Vacation Rentals & House Rentals in Hampshire County

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Wireless Internet
Air conditioning
Swimming pool
Private pool

Heated pool
Private indoor pool
Balcony or terrace
Washing machine
Jacuzzi or hot tub
Garden
Internet access
DVD player
Grill
Fireplace
Cot available
Sauna
High chair
Sea view
Safe
Dishwasher
Children's pool
Shared outdoor pool (unheated)
Shared indoor pool
Shared outdoor pool (heated)
Private outdoor pool (unheated)
Cribs
Ceiling Fans
Games room
Clothes dryer
Private outdoor pool (heated)
Trampoline
Table tennis
Pool or snooker table
Fax machine
Video player
Boat available
Staffed property
Private fishing lake or river
Swing set or jungle gym
Climbing frame
Bicycles available
Towels provided
Linen provided
Microwave
Freezer
Housekeeping Included

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Pets allowed
Parking
Car not required
Children under 5

Smoking allowed
Non-Smoking property
Smoking - Ask
Wheelchair adapted
Wheelchair accessible

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Beach or lakeside relaxation
City breaks
Skiing – property near ski resort
Walking trips

Tennis in town
Water sports
Horse riding
Fishing
Cycling trips
Golf course on site or within 15 min walk
Mountain Views
Golf within 30mins drive
Waterfront
Lakefront

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30 Houses

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Charming 2+2 Lakeside Cottage on Best Lake in CT

Salisbury cottage

2 bedrooms
2 bathrooms

sleeps 4

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Price per night from

$207

Enjoy horses and the largest recreational lake in Massachusetts

East Otis apartment

1 bedroom
1 bathroom

sleeps 4

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Price per night from

$127

New Timberframe House Rental in the Berkshire Mountains, Masschusetts

Hinsdale house

3 bedrooms
2 bathrooms

sleeps 6

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Price per night from

$218

Hillhouse Log Cabin

Hillsdale log cabin

3 bedrooms
2 bathrooms

sleeps 13

“rest,relax,recharge” It's a Beautiful home that has all the modern conveniences. It's quiet, quaint and had just what I needed to get away from it all. I enjoyed morning coffee on the back deck among the trees and afternoon walks in the woods. A perfect place to recharge.

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Price per night from

$488

Lake House

Lakeville house

5 bedrooms
3 bathrooms

sleeps 9

Responds fast! avg. 2 hours 27 minutes

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Price per night from

$688

The Meadow House 4 bdrm 4 bath house

Stephentown house

4 bedrooms
4 bathrooms

sleeps 12

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Price per night from

$723

Christmas in The Berkshires

Hancock condo

1 bedroom
2 bathrooms

sleeps 4

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Price per night from

$258

Charming Affordable Home for groups up to 14

Shelburne Falls house

7 bedrooms
3 bathrooms

sleeps 14

“Beautiful house in beautiful village!” Thank you for the use of your beautiful house. It was perfect for our wedding weekend. Everyone was very comfortable and had a great time. Looking forward to coming back again in the future.

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Price per night from

$574

Lakefront Berkshires Ski/Summer House, Great Views

Great Barrington house

4 bedrooms
2 bathrooms

sleeps 10

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Price per night from

$252

Quiet Comfortable Cabin 5 Min. Walk to Lake

Becket house

2 bedrooms
1 bathroom

sleeps 4

“awesome beautiful place” I can't say enough about this. Place, perfect I guess Serene, peaceful,beautiful, quiet. Djuna the owner is Sweet and very efficient and provides every detail. The Whole are is perfect Oct a getaway, things to do places To shop,eat or just cuddle in with a fire. We will Definetly be returning as soon as we can.:)))

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Price per night from

$171

Berkshires: Romantic Cottage with spectacular view

Great Barrington cottage

1 bedroom
1 bathroom

sleeps 3

“A Real Gem!!!” This cottage is the perfect place for two people. It is truly as beautiful as the pictures! The pool and grounds are exceptional and the view is breathtaking. The place is extremely well maintained and the owner is very kind and helpful. We had a fabulous weekend here and would gladly return!

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Price per night from

$274

Retreat in the Woods

Savoy house

2 bedrooms
1 bathroom

sleeps 4

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Price per night from

$230

Beautifully decorated & immaculate log chalet

Hillsdale log cabin

3 bedrooms
2 bathrooms

sleeps 6

Responds fast! avg. 3 hours 45 minutes

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Price per night from

$230

Lake House

Lee house

5 bedrooms
6 bathrooms

sleeps 9

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Price per night from

$819

One of the Finest Homes and Best location in the Berkshires

Stockbridge house

4 bedrooms
3 bathrooms

sleeps 10

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Price per night from

$803

Beautiful Lake Side Getaway, Quiet, and Peaceful

Winchester apartment

2 bedrooms
1 bathroom

sleeps 6

“Relaxing vacation” We vacationed here for the first two weeks of July. Bill and Sandy were fabulous hosts. They were attentive to our needs and generous with their time taking us out in their boat to view the fireworks. The space is decorated tastefully and was clean and welcoming. We spent almost all of our time outdoors enjoying the sun and water. We ate most of our meals outside on the patio. The only thing that could have made it any better would have been to have a screened in area so that we could have stayed out later at night after the mosquitos' came out. We are planning on returning next year.

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Price per night from

$144