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Vacation Rentals in Windsor, VT and nearby

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    1 / 12
    Windsor
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    The following rentals are within 25 kilometres of Windsor, Vermont.

    1 / 38
    5 of 5 bubbles (10) Excellent
    Woodstock
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    1 / 21
    4.5 of 5 bubbles (4) Very good
    Perkinsville
    5 Bedrooms, 4 Bathrooms, Sleeps 12 | Quick View
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    1 / 7
    Woodstock
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    Amenities & Details
    • Satellite TV
    • Shared Indoor Pool
    • Balcony
    • Hot Tub
    • Sauna
    • Washer
    • Air Conditioning
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Located minutes from the charming village of Woodstock, this new and charmingly furnished hotel apartment offers the privacy and convenience of your own home with all the benefits of staying in a premium hotel. Located on the grounds of 506 On the River Inn, you will have access to the indoor... View all property information
    Location Information
    Woodstock, Vermont 05091
    1 / 22
    5 of 5 bubbles (2) Excellent
    Woodstock
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Wi-Fi
    • DVD Player
    • Grill
    • Central Heating
    • Mountain Views
    • Satellite TV
    • Patio
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Brand new local Vermont stone patio with firepit- perfect for a Vermont evening! Located just south of the Woodstock Country Club golf course off of Route 106, Maplewoods is a 4 bedroom, 2.5 bath professionally decorated luxury home located just two miles from the Woodstock Village Green.... View all property information
    Location Information
    Woodstock, Vermont 05091
    1 / 7
    Woodstock
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Hot Tub
    • Sauna
    • Terrace
    • Washer
    • Balcony
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Located minutes from the charming village of Woodstock, this new and charmingly furnished hotel apartment offers the privacy and convenience of your own home with all the benefits of staying in a premium hotel. Located on the grounds of 506 On the River Inn, you will have access to the indoor... View all property information
    Location Information
    Woodstock, Vermont 05091
    1 / 28
    4 of 5 bubbles (1) Very good
    Bridgewater
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Internet Access
    • Grill
    • Waterfront
    • DVD Player
    • Hot Tub
    • Mountain Views
    • Satellite TV
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    It means no worries, for the rest of your vacation. No service, no problem! That’s what makes this home so special, the stress of work and everyday life seem to evaporate the second you arrive. Being surrounded by beautiful scenery, fresh clean air and the sounds of nature have made this a favorite... View all property information
    Location Information
    Bridgewater, Vermont 05035 4409
    1 / 22
    4.5 of 5 bubbles (6) Very good
    Grantham, NH
    3 Bedrooms, 3 Bathrooms, Sleeps 9 | Quick View
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    • Sauna
    • Shared Indoor Pool
    • Wi-Fi
    • DVD Player
    • Satellite TV
    • Mountain Views
    • Skiing: Property Is...
    • Central Heating
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Eastman Four Season Resort in Mount Sunapee / Dartmouth area.<BR>3 bedroom/3 bath townhouse available for short or long term vacation rental. <BR>Sleeps 9! <BR>Eastman is a unique resort community that offers a pristine mountain lake and unaffected natural beauty, combined with the convenience of... View all property information
    Location Information
    Grantham, New Hampshire 03753
    5 of 5 bubbles Reviewed 2 August 2016
    My family has actually had the good fortune to rent this property in summer and winter. Since we stayed longer during our ski holidays I know it best then, but it's great any...
    5 of 5 bubbles Reviewed 31 May 2016
    >>>> We spent a very enjoyable July vacation at this charming lake home with our two children and my sisters family of 4'. The house was charming, clean and comfortable...
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    1 / 46
    Sunapee, NH
    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
    My 3 season waterfront cabin is appointed with true "cabin style" charm but with all the modern amenities. The cabin is directly on Perkins Pond and provides amazing views and sunsets. There are 2 large decks, a wharf for sunning, and lighted landscaped pathway. Two kayaks are included to explore... View all property information
    Location Information
    Sunapee, New Hampshire 03782
    1 / 25
    Hanover, NH
    3 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
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    • DVD Player
    • Patio
    • Washer
    • Grill
    • Air Conditioning
    • Satellite TV
    • Parking
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Have the quintessential New England getaway at "Serendipity on the Hill" by staying at this 3-bedroom plus loft, 3-bath Hanover house. With wonderful amenities and a great location near the area’s best attractions, this home provides immense comfort for 7 guests! Settled among the natural beauty... View all property information
    Location Information
    Hanover, New Hampshire 03755
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    1 / 20
    5 of 5 bubbles (1) Excellent
    Reading
    3 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
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    • Porch
    • Washer
    • Mountain Views
    • Shared Garden
    • Grill
    • Internet Access
    • Outdoor Dining Area
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • x
    About this property
    Nestled in a private hundred-acre valley crisscrossed with trails, a quiet, beautifully situated antique cabin and fully renovated barn overlooking idyllic Vermont meadow, ponds, hills & creek awaits your discovery. Property abuts the world famous Jenne Farm located twenty minutes south of... View all property information
    Location Information
    Reading, Vermont 05062
    5 of 5 bubbles Reviewed 30 June 2014
    We were looking for a quiet spot for our family to get away from our crazy day-to-day life, and we found it! The cabin was great - clean, comfortable, well-stocked - and the porch...
