Holiday rentals near Berkshire Retreat Center
We found 711 holiday rentals — enter your dates for availability
Find the perfect holiday rental within close proximity to Berkshire Retreat Center. Holiday homes provide the best amenities for your family, friends or furry companion, such as air conditioning and cable TV. Whatever you're looking for, you'll find a property to rent that has what everyone needs, including a place that is accessible or non-smoking.
Holiday rentals with weekly discounts - Berkshire Retreat Center
Showing deals for:29 Aug - 5 Sept
Image gallery for Summertime at Left Bank Lodge
1010 out of 10 rating
Exceptional
(6 reviews)
Summertime at Left Bank Lodge
Hancock, MA
8% off
Price is NZ$10,881
NZ$10,881
NZ$1,554 per night
includes taxes & fees
Image gallery for Five-Star Family Friendly Townhouse in the Heart of Jiminy Peak
1010 out of 10 rating
Exceptional
(19 reviews)
Five-Star Family Friendly Townhouse in the Heart of Jiminy Peak
Hancock, MA
8% off
Price is NZ$8,630
NZ$8,630
NZ$1,233 per night
includes taxes & fees
Image gallery for Modern Creekside Stay with Hot Tub 10 mins to Downtown Hudson
9.69.6 out of 10 rating
Exceptional
(5 reviews)
Modern Creekside Stay with Hot Tub 10 mins to Downtown Hudson
Hudson, NY
8% off
Price is NZ$6,392
NZ$6,392
NZ$913 per night
includes taxes & fees
Image gallery for The Pinetop Cabin | Modern ∙ Surrounded by Trees ∙ Sustainably-built
1010 out of 10 rating
Exceptional
(19 reviews)
The Pinetop Cabin | Modern ∙ Surrounded by Trees ∙ Sustainably-built
Chatham, NY
8% off
Price is NZ$5,002
NZ$5,002
NZ$715 per night
includes taxes & fees
Image gallery for Woodland 5-BR Retreat 5-Min to Jiminy Peak
1010 out of 10 rating
Exceptional
(6 reviews)
Woodland 5-BR Retreat 5-Min to Jiminy Peak
Pittsfield, Massachusetts
8% off
Price is NZ$8,997
NZ$8,997
NZ$1,285 per night
includes taxes & fees
Image gallery for 200 yr old Historic Farmhouse in Walkable City Neighborhood - 35 min to Saratoga
1010 out of 10 rating
Exceptional
(6 reviews)
200 yr old Historic Farmhouse in Walkable City Neighborhood - 35 min to Saratoga
Albany, NY
17% off
Price is NZ$14,360
NZ$14,360
NZ$2,051 per night
includes taxes & fees
Image gallery for In the HEART of JIMINY PEAK MOUNTAIN RESORT slope side, shopping restaurants
8.68.6 out of 10 rating
Excellent
(10 reviews)
In the HEART of JIMINY PEAK MOUNTAIN RESORT slope side, shopping restaurants
Hancock, MA
8% off
Price is NZ$3,878
NZ$3,878
NZ$554 per night
includes taxes & fees
Image gallery for Perfect family getaway spot! Free standing private 4 BR home on Jiminy Peak.
1010 out of 10 rating
Exceptional
(39 reviews)
Perfect family getaway spot! Free standing private 4 BR home on Jiminy Peak.
Hancock, MA
12% off
Price is NZ$9,262
NZ$9,262
NZ$1,323 per night
includes taxes & fees
Image gallery for *Discounted weekly rates* Beautiful 52 acre Farmhouse! Catskills Family Getaway
1010 out of 10 rating
Exceptional
(33 reviews)
*Discounted weekly rates* Beautiful 52 acre Farmhouse! Catskills Family Getaway
West Coxsackie, NY
8% off
Price is NZ$3,969
NZ$3,969
NZ$567 per night
includes taxes & fees
Image gallery for Enchanting Country House on 18 acres, Sunset Views, <15 minutes from Tanglewood
9.89.8 out of 10 rating
Exceptional
(17 reviews)
Enchanting Country House on 18 acres, Sunset Views, <15 minutes from Tanglewood
West Stockbridge, MA
14% off
Price is NZ$4,424
NZ$4,424
NZ$632 per night
includes taxes & fees
Image gallery for "Family Cabin: Hot Tub, Golf, Games, Sunset, Pet!"
1010 out of 10 rating
Exceptional
(5 reviews)
"Family Cabin: Hot Tub, Golf, Games, Sunset, Pet!"
