The Berkshires of Massachusetts are chock-full of history, culture, and important sites. A branch of the Appalachian Mountains, Berkshires resorts are set against a rural and charming atmosphere famous for attracting metropolitans for generations. Guests of Berkshires vacation rentals have the opportunity to visit the home of Herman Melville, the Clark Museum of Art, or the world famous Norman Rockwell Museum. The summers bring guests of Tanglewood vacation rentals crisp blue skies, as well as the Boston Symphony. Wonderful outdoor activities draw droves of visitors, including downhill and cross-country skiing, hiking, biking, whitewater rafting, fishing and golf.
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Berkshires Vacation Rentals
Berkshires Vacation Rentals - Search Over 250,000 Listings
| Featured Rentals | Type | Beds | Baths | Sleeps | Rate | |
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Charming Falmouth Heights Vacation Rental - Walk to Beach and Vineyard FerryAmenities:Beach, Kitchen, Washer/Dryer, Pets OK, TV Description:You're invited to spend the week of 8/23 - 8/30 at a pleasant vacation home located in Falmouth, Massachusetts on Cape Cod. This welcoming 2 bedroom, 1 bathroom home sleeps 6 and includes amenities such as cable, dvd player, laundry, microwave, gas grill, and a screened porch well suited for relaxing. It is located in a quiet neighborhood a short distance from many area attractions. Walking distance to: Falmouth Heights and Bristol Beaches Falmouth Harbor Island Queen Ferry to Martha's Vine |
House |
2 Beds |
1 Baths |
6 People |
$167 - $167 |
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Ctr of Town 2 Bdrm Condo w/Gas Fireplace - ProvincetownAmenities:Beach, Pool, Kitchen, Dishwasher, Washer/Dryer, TV Description:2 Bedroom Condo with gas fireplace close to the center of town. Quiet neighborhood, private screened in porch, access to dipping pool/patio, wonderful biking and walks. All the amenities including washer and dryer, granite counter tops, flat screen TV, DVD, and wifi to list a few. Very private and close to the wonderful shops, galeries,and restaurants of Commercial Steet. Free TV on demand movies available. |
Condo |
2 Beds |
1 Baths |
4 People |
$125 - $150 |
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PLEASANT BAY CHATHAM/HARWICH/ORLEANS - East HarwichAmenities:Beach, Ski, Golf Course, Kitchen, Dishwasher, Washer/Dryer, TV Description:Beautiful, and private newer home,3 bedrooms,large livingroom, dining room, deck, private yard with lush gardens.Full kitchen, washer and dryer, everything you could possibly need or want in a home. Pleasant Bay beach at end of street,3 minutes to get there! Free parking, take sailing lessons there. Wequesset Inn is right there too, have cocktails in the early evening watch the sun set. All you need, in area close to shopping, several golf courses, restaurants, medical center, fresh water pond. |
House |
3 Beds |
3 Baths |
6 People |
$143 - $193 |
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HEART OF THE BERKSHIRES - AdamsAmenities:Beach, Ski, Golf Course, Kitchen, Washer/Dryer, Air Conditioning, TV Description:THE RENTAL IS LOCATED BELOW BEAUTIFUL MT. GREYLOCK, AND SITS ON AN ACRE PRIVATE LOT WITH ONLY ONE OTHER HOME ON THIS QUIET STREET. IT IS A 5 MIN. WALK ON THE ASHWILTICOOK BIKE TRAIL AT THE BOTTOM OF THE STREET, TO THE MAIN STREET OF ADAMS, AND THE BERKSHIRE VISITOR BUREAU. TO CONTACT PLEASE ''CALL'' THE NUMBER ATTACHED, INSTEAD OF E-MAIL TO RECEIVE A CALL BACK BY THE EVENING OF ITS RECEIPT. |
Condo |
2 Beds |
1 Baths |
4 People |
$55 - $80 |
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Harwichport - Fabulous Fun- Harwichport, MA!Amenities:Beach, Golf Course, Kitchen, Dishwasher, Washer/Dryer, TV Description:2100 s.f. 2 story cape cod. Ambiance ladden 4 bedroom, newly updated bedrooms. Large living room with fireplace for ambiance, separate formal dining room (seats 8), sun/reading room, fully appointed kitchen and large deck with gas grill. All on a very large fully landscaped private lot. This will be your best vacation ever! One block from quaint town of Harwichport and 3 blocks from the ocean and beautiful beach! Come and enjoy. |
House |
4 Beds |
2 Baths |
8 People |
$193 - $314 |
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Truro - WATERFRONT CAPE COD BAY BEACH HOUSEAmenities:Beach, Golf Course, Pool, Kitchen, Dishwasher, Washer/Dryer, Smoking OK, Pets OK, TV Description:THIS HOUSE HAS IT ALL overlooking Cape Cod Bay to the tip of Provincetown . . This Cape Beach House has been renovated to enhance the charm and include all the ammenities you will want for your vacation needs. This 3 bedroom house features , a massive brick fireplace , wood flooring upstairs ,sweeping waterviews from kitchen and livingroom and waterviwes from just about every other room. |
House |
3 Beds |
2 Baths |
6 People |
$257 - $414 |
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Chatham - CAPE COD S. CHATHAM CHARMER NEAR COCKLE COVE BEACHAmenities:Beach, Kitchen, Dishwasher, Washer/Dryer, Air Conditioning, Pets OK, TV Description:This charming Cape Cod style cottage is a delight! It is a 2 bedroom, 2 bath home (one large new one) on a large lot with much privacy. It has A/C, hi-speed internet, brand new carpeting throughout the house, is on a no-outlet street so it is safe for children and is just a stone's throw from lovely conservation land at the end of the street. Pets are also considered with the approval of the landlords. |
House |
2 Beds |
2 Baths |
6 People |
$174 - $200 |
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Rockport - Spacious Carriage HouseAmenities:Beach, Golf Course, Kitchen, Washer/Dryer, Pets OK, TV Description:Large one bedroom carriage house. Great location in seaside town. Walk to Bear Skin Neck shopping, art galleries and restaurants. Walk to Old Garden Beach. Rockport Train Station is located within a 5 minute drive drive. It is one hour train ride to Boston and even less time to Manchester-by-the-Sea, and historic Salem, MA sites. The historic fishing port of Gloucester borders the town of Rockport. |
House |
1 Beds |
1 Baths |
2 People |
$39 - $175 |
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Classic Cape Cod Getaway - DennisportAmenities:Beach, Golf Course, Kitchen, TV Description:WE ARE SOLD OUT UNTIL AUG 30 - ALL WEEKS AFTER THAT HAVE AVAILABILITY Come enjoy the nature, beauty and adventure of Cape Cod at this quintessential Cape Cod beach cottage. We are located on a family-friendly cul-de-sac of seven summer homes & vacation rentals. |
House |
2 Beds |
1 Baths |
4 People |
$113 - $114 |
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Superb Vacation Rental in the Berkshires - BecketAmenities:Kitchen, TV Description:Spectacular contemporary saltbox in the Berkshires on 18 wooded acres down the road from Jacob's Pillow, the internationally famous dance theater center in Becket, Mass. Tanglewood and all the other cultural and recreational attractions of the Berkshires are nearby. Magical secluded setting with majestic forest views. A superb vacation rental imaginatively decorated and in mint condition. |
House |
3 Beds |
2.5 Baths |
6 People |
$250 - $300 |
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