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Vacation Rentals in Greenfield, MA and nearby

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    The following rentals are within 30 kilometres of Greenfield, Massachusetts.

    1 / 7
    5 of 5 stars (1) Excellent
    West Halifax, VT
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    $396
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    Winchester, NH
    4 Bedrooms, 2 Bathrooms, Sleeps 9 | Quick View
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    $278
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    1 / 5
    5 of 5 stars (4) Excellent
    Guilford, VT
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    $188
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    Charlemont
    5 Bedrooms, 3 Bathrooms, Sleeps 14 | Quick View
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    $600
    / Night
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    Amenities & Details
    • Mountain Views
    • Internet Access
    • Parking
    • Grill
    • Central Heating
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    Hawk Mountain Lodge offers a year-round New England vacation experience! Enjoy comfortable accommodations conveniently located in Charlemont in the northern Berkshires, just 2.5 hours from Boston and 3.5 to 4 hours from New York City. Overlooking the Deerfield River Valley and Berkshire East Ski... View all property information
    Location Information
    Charlemont, Berkshires 01339
    1 / 11
    5 of 5 stars (9) Excellent
    Shelburne Falls
    7 Bedrooms, 3 Bathrooms, Sleeps 14 | Quick View
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    $695
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    Amenities & Details
    • Balcony
    • DVD Player
    • Grill
    • Internet Access
    • Patio
    • Satellite TV
    • Washer
    • Central Heating
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Our 7 bedroom, 3 bath, redone Federal House is the perfect place for family celebrations, school reunions, wellness, writing, quilting or other special interest gatherings. Your whole group can share our dining area and even enjoy the services of a gourmet chef should you desire. We have 8 quiet... View all property information
    Location Information
    Shelburne Falls, Massachusetts 01370
    5 of 5 stars Reviewed 3 January 2014
    I stayed in this house with a group of about 14 friends from college (we're a few years out) the weekend after Christmas, and we had a great time staying at Susan's place in...
    5 of 5 stars Reviewed 3 July 2012
    The home was so perfect. Just a short walk to the center of Shelburne Falls, 5 minute drive to rafting outfitters, swimming holes. Huge house with a great kitchen, but you'll...
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    1 / 22
    5 of 5 stars (5) Excellent
    Whitingham, VT
    3 Bedrooms, 2 Bathrooms, Sleeps 12 | Quick View
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    $208
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    Amenities & Details
    • DVD Player
    • Central Heating
    • Washer
    • Parking
    • Porch
    • Outdoor Dining Area
    • Internet Access
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    This very private 3 bedroom home sits on 10 acres. Three levels. Enjoy the rustic charm and tranquility of this great Vermont Vacation Home. No other houses in sight. 3 miles from boat launch on Harriman Reservoir. -Fully stocked kitchen! Coffee maker, toaster oven, dish washer, everything... View all property information
    Location Information
    Whitingham, Vermont 05361
    4 of 5 stars Reviewed 17 December 2015
    Hobbit Hollow is an ideal great-away for a large group of friends. The house is quirky and characterful. The kitchen and general amenities were perfect -- the former is very...
    5 of 5 stars Reviewed 17 November 2015
    We were like 7 people stayed in cabin, and the cabin is so spacious with extra beds. It is very near to the green mountains. The cabin is well maintained and lots of fire wood...
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    1 / 22
    5 of 5 stars (6) Excellent
    Hawley
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    $188
    / Night
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    Amenities & Details
    • Parking
    • Mountain Views
    • DVD Player
    • Satellite TV
    • Central Heating
    • Internet Access
    • Grill
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    3 Bedroom house, know as Flight's End, is for rent by day, weekend, week or month. Great for romantic get away or a family outdoor vacation. Not a party house. Fifteen minutes to Charlemont, Ashfield and Shelburne Falls. House is located on a brook and across the road from a private pond (not... View all property information
    Location Information
    Hawley, Massachusetts 01339
    5 of 5 stars Reviewed 26 August 2015
    Very pleasant place to stay. Felt like staying at Grandma's house in the country. The owner is a very pleasant and easy going fellow and the price is reasonable. House and...
    5 of 5 stars Reviewed 11 September 2014
    The house was very clean and cozy. Everything was as shown in the pictures. As my friends and I are from the city, we love how quiet the area is. BBQ grill and bonfire were the...
