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Greenfield Holiday Homes

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    Don't let other travellers get your favourite Greenfield area holiday rental. You're so close to securing your perfect getaway. Book today.
    All 28 Rentals in Greenfield
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    Greenfield
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    The following rentals are within 30 kilometres of Greenfield.
    Berkshire house w/ fireplace, A/C, WiFi & laundry1 / 27
    (16)Very good
    Plainfield
    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Winchester, NH
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Winchester, NH
    4 Bedrooms, 2 Bathrooms, Sleeps 9 Quick View
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    • Mountain Views
    • DVD Player
    • Air Conditioning
    • Hot Tub
    • Washer
    • Satellite TV
    • Wi-Fi
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Inquire today for Spring and Summer Getaways!! 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...
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    Winchester, New Hampshire 03470
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 9
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    Stone 'n Sky Lodge on an Ancient Stone Landscape1 / 32
    (4)Excellent
    New Salem
    4 Bedrooms, 3 Bathrooms, Sleeps 14 Quick View
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    • Internet Access
    • Washer
    • Grill
    • Porch
    • Mountain Views
    • DVD Player
    • Central Heating
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 weeks ago
    We visited New Salem for 5 days in the end of May. We were welcomed by a cheerful Sarah carrying a carton of organic eggs from her farm next door. Obviously a good start! For a...
    Reviewed 18 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...
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    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...
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    New Salem, Massachusetts 01355
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 14
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    PARADISE on EARTH! - Historic 4BR Farmhouse1 / 7
    (1)Excellent
    West Halifax, VT
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Mountain Views
    • DVD Player
    • Satellite TV
    • Porch
    • Wi-Fi
    • Patio
    • Central Heating
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 January 2015
    We rented this house to be close to Mount Snow so our boys could spend their vacation snowboarding. The house was as beautiful as described. The rooms were charming and...
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    About this property
    • 19th Century Farmhouse with beautiful mature gardens<BR>• 24 Park like acres - woods and streams <BR>• Perfect location to attend Marlboro Music Festival<BR>• Close to Brattleboro (10 miles) located in the Village of West Halifax <BR>• House has 4 bedrooms - 2 master bedrooms with Queen Beds...
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    Location Information
    West Halifax, Vermont 05358
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Unique People & Pet-Welcoming Country Haven1 / 37
    (156)Excellent
    Charlemont
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Internet Access
    • Outdoor Dining Area
    • Air Conditioning
    • Shared Garden
    • Satellite TV
    • Washer
    • Secure Parking
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 weeks ago
    We had a wonderful, relaxing weekend. This cottage is nestled in the woods, but a short drive to civilization. If you travel with your dog...stay here!
    Reviewed 4 weeks ago
    I was playing for a nearby festival and was so pleased to find Cavalier Cottage. It can be very hard to find a pet-friendly, affordable, quiet place that will rent for a short 2...
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    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 area of Western Massachusetts with or without their companion animals. Now in its sixth year,...
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    Charlemont, Berkshires 01339
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Whitingham, VT
    5 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Central Heating
    • Grill
    • Outdoor Dining Area
    • Parking
    • Satellite TV
    • Washer
    • Mountain Views
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Discounts and seasonal specials may be available - call Evolve at 877 818-1013 for more info! Please go to youtube and search "JohnsFarmDrone+Music1" to view aerial footage of the property! Mount Snow Farm is a secluded haven nestled in the Green Mountains near Whitingham, Vermont. This rustic,...
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    Location Information
    Whitingham, Vermont 05361
    Holiday Rental House - 5 Bedrooms, 2 Bathrooms, Sleeps 10
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    Adorable Studio apartment in Brattleboro1 / 5
    (2)Average
    Brattleboro, VT
    Studio, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Wi-Fi
    • Patio
    • Central Heating
    • Outdoor Dining Area
    • Grill
    • Shared Garden
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 July 2016
    You can't beat the location just off I-91, 5 minutes (15 if you walk) from downtown Brattleboro. The hosts were very nice and helpful, and we loved their cats and dog, when...
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    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....
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    Location Information
    Brattleboro, Vermont 05301
    Condo/Apartment - 1 Bathroom, Sleeps 2
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    Charming Affordable  Home for groups up to 141 / 11
    (9)Excellent
    Shelburne Falls
    7 Bedrooms, 3 Bathrooms, Sleeps 14 Quick View
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    Amenities & Details
    • Balcony
    • DVD Player
    • Grill
    • Internet Access
    • Patio
    • Satellite TV
    • Washer
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 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...
    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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    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...
