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Deerfield Holiday Homes

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    Don't let other travellers get your favourite Deerfield area holiday rental. You're so close to securing your perfect getaway. Book today.

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

    1 / 32
    5 of 5 bubbles (3) Excellent
    New Salem
    4 Bedrooms, 3 Bathrooms, Sleeps 14 | Quick View
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    1 / 7
    5 of 5 bubbles (1) Excellent
    West Halifax, VT
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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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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    1 / 22
    5 of 5 bubbles (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
    • 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 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 the...
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    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 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...
    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 / 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 / 27
    4.5 of 5 bubbles (16) Very good
    Plainfield
    3 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    • Mountain Views
    • Wi-Fi
    • Skiing: Property Is...
    • Air Conditioning
    • DVD Player
    • Satellite TV
    • Housekeeping...
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    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 bubbles 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 bubbles Reviewed 30 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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    1 / 18
    Colrain
    3 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    Amenities & Details
    • 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
    Winchester, NH
    4 Bedrooms, 2 Bathrooms, Sleeps 9 | Quick View
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    Amenities & Details
    • 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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    Amenities & Details
    • 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
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    1 / 21
    5 of 5 bubbles (3) Excellent
    Winchester, NH
    2 Bedrooms, Sleeps 6 | Quick View
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    Amenities & Details
    • 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 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 people" and...
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    1 / 14
    Hatfield
    Private Room, 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
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • 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 bubbles (152) Excellent
    Charlemont
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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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
    • 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 days ago
    Once again, for the third time in the past three years, Alexander,Pete and I drove the most scenic anywhere (RT 2) to our favorite vacation destination,Cavalier Cottage in...
    5 of 5 bubbles Reviewed 6 days ago
    We enjoyed a mini vacation at this beautiful cottage retreat with our golden retriever Ivy Grace. Ivy Grace in in a wheelchair and she was able to menover with no problem inside...
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    1 / 21
    5 of 5 bubbles (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
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Winchester, New Hampshire 03470
    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 / 28
    5 of 5 bubbles (2) Excellent
    Charlemont
    Studio, 1 Bathroom, Sleeps 4 | Quick View
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    Amenities & Details
    • Internet Access
    • Mountain Views
    • Parking
    • Air Conditioning
    • Satellite TV
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    BREAKING NEWS: Cavalier Cottage has received, for the 2nd consecutive year, two distinguished awards as 'Top Vacation Rental' and 'Rated Excellence' by FlipKey, a division of TripAdvisor. In their own words... 'Congratulations! Based on exceptional guest reviews and an impressive listing, you... View all property information
    Location Information
    Charlemont, Berkshires 01370
    1 / 13
    Hatfield
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Satellite TV
    • Wi-Fi
    • Air Conditioning
    • Parking
    Suitability
    • 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
    1 / 35
    West Halifax, VT
    5 Bedrooms, 4 Bathrooms, Sleeps 10 | Quick View
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    • Grill
    • Patio
    • Terrace
    • DVD Player
    • Central Heating
    • Balcony
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Beautiful house interior and out. Many rooms for privacy including TV room, pool table below, dining areas, living room with circular couch to sit around open glass wood stove and a small library, computer space. Dining room open to kitchen area and to living room. Upper balcony and outside... View all property information
    Location Information
    West Halifax, Vermont 05342
    1 / 18
    Greenfield
    Private Room, 1 Bathroom, Sleeps 4 | Quick View
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    • Balcony
    • Terrace
    • Housekeeping...
    • Central Heating
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Brandt House is a three-and-a-half-acre, turn-of-the-century estate located in a charming residential area of Greenfield, just minutes from I-91 and Route 2 in northwestern Massachusetts. Walking distance to downtown Greenfield and in the northern Pioneer Valley where culture, history, adventure,... View all property information
    Location Information
    Greenfield, Massachusetts 01301
    1 / 11
    Easthampton
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • Central Heating
    • Patio
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    About this property
    NEW 4 FOOT WALK-IN SHOWER, WASHER AND DRYER. LOCATED IN THE CENTER OF EASTHAMPTON. WALKING DISTANCE TO MANY BARS, RESTAURANTS, AND THE BOARDWALK AROUND THE NASHAWANNUCK POND. HBO, CINEMAX, WIFI INCLUDED. LOCATED 1 BLOCK FROM WILLISTON SCHOOL AND 4 MILES FROM DOWNTOWN NORTHAMPTON AND SMITH COLLEGE.... View all property information
    Location Information
    Easthampton, Hampshire County 01027
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    1 / 5
    Goshen
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Balcony
    • Waterfront
    • DVD Player
    • Terrace
    • Grill
    • Housekeeping...
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Goshen, Hampshire County 01032
    1 / 16
    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
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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... View all property information
    Location Information
    Guilford, Vermont 05301
    1 / 8
    Hawley
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    • Washer
    • Mountain Views
    • Central Heating
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Valley View is a charming one-bedroom house sitting on a hilltop at the edge of a large meadow. 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... View all property information
    Location Information
    Hawley, Massachusetts 01339