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Holiday rentals near Tanglewood Music Center
We found 912 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 NZ$6,845
NZ$6,845
NZ$978 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
13% off
Price is NZ$2,638
NZ$2,638
NZ$377 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 NZ$3,588
NZ$3,588
NZ$513 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 NZ$14,826
NZ$14,826
NZ$2,118 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 NZ$3,951
NZ$3,951
NZ$564 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
(45 reviews)
1500 sqft private entrance with beautiful views of the Berkshire Mountains
Lee, MA
8% off
Price is NZ$4,216
NZ$4,216
NZ$602 per night
includes taxes & fees
Image gallery for Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!
1010 out of 10 rating
Exceptional
(27 reviews)
Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!
Great Barrington, MA
8% off
Price is NZ$9,910
NZ$9,910
NZ$1,416 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 NZ$5,172
NZ$5,172
NZ$739 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 NZ$16,177
NZ$16,177
NZ$2,311 per night
includes taxes & fees
Image gallery for Konkapot Cottage, Pastoral Bliss With Wide Views
1010 out of 10 rating
Exceptional
(20 reviews)
Konkapot Cottage, Pastoral Bliss With Wide Views
New Marlborough, MA
8% off
Price is NZ$4,202
NZ$4,202
NZ$600 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 NZ$7,454
NZ$7,454
NZ$1,065 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 NZ$7,423
NZ$7,423
NZ$1,060 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 NZ$13,595
NZ$13,595
NZ$1,942 per night
includes taxes & fees
Image gallery for Beautiful Berkshire Home - Enjoy summer, fall & winter attractions
1010 out of 10 rating
Exceptional
(15 reviews)
Beautiful Berkshire Home - Enjoy summer, fall & winter attractions
Sheffield, MA
8% off
Price is NZ$7,234
NZ$7,234
NZ$1,033 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 NZ$6,562
NZ$6,562
NZ$937 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 NZ$5,061
NZ$5,061
NZ$723 per night
includes taxes & fees
Image gallery for Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
1010 out of 10 rating
Exceptional
(128 reviews)
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
West Stockbridge, MA
8% off
Price is NZ$5,360
NZ$5,360
NZ$766 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 NZ$2,150
NZ$2,150
NZ$307 per night
includes taxes & fees
Image gallery for Stunning Renovated Victorian
1010 out of 10 rating
Exceptional
(54 reviews)
Stunning Renovated Victorian
Great Barrington, MA
16% off
Price is NZ$12,710
NZ$12,710
NZ$1,816 per night
includes taxes & fees
Image gallery for Best of the Berkshires & Hudson Valley
1010 out of 10 rating
Exceptional
(13 reviews)
Best of the Berkshires & Hudson Valley
Canaan, NY
8% off
Price is NZ$6,571
NZ$6,571
NZ$939 per night
includes taxes & fees
Image gallery for 5 Minutes from Catamount Ski Area
9.09.0 out of 10 rating
Wonderful
(21 reviews)
5 Minutes from Catamount Ski Area
Great Barrington, MA
8% off
Price is NZ$3,234
NZ$3,234
NZ$462 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 NZ$5,125
NZ$5,125
NZ$732 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
(26 reviews)
Amore Estate - beautiful room with many places to explore and relax in.
Lenox, MA
8% off
Price is NZ$12,926
NZ$12,926
NZ$1,847 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
7% off
Price is NZ$22,014
NZ$22,014
NZ$3,145 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
962 reviews(962 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
4 reviews(4 reviews)
The Ponds at Foxhollow
Sleeps 4 · 1 bedroom
8.68.6 out of 10
Excellentexcellent
125 reviews(125 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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