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Holiday Rentals and Homes in Greenfield, MA

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

    1 / 14
    Hatfield
    Private Room, 1 Bathroom, Sleeps 4 | Quick View
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    1 / 27
    4.5 of 5 bubbles (16) Very good
    Plainfield
    3 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    1 / 12
    Hatfield
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    1 / 5
    Jacksonville, VT
    4 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Satellite TV
    • Private Garden
    • Air Conditioning
    • Internet Access
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Jacksonville, Vermont 05342
    1 / 32
    5 of 5 bubbles (3) 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
    • Child-friendly
    • ?
    • Smoking allowed
    • ?
    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 bubbles 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 bubbles 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 / 15
    Winchester, NH
    4 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    • Wi-Fi
    • Mountain Views
    • Hot Tub
    • DVD Player
    • Air Conditioning
    • Satellite TV
    • Washer
    • Waterfront
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • ?
    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. <BR>The Great room... View all property information
    Location Information
    Winchester, New Hampshire 03470
    1 / 21
    Winchester, NH
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Satellite TV
    • Grill
    • Internet Access
    • Air Conditioning
    • Waterfront
    • Patio
    • DVD Player
    • Washer
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • 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
    1 / 18
    Colrain
    3 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Washer
    • Waterfront
    • Central Heating
    • Shared Garden
    • Wi-Fi
    • Outdoor Dining Area
    • Mountain Views
    • Private Garden
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • 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
    1 / 11
    5 of 5 bubbles (9) Excellent
    Shelburne Falls
    7 Bedrooms, 3 Bathrooms, Sleeps 14 | Quick View
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    • Balcony
    • DVD Player
    • Grill
    • Internet Access
    • Patio
    • Satellite TV
    • Washer
    • Central Heating
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • 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 bubbles 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 bubbles 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 / 8
    Charlemont
    5 Bedrooms, 3 Bathrooms, Sleeps 14 | Quick View
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    • Mountain Views
    • Internet Access
    • Parking
    • Grill
    • Central Heating
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • 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
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    1 / 21
    5 of 5 bubbles (3) 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
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Winchester, New Hampshire 03470
    5 of 5 bubbles 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 will...
    5 of 5 bubbles Reviewed 12 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 people" and...
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    1 / 22
    5 of 5 bubbles (6) Excellent
    Hawley
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Parking
    • Mountain Views
    • DVD Player
    • Satellite TV
    • Central Heating
    • Internet Access
    • Grill
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • 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 bubbles 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...
    5 of 5 bubbles 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 / 37
    5 of 5 bubbles (149) 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
    • Child-friendly
    • Smoking allowed
    • 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 bubbles Reviewed 4 weeks ago
    My husband and I had a three-day, out-of-this-world-relaxing stay at Cavalier Cottage. Not only were we able to bring our two rescue companions, but the inside of this adorable...
    5 of 5 bubbles Reviewed 17 December 2016
    Patricia was wonderful throughout the stay, and served up terrific scones and OJ each morning. A great quiet place to stay that is truly dog friendly. Highly recommended.
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    1 / 22
    5 of 5 bubbles (5) Excellent
    Whitingham, VT
    3 Bedrooms, 2 Bathrooms, Sleeps 12 | Quick View
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    • DVD Player
    • Central Heating
    • Washer
    • Parking
    • Porch
    • Outdoor Dining Area
    • Internet Access
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • 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 bubbles 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 bubbles 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 / 11
    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
    • Child-friendly
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Winchester, New Hampshire 03470
    1 / 15
    Colrain
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Mountain Views
    • Secure Parking
    • Wi-Fi
    • Outdoor Dining Area
    • Central Heating
    • Grill
    • DVD Player
    • Porch
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • x
    About this property
    I am booked through to the end of May 2017. Come and delight in this laid back, serene spot. Cell service has not reached us here so you will need to tap into the wireless service provided here. Password is provided when you arrive. This is a lovely fragrance free, efficiency apartment off the... View all property information
    Location Information
    Colrain, Massachusetts 01340
    1 / 11
    Conway
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    • Secure Parking
    • Mountain Views
    • Wi-Fi
    • Skiing: Property Is...
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • 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
    1 / 7
    5 of 5 bubbles (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
    • Child-friendly
    • ?
    • Smoking allowed
    • ?
    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... View all property information
    Location Information
    West Halifax, Vermont 05358
    5 of 5 bubbles 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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    1 / 5
    5 of 5 bubbles (4) Excellent
    Guilford, VT
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    • Grill
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Guilford, Vermont 05301
    5 of 5 bubbles 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 (who needs...
    5 of 5 bubbles Reviewed 3 December 2013
    When we first booked it we were not excepting anything that great for the price. Just wanted to get away for thanksgiving with the kids and try something different. The weather...
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    1 / 5
    3.5 of 5 bubbles (2) Average
    Brattleboro, VT
    Studio, 1 Bathroom, Sleeps 2 | Quick View
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    • Wi-Fi
    • Patio
    • Central Heating
    • Outdoor Dining Area
    • Grill
    • Shared Garden
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • 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
    4 of 5 bubbles Reviewed 9 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 we'd...
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    1 / 28
    Northampton
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Pet-friendly
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    • x
    • x
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    • 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
    1 / 31
    Jacksonville, VT
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Parking
    • Patio
    • Internet Access
    • Waterfront
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Jacksonville, Vermont 05342
    1 / 13
    Hatfield
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Satellite TV
    • Wi-Fi
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Hatfield, Hampshire County 01038