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Hinsdale Vacation Rentals

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    Don't let other travelers get your favorite Hinsdale area vacation rental. You're so close to securing your perfect getaway. Book today.
    All 19 Rentals in Hinsdale
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    Hinsdale
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    The following rentals are within 10 miles of Hinsdale.
    Stone School Cottage1 / 10
    (17)Excellent
    Lanesboro
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Gartner House, a charming home in Lenox1 / 21
    (28)Excellent
    Lenox
    4 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    Berkshires Waterfront Lakehouse Sanctuary1 / 31
    (4)Excellent
    Lanesboro
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Washer
    • DVD Player
    • Hot Tub
    • Mountain Views
    • Waterfront
    • Cable/satellite TV
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 weeks ago
    We were extremely grateful to have an opportunity to vacation with our black lab and were pleasantly surprised with not only the attractive amenities of the home, but the...
    Reviewed November 13, 2017
    We spent two nights here on short notice and couldn’t have been happier with everything. This is a home done right - it’s homey and perfectly furnished and oh-so-cozy. Quaint...
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    About this property
    Beautiful private peninsula like setting surrounded by a cove , stream and lake adorn this location. Waterfowl and birds are everywhere in this quiet spot just a few minute walk from the 11 mile Ashuwilticook Rail Trail. The house has undergone a total renovation and all the furnishings are new...
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    Lanesboro, Berkshires 01224
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    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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    Quiet Comfortable Cabin 5 Min. Walk to Lake1 / 13
    (13)Very good
    Becket
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Parking
    • Grill
    • Porch
    • Washer
    • Air Conditioning
    • DVD Player
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed February 19, 2017
    The location was easy to get to (even in the dead of winter).The place was clean, spacious and exactly as described. The wood stove was a great heat source as it was really cold...
    Reviewed October 25, 2016
    A charming cozy cottage in a quiet setting with all you need for comfort included. We hiked, canoed and visited farms and museums close by. It was a lovely fall getaway!
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    About this property
    Remember the simple pleasures of a country, lakeside vacation where you can spend the day swimming or boating, exploring new towns and attractions, or just spending a lazy afternoon reading on the screened-in porch? Get back to those simple pleasures in our cabin, which is located in a beautiful,...
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    Location Information
    Becket, Berkshires 01223
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Escape to the Berkshires!1 / 20
    (4)Excellent
    Becket
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 21, 2016
    My family and friends - group of 8 just spent an amazing week at this home. The house was a perfect size, clean and fully stocked. We made gourmet breakfasts, lunches &amp...
    Reviewed May 14, 2016
    The Levy's home was perfect for our intergenerational family, including a 7month old grandaughter. We were pleasantly surprised by how well the home was supplied and organized...
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    About this property
    Come to the Berkshires and stay in one of the most beloved areas of Massachusetts. We are located close to Lenox, Stockbridge, Lee, Great Barrington and more. Our 3400 square foot ranch home is located in the heart of the Berkshires awaiting memorable times with your family and friends. Our...
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    Becket, Berkshires 01223
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    Pittsfield
    7 Bedrooms, 3 Bathrooms, Sleeps 18 Quick View
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    Amenities & Details
    • Central Heating
    • Grill
    • Terrace
    • Washer
    • Balcony
    • Patio
    • Hot Tub
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is a beautiful 7 bedroom home with over 4000 sq. ft. of nicely furnished large rooms. Nestled in the heart of the Berkshire Mountains, between 2 lakes and located in a quiet family friendly neighborhood. Just minutes from the New York border. Our home is a fantastic deal for the wonderfully...
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    Location Information
    Pittsfield, Berkshires 01201
    Rental Home - 7 Bedrooms, 3 Bathrooms, Sleeps 18
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    INTERIOR DESIGNERS BOTANICAL GARDENS1 / 30
    (1)Excellent
    Lenox
    1 Bedroom, 1 Bathroom, Sleeps 5 Quick View
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    Amenities & Details
    • Wi-Fi
    • Private Yard
    • Patio
    • Parking
    • Air Conditioning
    • Cable/satellite TV
    • Grill
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 4, 2017
    We have been traveling to the Berkshires for several years to attend Shakespeare & Company plays. We have stayed at Inns and Hotels. This was our first time, in this area...
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    About this property
    AS YOU OPEN THE GATE FROM THE DRIVE YOU WALK ONTO YR FRONT DECK LEADING TO THE ENTRY , MUD ROOM WHICH HOLDS YR SUMMER NEEDS, SKIS AND BOOTS. THIS LEADS TO THE COTTAGE APT. [attached to the owner`s quarters} LIVING RM- HAS A SOFA SLEEPER TO ACCOMMODATE 2 MORE GUESTS. KITCHENETTE W/ LG CEILING...
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    Location Information
    Lenox, Berkshires 01240
    Rental Home - 1 Bedroom, 1 Bathroom, Sleeps 5
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    Heart of Lenox1 / 10
    (2)Excellent
    Lenox
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Private Yard
    • Parking
    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 14, 2018
    1/2 house, with owners in other half, which was handy for questions and suggestions. Very clean, and queen bed was really comfortable. Other BR has twin bedsKitchen has...
    Reviewed May 27, 2017
    Title sums it up! Excellent choice for our recent visit to Lenox. The house is very clean and comfortable and the owners are very accommodating. Location is great, just steps...