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    1 / 53
    5 of 5 bubbles (4) Excellent
    Reading
    15 Bedrooms, 12 Bathrooms, Sleeps 44 | Quick View
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    • Hot Tub
    • Wi-Fi
    • Satellite TV
    • DVD Player
    • Washer
    • Private Outdoor...
    • Mountain Views
    • Central Heating
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Reading Farms lies in the heart of Vermont. A completely private 400 acre estate. One of Vermont's most majestic properties has been held by the same owners for nearly 100 years. The secluded estate is conveniently located minutes from Woodstock Vermont and two of the best Vermont ski areas... View all property information
    Location Information
    Reading, Vermont 05062
    5 of 5 bubbles Reviewed 27 July 2015
    We just returned from our stay at Reading Farms and it was truly amazing, the chef cooked us a to die for meal and the staff did a firework show for us our last night that was...
    5 of 5 bubbles Reviewed 26 June 2014
    I had a lovely time at Reading Farms Estate over the Memorial Day weekend. The property is stunning, with sweeping views of the surrounding mountains and excellent service and...
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    1 / 18
    Grantham, NH
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    Amenities & Details
    • Waterfront
    • Internet Access
    • Parking
    • Central Heating
    • Balcony
    • Washer
    • Grill
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Enjoy the Fall colors, Dartmouth football games, Sunapee ski weekends, and all that this beautiful region has to offer. 2BR, 2BA lakefront condo in Eastman, a planned recreational community located in the NH Upper Valley area. This condo was completely renovated in 2015 and features bamboo... View all property information
    Location Information
    Grantham, New Hampshire 03753
    1 / 6
    Woodstock
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Wi-Fi
    • Central Heating
    • Shared Garden
    • Mountain Views
    • Parking
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    About this property
    NEW! 2013 Renovation: Country Serenity Meets Urban Amenity (2 apartments)<BR><BR>This wonderful escape combines a soothing minimalist aesthetic with the pleasures of a rural landscape. <BR><BR>Renovated in November 2013, the spacious apartment features brand new whitewashed parquet hardwood... View all property information
    Location Information
    Woodstock, Vermont 05071
    1 / 32
    Sunapee, NH
    3 Bedrooms, 2 Bathrooms, Sleeps 9 | Quick View
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    • Central Heating
    • Grill
    • Parking
    • Waterfront
    • Washer
    • Internet Access
    • Porch
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    You’ll feel like you’re vacationing inside the pages of DWELL magazine in this brand new three/four bedroom lakefront house designed by a prominent Boston architect. Charming Kezar Lake, dotted with old farmhouses and inns, is a well-kept secret in the area. Old-fashioned Vernondale General Store,... View all property information
    Location Information
    Sunapee, New Hampshire 03260
    1 / 27
    5 of 5 bubbles (5) Excellent
    Woodstock
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Satellite TV
    • Air Conditioning
    • Grill
    • Mountain Views
    • Internet Access
    • Washer
    • DVD Player
    • Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • x
    About this property
    This exceptionally nice, newly renovated 2 bedroom converted carriage house sits on a private 250 acre estate. All windows overlook undisturbed fields, mountains, and the Woodstock valley. It is completely furnished, has outside deck with beautiful views, a slate floor ski/mud room, and doorstep... View all property information
    Location Information
    Woodstock, Vermont 05091
    5 of 5 bubbles Reviewed 20 June 2016
    Wonderful location and a comfortable home for a thoroughly relaxing vacation. We stayed at the Carriage House as a base while taking a baking class at the Kung Arthur Flour...
    5 of 5 bubbles Reviewed 20 May 2016
    Immaculate space atop a mile high road with beautiful views out the windows and deck. Very peaceful. We especially enjoyed walking down to the little pond and sitting on the...
