Holiday rentals near Colonial Theater
We found 949 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:31 Oct - 7 Nov
Image gallery for Taggart River House: Modern Luxury Meets Nature: Stunning river views, sleeps 10
1010 out of 10 rating
Exceptional
(6 reviews)
Taggart River House: Modern Luxury Meets Nature: Stunning river views, sleeps 10
Stockbridge, MA
8% off
Price is AU$13,382
AU$13,382
AU$1,912 per night
includes taxes & fees
Image gallery for Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!
1010 out of 10 rating
Exceptional
(26 reviews)
Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!
Great Barrington, MA
8% off
Price is AU$9,157
AU$9,157
AU$1,308 per night
includes taxes & fees
Image gallery for Waterfront Cottage 10 Min From Great Barrington
1010 out of 10 rating
Exceptional
(97 reviews)
Waterfront Cottage 10 Min From Great Barrington
Great Barrington, MA
8% off
Price is AU$4,820
AU$4,820
AU$689 per night
includes taxes & fees
Image gallery for 1500 sqft private entrance with beautiful views of the Berkshire Mountains
1010 out of 10 rating
Exceptional
(44 reviews)
1500 sqft private entrance with beautiful views of the Berkshire Mountains
Lee, MA
8% off
Price is AU$3,870
AU$3,870
AU$553 per night
includes taxes & fees
Image gallery for Indoor Pool & Lofted Game Area | Sunroom w/ Sweeping Mountain Views | Wellspring
1010 out of 10 rating
Exceptional
(13 reviews)
Indoor Pool & Lofted Game Area | Sunroom w/ Sweeping Mountain Views | Wellspring
West Stockbridge, Massachusetts
17% off
Price is AU$12,115
AU$12,115
AU$1,731 per night
includes taxes & fees
Image gallery for Beautiful Home in AMAZING Berkshire Location
1010 out of 10 rating
Exceptional
(17 reviews)
Beautiful Home in AMAZING Berkshire Location
Lee, MA
8% off
Price is AU$6,892
AU$6,892
AU$985 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
(13 reviews)
Half Moon by AvantStay | 4BR Cabin w/ Large Deck & Yard
Great Barrington, MA
6% off
Price is AU$7,172
AU$7,172
AU$1,025 per night
includes taxes & fees
Image gallery for A-Frame Cabin w/ Furnished Deck in Becket!
8.68.6 out of 10 rating
Excellent
(8 reviews)
A-Frame Cabin w/ Furnished Deck in Becket!
Becket, Massachusetts
10% off
Price is AU$2,249
AU$2,249
AU$321 per night
includes taxes & fees
Image gallery for Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.
9.69.6 out of 10 rating
Exceptional
(14 reviews)
Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.
Hinsdale, MA
8% off
Price is AU$2,112
AU$2,112
AU$302 per night
includes taxes & fees
Image gallery for BEAUTIFUL ESTATE: POOL, POND, ARCADE, GYM, TRAILS! REDUCED RATE FOR SMALL GROUPS
9.69.6 out of 10 rating
Exceptional
(88 reviews)
BEAUTIFUL ESTATE: POOL, POND, ARCADE, GYM, TRAILS! REDUCED RATE FOR SMALL GROUPS
Old Chatham, NY
8% off
Price is AU$18,000
AU$18,000
AU$2,571 per night
includes taxes & fees
Image gallery for Private Berkshire Cabin on 27acres near Jiminy Peak.
9.69.6 out of 10 rating
Exceptional
(7 reviews)
Private Berkshire Cabin on 27acres near Jiminy Peak.
