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Holiday Rentals nearby Maine DaySail and the Schooner Timberwind

Portland, Maine 04101
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    Travellers to Portland are booking October dates now. Secure your holiday home today, and have the perfect trip.
    All 31 Rentals in Portland
    4.3 kilometres from Maine DaySail and the Schooner Timberwind
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Chez Seeger, Belfast First floor apartment1 / 17
    (1)Excellent
    1.4 kilometres from Maine DaySail and the Schooner Timberwind
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    6.0 kilometres from Maine DaySail and the Schooner Timberwind
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    5.2 kilometres from Maine DaySail and the Schooner Timberwind
    5 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Hot Tub
    • Wi-Fi
    • Grill
    • Cable/satellite TV
    • Patio
    • Air Conditioning
    • Porch
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Original sea captain's home; recently renovated with period details intact. Large living room, dining room with fireplace, eat-in farm kitchen with new appliances, granite countertops, and a restored wood cook stove for ambiance and warmth on a chilly evening. The house is available with 2 to 5...
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    Searsport, Mid Coast Maine
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 10
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    Bayside / Northport / Belfast Shorefront Weekly Rental #11 / 12
    (5)Very good
    4.6 kilometres from Maine DaySail and the Schooner Timberwind
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Central Heating
    • Outdoor Dining Area
    • Shared Garden
    • Grill
    • Cable/satellite TV
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 23 July 2014
    The cottage was quaint, clean, and well-equipped with kitchen pots, pans and utensils. We were disappointed with the lack of a water view from the cottage. We could see the...
    Reviewed 14 July 2014
    There is a beautiful ocean view. The owner is extremely helpful if you need anything. It is very private and quiet.
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    About this property
    21 beautiful acres w/660 feet of oceanfront all to yourself. 3 miles to Belfast. 15 miles to Camden. Vintage gardens and apple orchard. Only two rentals on the entire property. Caretakers Cottage - One bedroom, bathroom w/shower living room and full kitchen - $850 wk. max 2 people All weekly...
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    Northport, Mid Coast Maine
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Starry Nights Cottage- Bayside Village, Northport1 / 19
    (1)Very good
    6.1 kilometres from Maine DaySail and the Schooner Timberwind
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
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    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 October 2014
    This property is everything it is described to be and more. We enjoyed our stay in Maine and Starry Nights was a large part of our enjoyment. As it turns out this cottage is far...
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    About this property
    Roomy gambrel ~ features three bedrooms including a king bed, two baths and is very light and bright. It has a waterview from the large yard and sneaks a couple of water views upstairs. A more modern design and construction, this cottage offers a family ample space for an extended vacation....
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    Northport, Mid Coast Maine
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    7.3 kilometres from Maine DaySail and the Schooner Timberwind
    3 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    • DVD Player
    • Secure Parking
    • Waterfront
    • Wi-Fi
    • Washer
    • Grill
    • Ocean Views
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Kelly Cove Cottage offers a comfortable, modest home perfectly located for plenty of Maine adventures. The adjacent beach is on a calm cove within Penobscot Bay, great for swimming, paddling, boating and even SUPing. The house is a cozy retreat, a short walk into Bayside Village and quick drives to...
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    Northport, Mid Coast Maine
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 9
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    The LUV Cottage, Northport, Maine (in Bayside)1 / 56
    (4)Excellent
    6.2 kilometres from Maine DaySail and the Schooner Timberwind
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
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    • Internet Access
    • Grill
    • Porch
    • Outdoor Dining Area
    • Washer
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 July 2017
    The location was so convenient! We were right down the street from the bridge, playground, sailing camp, basketball courts, and they have a Market on Tuesdays. The people are...
    Reviewed 2 August 2015
    We love Luv cottage! (HAHA) We have been coming here for three years now. The company that manages the cottage is ONTHEWATERINMAINE. (Shout out to Ben!) And, the owners are...
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    About this property
    PLEASE NOTE THAT THE DEFAULT RATE LISTED IS THE PEAK SUMMER RATE (last 3 and first 3 weeks in July/August) .....DISCOUNTS AVAILABLE FOR OTHER TIMES AND FOR MORE THAN ONE WEEK STAYS...SEND INQUIRY TO DISCUSS...Deep in the heart of Bayside is this classic Maine cottage. The 90+ year old LUV cottage...
