Holiday rentals near Undermountain Golf Course
We found 725 holiday rentals — enter your dates for availability
If you want to to stay within easy reach of Undermountain Golf Course, scroll through and discover holiday rentals to find the perfect home base for your trip. Whether you’re staying in a holiday home with a group or just with your pet, you'll find the best amenities for hanging out with the people that matter most, which might include a pool and a washer and dryer. Whatever you're looking for, you'll be sure to find a property to rent that has what everyone needs, including accessible or non-smoking choices.
Holiday rentals with weekly discounts - Undermountain Golf Course
Showing deals for:19 Sept - 26 Sept
Image gallery for 5-bed Colonial Berkshires Farmhouse, aka Grandaddy's House, Family Friendly home
1010 out of 10 rating
Exceptional
(9 reviews)
5-bed Colonial Berkshires Farmhouse, aka Grandaddy's House, Family Friendly home
New Marlborough, MA
12% off
Price is AU$6,931
AU$6,931
AU$990 per night
includes taxes & fees
Image gallery for Newly renovated charming home , Brand new chefs kitchen very comfortable home .
9.89.8 out of 10 rating
Exceptional
(9 reviews)
Newly renovated charming home , Brand new chefs kitchen very comfortable home .
Lakeville, CT
12% off
Price is AU$4,418
AU$4,418
AU$631 per night
includes taxes & fees
Image gallery for Converted Berkshire schoolhouse on a quiet river
1010 out of 10 rating
Exceptional
(32 reviews)
Converted Berkshire schoolhouse on a quiet river
Great Barrington, MA
8% off
Price is AU$3,349
AU$3,349
AU$478 per night
includes taxes & fees
Image gallery for Spacious, Modern House 5 Bedrooms, 2.5 Bathrooms, Sleep 12 on small horse farm.
1010 out of 10 rating
Exceptional
(63 reviews)
Spacious, Modern House 5 Bedrooms, 2.5 Bathrooms, Sleep 12 on small horse farm.
Great Barrington, MA
8% off
Price is AU$7,694
AU$7,694
AU$1,099 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$8,225
AU$8,225
AU$1,175 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$7,320
AU$7,320
AU$1,046 per night
includes taxes & fees
Image gallery for Gorgeous Sheffield Home in Heart of Berkshires
1010 out of 10 rating
Exceptional
(50 reviews)
Gorgeous Sheffield Home in Heart of Berkshires
Sheffield, MA
8% off
Price is AU$8,462
AU$8,462
AU$1,209 per night
includes taxes & fees
Image gallery for Elegant Modern Farmhouse with Pool and Gardens, steps from Nature Preserve
1010 out of 10 rating
Exceptional
(15 reviews)
Elegant Modern Farmhouse with Pool and Gardens, steps from Nature Preserve
Sharon, CT
8% off
Price is AU$10,568
AU$10,568
AU$1,510 per night
includes taxes & fees
Image gallery for Cozy Log Cabin Retreat with Pool on 4 Acres
9.69.6 out of 10 rating
Exceptional
(8 reviews)
Cozy Log Cabin Retreat with Pool on 4 Acres
Canaan, CT
7% off
Price is AU$3,936
AU$3,936
AU$562 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$11,991
AU$11,991
AU$1,713 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$4,524
AU$4,524
AU$646 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$2,175
AU$2,175
AU$311 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$6,195
AU$6,195
AU$885 per night
includes taxes & fees
Image gallery for Taghkanic Glass House
1010 out of 10 rating
Exceptional
(6 reviews)
Taghkanic Glass House
Hudson, NY
9% off
Price is AU$51,031
AU$51,031
AU$7,290 per night
includes taxes & fees
Image gallery for Salisbury Cottage Retreat
1010 out of 10 rating
Exceptional
(12 reviews)
Salisbury Cottage Retreat
Salisbury, CT
16% off
Price is AU$2,839
AU$2,839
AU$406 per night
includes taxes & fees
Image gallery for TREEMENDOUS VIEWS COTTAGE
1010 out of 10 rating
Exceptional
(21 reviews)
TREEMENDOUS VIEWS COTTAGE
Amenia, NY
19% off
Price is AU$4,225
AU$4,225
AU$604 per night
includes taxes & fees
Image gallery for Near Hudson - Gorgeous Sunsets + Catskill Mountain Views
1010 out of 10 rating
Exceptional
(5 reviews)
Near Hudson - Gorgeous Sunsets + Catskill Mountain Views
Ancram, NY
8% off
Price is AU$3,983
AU$3,983
AU$569 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$4,461
AU$4,461
AU$637 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$2,756
AU$2,756
AU$394 per night
includes taxes & fees
Image gallery for Incredible Ski Lodge - 7500 Square ft - Log Cabin - Moose Lodge
1010 out of 10 rating
Exceptional
(49 reviews)
Incredible Ski Lodge - 7500 Square ft - Log Cabin - Moose Lodge
Great Barrington, MA
8% off
Price is AU$20,455
AU$20,455
AU$2,922 per night
includes taxes & fees
Image gallery for Doodletown Cabin: Pond—Outdoor Dining—Games Barn!
9.69.6 out of 10 rating
Exceptional
(65 reviews)
Doodletown Cabin: Pond—Outdoor Dining—Games Barn!
Ancram, NY
12% off
Price is AU$6,867
AU$6,867
AU$981 per night
includes taxes & fees
Image gallery for Luxurious Mountain Retreat - Private 40-Acre Family Haven
9.69.6 out of 10 rating
Exceptional
(9 reviews)
Luxurious Mountain Retreat - Private 40-Acre Family Haven
New Marlborough, MA
16% off
Price is AU$8,835
AU$8,835
AU$1,262 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
10% off
Price is AU$12,490
AU$12,490
AU$1,784 per night
includes taxes & fees
Image gallery for Escape to an Exclusive Mountain Retreat: Experience the Splendor of all seasons.
1010 out of 10 rating
Exceptional
(121 reviews)
Escape to an Exclusive Mountain Retreat: Experience the Splendor of all seasons.
Hillsdale, NY
16% off
Price is AU$3,450
AU$3,450
AU$493 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Undermountain Golf Course
Elegant Historic Hudson Valley Gilded Age Mansion On 4+ Parklike Acres
Sleeps 22 · 9 bedrooms · 9+ bathrooms
1010 out of 10
Exceptionalexceptional
147 reviews(147 reviews)
Charming Lakefront Cottage; Boat, Swim, Fish, Hike, Bike, Golf, majestic Views
Sleeps 6 · 2 bedrooms · 1 bathroom
9.69.6 out of 10
Exceptionalexceptional
200 reviews(200 reviews)
Prana Residence Spa with Indoor Pool, Sauna, Jacuzzi & Solarium - near Kent
Sleeps 7 · 3 bedrooms · 3 bathrooms
9.89.8 out of 10
Exceptionalexceptional
52 reviews(52 reviews)
An acclaimed photographers country estate, arts community, near private schools!
Sleeps 10 · 5 bedrooms · 2+ bathrooms
9.49.4 out of 10
Exceptionalexceptional
23 reviews(23 reviews)
Pet-friendly Cottage at Historic Millbrook Farm Estate
Sleeps 5 · 3 bedrooms · 1+ bathroom
1010 out of 10
Exceptionalexceptional
3 reviews(3 reviews)
Lakefront Summer Spectacular in New England Just 2 Hours From NYC
Sleeps 4 · 2 bedrooms · 1 bathroom
1010 out of 10
Exceptionalexceptional
72 reviews(72 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