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    1 / 13
    White River Junction
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Internet Access
    • Washer
    • Mountain Views
    • Parking
    • Satellite TV
    • Patio
    • Central Heating
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    On the border of Vermont and New Hampshire, Savage Hart Farm is a perfect place to stay for a memorable visit to the heart of New England. You'll find a retreat-type setting close to the center of the towns of Hanover, NH, and Norwich, VT in a bucolic locale even the locals talk about. Quechee is... View all property information
    Location Information
    White River Junction, Hartford 05001
    1 / 27
    Cavendish
    6 Bedrooms, 10 Bathrooms, Sleeps 17 | Quick View
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    • DVD Player
    • Grill
    • Hot Tub
    • Mountain Views
    • Patio
    • Air Conditioning
    • Skiing: Property Is...
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    The property includes 7 bedrooms (robes, bath amenities, tempurpedic beds, fireplaces, vable television, DVD and ensuite baths in all but 2), 8-person hot tub, dining for 24. Great for large groups or big families or specialb events. Warm weather Rustic Barn with bar can seat up to 115 guest... View all property information
    Location Information
    Cavendish, Vermont 05142
    1 / 12
    5 of 5 bubbles (1) Excellent
    Newport, NH
    3 Bedrooms, 1 Bathroom, Sleeps 7 | Quick View
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    • Grill
    • Wi-Fi
    • Waterfront
    • Mountain Views
    • DVD Player
    • Satellite TV
    • Patio
    • Central Heating
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Located on a quiet, pristine New Hampshire lake, this home and scenic surroundings provide a haven of rest for your vacation. Our private sandy beach sits on 510 feet of shoreline and invites you to enjoy carefree sunbathing and swimming in a safe, beautiful setting. Shade trees on the grounds... View all property information
    Location Information
    Newport, New Hampshire 03773
    1 / 15
    Brownsville
    Studio, 3 Bathrooms, Sleeps 6 | Quick View
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    • Porch
    • Internet Access
    • Parking
    • Mountain Views
    • DVD Player
    • Washer
    • Shared Indoor Pool
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    The condominium lies on the West face of historical Ascutney Mt in the small town of Brownsville. The condominium consists of 3 bedrooms, 2 1/2 bathrooms, a small family rec room, living room, and dining area. A very comfy and warm atmosphere with access to a full service sports and fitness center.... View all property information
    Location Information
    Brownsville, Vermont 05089
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    1 / 34
    Perkinsville
    Private Room, 1 Bathroom, Sleeps 2 | Quick View
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    • Mountain Views
    • Grill
    • Washer
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    • DVD Player
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Come and enjoy a beach view in VT! refreshing yourself in a lovely beach painting room. Our place is a 200 year old farmhouse which is located in a big farm scenic private area in Perkinsville, Vermont. We have a covered bridge at one end of our road. It's quiet dirt road which is perfect for... View all property information
    Location Information
    Perkinsville, Vermont 05151
    1 / 6
    Woodstock
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Skiing: Property Is...
    • Patio
    • Wi-Fi
    • Waterfront
    • Washer
    • Mountain Views
    • Central Heating
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    New! 2013 renovation: country serenity meets urban amenity. This wonderful escape combines a soothing minimalist aesthetic with the pleasures of a rural landscape. <BR><BR>Renovated in fall 2013, the spacious apartment features brand new hardwood floors, granite counter tops, stainless steel... View all property information
    Location Information
    Woodstock, Vermont 05071
    1 / 10
    Proctorsville
    3 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    • DVD Player
    • Satellite TV
    • Washer
    • Patio
    • Hot Tub
    • Mountain Views
    • Air Conditioning
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Our home is a beautiful 3 bedroom, 2 bath with large family room and sleeps 10. In winter we are 4 minutes to skiing at the fabulous resort of Okemo/Jackson Gore. You ski, board, ice skate, snowmobile, snow shoe, cross country or go to the spa for a day of fun. At our house we have an outdoor hot... View all property information
    Location Information
    Proctorsville, Vermont 05153
    1 / 12
    5 of 5 bubbles (1) Excellent
    White River Junction
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Satellite TV
    • Patio
    • Washer
    • Grill
    • Mountain Views
    • Air Conditioning
    • Parking
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    On the border of Vermont and New Hampshire, Savage Hart Farm is a perfect place to stay for a memorable visit to the heart of New England. You'll find a retreat-type setting close to the center of the towns of Hanover, NH, and Norwich, VT in a bucolic locale even the locals talk about. Quechee is... View all property information
    Location Information
    White River Junction, Hartford 05001
    5 of 5 bubbles Reviewed 30 September 2014
    Modern, clean apartment with beautiful views. Quintessential New England! Fully equipped kitchen (and BBQ grill) made cooking in easy. Todd was a gracious host and most...
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    1 / 32
    Perkinsville
    Private Room, 1 Bathroom, Sleeps 2 | Quick View
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    • Grill
    • Air Conditioning
    • DVD Player
    • Washer
    • Mountain Views
    • Housekeeping...