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    1 / 32
    5 of 5 stars (3) Excellent
    New Salem
    4 Bedrooms, 3 Bathrooms, Sleeps 14 | Quick View
    other travellers have booked this property
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    $354
    / Night
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    Amenities & Details
    • Internet Access
    • Washer
    • Grill
    • Porch
    • Mountain Views
    • DVD Player
    • Central Heating
    • Balcony
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    About this property
    Gorgeous, spacious, red-oak post and beam home on 11.25 acres abutting 2,700 acre Wildlife Preserve. 3-5 bedroom, 3 bath, 2600 sq ft, fully furnished and appointed, Stone 'n Sky Lodge offers extraordinary privacy and local convenience. Located on a paved, town-maintained, dead-end road surrounded... View all property information
    Location Information
    New Salem, Massachusetts 01355
    5 of 5 stars Reviewed 17 October 2014
    The house was clean, had three bedrooms with many beds, and had an amazing back yard with frog pond and patio with two barbeque grills. Coffee was left for us to drink in the...
    5 of 5 stars Reviewed 26 July 2014
    The Stone & Sky Lodge was perfect for our retreat getaway. New Salem is a peaceful area that's out of the way from the hustle and bustle of bigger Massachusetts cities. We...
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    1 / 7
    5 of 5 stars (5) Excellent
    Guilford, VT
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
    other travellers have booked this property
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    $208
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    Amenities & Details
    • Outdoor Dining Area
    • Air Conditioning
    • Hot Tub
    • Internet Access
    • Washer
    • Parking
    • Mountain Views
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Schoolhouse No. 10 is a fully renovated 18th century schoolhouse in scenic southern Vermont. Located on a country road in a very special neighborhood, the Schoolhouse offers a romantic private getaway for one or two couples, or a creative art spa for friends who want to come share an historic... View all property information
    Location Information
    Guilford, Vermont 05301
    5 of 5 stars Reviewed 25 October 2014
    A beautifully restored schoolhouse with abundant charm. The owners Susan and Gilbert are genuinely the nicest people you could meet. The refrigerator was stocked with farm fresh...
    5 of 5 stars Reviewed 7 October 2013
    My husband and I just returned from a glorious fall weekend in VT. Schoolhouse No. 10 is situated on a quiet country dirt road and far exceeded all expectations. The Schoolhouse...
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    Winchester, NH
    4 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
    From
    $278
    / Night
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    Amenities & Details
    • Wi-Fi
    • Mountain Views
    • Hot Tub
    • DVD Player
    • Air Conditioning
    • Satellite TV
    • Washer
    • Waterfront
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    A Stunning Lakefront home on crystal clear, sandy bottomed, 110 acre Forest Lake at the junction of NH,VT,& MA will be your long awaited retreat in the whispering pines, shimmering lakes, and beautiful foliage of New Hampshire. Bring the kids & dogs or just enjoy by yourselves. The Great room with... View all property information
    Location Information
    Winchester, New Hampshire 03470
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    1 / 12
    5 of 5 stars (2) Excellent
    Winchester, NH
    4 Bedrooms, 1 Bathroom, Sleeps 9 | Quick View
    other travellers have booked this property
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    $278
    / Night
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    Amenities & Details
    • Air Conditioning
    • Satellite TV
    • Washer
    • Waterfront
    • Internet Access
    • Mountain Views
    • DVD Player
    • Hot Tub
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    A Stunning Lakefront home on crystal clear,sandy bottomed, 110 acre Forest Lake at the junction of NH,VT,& MA will be your long awaited retreat in the whispering pines, shimmering lakes, and beautiful foliage of New Hampshire. Also check out our new home on Rockwood Pond in Fitzwilliam. NH! The... View all property information
    Location Information
    Winchester, New Hampshire 03470
    5 of 5 stars Reviewed 13 October 2014
    this large home is extremely well equipped. Each of our party had a separate bedroom and the communal spaces, and there are many of them, are extremely well equipped with...
    5 of 5 stars Reviewed 31 July 2012
    We could not have asked for a better vacation. It is definitely a home away from home with all the amenities you could ask for. Thoughtful details are everywhere. We enjoyed...
