Berkshires with Pools(96)
Vue de L'est - The East View
- 5 Bedrooms,
- 4 Bathrooms,
- 1 Half Bath, Sleeps 11
$600 -
$860
per night
3 - 7 night minimum stay
- 5 BR,
- 4 BA,
- 1 HF BA,
- Sleeps 11
Unique Luxury Property in Williamstown with Spectacular Views...Multiple Suites
- 5 Bedrooms,
- 4 Bathrooms,
- 1 Half Bath, Sleeps 10
$400 -
$800
per night
2 - 3 night minimum stay
- 5 BR,
- 4 BA,
- 1 HF BA,
- Sleeps 10
Berkshire Monarch Hill Retreat , Pool, Views, Secluded Setting
- 4 Bedrooms,
- 3 Bathrooms,
- 1 Half Bath, Sleeps 8
- 4 BR,
- 3 BA,
- 1 HF BA,
- Sleeps 8
Bright & Open, High Up Jiminy Peak, Panoramic Views, Close to Williamstown
- 4 Bedrooms,
- 3 Bathrooms, Sleeps 10
$275 -
$450
per night
2 - 3 night minimum stay
- 4 BR,
- 3 BA,
- Sleeps 10
Beautifully Renovated Barn With Pool
- 4 Bedrooms,
- 2 Bathrooms,
- 1 Half Bath, Sleeps 8
$250 -
$1,000
per night
2 night minimum stay
- 4 BR,
- 2 BA,
- 1 HF BA,
- Sleeps 8
Berkshires Comfort, Convenience & Privacy
- 3 Bedrooms,
- 1 Bathroom,
- 1 Half Bath, Sleeps 6
$257 -
$450
per night
5 night minimum stay
- 3 BR,
- 1 BA,
- 1 HF BA,
- Sleeps 6
Rustic Home in Exclusive Lakeside Community
- 4 Bedrooms,
- 2 Bathrooms,
- 1 Half Bath, Sleeps 10
$2,000
per week
3 - 14 night minimum stay
- 4 BR,
- 2 BA,
- 1 HF BA,
- Sleeps 10
Beautiful Stockbridge Contempt, on 16 wooded acres, Pool and Gardens
- 3 Bedrooms,
- 2 Bathrooms,
- 1 Half Bath, Sleeps 8
- 3 BR,
- 2 BA,
- 1 HF BA,
- Sleeps 8
A Home that feels like a Resort
- 4 Bedrooms,
- 3 Bathrooms,
- 1 Half Bath, Sleeps 8
$350 -
$500
per night
3 - 4 night minimum stay
- 4 BR,
- 3 BA,
- 1 HF BA,
- Sleeps 8
Exclusive Property
- 2 Bedrooms,
- 1 Bathroom,
- 1 Half Bath, Sleeps 4
$2,275
per week
7 night minimum stay
- 2 BR,
- 1 BA,
- 1 HF BA,
- Sleeps 4
4Br Lakefront/Ski House on Otis Res: now with Internet
- 4 Bedrooms,
- 3 Bathrooms, Sleeps 10
$175 -
$200
per night
2 - 7 night minimum stay
- 4 BR,
- 3 BA,
- Sleeps 10
Berkshires, Lake Buel, Beautiful Cottage,Walk 2 Private Dock Beach
- 2 Bedrooms,
- 1 Bathroom, Sleeps 6
$150 -
$215
per night
2 night minimum stay
- 2 BR,
- 1 BA,
- Sleeps 6
JIMINY PEAK ALL YEAR ROUND RESORT 20 MINUTES FROM ALL CULTURAL ACTIVITIES
- 4 Bedrooms, Sleeps 10
$200 -
$500
per night
3 - 30 night minimum stay
- 4 BR,
- Sleeps 10
Historic Home on 8.5 Acres Heated Pool A/C ALL sleeping areas
- 3 Bedrooms,
- 2 Bathrooms,
- 1 Half Bath, Sleeps 9
$2,000
per week
7 night minimum stay
- 3 BR,
- 2 BA,
- 1 HF BA,
- Sleeps 9
Summer Savings. Book Now! Stunning Post & Beam
- 5 Bedrooms,
- 2 Bathrooms,
- 2 Half Baths, Sleeps 12
$600 -
$750
per night
2 - 7 night minimum stay
- 5 BR,
- 2 BA,
- 2 HF BA,
- Sleeps 12
Special Offer
July Get-Away Specials -- Discounts (June 28 - July 25)
Williamstown Rental
- 3 Bedrooms,
- 2 Bathrooms,
- 1 Half Bath, Sleeps 8
$300 -
$350
per night
4 night minimum stay
- 3 BR,
- 2 BA,
- 1 HF BA,
- Sleeps 8
Time to plan for the Fall and Winter - Good foliage dates still open
- 5 Bedrooms,
- 2 Bathrooms, Sleeps 10
$2,000 -
$2,200
per week
2 - 6 night minimum stay
- 5 BR,
- 2 BA,
- Sleeps 10
Spacious architect designed clapboard house on 17 secluded acres w. pool.