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    Northport, Mid Coast Maine
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Ocean View Cape on 14 Private Acres1 / 15
    (3)Very good
    6.0 kilometres from Maine DaySail and the Schooner Timberwind
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Parking
    • Patio
    • Central Heating
    • Internet Access
    • Porch
    • Grill
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 September 2016
    Rambling country property on a large plot. Well equipped kitchen. About an hours drive from Acadia National Park. Grocery shopping close by in either Searsport or Belfast...
    Reviewed 6 October 2015
    Had such a nice time walking along Penobscot Bay beach and to Moose Point State Park. Very convenient to Searsport and Belfast but feels secluded and very cozy. It is obvious...
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    About this property
    The Space Resting on over 14 private acres, Heroncrest was built circa 1840 and boasts scenic ocean views, gracious lawns, perennial gardens and southern exposure. Enjoy sunrises, sunsets and moonlight over picturesque Penobscot Bay in this house furnished with antiques and original art. There...
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    Searsport, Mid Coast Maine
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    1.5 kilometres from Maine DaySail and the Schooner Timberwind
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Cable/satellite TV
    • Internet Access
    • Private Garden
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Fabulous Belfast Harbor location looking out towards Penobscot Bay, this lovely vacation rental has water views and direct access with a sweeping lawn down to the water. This unique property has over 200ft of waterfront and there is a private fire-pit on the beach. The yard has mature plantings and...
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    Belfast, Mid Coast Maine
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    The Beehive Cottage, Northport, Maine (in Bayside)1 / 45
    (5)Excellent
    6.7 kilometres from Maine DaySail and the Schooner Timberwind
    5 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Washer
    • DVD Player
    • Grill
    • Patio
    • Balcony
    • Waterfront
    • Ocean Views
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 September 2017
    My husband and I stayed at the Beehive for our 10 year anniversary trip. We were looking for somewhere comfortable, quiet & laid back and this hit all the marks. The house...
    Reviewed 5 July 2017
    Very nice location directly on the bay with beautiful views. Plenty of amenities and easy access to local restaurants. Highly recommended.
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    About this property
    PLEASE NOTE THAT THE DEFAULT RATE LISTED IS THE PEAK SUMMER RATE (last 3 and first 3 weeks in July/August) .....DISCOUNTS AVAILABLE FOR OTHER TIMES AND FOR MORE THAN ONE WEEK STAYS...SEND INQUIRY TO DISCUSS....A stone's throw from the Bayside village wharf, this 3,500 square foot oceanfront cottage...
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    Northport, Mid Coast Maine
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 12
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    Sea Smoke - Waterfront1 / 20
    (3)Very good
    6.4 kilometres from Maine DaySail and the Schooner Timberwind
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Porch
    • Secure Parking
    • Washer
    • Waterfront
    • Outdoor Dining Area
    • Grill
    • DVD Player
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 August 2015
    This was a lovely old camp type home with many modern upgrades. The house was charming with the sea glass window in the old fashion bathroom. It was very comfortable and well...
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    About this property
    The graceful white cottage with dark green shutters is located in a quaint Victorian village on the coast of Maine. Bayside is a boating and sailing paradise with an active village wharf for adults and children with a swim float and lifeguard. 'Sea Smoke' is at the far corner of Bayview Park...
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    Northport, Mid Coast Maine
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    Ocean Front Cottage on Penobscot Bay1 / 10
    (6)Excellent
    3.2 kilometres from Maine DaySail and the Schooner Timberwind
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Ocean Views
    • Cable/satellite TV
    • Patio
    • Wi-Fi
    • Grill
    • Air Conditioning
    • DVD Player
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 June 2018
    Watched the tide come and and go out from the deck, or from the cozy cottage's front window. The sounds of the water was so relaxing. Steps to the beach. We watched the moon...
    Reviewed 5 July 2017
    We watched seals and loons in the morning. Neighboring cottages were very quiet. Beach is rocky, mid-coast Maine. The cottage is beautifully renovated and lovely. Fran and Ellen...
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    About this property
    Surfside cottage sits just 100 feet from the high tide mark. This is rare along the coast and allows you to experience both the spectacular views of the ocean, and the sound of the coast. Relax to the sound of the surf, loons and harbor bell and watch lobster boats pass by. Plenty to do right at...
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    Belfast, Mid Coast Maine
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    See Sea Cottage, Northport Maine (in Bayside)1 / 18
    (7)Very good
    6.2 kilometres from Maine DaySail and the Schooner Timberwind
    5 Bedrooms, 3 Bathrooms, Sleeps 5 Quick View
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    • Washer
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    • Outdoor Dining Area
    • Porch
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    • Grill
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 June 2013
    Six college friends have been traveling for 35 years. We are all retired from teaching and are in our early 70's. We used to be right in the middle of everything and...
