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Pet Friendly Holiday Rentals in Chestertown

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    ₹ 15,139 Average
    ₹ 64,000+
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    1 / 10
    5 of 5 bubbles (6) Excellent
    Chestertown
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    1 / 14
    4.5 of 5 bubbles (3) Very good
    Chestertown
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    1 / 16
    5 of 5 bubbles (1) Excellent
    Chestertown
    4 Bedrooms, 9 Bathrooms, Sleeps 8 | Quick View
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    1 / 11
    4 of 5 bubbles (2) Very good
    Chestertown
    3 Bedrooms, 1 Bathroom, Sleeps 7 | Quick View
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    • Pet-friendly
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    • x
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    About this property
    A 3 bedroom house on the Chester River with amazing sunsets over the dock. Fully equipped, with central air conditioning, dishwasher, washer, dryer and parking - also free use of kayaks to enjoy the Chester River. An ideal property for those dropping off, picking up, or just visiting a student at... View all property information
    Location Information
    Chestertown, Maryland 21620
    3 of 5 bubbles Reviewed 15 August 2015
    The sunsets are magnificent. The house is comfy, but showing some deferred maintenance like grass growing from the gutters, green stuff on the exterior, landscaping so very...
    5 of 5 bubbles Reviewed 30 August 2014
    what a beautiful area of md. to stay at for an relaxing get away.the beautiful sun sets and sunrise.
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    1 / 28
    5 of 5 bubbles (3) Excellent
    Chestertown
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Porch
    • Grill
    • Wi-Fi
    • Air Conditioning
    • Private Garden
    • Patio
    • Parking
    • Outdoor Dining Area
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Quaint, modest one-bedroom cottage near the Chesapeake Bay. Relax and discover the culture, history, nature & cuisine of Maryland's Eastern Shore. Perfect for families, couples and friends. Guests can enjoy great views of the bay and sunsets from the owner's property, which is adjacent to... View all property information
    Location Information
    Chestertown, Maryland 21620
    5 of 5 bubbles Reviewed 9 September 2016
    We have been at this rental for 5 nights now, so thought we would review before we leave the day after tomorrow. The accommodation is set amongst trees near the owners home, with...
    5 of 5 bubbles Reviewed 10 June 2014
    My husband and I were lucky enough to stay in a charming little guest house on the Bay (Tolchester area of Chestertown, MD). House is almost right on the water, very clean, very...
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    1 / 22
    5 of 5 bubbles (1) Excellent
    Chestertown
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    • Air Conditioning
    • Grill
    • Parking
    • Outdoor Dining Area
    • Private Garden
    • Wi-Fi
    • Washer
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Modern, Cozy 2-Bedroom Cottage with sleeping loft. Views of the Chesapeake Bay from house and wraparound deck. Perfect destination for a couples getaway, family trip or friends gathering to enjoy the Bay & Sunsets. Located in the scenic, serene environs of the Eastern Shore of Maryland in... View all property information
    Location Information
    Chestertown, Maryland 21620
    5 of 5 bubbles Reviewed 24 September 2015
    I took my mother here for a getaway birthday weekend. I wanted somewhere we could relax but also be inspired by our surroundings. This quaint cottage was perfect. Nestled close to...
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    1 / 7
    Chestertown
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Satellite TV
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    A delightful one-bedroom apartment located in historic Chestertown. Close to Washington College & Heron Point. Apartment accommodates 2 guests. It is the perfect place for enjoying this historic, artistic town on Maryland's Eastern Shore. The space includes kitchen/living room combo, bedroom with... View all property information
    Location Information
    Chestertown, Maryland 21620

    The following rentals are within 40 kilometres of Chestertown, Maryland.