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    Shelburne Falls, Massachusetts 01370
    Holiday Rental House - 7 Bedrooms, 3 Bathrooms, Sleeps 14
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    Conway
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Amenities & Details
    • Secure Parking
    • Mountain Views
    • Wi-Fi
    • Skiing: Property Is In A Ski Resort
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Location Information
    Conway, Massachusetts 01341
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Flight's End-A Country Home with Babbling Brook1 / 22
    (6)Excellent
    Hawley
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Parking
    • Mountain Views
    • DVD Player
    • Satellite TV
    • Central Heating
    • Internet Access
    • Grill
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 27 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...
    Reviewed 12 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...
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    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...
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    Location Information
    Hawley, Massachusetts 01339
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Vermont Log Cabin available for weekend and weekly1 / 5
    (5)Excellent
    Guilford, VT
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Grill
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 May 2017
    Beautiful mountain retreat! Has all of the comforts of home minus wifi and cell service. A perfect way to unwind and disconnect. Pictures do not do this quaint log cabin...
    Reviewed 30 May 2014
    The word "cabin" doesn't do this property justice. It is actually a comfortable two bedroom log home which is immaculate and well secluded. There is no internet service...
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    About this property
    If you want to get away from the hustle and bustle of our technologically driven lives and slow down, breath and relax, our cabin is the perfect place for you. No phones, television or internet, just a nice comfortable and affordable country log cabin nestled in the foothills of the Green...
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    Location Information
    Guilford, Vermont 05301
    Cabin Holiday Rental - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    Hatfield
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Washer
    • Wi-Fi
    • Air Conditioning
    • Porch
    • Satellite TV
    • Parking
    • Outdoor Dining Area
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Location Information
    Hatfield, Hampshire County 01038
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Jacksonville, VT
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Satellite TV
    • Private Garden
    • Air Conditioning
    • Internet Access
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful spacious 3200/sf. log home situated on ten acres very close to Mount Snow Resort. Private and secluded, this property features a wonderful outdoor fire-pit, babbling brook, many hiking, ATV and snowmobile trails. Quaint country living at its finest. Year-round weekly rentals...
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    Location Information
    Jacksonville, Vermont 05342
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Goshen
    2 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    Amenities & Details
    • Porch
    • Patio
    • Grill
    • Satellite TV
    • Parking
    • DVD Player
    • Air Conditioning
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Escape to the New England woodlands and reconnect with the outdoors when you stay at this 2-bedroom, 1-bathroom Goshen vacation rental cabin that sleeps 8. This quiet, 725-square-foot cabin offers peace and comfort, with an open-concept living space, a large deck with a patio set and grill, a...
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    Location Information
    Goshen, Hampshire County 01032
    Cabin Holiday Rental - 2 Bedrooms, 1 Bathroom, Sleeps 8
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    Hatfield
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Satellite TV
    • Wi-Fi
    • Air Conditioning
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    new condo with open floor plan and first floor master with view across the Connecticut River to Mount Holyoke. Quartz countertops and high end appliances make it a dream kitchen. Master bedroom has steam shower and soaking tub. Second floor has one single bedroom (with room for inflatable bed or...
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    Location Information
    Hatfield, Hampshire County 01038
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Beautiful Lake side get away, quiet and peaceful1 / 21
    (1)Excellent
    Winchester, NH
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Amenities & Details
    • Mountain Views
    • Patio
    • Internet Access
    • Air Conditioning
    • Waterfront
    • Washer
    • Satellite TV
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    It is an apartment with: Private beach, dock, raft, rowboat, canoe, 5 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 (Can be made into Queen bed), and a full size pullout couch...
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    Location Information
    Winchester, New Hampshire 03470
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Test Listing - Do Not Rent1 / 4
    (2)Very good
    Hawley
    1 Bedroom, 50 Bathrooms, Sleeps 50 Quick View
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    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 23 May 2017
    What an experience-great expanse inside with lots of room to explore. All of our guests enjoyed the plethora of bathrooms the place had to offer. Minus one star for only having...
    Reviewed 23 May 2017
    It is a pretend cave, but it is a nice pretend cave. I have never stayed in a cave with so many bathrooms. The best part is the location, though - there is a gold course o site...
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    About this property
    Test listing. Test listing. Test listing. Test listing. Test listing. Test listing. Test listing. Test listing. Test listing. Test listing. Test listing. Test listing. Test listing. Test listing. Test listing. Test listing. Test listing. Test listing. Test listing. Test listing. Test listing. Test...