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    About this property
    The See Sea Cottage began almost 100 years ago as a boat barn. In 2015 it was converted and expanded into a cottage. It has frontage on both Main and Maple Streets It has three bedrooms and 2.5 completely renovated bathrooms. The cottage has a master bedroom loft with a king size bed, a bedroom...
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    Northport, Mid Coast Maine
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 5
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    3.9 kilometres from Maine DaySail and the Schooner Timberwind
    6 Bedrooms, 7 Bathrooms, Sleeps 12 Quick View
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    • Central Heating
    • Waterfront
    • Washer
    • Parking
    • DVD Player
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Fall in love at Portside Manor with the stunning ocean views, lavish living space and pristine landscaping. Located in Searsport Maine, home of the famous sea captains. This rental property features a stylish coastal-beach interior with rolling lawns spilling down to the water’s edge. It is the...
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    Searsport, Mid Coast Maine
    Holiday Rental House - 6 Bedrooms, 7 Bathrooms, Sleeps 12
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    1.4 kilometres from Maine DaySail and the Schooner Timberwind
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
    • Private Garden
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    Pet friendly
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    Smoking allowed
    About this property
    Originally a farmhouse built by a ship-builder in 1855, this second floor apartment has charm of a by-gone era yet all the comfort and convenience of today. Two bedrooms with pumpkin pine floors, a fully equipped kitchen, cozy living room with 50' TV and Amazon service, plus bathroom with antique...
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    Belfast, Mid Coast Maine
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    0.2 kilometres from Maine DaySail and the Schooner Timberwind
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Central Heating
    • Terrace
    • DVD Player
    • Balcony
    • Ocean Views
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is a very unique property. It is a brand new, 165 year old home. As you move from room to room in this recently renovated farmhouse style home there are hints of its history in the wavy (occasionally creaky) floors and slanted roofline. While admiring its unique features, you'll appreciate...
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    Belfast, Mid Coast Maine
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    Modern luxury home & the kids can run free. :-)1 / 26
    (2)Excellent
    1.5 kilometres from Maine DaySail and the Schooner Timberwind
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Central Heating
    • DVD Player
    • Washer
    • Ocean Views
    • Mountain Views
    • Cable/satellite TV
    • Patio
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 weeks ago
    We had such an incredible stay one night end of April 2018, and so welcomed by the owner's and enjoyed listening to all their stories, that I kept in touch with them and worked...
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    About this property
    A 6 acre plot with huge lawn, woodland walks & a tire swing. A totally safe space for kids to run wild. Close to Belfast with fabulous independent stores, bars & restaurants, a legendary movie theatre and moments away from hiking spots, boating opportunities & parks. Day trips to Acadia National...
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    Belfast, Mid Coast Maine
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    4.7 kilometres from Maine DaySail and the Schooner Timberwind
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Outdoor Dining Area
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    • Waterfront
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    • Shared Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    21 beautiful acres w/660 feet of oceanfront all to yourself. 3 miles to Belfast. 15 miles to Camden.Vintage gardens and apple orchard. Only two rentals on the entire property. Chauffeurs Garage Apt. (second floor) - One bedroom, bathroom w/shower living room and kitchen dining room - $750 wk. max...
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    Northport, Mid Coast Maine
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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    5.5 kilometres from Maine DaySail and the Schooner Timberwind
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
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    Smoking allowed
    About this property
    Built in 1900 as a church for the historic Bayside community of Northport, our home has been converted into a beautiful, comfortable home. Surrounded by organic gardens and overlooking Penobscot Bay, we are conveniently located, five minutes to downtown Belfast, and a perfect jumping off point for...
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    Northport, Mid Coast Maine
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    1.2 kilometres from Maine DaySail and the Schooner Timberwind
    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Porch
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    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 August 2016
    We had a nice trip to the Charming House near Ocean. One tv in master bead room but nice place to unwind and escape.
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    About this property
    ENTIRE CONTEMPORARY HOUSE NEAR THE OCEAN.....ALL MODERN CONVIENENCES...BEAUTIFULLY LANDSCAPED WITH MANICURED GARDENS AND 2 MINUTESFROM THE OCEAN AND BOATING ,RESTAURANTS ,SHOPPING AND HOSPITALS........ 3 BEDROOMS, 1.5 BATHS , WASHER AND DRYER, 3 SUNNY DECKS AND A MASTER BEDROOM WITH A...
