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Holiday Rentals in Winchendon, MA

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    ₹ 12,400 Average
    ₹ 68,000+
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    The following rentals are within 25 kilometres of Winchendon, Massachusetts.

    1 / 9
    4 of 5 stars (1) Very good
    Jaffrey, NH
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    1 / 24
    4.5 of 5 stars (2) Very good
    Rindge, NH
    2 Bedrooms, 1 Bathroom, Sleeps 7 | Quick View
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    1 / 37
    5 of 5 stars (15) Excellent
    Ashburnham
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    1 / 12
    5 of 5 stars (2) Excellent
    Fitzwilliam, NH
    3 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    Amenities & Details
    • Washer
    • Satellite TV
    • Internet Access
    • DVD Player
    • Waterfront
    • Mountain Views
    • Air Conditioning
    • Hot Tub
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    3 Bedrooms (Queen, Queen and single) and an upstairs expansive family sleeping loft/entertainment center with a King,2 single beds and a hideabed. The great room has a full modern kitchen with all Brand New appliances, glasses, dishes, pots, spices, condiments and a dining table with room for 10.... View all property information
    Location Information
    Fitzwilliam, New Hampshire 03447
    5 of 5 stars Reviewed 2 January 2013
    With older family members in retirement housing in Keene, NH, we needed to find a way to continue our tradition of large family Christmas celebrations. When I found this Rockwood...
    5 of 5 stars Reviewed 10 December 2010
    We recently stayed at Rockwood Pond's and we can't say enough good things about our experience! First, Paul and anne were extermely accomodating and made the booking process a...
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    Fitzwilliam, NH
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Porch
    • Central Heating
    • Waterfront
    • Washer
    • Wi-Fi
    • Mountain Views
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    (Please note that the FlipKey 'per night' quote is for a weekly rental and their 'Ready to book?' quote does not include the security deposit amount.) We book Sunday to Sunday. If we are not booked within three weeks of a date, then we open up to partial week rentals. Our minimal rental is 2... View all property information
    Location Information
    Fitzwilliam, New Hampshire 03447
    Troy, NH
    3 Bedrooms, 2 Bathrooms, Sleeps 9 | Quick View
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    • Grill
    • Hot Tub
    • Wi-Fi
    • Parking
    • Air Conditioning
    • Balcony
    • Terrace
    • Mountain Views
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Inquire today late Summer and Fall Foliage vacations! Relax in peaceful private comfort on 1.5 acres on serene 110 acre Rockwood Pond. The view out the full length deck across the lake will make it easy to fully enjoy the Great Room with cathedral ceilings, wood stove, new appliances and lots of... View all property information
    Location Information
    Troy, New Hampshire 03447
    Richmond, NH
    5 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Outdoor Dining Area
    • Balcony
    • Mountain Views
    • Wi-Fi
    • Washer
    • Patio
    • Parking
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • x
    About this property
    This historic home on 24 wooded acres in New Hampshire about 20 minutes south of Keene was built in 1774 and occupied by a Revolutionary War family. Additions over the centuries make it a rich experience of history, nature, fireplaces and wood-burning stoves, rich furnishings, and modern amenities!... View all property information
    Location Information
    Richmond, New Hampshire 03470
    Jaffrey, NH
    6 Bedrooms, 8 Bathrooms, Sleeps 12 | Quick View
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    Amenities & Details
    • Washer
    • Balcony
    • Porch
    • Patio
    • Grill
    • Mountain Views
    • Internet Access
    • Central Heating
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    1) Beautiful historic property, originally an early 1800's tavern with a rich history as a working farm, seasonal vacation home, inn and year round residence. Property sits at the base of Mt. Monadnock with beautiful mountain and pastoral views. Our street address is Mountain Rd., 2) One of... View all property information
    Location Information
    Jaffrey, New Hampshire 034526002
    1 / 18
    Rindge, NH
    3 Bedrooms, 1 Bathroom, Sleeps 7 | Quick View
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    Amenities & Details
    • DVD Player
    • Washer
    • Grill
    • Patio
    • Central Heating
    • Satellite TV
    • Waterfront
    • Parking
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    On the Lake, 80 Feet Sandy Beach Frontage, facing west with beautiful sunset view Docks and Nice Swimming Area all part of this nice private property NEW DOCKS MAY 2014 Patio spaces at the Beach Picnic Tables/Barbeque Area (all part of the property) Sunny Deck (NEW DECK MAY May 2011!!)... View all property information
    Location Information
    Rindge, New Hampshire 03461
    Richmond, NH
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    Amenities & Details
    • Patio
    • Wi-Fi
    • Air Conditioning
    • Satellite TV
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Enjoy a quiet entire apartment with your friend and family in historic town Richmond,Va This is a apartment on first floor in byrd park area with all renovation, it is between byrd park and Cary town (good neighborhood) first floor apartment has a 1 year lease tenant live there. it is pretty... View all property information
    Location Information
    Richmond, New Hampshire 23220
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    1 / 20
    Rindge, NH
    8 Bedrooms, 6 Bathrooms, Sleeps 22 | Quick View
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    Amenities & Details
    • Balcony
    • Private Outdoor...
