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Hawley Family & Kid Friendly Rentals

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    Don't let other travelers get your favorite Hawley area vacation rental. You're so close to securing your perfect getaway. Book today.
    21 Matching Rentals in the Hawley AreaView all 25 rentals
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    Flight's End-A Country Home with Babbling Brook1 / 22
    (9)Very good
    Hawley
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Hawley
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Valley View1 / 8
    (2)Excellent
    Hawley
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Hawley
    3 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Mountain Views
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Pudding Hollow sits nestled into the woods at a corner of our private drive. This cozy cottage with both deck and screen porch looks out over a grassy lawn and wooded hillside. The fully-equipped kitchen and family room with wood stove run across the front of the house, while the bedrooms and bath...
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    Location Information
    Hawley, Massachusetts 01339
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 5
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    The following rentals are within 15 miles of Hawley.
    Retreat in the Woods1 / 6
    (6)Excellent
    Savoy
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Internet Access
    • DVD Player
    • Grill
    • Hot Tub
    • Parking
    • Porch
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 23, 2017
    My husband and I vacationed in the Berkshires to hike and visit the MA state parks. This home is conveniently located within a 30 min. drive to many state parks and hiking...
    Reviewed July 19, 2017
    Lovely home - the pictures don't fully do it justice! The house is shielded from the road and set in a small clearing, so it gets plenty of light and a pleasant breeze at night...
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    About this property
    Located in a quiet corner of the northern Berkshires, this lovely two-bedroom home has a combined living room/kitchen with cathedral ceilings and a spacious bathroom complete with a 2-person jacuzzi tub. The house is located about a mile from beautiful Tannery Falls in the Savoy State Forest and...
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    Savoy, Berkshires 01256
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Unique People & Pet-Welcoming Country Haven1 / 37
    (173)Excellent
    Charlemont
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Internet Access
    • Outdoor Dining Area
    • Air Conditioning
    • Shared Yard
    • Cable/satellite TV
    • Washer
    • Secure Parking
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 weeks ago
    A cute cottage off the beaten trackDefinitely in the country but close enough to lovely cities. The scones and juice every morning were a treat.. the kitchen came in...
    Reviewed July 27, 2018
    We like to travel with our dogs, and it was so easy to stay with them at Cavalier Cottage. Comfortable and charming for humans and canines alike. We loved the quiet woodsy area...
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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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    PARADISE on EARTH! - Historic 4BR Farmhouse1 / 7
    (1)Excellent
    West Halifax, VT
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Mountain Views
    • DVD Player
    • Cable/satellite TV
    • Porch
    • Wi-Fi
    • Patio
    • Central Heating
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed January 16, 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 • 24 Park like acres - woods and streams • Perfect location to attend Marlboro Music Festival • Close to Brattleboro (10 miles) located in the Village of West Halifax • House has 4 bedrooms - 2 master bedrooms with Queen Beds • 2...
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    Location Information
    West Halifax, Vermont 05358
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    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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    Amenities & Details
    • Waterfront
    • Wi-Fi
    • DVD Player
    • Air Conditioning
    • Cable/satellite TV
    • Mountain Views
    • Housekeeping Included
    • Skiing: Property Is In A Ski Resort
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 25, 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...
    Reviewed May 29, 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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    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...
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    Location Information
    Plainfield, Hampshire County 01070
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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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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    North Adams
    3 Bedrooms, 1 Bathroom, Sleeps 15 Quick View
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    Amenities & Details
    • Patio
    • DVD Player
    • Central Heating
    • Mountain Views
    • Skiing: Property Is In A Ski Resort
    • Cable/satellite TV
    • Wi-Fi
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The house is located at the end of a dead end street. It has a huge, private backyard with 2 firepits, hammock, portable bar, grill and ample seating. Under one mile to downtown North Adams and about a 5 minute drive to Williamstown. This is a 3 bedroom, upstairs apartment (one bedroom has a...
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    Location Information
    North Adams, Berkshires 01247
    Condo/Apartment - 3 Bedrooms, 1 Bathroom, Sleeps 15
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    Readsboro, VT
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Amenities & Details
    • Washer
    • Grill
    • Wi-Fi
    • Mountain Views
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Recharge your batteries at this cozy, newly renovated mountain retreat. This 3br/1ba open floor plan comfortably accommodates 6. Perfect for couples or a small family. Located on route 100 in Readsboro, VT, makes you centrally located to the best area attractions. Whether you love hiking,...
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    Location Information
    Readsboro, Green Mountains 05350
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    Apartment walking distance to Mass MoCa!!1 / 39
    (2)Excellent
    North Adams
    2 Bedrooms, 1 Bathroom, Sleeps 10 Quick View
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    Amenities & Details
    • Air Conditioning
    • Mountain Views
    • Cable/satellite TV
    • Wi-Fi
    • Grill
    • Patio
    • Skiing: Property Is In A Ski Resort
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 11, 2015
    Owners were very friendly and helpful. We enjoyed our stay very much. this is the place for a quiet vacation.