Williamstown, MA
13% off
Price is AU$3,670
AU$3,670
AU$524 per night
includes taxes & fees
Image gallery for 3 BR+ 4level WINTER SKI RENTAL LOOKING 4 SEASONAL RENTER 1 MILE OFF OF JIMINEY
9.69.6 out of 10 rating
Exceptional
(17 reviews)
3 BR+ 4level WINTER SKI RENTAL LOOKING 4 SEASONAL RENTER 1 MILE OFF OF JIMINEY
Lanesborough, MA
23% off
Price is AU$5,596
AU$5,596
AU$799 per night
includes taxes & fees
Image gallery for Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
1010 out of 10 rating
Exceptional
(126 reviews)
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
West Stockbridge, MA
8% off
Price is AU$4,920
AU$4,920
AU$703 per night
includes taxes & fees
Image gallery for Picture-perfect farmhouse nestled in Berkshire County, MA near Tanglewood
1010 out of 10 rating
Exceptional
(11 reviews)
Picture-perfect farmhouse nestled in Berkshire County, MA near Tanglewood
Lee, MA
8% off
Price is AU$6,933
AU$6,933
AU$990 per night
includes taxes & fees
Image gallery for Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
9.89.8 out of 10 rating
Exceptional
(29 reviews)
Beautiful 2-Bedroom + Loft with Hot Tub at Lake Ashmere
Hinsdale, MA
12% off
Price is AU$3,697
AU$3,697
AU$528 per night
includes taxes & fees
Image gallery for Best of the Berkshires & Hudson Valley
1010 out of 10 rating
Exceptional
(12 reviews)
Best of the Berkshires & Hudson Valley
Canaan, NY
8% off
Price is AU$5,856
AU$5,856
AU$837 per night
includes taxes & fees
Image gallery for Cozy lake house with hot tub. Enjoy everything the Berkshires have to offer!
1010 out of 10 rating
Exceptional
(5 reviews)
Cozy lake house with hot tub. Enjoy everything the Berkshires have to offer!
Lanesborough, MA
12% off
Price is AU$4,777
AU$4,777
AU$682 per night
includes taxes & fees
Image gallery for Stunning Renovated Victorian
1010 out of 10 rating
Exceptional
(53 reviews)
Stunning Renovated Victorian
Great Barrington, MA
15% off
Price is AU$11,684
AU$11,684
AU$1,669 per night
includes taxes & fees
Image gallery for Forget-Me-Not by AvantStay | Bold Lakefront Escape
9.09.0 out of 10 rating
Wonderful
(6 reviews)
Forget-Me-Not by AvantStay | Bold Lakefront Escape
Monterey, Massachusetts
9% off
Price is AU$10,821
AU$10,821
AU$1,546 per night
includes taxes & fees
Image gallery for Amore Estate - beautiful room with many places to explore and relax in.
9.09.0 out of 10 rating
Wonderful
(25 reviews)
Amore Estate - beautiful room with many places to explore and relax in.
Lenox, MA
8% off
Price is AU$11,643
AU$11,643
AU$1,663 per night
includes taxes & fees
Image gallery for Modern Victorian Walk to Main Street
1010 out of 10 rating
Exceptional
(25 reviews)
Modern Victorian Walk to Main Street
Great Barrington, MA
15% off
Price is AU$5,411
AU$5,411
AU$773 per night
includes taxes & fees
Image gallery for Walk to Town/Lake – Spring ’25 Renovation!
9.89.8 out of 10 rating
Exceptional
(7 reviews)
Walk to Town/Lake – Spring ’25 Renovation!
Great Barrington, Massachusetts
14% off
Price is AU$4,336
AU$4,336
AU$619 per night
includes taxes & fees
Image gallery for Quiet Cabin On Over 12 Acres Of Woods!
1010 out of 10 rating
Exceptional
(11 reviews)
Quiet Cabin On Over 12 Acres Of Woods!
Becket, Massachusetts
14% off
Price is AU$2,467
AU$2,467
AU$352 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$4,645
AU$4,645
AU$664 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
28 reviews(28 reviews)
Vacation Village in the Berkshires
Sleeps 4 · 1 bedroom
8.68.6 out of 10
Excellentexcellent
1,920 reviews(1,920 reviews)
Jiminy Peak Mountain Resort
Sleeps 8 · 3 bedrooms
8.28.2 out of 10
Very goodvery good
957 reviews(957 reviews)
Berkshire Village Carriage House - Super Private!!
Sleeps 2 · 1 bedroom · 1 bathroom
9.89.8 out of 10
Exceptionalexceptional
253 reviews(253 reviews)
Spacious Berkshire Summer Rental, Private Dock on Lake 3 BR/2b
Sleeps 7 · 3 bedrooms · 2 bathrooms
9.69.6 out of 10
Exceptionalexceptional
100 reviews(100 reviews)
A Beautiful Log Cabin In The Woods, On Pontoosuc Lake, Yet Near Everything
Sleeps 5 · 2 bedrooms · 1 bathroom
1010 out of 10
Exceptionalexceptional
122 reviews(122 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