    1 / 17
    5 of 5 bubbles (3) Excellent
    Rock Hall
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    • Air Conditioning
    • Shared Outdoor Pool...
    • Washer
    • Satellite TV
    • Patio
    • DVD Player
    • Porch
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    This Spacious Home provides 3 Bedrooms and 2 bathrooms. Each room sleeps 2 people comfortably, and an old fashion cot is provided to sleep one more. This home is completely equipped with all the comforts of home. The Central location is in the heart of the Marina district, steps from Waterman’s... View all property information
    Location Information
    Rock Hall, Maryland 21661
    1 / 34
    5 of 5 bubbles (21) Excellent
    Centreville
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Washer
    • Internet Access
    • Porch
    • Satellite TV
    • Grill
    • Waterfront
    • Private Outdoor...
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    This house is on the estate of John Raskob, builder of the Empire State Building. The four-bedroom, two-bath house is one of seven that Raskob built for his farm employees. Now it has its own dock and swimming pool fronting on Grove Creek, with access to the two-mile-wide Chester River and... View all property information
    Location Information
    Centreville, Maryland 21617
    1 / 11
    Stevensville
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    Come to our beautiful vacation home and enjoy the scenic view while having fun on the water. Love Point Bay Vacation Home is at the mouth of the Chester River, where it connects to the Chesapeake Bay on Maryland's Eastern Shore. You will feel right at home, yet free of your everyday stress. Leave... View all property information
    Location Information
    Stevensville, Kent Island 21666
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    1 / 12
    5 of 5 bubbles (1) Excellent
    Rock Hall
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Pet-friendly
    • Child-friendly
    • ?
    • ?
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    • x
    About this property
    Enjoy the gentle tidal waters of the Chesapeake Bay and its tributaries from your private overlook. The Captain’s Quarters at Spring Cove is a crisp and contemporary second floor living space with great water views. An exterior stairway leads to an ample deck where you can enjoy breakfast and... View all property information
    Location Information
    Rock Hall, Maryland 21661
    5 of 5 bubbles Reviewed 2 January 2017
    Lovely, comfortable,clean, friendly with direct access to dock and bay. Lovely views from the many windows. Space is bright and modern while still sortingva large claw foot tube...
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    1 / 15
    4 of 5 bubbles (2) Very good
    Rock Hall
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • ?
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    • x
    About this property
    The Cottage takes advantage of its unique environment with a large deck overlooking the extensive lawn and the tranquil waters of Spring Cove. The deck includes a dining set and barbeque grill.The first level includes a screened porch accessed through a first floor bedroom The Cottage is oriented... View all property information
    Location Information
    Rock Hall, Maryland 21661
    4 of 5 bubbles Reviewed 17 September 2014
    My sisters and mother stayed three nights in this quaint house with great views of one of the marina's and cove area. The downstairs was perfect my mother, with a screened in...
    4 of 5 bubbles Reviewed 19 August 2014
    My family was looking for a relaxing getaway that would be an alternative to another week at the beach. We found the perfect spot at this cottage near Rock Hall. We rented with no...
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    1 / 12
    Stevensville
    3 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • Satellite TV
    • Private Garden
    • Parking
    • Wi-Fi
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Watch the beautiful sunrise and sunset from the privacy of the guest house. House has separate entrance for your privacy. 3 bedrooms and 2 full bath - with a spa bath in the master bath. Ample living room with ample dining and kitchen areas. Guests can enjoy their home cooking as kitchen is fully... View all property information
    Location Information
    Stevensville, Kent Island 21666
    1 / 10
    Rock Hall
    3 Bedrooms, 1 Bathroom, Sleeps 8 | Quick View
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    Amenities & Details
    • DVD Player
    • Air Conditioning
    • Satellite TV
    • Washer
    • Grill
    • Parking
    • Porch
    • Patio
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • ?
    About this property
    Charming 3 bed / 1 bath single family home with screened in front porch. Relax on the rocking chairs as you take in the charm of this lovely town on one of the prettiest streets in Rock Hall. Ample parking, large back yard with BBQ, tables and chairs to relax with family and friends after spending... View all property information
    Location Information
    Rock Hall, Maryland 21661
    1 / 35
    5 of 5 bubbles (13) Excellent
    Chester
    4 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    Amenities & Details
    • Hot Tub
    • Waterfront
    • Wi-Fi
    • Satellite TV
    • Air Conditioning
    • Secure Parking
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Swan Cove Condominiums at Kent Narrows(#49064) with private beach and views of the Chesapeake bay! - Brand new luxury condominium with 3000 sq ft, 4 bedrooms, 3 ½ bathrooms, one large family room with open kitchen, one large sunny living room and dinning area. There are 2 king size bed, 2 queen... View all property information
    Location Information
    Chester, Kent Island 21619
    5 of 5 bubbles Reviewed 11 January 2016
    My family used this home for 10 days over Christmas and New Year. It was just perfect. Plenty of room for our Christmas tree, decorations and packages. Spotlessly clean bedrooms...
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    1 / 26
    5 of 5 bubbles (1) Excellent
    Stevensville
    3 Bedrooms, 5 Bathrooms, Sleeps 8 | Quick View
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    • Washer
    • Private Outdoor...
    • Satellite TV
    • Hot Tub
    • Air Conditioning
    • DVD Player
    • Internet Access
    • Waterfront
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Have the ultimate Maryland getaway by staying at this remarkable Stevensville vacation rental home, surrounded by approximately 20 breathtaking acres of open space with picturesque Eastern Shore views. Whether you're in the mood for a relaxing escape in the great outdoors or a vacation filled with... View all property information
    Location Information
    Stevensville, Kent Island 21666
    5 of 5 bubbles Reviewed 11 May 2016
    From the moment you ride up the driveway you already know you are in for a wonderful experience. From the cathedral ceilings to the beautiful decor this home welcomes you. The...
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    1 / 21
    5 of 5 bubbles (3) Excellent
    Chester
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    Amenities & Details
    • DVD Player
    • Patio
    • Satellite TV
    • Waterfront
    • Wi-Fi
    • Washer
    • Grill
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Waterfront Rancher on 3 acres, centrally located between Washington DC, St. Michaels, Annapolis, and Baltimore. 4 Bed/2 Bath home with central air sleeps 8. This home has been in our family for over 50 years and is a special place. Over the years there have been many updates to the home. The... View all property information
    Location Information
    Chester, Kent Island 21619
    5 of 5 bubbles Reviewed 6 January 2016
    We have stayed in this home several times and will return in July. It is a wonderful house with a private master suite at one end, two bedrooms with a 2nd bath at the other.The...
    5 of 5 bubbles Reviewed 29 July 2013
    First I would like to say thanks, to Harry, and Scott. They were the best host, I've encountered. They have a property, they can be proud of. The house was just excellent. The...
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