    Reviewed July 6, 2014
    Stephanie was helpful and accommodating of us and our last minute request . Sheafs it easy to stay, come and go and we found the location convenient yet private and remote from...
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    About this property
    I have a 2 to 3 bedroom first floor apartment located in a dead end street. This spacious 8 room apartment is surrounded by woods and minutes from downtown North Adams or Williamstown!! It is also walking distance to Mass MoCa (about a 10 minute walk)!!! Animals are welcome if needed. The master...
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    Location Information
    North Adams, Berkshires 01247
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 10
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    Berkshire Getaway1 / 7
    (8)Excellent
    North Adams
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Housekeeping Included
    • Parking
    • Outdoor Dining Area
    • Grill
    • Porch
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 25, 2015
    Descriptions are accurate. The house and grounds are very well kept. Extremely clean especially bathroom and kitchen. It is located at the end of a hard pack dirt road with no...
    Reviewed August 24, 2015
    The minute we entered the cottage we felt at home. A perfect secluded, warm and cosy getaway. Our only sorrow was that we could only stay for one night. We prepared dinner in...
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    About this property
    Cozy cottage with complete privacy on 142 acres and borders Monroe State Forest. Cottage offers 2 bedrooms, 1 bathroom, large living room, eat in kitchen, deck with grill, TV and DVD. Hiking and biking is available right outside your door. The Dunbar Brook Trail boasts great hiking and a grove of...
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    Location Information
    North Adams, Berkshires 01247
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Lakefront Summer Vacation Cottages1 / 16
    (4)Excellent
    Goshen
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Amenities & Details
    • Grill
    • Parking
    • Wi-Fi
    • DVD Player
    • Housekeeping Included
    • Waterfront
    • Balcony
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 weeks ago
    Wonderful Labor Day weekend trip with our grandchildren, ages 5 and 8, and out 2 year old Great Pyrenees. Clean and comfortable cottage, appropriately stocked kitchen, and the...
    Reviewed April 20, 2018
    This review is a little late but we lived here last August through October while I was working in the area. We loved it. The Lake and the views were from late summer through...
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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
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    North Adams
    1 Bedroom, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Housekeeping Included
    • Air Conditioning
    • DVD Player
    • Mountain Views
    • Washer
    • Patio
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    I have a two bedroom downstairs apartment and a three bedroom upstairs apartment (all of the rooms are available to rent). I also rent out the full apartments but I also rent out rooms (please ask for information). The house is located on a dead end street with a huge wooded backyard that...
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    Location Information
    North Adams, Berkshires 01247
    Condo/Apartment - 1 Bedroom, 2 Bathrooms, Sleeps 8
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    West Halifax, VT
    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Air Conditioning
    • Private Yard
    • Secure Parking
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
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    Location Information
    West Halifax, Vermont 05358
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 12
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    Whitingham, VT
    5 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Central Heating
    • Washer
    • Parking
    • Grill
    • Cable/satellite TV
    • Skiing: Property Is In A Ski Resort
    • Mountain Views
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    ** Discounts and seasonal specials may be available - call Evolve at (877) ******** for more info! ** James Gandolfini stayed here! 'Mount Snow Farm' is a 120-acre former dairy farm and secluded haven nestled in the Green Mountains near Whitingham, Vermont. The top of this property sits 2,300...
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    Location Information
    Whitingham, Vermont 05361
    Rental Home - 5 Bedrooms, 2 Bathrooms, Sleeps 10
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    Adams
    7 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    • Secure Parking
    • Private Yard
    • Cable/satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Manor is an elegant home built in the 1800's with a beautiful story and rich history. It offers amazing architecture and style with modern conveniences. Once encompassed within its walls guests will feel its unique small town warmth which adds significantly to its charm. Located in...
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    Location Information
    Adams, Berkshires 01220
    Rental Home - 7 Bedrooms, 4 Bathrooms, Sleeps 14
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    Jacksonville, VT
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Parking
    • Washer
    • Cable/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
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Goshen
    2 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    • Cable/satellite TV
    • Air Conditioning
    • DVD Player
    • Wi-Fi
    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 - 2 Bedrooms, 1 Bathroom, Sleeps 8
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    Shelburne Falls
    Studio, 1 Bathroom, Sleeps 6 Quick View
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    • Patio
    • Central Heating
    • DVD Player
    • Private Outdoor Pool (Unheated)
    • Wi-Fi
    • Skiing: Property Is In A Ski Resort
    • Mountain Views
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Pack your bags for a peaceful nature retreat at this charming vacation rental studio cabin! Ideally situated on 65 expansive acres, this Shelburne escape offers accommodations for 6 and upgraded amenities such as a floor-to-ceiling fieldstone fireplace and stainless steel appliances. Whether you're...
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    Location Information
    Shelburne Falls, Massachusetts 01370
    Condo/Apartment - 1 Bathroom, Sleeps 6
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