    • Wi-Fi
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    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    A cozy and comfortable room with the sun shines all day! It is an opened bright space with big windows all around. Our place is a 200 year old farmhouse which is located in a big farm scenic private area in Perkinsville, Vermont. We have a covered bridge at one end of our road. It's quiet dirt road... View all property information
    Location Information
    Perkinsville, Vermont 05151
    1 / 8
    Quechee
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Washer
    • Grill
    • Internet Access
    • Satellite TV
    • Mountain Views
    • Sauna
    • DVD Player
    • Shared Indoor Pool
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Quechee VT townhouse located on top of the ski hill. This two bed, lofted condo is located close to all Queschee Lakes amenties and is close to Woodstock VT and Hanover NH. View all property information
    Location Information
    Quechee, Hartford 05001
    1 / 51
    Perkinsville
    Private Room, 2 Bathrooms, Sleeps 8 | Quick View
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    • DVD Player
    • Washer
    • Air Conditioning
    • Grill
    • Mountain Views
    • Housekeeping...
    • Wi-Fi
    • Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    A beautiful bed and breakfast Vermont getaway! with 3 comfortable bedrooms available. Our place is a 200 year old farmhouse which is located in a big farm scenic private area in Perkinsville, Vermont. We have a covered bridge at one end of our road. It's quiet dirt road which is perfect for biking,... View all property information
    Location Information
    Perkinsville, Vermont 05151
    1 / 26
    Woodstock
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Grill
    • Waterfront
    • Parking
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    A quintessential Vermont getaway, this three-bedroom, two-bathroom Woodstock vacation rental features an outdoor fireplace, access to great skiing, plenty of room for up to six guests, and picturesque views next to the Ottauquechee River - all within a secluded woodland setting! If you like to play... View all property information
    Location Information
    Woodstock, Vermont 05091
    1 / 15
    Woodstock
    2 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
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    • Shared Indoor Pool
    • Washer
    • Wi-Fi
    • Air Conditioning
    • DVD Player
    • Sauna
    • Grill
    • Hot Tub
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • ?
    About this property
    Summer Seasonal Rental: This 2 Bedroom Condo has a great set up with 2 Full Baths for each bedroom and 1/2 bath on Main Floor. Fully Equipped Kitchen with a Keurig and Coffee Maker. Washer/Dryer, Built in AC Unit and deck to enjoy the White Mountains. Wireless Internet and Expanded Cable as well!!... View all property information
    Location Information
    Woodstock, Vermont 3262
    1 / 34
    Perkinsville
    Private Room, 1 Bathroom, Sleeps 2 | Quick View
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    • Wi-Fi
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    • Washer
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    • Mountain Views
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    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    You will definitely love this classic, unique, beautiful and comfortable studio room. It's a great space for your vocation. Our place is a 200 year old farmhouse which is located in a big farm scenic private area in Perkinsville, Vermont. We have a covered bridge at one end of our road. It's quiet... View all property information
    Location Information
    Perkinsville, Vermont 05151
    1 / 24
    Bridgewater
    4 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    • Pet-friendly
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    • Smoking allowed
    • x
    About this property
    Winter, spring, summer and fall, there is always something to do and something to fall in love with at this cozy Vermont vacation home. Kids will love the rustic sturdy bunk beds and folks just love to relax in front of the fire, cozying up to a good book. There are many downhill and cross... View all property information
    Location Information
    Bridgewater, Vermont 05035
    1 / 24
    Grantham, NH
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Central Heating
    • Private Indoor Pool
    • Waterfront
    • Patio
    • Satellite TV
    • Washer
    • Internet Access
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Forget all your troubles at this 3-bedroom, 2-bathroom tranquil Grantham condo, which comfortably sleeps 6. From the spacious back deck, enjoy lakefront views and lush green pines before beginning a kayaking, biking, fishing or golfing adventure! You’ll know you made the right choice upon your... View all property information
    Location Information
    Grantham, New Hampshire 03753
    1 / 12
    Brownsville
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Private Garden
    • Parking
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    This exceedingly charming cottage on a wooded hilltop just outside of Brownsville has great views of Mt Ascutney and a burbling brook at the base of the hill. The historic converted early 1800's one room school house is filled with many antique furnishings. Hanging in the stairway are photographs... View all property information
    Location Information
    Brownsville, Vermont 05047
    1 / 24
    Bridgewater
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Internet Access
    • Washer
    • Parking
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    It means no worries, for the rest of your vacation. No service, no problem! That's what makes this home so special, the stress of work and everyday life seem to evaporate the second you arrive. Being surrounded by beautiful scenery, fresh clean air and the sounds of nature have made this a... View all property information
    Location Information
    Bridgewater, Vermont 05035