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    About this property
    Just rated Best Small Town in the Northeast by USA Today, our home is located in the heart of Lenox MA! Come relax in our lovely home, situated in a quiet neighborhood just steps from downtown. Walk to Zagat rated restaurants, shop unique boutique shops, hike in Kennedy Park. Whether you love the...
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    Location Information
    Lenox, Berkshires 01240
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Heart of the Berkshires!1 / 12
    (2)Very good
    Lenox
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    Amenities & Details
    • Air Conditioning
    • Private Yard
    • Wi-Fi
    • Parking
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 29, 2017
    A friend and I rented this charming home for 3 nights. It was immaculate, the kitchen was well stocked, furniture/beds comfortable. The bedrooms had window a/c units. What...
    Reviewed June 29, 2017
    I was looking for a place for two couples for a weekend in the Berkshires, and stayed at this house. It was a perfect fit for my needs. The house is on a road that has very...
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    About this property
    This sophisticated ranch is privately sited on a premier road in Stockbridge. Less than a mile to Tanglewood, Stockbridge Bowl, and local theatre companies. Nestled between Lenox and Stockbridge, this is perfect location for your vacation. 3 bedroom and 1 bath, an open floor plan with the guest...
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    Location Information
    Lenox, Berkshires 01240
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 6
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    Becket
    4 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Central Heating
    • Terrace
    • Balcony
    • Private Yard
    • Grill
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Large home in wooded area of the Berkshires. Ideal for all the summer events such as visiting Great Barrington, Lenox, Lee, Stockbridge. Many mountain areas for picnics, biking, hiking in the summer and winter events such as skiing and snowboarding. Near Center pond where there are many boating...
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    Location Information
    Becket, Berkshires 01223
    Rental Home - 4 Bedrooms, 6 Bathrooms, Sleeps 12
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    Lenox
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Air Conditioning
    • Parking
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Completely renovated 2 bedroom downtown apartment with open floor plan in Lenox MA. Enjoy walks around the downtown area and visit the many attractions in Berkshire County. Endless restaurants to choose from, golf courses within 7 miles, Kennedy Park and Tanglewood close by. Minutes down the road...
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    Location Information
    Lenox, Berkshires 01240
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Dalton
    3 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    Amenities & Details
    • Mountain Views
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • DVD Player
    • Washer
    • Patio
    • Wi-Fi
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This home is an exact replica of the first Colonial ever built in Massachusetts back in the 1600's. It is called the 'Parson Capens Home' and is located in Topsfield Mass. It has the design of the old but all the modern features. The home is nestled in the mountains of Berkshire County which have...
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    Location Information
    Dalton, Berkshires 01226
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 9
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    Lenox
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    No matter the season, you'll find the getaway you crave while staying at this 3-bed, 2.5-bath house in Lenox! This welcoming vacation rental features room for 6, numerous amenities, and an incredible location just minutes from the Tanglewood Music Center. In addition, enjoy easy access to the...
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    Location Information
    Lenox, Berkshires 01240
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Becket
    2 Bedrooms, 2 Bathrooms, Sleeps 2 Quick View
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    Amenities & Details
    • Waterfront
    • Wi-Fi
    • Washer
    • Cable/satellite TV
    • Private Yard
    • DVD Player
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Lovely house on pond, Beautiful views of pond from every room, except one. Lounge on the deck with a glass of wine watch the Great Blue Heron has he stalks his fish, see the beavers swim lazily across the pond, flapping their tails to let you know they are there. Every room but one has a water...
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    Location Information
    Becket, Berkshires 01223
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 2
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    Serene Lakefront Cottage1 / 17
    (12)Excellent
    Becket
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Grill
    • Air Conditioning
    • Parking
    • Wi-Fi
    • Cable/satellite TV
    • Washer
    • Waterfront
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed July 16, 2016
    We stayed for a week with two teenaged boys and two dogs. We had a wonderful time. The lake was fully accessible and the boats and life vests well cared for. The photos are...
    Reviewed September 1, 2015
    My husband and I plus our two dogs recently took one last family vacation before our first son arrives later this year. We were looking for a private and peaceful place where we...
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    About this property
    Pretty cottage in the woods on a beautiful clean private lake with a stream running through the property's two acres of land. Newly constructed, spacious and sunny second floor with views of the lake. Hardwood floors throughout the house. Swim, kayak, canoe (both supplied with life vests) or...
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    Location Information
    Becket, Berkshires 01223
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Becket
    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Central Heating
    • Patio
    • Wi-Fi
    • Skiing: Property Is In A Ski Resort
    • Grill
    • Washer
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A beautiful retreat awaits you at this 3-bedroom, 3-bathroom vacation rental house in Beckett! Up to 8 guests can share this peaceful home, situated on 11 private acres of wooded land with a swimming pond. Venture out to explore the Berkshires where you'll find 9 lakes, watersports, renowned spas,...
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    Location Information
    Becket, Berkshires 10021
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Lenox
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Skiing: Property Is In A Ski Resort
    • Wi-Fi
    • Patio
    • Washer
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Enjoy leisurely lakeside days just a walk away as you stay at this 3-bed, 1.5-bath vacation rental house that sleeps 6 in Stockbridge! With mossy grounds below and age-old oaks towering above, this cozy cottage is a dreamy retreat, perfect for those looking for a bit of the great outdoors without...
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    Location Information
    Lenox, Berkshires 01262
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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