- 5 Bedrooms,
- 3 Bathrooms, Sleeps 13
$200 -
$700
per night
3 - 7 night minimum stay
- 5 BR,
- 3 BA,
- Sleeps 13
Year Round Retreat Near Jiminy Peak
- 4 Bedrooms,
- 2 Bathrooms, Sleeps 10
$350 -
$500
per night
2 night minimum stay
- 4 BR,
- 2 BA,
- Sleeps 10
Lovingly Cared 4, Ranch- 1 level- Piano,Private deck. Ask rent price.
- 2 Bedrooms,
- 2 Bathrooms, Sleeps 6
$182 -
$250
per night
4 night minimum stay
- 2 BR,
- 2 BA,
- Sleeps 6
Modern Summer/Ski Retreat Sleeps 10
- 4 Bedrooms,
- 3 Bathrooms,
- 1 Half Bath, Sleeps 10
$2,338 -
$4,086
per week
7 - 30 night minimum stay
- 4 BR,
- 3 BA,
- 1 HF BA,
- Sleeps 10
Charming Condo with Jacuzzi on Mountain Ski on/Ski off
- 2 Bedrooms,
- 2 Bathrooms, Sleeps 8
$150 -
$580
per night
2 - 3 night minimum stay
- 2 BR,
- 2 BA,
- Sleeps 8
The Pastures: an Experience Not to Miss - Now with Gorgeous in-ground Pool!
- 6 Bedrooms,
- 4 Bathrooms,
- 2 Half Baths, Sleeps 12
$9,500 -
$11,000
per week
4 night minimum stay
- 6 BR,
- 4 BA,
- 2 HF BA,
- Sleeps 12
WE ARE SOLD OUT!!!...PLEASE CHECK BACK FOR NEXT YEAR
- 2 Bedrooms,
- 2 Bathrooms, Sleeps 8
$350
per night
4 night minimum stay
- 2 BR,
- 2 BA,
- Sleeps 8
Beautifully Renovated Old Colonial In Secluded Berkshires
- 6 Bedrooms,
- 2 Bathrooms,
- 1 Half Bath, Sleeps 11
$250
per night
6 night minimum stay
- 6 BR,
- 2 BA,
- 1 HF BA,
- Sleeps 11
Vacation House in Otis Woodlands Community
- 4 Bedrooms,
- 2 Bathrooms, Sleeps 8
$150
per night
2 night minimum stay
- 4 BR,
- 2 BA,
- Sleeps 8
Bentley Brook Mountain Club at Jiminy Peak
- 2 Bedrooms,
- 2 Bathrooms, Sleeps 8
$175 -
$375
per night
2 - 3 night minimum stay
- 2 BR,
- 2 BA,
- Sleeps 8
Fabulous GB Estate w/ Pool, Hot Tub, Views, 120 acres + Guest House!
- 9 Bedrooms,
- 6 Bathrooms,
- 1 Half Bath, Sleeps 20
$13,000 -
$15,000
per week
2 night minimum stay
- 9 BR,
- 6 BA,
- 1 HF BA,
- Sleeps 20
Converted Barn on 120 Acres w/ Private Swimming Pond & All Amenities.
- 5 Bedrooms,
- 2 Bathrooms,
- 1 Half Bath, Sleeps 11
$8,000
per month
6 night minimum stay
- 5 BR,
- 2 BA,
- 1 HF BA,
- Sleeps 11
Wyndham Bentley Brook - Click “Book Now” to securely book online
- Studio,
- 1 Bathroom, Sleeps 4
$104 -
$286
per night
2 night minimum stay
- Studio,
- 1 BA,
- Sleeps 4
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Berkshires
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