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    Location Information
    Hawley, Massachusetts 01339
    Holiday Rental House - 1 Bedroom, 50 Bathrooms, Sleeps 50
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    Plainfield
    7 Bedrooms, 1 Bathroom, Sleeps 10 Quick View
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    • Parking
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Apartment/Flat, in Plainfield at Perry's, from 232 USD per night per person and 233 USD for 2! Discover Plainfield, and enjoy the advantages of staying at a locals': practical advice, a welcoming atmosphere and great prices. A Whole Lodging (for cottage, appartment, house), from 1 to 10 people. At...
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    Location Information
    Plainfield, Hampshire County 01070
    Condo/Apartment - 7 Bedrooms, 1 Bathroom, Sleeps 10
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    Beautiful Lake Side Getaway, Quiet, and Peaceful1 / 21
    (4)Excellent
    Winchester, NH
    2 Bedrooms, Sleeps 6 Quick View
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    • Internet Access
    • Satellite TV
    • DVD Player
    • Air Conditioning
    • Waterfront
    • Grill
    • Patio
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 September 2014
    Great off the beaten track place to stay yet only 20 minutes from Keene. Bill and Sandie very gracious hosts both before and during your stay. Accommodations very modern. We...
    Reviewed 13 July 2014
    My fiancé and another couple stayed here for a few days in May. It was absolutely beautiful and exactly what we were looking for! My fiancé and I are avid "outdoors...
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    About this property
    2 Bedrooms, 1 bath, sleeps 6. Private beach, dock, raft, rowboat, canoe, 5 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 (can be made into Queen), and a full size pullout couch in...
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    Winchester, New Hampshire 03470
    Condo/Apartment - 2 Bedrooms, Sleeps 6
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    Northampton
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The White Room has a single queen sized bed and a beautiful cherry desk built by your host, John. This room has its own bathroom (ensuite) with a shower, toilet, sink, and toiletries. Sitting at the desk, you will see the east pasture where the llamas like to sleep in the summer. The rear window...
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    Location Information
    Northampton, Hampshire County 01062
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Jacksonville, VT
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Parking
    • Washer
    • Satellite TV
    • Internet Access
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Plan a relaxing escape to this three-bedroom Jacksonville cabin, a lakefront home with a private deck, lovely lily pond views, and a wonderful location close to outdoor adventures in every season. This three-level home sits atop a small hill on the eastern shores of Gates Pond, where you'll enjoy...
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    Location Information
    Jacksonville, Vermont 05342
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Lakefront Summer Vacation Cottages1 / 5
    (1)Excellent
    Goshen
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Balcony
    • Waterfront
    • DVD Player
    • Terrace
    • Grill
    • Housekeeping Included
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 days ago
    Very nice and quiet, clean and confortable. Kids enjoy Adults love it and i will say we will go back
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    About this property
    We have shared the beauty of our lakefront property for many summers. We live on the property year round and rent three cottages from late June through September.We love our guests and honor their privacy. We are a family and pet (dog) friendly vacation spot,unique and enjoyable! The property is...
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    Location Information
    Goshen, Hampshire County 01032
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    Hawley
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Mountain Views
    • Central Heating
    • Parking
    • Private Garden
    • Grill
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Valley View is a charming one-bedroom house looking out over a large meadow from the top of a hill. The house features a wraparound deck which extends the living space into the outdoors, and large picture windows and sliding glass doors bring light and views inside. A woodstove in the living room...
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    Location Information
    Hawley, Massachusetts 01339
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Guilford, VT
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Air Conditioning
    • Private Garden
    • Satellite TV
    • Secure Parking
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    House is inset from a 1/2 mile driveway off the main road. Set up on a hill with a beautiful view across the mountain over to another mountain. Very large 1000 sq ft deck to relax and enjoy the view from. 3 open acres of yard with large fire pit and gas grill for barbecuing. Inside has a full...
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    Location Information
    Guilford, Vermont 05301
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Northampton
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Lavender Room, or Inside room as we often call it, is nestled inside the house, and is located off the kitchen. It is the largest of the three rooms and was recently painted a lovely 'amethyst' or rich lavender color. Its bathroom, while not in the room, is located directly across the private...
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    Location Information
    Northampton, Hampshire County 01062
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Northampton
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Actually, the Pink room is painted a lovely 'Santa Fe red' and is a mirror image to the White Room. The Pink room has a single queen sized bed, and its own bath in the room (ensuite) with a shower, toilet, freestanding sink, and toiletries. Sitting at the spinette (an antique desk that once housed...
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    Location Information
    Northampton, Hampshire County 01062
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
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