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    Hatfield
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
    From
    $313
    / Night
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    Amenities & Details
    • Air Conditioning
    • Wi-Fi
    • Terrace
    • Porch
    • Balcony
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Very unique apartments in beautifully restored 19th-century grist mill with private dam and waterfall, available for daily, weekly or monthly stays. As little as $76/night for longer stays, and additional days are prorated based on weekly/monthly rate. All utilities, WiFi and cable included, and... View all property information
    Location Information
    Hatfield, Hampshire County 01038
    Colrain
    3 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
    other traveller has booked this property
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    $347
    / Night
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    Amenities & Details
    • Waterfront
    • Central Heating
    • Outdoor Dining Area
    • Mountain Views
    • Internet Access
    • Shared Garden
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    This eco-friendly, river front home in Colrain, Massachusetts is situated in a slice of rural paradise, yet close to the charming village of Shelburne Falls and year-round recreational activities. The house is situated on 2.9 acres of flatland and wooded path down to the beach edge of the North... View all property information
    Location Information
    Colrain, Massachusetts 01340
    Hatfield
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
    other traveller has booked this property
    From
    $278
    / Night
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    Amenities & Details
    • Washer
    • Wi-Fi
    • Air Conditioning
    • Porch
    • Satellite TV
    • Parking
    • Outdoor Dining Area
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Very unique apartments in beautifully restored 19th-century grist mill with private dam and waterfall, available for daily, weekly or monthly stays. As little as $76/night for longer stays, and additional days are prorated based on weekly/monthly rate. All utilities, WiFi and cable included, and... View all property information
    Location Information
    Hatfield, Hampshire County 01038
    1 / 37
    5 of 5 stars (132) Excellent
    Charlemont
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    $181
    / Night
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    Amenities & Details
    • Internet Access
    • Outdoor Dining Area
    • Air Conditioning
    • Shared Garden
    • Satellite TV
    • Washer
    • Secure Parking
    • Mountain Views
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Discover Cavalier Cottage B&B, a pet-friendly home away from your home and an attractive alternative to conventional hotels, motels and B&B's. We warmly welcome visitors who come to this beautiful and diverse area of Western Massachusetts with or without their companion animals. Since opening the... View all property information
    Location Information
    Charlemont, Berkshires 01339
    5 of 5 stars Reviewed 2 weeks ago
    Berkshire East is a nice vacation spot and Cavalier Cottage is a great place to stay. The accommodations are set up like an apartment with a living/sleeping area, and fully...
    5 of 5 stars Reviewed 4 January 2016
    Not many places are pet-friendly, and when they are they are "friendly" only to dogs. Cavalier Cottage welcomed our feline baby and made her feel at home. The cottage is warm...
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    1 / 24
    4.5 of 5 stars (16) Very good
    Plainfield
    3 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    $295
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    • Mountain Views
    • Wi-Fi
    • Skiing: Property Is...
    • Air Conditioning
    • DVD Player
    • Satellite TV
    • Housekeeping...
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • Smoking allowed
    • Elder access
    • ?
    About this property
    Experience a Berkshire get-away in this huge secluded luxury modern house. It's the only house that is surrounded by 10,000 Acres of protected Hawley State forest. Escape from headaches and the rat race. No cell phone reception here! But we have WiFi and a house phone. We like to define our country... View all property information
    Location Information
    Plainfield, Hampshire County 01070
    3 of 5 stars Reviewed 25 August 2014
    The home and grounds were lovely but need some updating,and a good cleaning. Location was secluded with plenty of forest and hiking trails, and a scenic lake for fishing. The...
    5 of 5 stars Reviewed 29 May 2014
    We all thoroughly enjoyed our long weekend at this lovely house. It was spacious, well situated, and well equipped. We were sorry our stay was so short, and the time in the...
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    Brattleboro, VT
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    $188
    / Night
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    Amenities & Details
    • Wi-Fi
    • Patio
    • Central Heating
    • Outdoor Dining Area
    • Grill
    • Shared Garden
    • Parking
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Welcome to the Culbertson House! This adorable studio apartment was completely refinished a few years ago. It features a gorgeous stone fireplace, tasteful furnishings and decoration, a comfortable king-size bed, fully equipped kitchen, full bath with shower, and exquisite hardwood walls and floor.... View all property information
    Location Information
    Brattleboro, Vermont 05301
    Conway
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
    From
    $229
    / Night
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    Amenities & Details
    • Secure Parking
    • Mountain Views
    • Wi-Fi
    • Skiing: Property Is...
