Holiday rentals near Colonial Theater
We found 937 holiday rentals — enter your dates for availability
Scroll through and discover private holiday rentals within easy reach of Colonial Theater that are perfect for your trip. Whether you're travelling with family, friends or just your furry companion, holiday rentals have the amenities that you expect for your stay, which might include a hot tub and a washer and dryer. You'll be able to choose a property to rent for everyone's needs, including places that are non-smoking or accessible.
Holiday rentals with weekly discounts - Colonial Theater
Showing deals for:19 Sept - 26 Sept
Image gallery for Private river-front home with tennis court and hot tub in the Berkshire hills!
1010 out of 10 rating
Exceptional
(5 reviews)
Private river-front home with tennis court and hot tub in the Berkshire hills!
Cummington, MA
13% off
Price is AU$8,096
AU$8,096
AU$1,157 per night
includes taxes & fees
Image gallery for 11 acre mid-century estate, newly renovated, seasonally available pool.
1010 out of 10 rating
Exceptional
(22 reviews)
11 acre mid-century estate, newly renovated, seasonally available pool.
Williamstown, MA
8% off
Price is AU$9,474
AU$9,474
AU$1,353 per night
includes taxes & fees
Image gallery for Tranquil 3-BR Waterfront Retreat
1010 out of 10 rating
Exceptional
(13 reviews)
Tranquil 3-BR Waterfront Retreat
Becket, MA
8% off
Price is AU$5,770
AU$5,770
AU$824 per night
includes taxes & fees
Image gallery for COZY LOFT w/ PRIVATE BEACH ON GORGEOUS MOUNTAIN LAKE IN THE BERKSHIRES
9.89.8 out of 10 rating
Exceptional
(159 reviews)
COZY LOFT w/ PRIVATE BEACH ON GORGEOUS MOUNTAIN LAKE IN THE BERKSHIRES
Lee, MA
12% off
Price is AU$2,592
AU$2,592
AU$370 per night
includes taxes & fees
Image gallery for Enchanting Modern Farmhouse with Picturesque Views
1010 out of 10 rating
Exceptional
(17 reviews)
Enchanting Modern Farmhouse with Picturesque Views
Sand Lake, NY
8% off
Price is AU$5,002
AU$5,002
AU$715 per night
includes taxes & fees
Image gallery for Half Moon by AvantStay | 4BR Cabin w/ Large Deck & Yard
9.89.8 out of 10 rating
Exceptional
(12 reviews)
Half Moon by AvantStay | 4BR Cabin w/ Large Deck & Yard
Great Barrington, MA
6% off
Price is AU$7,366
AU$7,366
AU$1,052 per night
includes taxes & fees
Image gallery for 5 STAR ESTATE: POOL, POND, ARCADE, GYM, TRAILS! DON'T MISS OUT! JULY 13-20 OPEN!
9.69.6 out of 10 rating
Exceptional
(87 reviews)
5 STAR ESTATE: POOL, POND, ARCADE, GYM, TRAILS! DON'T MISS OUT! JULY 13-20 OPEN!
Old Chatham, NY
8% off
Price is AU$17,566
AU$17,566
AU$2,509 per night
includes taxes & fees
Image gallery for Ashmere Lake Log Cabin with privacy / 2 Bedrooms/ 3 night minimum
9.89.8 out of 10 rating
Exceptional
(57 reviews)
Ashmere Lake Log Cabin with privacy / 2 Bedrooms/ 3 night minimum
Hinsdale, MA
8% off
Price is AU$2,702
AU$2,702
AU$386 per night
includes taxes & fees
Image gallery for Modern, private, spacious vacation home, deck, mountain views, 5 mi to Catamount
1010 out of 10 rating
Exceptional
(10 reviews)
Modern, private, spacious vacation home, deck, mountain views, 5 mi to Catamount
Hillsdale, NY
8% off
Price is AU$8,219
AU$8,219
AU$1,174 per night
includes taxes & fees
Image gallery for Berkshire Lake at the Pillow, and EV!
9.49.4 out of 10 rating
Exceptional
(15 reviews)
Berkshire Lake at the Pillow, and EV!
Lee, MA
8% off
Price is AU$4,532
AU$4,532
AU$647 per night
includes taxes & fees
Image gallery for Stay at Beaver Lodge!
1010 out of 10 rating
Exceptional
(29 reviews)
Stay at Beaver Lodge!
