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Holiday rentals near Tanglewood Music Center
We found 911 holiday rentals — enter your dates for availability
Find the perfect holiday rental within close proximity to Tanglewood Music Center. Holiday homes offer the amenities that you expect for you and your friends, family or even pets, such as Wi-Fi and a washer and dryer. Whatever you're looking for, you're sure to find a property to rent for everyone's needs, including a place that's non-smoking or offers accessibility.
Holiday rentals with weekly discounts - Tanglewood Music Center
Showing deals for:14 Nov - 21 Nov
Image gallery for Berkshires Summer Chalet w/ Pool + Private Hiking Trails
1010 out of 10 rating
Exceptional
(7 reviews)
Berkshires Summer Chalet w/ Pool + Private Hiking Trails
Great Barrington, MA
16% off
Price is AU$6,237
AU$6,237
AU$891 per night
includes taxes & fees
Image gallery for Peaceful, Post and Beam Loft, Sleeps 9
1010 out of 10 rating
Exceptional
(20 reviews)
Peaceful, Post and Beam Loft, Sleeps 9
Great Barrington, MA
14% off
Price is AU$2,409
AU$2,409
AU$344 per night
includes taxes & fees
Image gallery for Cheerful 3-bedroom cottage with woodstove
1010 out of 10 rating
Exceptional
(39 reviews)
Cheerful 3-bedroom cottage with woodstove
Sheffield, MA
9% off
Price is AU$3,243
AU$3,243
AU$463 per night
includes taxes & fees
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$13,184
AU$13,184
AU$1,883 per night
includes taxes & fees
Image gallery for Lakeside 3-BR Berkshires Residence
1010 out of 10 rating
Exceptional
(5 reviews)
Lakeside 3-BR Berkshires Residence
Becket, MA
7% off
Price is AU$3,579
AU$3,579
AU$511 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$8,972
AU$8,972
AU$1,282 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$3,813
AU$3,813
AU$545 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$4,679
AU$4,679
AU$668 per night
includes taxes & fees
Image gallery for 5-bed Colonial Berkshires Farmhouse, aka Grandaddy's House, Family Friendly home
1010 out of 10 rating
Exceptional
(10 reviews)
5-bed Colonial Berkshires Farmhouse, aka Grandaddy's House, Family Friendly home
New Marlborough, MA
16% off
Price is AU$7,402
AU$7,402
AU$1,057 per night
includes taxes & fees
Image gallery for General Williams Estate House Lenox/Stockbridge
9.89.8 out of 10 rating
Exceptional
(110 reviews)
General Williams Estate House Lenox/Stockbridge
Stockbridge, MA
8% off
Price is AU$14,347
AU$14,347
AU$2,050 per night
includes taxes & fees
Image gallery for Stonebridge Cabin: Modern Amenities, Enjoy Nature!
9.09.0 out of 10 rating
Wonderful
(6 reviews)
Stonebridge Cabin: Modern Amenities, Enjoy Nature!
Lee, MA
14% off
Price is AU$3,957
AU$3,957
AU$565 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$6,790
AU$6,790
AU$970 per night
includes taxes & fees
Image gallery for Peaceful Retreat Compound 10 Minutes to Great Barrington!
1010 out of 10 rating
Exceptional
(28 reviews)
Peaceful Retreat Compound 10 Minutes to Great Barrington!
Great Barrington, MA
8% off
Price is AU$12,067
AU$12,067
AU$1,724 per night
includes taxes & fees
Image gallery for Modern home with Catskill views, guesthouse and heated pool near Chatham/Hudson
9.49.4 out of 10 rating
Exceptional
(6 reviews)
Modern home with Catskill views, guesthouse and heated pool near Chatham/Hudson
Chatham, NY
8% off
Price is AU$15,054
AU$15,054
AU$2,151 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$6,835
AU$6,835
AU$976 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$6,763
AU$6,763
AU$966 per night
includes taxes & fees
Image gallery for Woodland 5-BR Retreat 5-Min to Jiminy Peak
1010 out of 10 rating
Exceptional
(8 reviews)
Woodland 5-BR Retreat 5-Min to Jiminy Peak
Pittsfield, MA
8% off
Price is AU$4,575
AU$4,575
AU$654 per night
includes taxes & fees
Image gallery for Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
1010 out of 10 rating
Exceptional
(127 reviews)
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
West Stockbridge, MA
8% off
Price is AU$4,848
AU$4,848
AU$693 per night
includes taxes & fees
Image gallery for Completely Renovated Historic Home in the Heart of the Berkshires
1010 out of 10 rating
Exceptional
(13 reviews)
Completely Renovated Historic Home in the Heart of the Berkshires
South Lee, MA
8% off
Price is AU$3,755
AU$3,755
AU$536 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$11,471
AU$11,471
AU$1,639 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$5,770
AU$5,770
AU$824 per night
includes taxes & fees
Image gallery for Entire cottage in Berkshire Villiage
9.69.6 out of 10 rating
Exceptional
(5 reviews)
Entire cottage in Berkshire Villiage
Lanesborough, MA
12% off
Price is AU$1,944
AU$1,944
AU$278 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
16% off
Price is AU$11,278
AU$11,278
AU$1,611 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$4,636
AU$4,636
AU$662 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Tanglewood Music Center
Villa with Access to Amazing Amenities!
Sleeps 6 · 2 bedrooms · 2 bathrooms
9.49.4 out of 10
Exceptionalexceptional
127 reviews(127 reviews)
Jiminy Peak Mountain Resort
Sleeps 8 · 3 bedrooms
8.28.2 out of 10
Very goodvery good
959 reviews(959 reviews)
NEW RENO - Historic Loft w/views of the Berkshires
Sleeps 5 · 2 bedrooms · 1 bathroom
1010 out of 10
Exceptionalexceptional
6 reviews(6 reviews)
Deluxe Queen Room with 2 Queen Beds
Sleeps 4 · 1 bedroom · 1 bathroom
2.02.0 out of 10
3 reviews(3 reviews)
The Ponds at Foxhollow
Sleeps 4 · 1 bedroom
8.68.6 out of 10
Excellentexcellent
124 reviews(124 reviews)
Charming 3-bedroom Cabin for nature lovers
Sleeps 8 · 3 bedrooms · 1 bathroom
8.08.0 out of 10
Very goodvery good
1 review(1 review)
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
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