Updating...

More filters

Wireless Internet
Air conditioning
Swimming pool
Private pool

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

See all

Less

Pets
Pets allowed
Parking
Car not required

Children under 5
Smoking allowed
Non-Smoking property
Smoking - Ask
Wheelchair adapted
Wheelchair accessible

See all

Less

Beach or lakeside relaxation
City breaks
Skiing – property near ski resort
Tennis in town

Water sports
Horse riding
Fishing
Cycling trips
Waterfront

See all

Less

72 Houses

Sort by:

nesteldown pet friendly

Old Chatham guest house

4 bedrooms
3 bathrooms

sleeps 8

Price per night from

$458

Beautiful, Special 5 Star Estate! Perfect for Family/Friend Reunions & Retreats!

Old Chatham villa

9 bedrooms
5 bathrooms

sleeps 16

Price per night from

$1,260

Charming Guest Suite

Old Chatham apartment

1 bedroom
1 bathroom

sleeps 2

Price per night from

$155

Great rentals within 20 miles that match your search

Iris Room

Stockbridge farmhouse

1 bedroom
1 bathroom

sleeps 2

Price per night from

$172

Horse Room

Stockbridge farmhouse

1 bedroom
1 bathroom

sleeps 3

Price per night from

$172

Thanksgiving week lux condo/4 Berkshires

Williamstown condo

2 bedrooms
1 bathroom

sleeps 4

Price per night from

$263

Berkshires Spacious Comfortable Charming Farmhouse

Lee apartment

3 bedrooms
2 bathrooms

sleeps 8

“lovely stay” The house is comfortable, clean, and convenient to Lenox, Stockbridge, and the rest of the Berkshires. Traffic from the street can be a bit loud at times, but it quiets down at night.

Price per night from

$373

Berkshire Farmhouse Vacation

West Stockbridge house

5 bedrooms
2 bathrooms

sleeps 15

“Quaint Getaway” We were 2 families with 5 kids staying for the weekend. We had plenty of space to spread out, cook & dine together and lots of bedroom options to meet everyone's needs. The house had a lot of antique charm like exposed beams in the living room and paneled walls in the dining room. We were there on a rainy, cold weekend, so did not have an opportunity to enjoy the grounds or porch, but imagine it would be lovely in the warmer weather. Elaine (and her shop) were on the same grounds and she was available for questions about the area. Overall a very relaxing & convenient experience.

Price per night from

$298

Bentley/Wyndham Hancock Mass at Jiminy Peak

Hancock condo

2 bedrooms
2 bathrooms

sleeps 6

Price per night from

$430

Eco-friendly cozy home in Gt. Barrington

Great Barrington house

3 bedrooms
2 bathrooms

sleeps 4

Price per night from

$172

Golden Triangle in the Berkshires

Hancock house

2 bedrooms
2 bathrooms

sleeps 4

Price per night from

$2,863

Beautifully decorated & immaculate log chalet

Hillsdale log cabin

3 bedrooms
2 bathrooms

sleeps 6

Responds fast! avg. 3 hours 45 minutes

Price per night from

$229

Gartner House, a charming home in Lenox

Lenox apartment

4 bedrooms
1 bathroom

sleeps 7

“Great Location In Lenox” My family, friends, & I had a wonderful 2 weeks at Gartner House. It is within easy walking distance of nice shops, terrific restaurants, & a friendly library. Not far are Chesterwood, Tanglewood, Jacob's Pillow, Mass MoCa, Norman Rockwell, & a great, newly renovated Beshire Museum in Pittsfield.

Price per night from

$229