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Charming one-bedroom apartment situated on 8 beautiful and peaceful acres in the rolling hills of Conway Massachusetts. The apartment has a large kitchen, a sitting room, study 'nook', private bath with laundry facilities and a separate entrance. Guests are greeted every morning by two friendly... View all property information
    Location Information
    Conway, Massachusetts 01341
    Northampton
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
    From
    $263
    / Night
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    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Light, airy, tasteful, contemporary and comfortable 5 room apartment with kitchen, dining room, living room with fireplace, den/study, bedroom with queen size platform bed. Bathroom has claw foot tub for showers or bath. Private garage bay. Keyless apartment entry. Ten minute walk to downtown... View all property information
    Location Information
    Northampton, Hampshire County 01060
    Northampton
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
    From
    $486
    / Night
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    Amenities & Details
    • Patio
    • Grill
    • Parking
    • Porch
    • Washer
    • Air Conditioning
    • Internet Access
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Beautiful in-town single family home for weekly or extended rental in Northampton's tranquil Smith College neighborhood. 3 Bedroom, 1.5 bath. Max 6. Great for walking the home is close to town, easy to find, and on a very nice street in a gorgeous part of town. This New England home has original... View all property information
    Location Information
    Northampton, Hampshire County 01060
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    1 / 23
    5 of 5 stars (2) Excellent
    Charlemont
    1 Bedroom, 1 Bathroom, Sleeps 6 | Quick View
    From
    $1,112
    / Week
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    Amenities & Details
    • Grill
    • Mountain Views
    • Porch
    • Parking
    • Washer
    • Central Heating
    • Wi-Fi
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    If you're looking for gorgeous mountain views in a peaceful setting, come stay in the Berkshires Log Cabin with Views - we call it Comsomore Cottage - a mountainside log cabin located on the 50 acre mountain top estate, the Rose and Goat Retreat in the beautiful Berkshires, USA. Great for a long... View all property information
    Location Information
    Charlemont, Berkshires 01247
    5 of 5 stars Reviewed 21 September 2015
    Beautiful rustic cabin set back in the woods with incredible views of the mountains--- great amenities and comfort--- warm and inviting in a quiet setting amongst natures...
    5 of 5 stars Reviewed 20 September 2015
    Every year I go on a retreat with my two best friends from childhood, and this year we settled on a weekend in the Berkshires, and the Freshgrass music festival at Mass MOCA...
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    Colrain
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
    From
    $174
    / Night
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    Amenities & Details
    • Mountain Views
    • Secure Parking
    • Wi-Fi
    • Outdoor Dining Area
    • Central Heating
    • Grill
    • DVD Player
    • Porch
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    This is a NEW Place being offered. Come and delight in this laid back, serene spot and then write my 1st review! This is a lovely fragrance free, efficiency apartment off the back wing of my rural home and Studio/Gallery. Very private, quiet, light-filled, clean cozy and spacious with pastoral... View all property information
    Location Information
    Colrain, Massachusetts 01340
    Conway
    3 Bedrooms, 3 Bathrooms, Sleeps 7 | Quick View
    From
    $208
    / Night
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    Amenities & Details
    • Secure Parking
    • Air Conditioning
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Nice to rent Cape Cod, Massachusetts .Here is the address apartment : 660 Washington Street, Theatre District, Boston, MA 02111 .Theare are two flats on same floorand the two street-facing sunny suites share an inside chill-out garden that is warmly and exquisitely decorated to provide our guests... View all property information
    Location Information
    Conway, Massachusetts 02111
    1 / 30
    5 of 5 stars (1) Excellent
    Guilford, VT
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
    other travellers have booked this property
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    $313
    / Night
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    Amenities & Details
    • Mountain Views
    • Internet Access
    • Hot Tub
    • Grill
    • Washer
    • Air Conditioning
    • Porch
    • Waterfront
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • 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
    Guilford, Vermont 05301
    5 of 5 stars Reviewed 4 March 2015
    We did our ski trip with total of six people and two dogs. The cabin is big enough for six people. The living room with double height space is nice and cozy, especially with the...
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    1 / 21
    Winchester, NH
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
    From
    $139
    / Night
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    Amenities & Details
    • Satellite TV
    • Grill
    • Internet Access
    • Air Conditioning
    • Waterfront
    • Patio
    • DVD Player
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    It is an apartment with: Private beach, dock, raft, rowboat, canoe, 4 Kayaks, or launch your boat. Cable TV, high speed internet, WIFI, 42' flat screen internet TV. Sleeps 6 - two bedrooms - One with Queen bed, one with two single beds, and a full size pullout couch in the family/living... View all property information
    Location Information
    Winchester, New Hampshire 03470