Castleton-on-Hudson, NY
8% off
Price is NZ$12,450
NZ$12,450
NZ$1,779 per night
includes taxes & fees
Image gallery for Boho Chic Cape
9.89.8 out of 10 rating
Exceptional
(16 reviews)
Boho Chic Cape
Albany, NY
8% off
Price is NZ$6,316
NZ$6,316
NZ$902 per night
includes taxes & fees
Image gallery for Mini Mansion newly furnished with Italian furniture 8kslim televisions all rooms
9.29.2 out of 10 rating
Wonderful
(16 reviews)
Mini Mansion newly furnished with Italian furniture 8kslim televisions all rooms
Albany, NY
8% off
Price is NZ$6,030
NZ$6,030
NZ$861 per night
includes taxes & fees
Image gallery for Modern Country Farmhouse, Walking Distance to Lake
1010 out of 10 rating
Exceptional
(7 reviews)
Modern Country Farmhouse, Walking Distance to Lake
Averill Park, NY
8% off
Price is NZ$4,124
NZ$4,124
NZ$589 per night
includes taxes & fees
Image gallery for A MAGIC SPOT: Booking all year Weekly, monthly discounts available
9.69.6 out of 10 rating
Exceptional
(30 reviews)
A MAGIC SPOT: Booking all year Weekly, monthly discounts available
Stephentown, NY
8% off
Price is NZ$3,592
NZ$3,592
NZ$513 per night
includes taxes & fees
Image gallery for Ghent Getaway, Minutes from Hudson
1010 out of 10 rating
Exceptional
(6 reviews)
Ghent Getaway, Minutes from Hudson
Ghent, NY
8% off
Price is NZ$1,364
NZ$1,364
NZ$195 per night
includes taxes & fees
Image gallery for Hennett Road Hideaway with Hot Tub, Pool and Pellet Stove
1010 out of 10 rating
Exceptional
(16 reviews)
Hennett Road Hideaway with Hot Tub, Pool and Pellet Stove
Valatie, NY
8% off
Price is NZ$5,469
NZ$5,469
NZ$781 per night
includes taxes & fees
Image gallery for Hudson Valley Chalet
9.29.2 out of 10 rating
Wonderful
(7 reviews)
Hudson Valley Chalet
East Chatham, NY
25% off
Price is NZ$7,777
NZ$7,777
NZ$1,111 per night
includes taxes & fees
Image gallery for Tutti Farmhouse - 6 bedroom 3 bath 1847 Farmhouse Upstate NY
1010 out of 10 rating
Exceptional
(6 reviews)
Tutti Farmhouse - 6 bedroom 3 bath 1847 Farmhouse Upstate NY
Cropseyville, NY
8% off
Price is NZ$12,475
NZ$12,475
NZ$1,782 per night
includes taxes & fees
Image gallery for Utopian Country Retreat w Glowing Flowers
9.89.8 out of 10 rating
Exceptional
(18 reviews)
Utopian Country Retreat w Glowing Flowers
Voorheesville, NY
13% off
Price is NZ$3,603
NZ$3,603
NZ$515 per night
includes taxes & fees
Image gallery for Snowdrop Lodge - Beautiful Condo on Jiminy Peak Grounds
9.69.6 out of 10 rating
Exceptional
(18 reviews)
Snowdrop Lodge - Beautiful Condo on Jiminy Peak Grounds
Hancock, MA
5% off
Price is NZ$3,298
NZ$3,298
NZ$471 per night
includes taxes & fees
Image gallery for Berkshire Rural Retreat
1010 out of 10 rating
Exceptional
(21 reviews)
Berkshire Rural Retreat
Canaan, NY
8% off
Price is NZ$6,047
NZ$6,047
NZ$864 per night
includes taxes & fees
Image gallery for Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn
9.49.4 out of 10 rating
Exceptional
(16 reviews)
Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn
Hancock, MA
8% off
Price is NZ$3,454
NZ$3,454
NZ$493 per night
includes taxes & fees
Image gallery for / New Giant Victorian \ 7beds 6 baths
1010 out of 10 rating
Exceptional
(12 reviews)
/ New Giant Victorian \ 7beds 6 baths
Albany, NY
17% off
Price is NZ$8,100
NZ$8,100
NZ$1,157 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Berkshire Retreat Center
6BR Berkshire Bliss - 38 Acres of nature - minutes from Jiminy Peak Ski Resort
Sleeps 14 · 6 bedrooms · 4+ bathrooms
9.89.8 out of 10
Exceptionalexceptional
27 reviews(27 reviews)
Vacation Village in the Berkshires
Sleeps 4 · 1 bedroom
8.68.6 out of 10
Excellentexcellent
1,813 reviews(1,813 reviews)
Berkshire Village Carriage House - Super Private!!
Sleeps 2 · 1 bedroom · 1 bathroom
9.89.8 out of 10
Exceptionalexceptional
248 reviews(248 reviews)
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table
Sleeps 28 · 8 bedrooms · 3 bathrooms
9.89.8 out of 10
Exceptionalexceptional
142 reviews(142 reviews)
Comfortable Berkshires retreat on mtn resort, SISO
Sleeps 12 · 4 bedrooms · 3 bathrooms
9.69.6 out of 10
Exceptionalexceptional
4 reviews(4 reviews)
Jiminy Peak Mountain Resort
Sleeps 8 · 3 bedrooms
8.28.2 out of 10
Very goodvery good
931 reviews(931 reviews)
Peace of mindOur Book with Confidence guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value