Holiday rentals near Undermountain Golf Course
We found 743 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:21 Nov - 28 Nov
Image gallery for Navywood: Scandi | Peaceful | Red Hook/Rhinebeck
9.89.8 out of 10 rating
Exceptional
(9 reviews)
Navywood: Scandi | Peaceful | Red Hook/Rhinebeck
Elizaville, NY
11% off
Price is NZ$5,126
NZ$5,126
NZ$732 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$14,646
NZ$14,646
NZ$2,092 per night
includes taxes & fees
Image gallery for Charming cottage with lake access, wood burning fire place, and WiFi
9.09.0 out of 10 rating
Wonderful
(8 reviews)
Charming cottage with lake access, wood burning fire place, and WiFi
Elizaville, NY
12% off
Price is NZ$2,669
NZ$2,669
NZ$381 per night
includes taxes & fees
Image gallery for Taghkanic Glass House
1010 out of 10 rating
Exceptional
(7 reviews)
Taghkanic Glass House
Hudson, NY
8% off
Price is NZ$59,641
NZ$59,641
NZ$8,520 per night
includes taxes & fees
Image gallery for A Country Lodge Straight Out of the Pages of a Great Novel
1010 out of 10 rating
Exceptional
(12 reviews)
A Country Lodge Straight Out of the Pages of a Great Novel
Pine Plains, NY
8% off
Price is NZ$12,506
NZ$12,506
NZ$1,787 per night
includes taxes & fees
Image gallery for Mountain View Getaway
1010 out of 10 rating
Exceptional
(56 reviews)
Mountain View Getaway
West Cornwall, CT
8% off
Price is NZ$4,121
NZ$4,121
NZ$589 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$20,730
NZ$20,730
NZ$2,961 per night
includes taxes & fees
Image gallery for West Cornwall Cabin ~ 4 Mi to Covered Bridge!
9.69.6 out of 10 rating
Exceptional
(8 reviews)
West Cornwall Cabin ~ 4 Mi to Covered Bridge!
West Cornwall, CT
7% off
Price is NZ$3,996
NZ$3,996
NZ$571 per night
includes taxes & fees
Image gallery for Charming Columbia County Farm House
9.49.4 out of 10 rating
Exceptional
(25 reviews)
Charming Columbia County Farm House
Hillsdale, NY
8% off
Price is NZ$4,191
NZ$4,191
NZ$599 per night
includes taxes & fees
Image gallery for Fun Getaway Lakehouse in the Hudson Valley
1010 out of 10 rating
Exceptional
(15 reviews)
Fun Getaway Lakehouse in the Hudson Valley
Craryville, NY
12% off
Price is NZ$4,451
NZ$4,451
NZ$636 per night
includes taxes & fees
Image gallery for Charming Cabin On Scenic Road
1010 out of 10 rating
Exceptional
(5 reviews)
Charming Cabin On Scenic Road
Great Barrington, MA
28% off
Price is NZ$97,885
NZ$97,885
NZ$13,984 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$7,351
NZ$7,351
NZ$1,050 per night
includes taxes & fees
Image gallery for Mid-Century Home Surrounded by Meadows
1010 out of 10 rating
Exceptional
(7 reviews)
Mid-Century Home Surrounded by Meadows
Pine Plains, NY
8% off
Price is NZ$8,112
NZ$8,112
NZ$1,159 per night
includes taxes & fees
Image gallery for An acclaimed photographers country estate, arts community, near private schools!
9.49.4 out of 10 rating
Exceptional
(23 reviews)
An acclaimed photographers country estate, arts community, near private schools!
Sharon, CT
16% off
Price is NZ$7,442
NZ$7,442
NZ$1,063 per night
includes taxes & fees
Image gallery for Charming Berkshire Farmhouse: Your Cozy Retreat Awaits!
1010 out of 10 rating
Exceptional
(6 reviews)
Charming Berkshire Farmhouse: Your Cozy Retreat Awaits!
Monterey, MA
8% off
Price is NZ$4,798
NZ$4,798
NZ$685 per night
includes taxes & fees
Image gallery for Lakefront 4-Season Stunning Home and Guest House W/Tennis Court & Full Gym
9.89.8 out of 10 rating
Exceptional
(97 reviews)
Lakefront 4-Season Stunning Home and Guest House W/Tennis Court & Full Gym
Copake, NY
8% off
Price is NZ$11,545
NZ$11,545
NZ$1,649 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
12% off
Price is NZ$16,314
NZ$16,314
NZ$2,331 per night
includes taxes & fees
Image gallery for NEWLY REMODELED 3 BEDROOM COUNTRY CASTLE
1010 out of 10 rating
Exceptional
(37 reviews)
NEWLY REMODELED 3 BEDROOM COUNTRY CASTLE
Great Barrington, MA
8% off
Price is NZ$7,643
NZ$7,643
NZ$1,092 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$3,286
NZ$3,286
NZ$469 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 NZ$9,996
NZ$9,996
NZ$1,428 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 NZ$4,219
NZ$4,219
NZ$603 per night
includes taxes & fees
Image gallery for TREEMENDOUS VIEWS COTTAGE
1010 out of 10 rating
Exceptional
(22 reviews)
TREEMENDOUS VIEWS COTTAGE
Amenia, NY
15% off
Price is NZ$5,720
NZ$5,720
NZ$817 per night
includes taxes & fees
Image gallery for Waterfront Escape +dock +kayaks +firepit +fireplace +games
9.89.8 out of 10 rating
Exceptional
(10 reviews)
Waterfront Escape +dock +kayaks +firepit +fireplace +games
Copake, NY
8% off
Price is NZ$4,670
NZ$4,670
NZ$667 per night
includes taxes & fees
Image gallery for Taconic Hideaway – Swimming, BBQ Pit, Hiking
1010 out of 10 rating
Exceptional
(6 reviews)
Taconic Hideaway – Swimming, BBQ Pit, Hiking
Copake, NY
11% off
Price is NZ$3,531
NZ$3,531
NZ$504 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
150 reviews(150 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)
Charming Lakefront Cottage; Boat, Swim, Fish, Hike, Bike, Golf, majestic Views
Sleeps 6 · 2 bedrooms · 1 bathroom
9.69.6 out of 10
Exceptionalexceptional
202 reviews(202 reviews)
Summer Lake Cottage, private beach, Berkshire Hills, small village
Sleeps 18 · 5 bedrooms · 3 bathrooms
9.49.4 out of 10
Exceptionalexceptional
81 reviews(81 reviews)
Enjoy the ambiance of the Spirit Horse Farm just 1 mile from the town of Kent CT
Sleeps 14 · 3 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
3 reviews(3 reviews)
Lakefront Fall Foliage in New England Just 2 Hours From NYC
Sleeps 4 · 2 bedrooms · 1 bathroom
1010 out of 10
Exceptionalexceptional
79 reviews(79 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