    • Air Conditioning
    • Hot Tub
    • Grill
    • Satellite TV
    • Internet Access
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Located atop of a hill, amidst 500 acres with miles of walking & groomed x-country ski trails, outdoor hot tub, & 5000 gallon swimming pool. This extraordinary 11,000 sq. ft. castle has incredible views of Mt. Monadnock from the N & lake/ beach from the S. Enjoy the solitude & amazing sunsets on... View all property information
    Location Information
    Rindge, New Hampshire
    Fitzwilliam, NH
    3 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    Amenities & Details
    • Mountain Views
    • Hot Tub
    • Air Conditioning
    • Satellite TV
    • Internet Access
    • Washer
    • DVD Player
    • Waterfront
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    About this property
    Relax in peaceful private comfort on 1.5 acres on serene 110 acre Rockwood Pond. The view out the full length deck across the lake will make it easy to fully enjoy the Great Room with cathedral ceilings, wood stove, new appliances and lots of seating and the Private Hot Tub under the stars. 3... View all property information
    Location Information
    Fitzwilliam, New Hampshire 03447
    1 / 26
    5 of 5 stars (2) Excellent
    New Ipswich, NH
    3 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    Amenities & Details
    • DVD Player
    • Parking
    • Washer
    • Internet Access
    • Central Heating
    • Grill
    • Hot Tub
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Home built in 2000 with complete makeover in 2013 features hardwood and tile floors throughout, granite kitchen countertops, fridge, dishwasher, gas stove, microwave, toaster, coffee maker, washer, dryer, whirlpool tub, central vac, gas grill, and gas fireplace. All new furniture in 2014 throughout... View all property information
    Location Information
    New Ipswich, New Hampshire 03071
    5 of 5 stars Reviewed 29 December 2015
    I belong to a music group based out of Boston, and we were looking for a relaxing retreat for one night away from the city. This could not have been a more perfect location. It...
    5 of 5 stars Reviewed 21 July 2015
    We were surprised at how clean and comfortable and well stocked this home is. We traveled to New Hampshire from Florida. We had family from Florida, Pennsylvania, Delaware and...
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    Richmond, NH
    2 Bedrooms, 3 Bathrooms, Sleeps 3 | Quick View
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Stunningly beautiful two bedroom, t.5 bath condominium in the Oregon Hill section of Richmond, along the James River within easy walking access to the Canal Walk, numerous restaurants and with the heart of downtown Richmond less than five minutes away; walk if you feel like it. Rents fully... View all property information
    Location Information
    Richmond, New Hampshire 23220
    Peterborough, NH
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Parking
    • Balcony
    • Satellite TV
    • Wi-Fi
    • Washer
    • Air Conditioning
    • DVD Player
    • Waterfront
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    An easy one mile walk from downtown Peterborough (sidewalks all the way) with all its fantastic shopping, dining, parks, and quintessential New England charm. This recently renovated two bedroom riverside cottage sleeps four people. With its updated kitchen, spacious living room, screened-in porch,... View all property information
    Location Information
    Peterborough, New Hampshire 03458
    Fitzwilliam, NH
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Amenities & Details
    • Central Heating
    • Grill
    • Waterfront
    • Washer
    • DVD Player
    • Wi-Fi
    • Satellite TV
    • Porch
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Come to MountainShadow for an escape from stress and the city! Our location is perfect for summer outdoor activities, blueberry picking, mountain hiking, fall foliage and visiting farms for organic meat, pork, lamb, eggs, maple syrup, apples, and cider. We are on Scott Pond and in the shadow of... View all property information
    Location Information
    Fitzwilliam, New Hampshire 03447