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    Belfast, Mid Coast Maine
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 5
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    6.0 kilometres from Maine DaySail and the Schooner Timberwind
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
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    • Balcony
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    • Waterfront
    • Central Heating
    • DVD Player
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Windy Corner Cottage has become our most desired waterfront rental. The cottage has undergone a fantastic upgrade with new bathrooms, a fireplace, 2 sets of sliding glass doors across the front of the cottage and a deck at the shore. The owners had the vision to make a historic cottage meet the...
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    Northport, Mid Coast Maine
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    0.2 kilometres from Maine DaySail and the Schooner Timberwind
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
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    • Balcony
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This fantastic new apartment is perfect for 3 couples as each bedroom has its own private space and there are three bathrooms, each more distinctive than the next. The apartment is on the top two floors of the Ocean House, a recently renovated 1865 building in the heart of downtown Belfast. The two...
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    Belfast, Mid Coast Maine
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    5.2 kilometres from Maine DaySail and the Schooner Timberwind
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Charming newly renovated apartment includes living room with flat-screen TV, wifi, queen size bedroom, new kitchen, large bath, and a private patio with picnic table and grill. Apartment has a private entrance and is on the second floor. Beds: 1 Queen Bed...
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    Searsport, Mid Coast Maine
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    1.0 kilometres from Maine DaySail and the Schooner Timberwind
    3 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Great location on quiet street in charming neighborhood. Sunny, cheerful house with views of bay and an open floor plan, large sectional sofa with big screen TV! Great house for kids and adults alike. 3 blocks from shore and 6 blocks from charming downtown Belfast. Free WIFI and Netflix! 2 large...
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    Belfast, Mid Coast Maine
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 9
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    2.4 kilometres from Maine DaySail and the Schooner Timberwind
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Ocean Views
    • DVD Player
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    • Housekeeping Included
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    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy breakfast on Belfast Bay from your ocean view deck while staying in this newly renovated suite. Featuring ocean views from the living room, dining room, and kitchen of this open concept suite. the dining room seats 8 and the granite island in the kitchen offers ocean views while your lobsters...
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    Location Information
    Belfast, Mid Coast Maine
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    6.2 kilometres from Maine DaySail and the Schooner Timberwind
    2 Bedrooms, 5 Bathrooms, Sleeps 5 Quick View
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    Smoking allowed
    About this property
    Take a step back in time and enjoy 'THE HISTORIC BAYSIDE INN'. The stately 'BAYSIDE INN' has has a dominating view at the head of the village green with unobstructed views of Penobscot Bay. A true piece of Maine history completely up-dated with today's amenities to make your stay one you will never...
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    Northport, Mid Coast Maine
    Condo/Apartment - 2 Bedrooms, 5 Bathrooms, Sleeps 5
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    0.6 kilometres from Maine DaySail and the Schooner Timberwind
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
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    • Waterfront
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    • Ocean Views
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Step into your dream home when you book this Belfast, Maine getaway. Built in the 1890s but full of modern updates, this 3-bedroom, 1.5-bathroom vacation rental home is packed with New England charm, including sleeping for 6, cozy furnishings and contemporary decor. With the Passagassawakeag River...
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    Belfast, Mid Coast Maine
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    7.5 kilometres from Maine DaySail and the Schooner Timberwind
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Housekeeping Included
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    Smoking allowed
    About this property
    The beautiful 1863 Sea Captain's Cottage has over 3500 square feet of luxuriously renovated space. Walk to everything Searsport has to offer. We are only minutes from Penobscot Bay and one block from the famous maritime museum. The house has three bedrooms and 2 and 1/2 bathes. The third bedroom...
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    Location Information
    Searsport, Mid Coast Maine
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    5.3 kilometres from Maine DaySail and the Schooner Timberwind
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Central Heating
    • Grill
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Newly renovated apartment on ground floor with private entrance, large, fully equipped kitchen, living room with cable TV, large bath, and a deck with grill and patio furniture. Wifi, all utilities, and parking are included. The property is on 2 private acres with trees and wildlife. Building is...
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    Location Information
    Searsport, Mid Coast Maine
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    3.9 kilometres from Maine DaySail and the Schooner Timberwind
    6 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Washer
    • Waterfront
    • Central Heating
    • DVD Player
    • Ocean Views
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Fall in love at Portside Manor with the stunning ocean views, lavish living space and pristine landscaping. Located in Searsport Maine, home of the famous sea captains. This rental property features a stylish coastal-beach interior with rolling lawns spilling down to the water’s edge. It is the...
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    Location Information
    Searsport, Mid Coast Maine
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 12
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