Monterey, MA
8% off
Price is AU$2,174
AU$2,174
AU$311 per night
includes taxes & fees
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 AU$9,586
AU$9,586
AU$1,369 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 AU$7,356
AU$7,356
AU$1,051 per night
includes taxes & fees
Image gallery for The Pinetop Cabin | Modern ∙ Surrounded by Trees ∙ Sustainably-built
1010 out of 10 rating
Exceptional
(20 reviews)
The Pinetop Cabin | Modern ∙ Surrounded by Trees ∙ Sustainably-built
Chatham, NY
8% off
Price is AU$4,521
AU$4,521
AU$646 per night
includes taxes & fees
Image gallery for Ashintully Cottage in spectacular setting
1010 out of 10 rating
Exceptional
(33 reviews)
Ashintully Cottage in spectacular setting
Lee, MA
17% off
Price is AU$3,784
AU$3,784
AU$541 per night
includes taxes & fees
Image gallery for Family-friendly, private three bedroom cottage in the beautiful Berkshires
9.29.2 out of 10 rating
Wonderful
(15 reviews)
Family-friendly, private three bedroom cottage in the beautiful Berkshires
Williamstown, MA
12% off
Price is AU$4,343
AU$4,343
AU$620 per night
includes taxes & fees
Image gallery for Views of Catamount! Tanglewood, Skiing, Bash Bish Falls, Barn At Liberty Farms!
1010 out of 10 rating
Exceptional
(43 reviews)
Views of Catamount! Tanglewood, Skiing, Bash Bish Falls, Barn At Liberty Farms!
Hillsdale, NY
8% off
Price is AU$11,983
AU$11,983
AU$1,712 per night
includes taxes & fees
Image gallery for Stunning Lake Views & Privacy Only Mins. to Downtown Lenox, Stockbridge, Lee.
1010 out of 10 rating
Exceptional
(22 reviews)
Stunning Lake Views & Privacy Only Mins. to Downtown Lenox, Stockbridge, Lee.
Lee, MA
12% off
Price is AU$7,397
AU$7,397
AU$1,057 per night
includes taxes & fees
Image gallery for Two Rooms with En-Suite in Quiet Woodland
1010 out of 10 rating
Exceptional
(30 reviews)
Two Rooms with En-Suite in Quiet Woodland
Hillsdale, NY
8% off
Price is AU$2,754
AU$2,754
AU$393 per night
includes taxes & fees
Image gallery for Secluded Family Home in Serene Stockbridge Woods
1010 out of 10 rating
Exceptional
(21 reviews)
Secluded Family Home in Serene Stockbridge Woods
South Lee, MA
8% off
Price is AU$6,191
AU$6,191
AU$884 per night
includes taxes & fees
Image gallery for Spacious Berkshire Summer Rental, Private Dock on Lake 3 BR/2b
9.69.6 out of 10 rating
Exceptional
(97 reviews)
Spacious Berkshire Summer Rental, Private Dock on Lake 3 BR/2b
Richmond, MA
8% off
Price is AU$3,497
AU$3,497
AU$500 per night
includes taxes & fees
Image gallery for Sunny, Stylish Berkshire Mountain Retreat near Jacob's Pillow
9.89.8 out of 10 rating
Exceptional
(54 reviews)
Sunny, Stylish Berkshire Mountain Retreat near Jacob's Pillow
Middlefield, MA
12% off
Price is AU$5,181
AU$5,181
AU$740 per night
includes taxes & fees
Image gallery for A simple kind of paradise
1010 out of 10 rating
Exceptional
(19 reviews)
A simple kind of paradise
Worthington, MA
8% off
Price is AU$2,629
AU$2,629
AU$376 per night
includes taxes & fees
Image gallery for Classic Stockbridge Cottage
1010 out of 10 rating
Exceptional
(15 reviews)
Classic Stockbridge Cottage
Stockbridge, Massachusetts
14% off
Price is AU$4,473
AU$4,473
AU$639 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Colonial Theater
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
1,829 reviews(1,829 reviews)
Berkshire Village Carriage House - Super Private!!
Sleeps 2 · 1 bedroom · 1 bathroom
9.89.8 out of 10
Exceptionalexceptional
248 reviews(248 reviews)
Jiminy Peak Mountain Resort
Sleeps 8 · 3 bedrooms
8.28.2 out of 10
Very goodvery good
933 reviews(933 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
144 reviews(144 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)
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