Holiday rentals near Cheshire Golf Course
We found 674 holiday rentals — enter your dates for availability
Discover a selection of private holiday rentals close to Cheshire Golf Course that provide the perfect home base 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 garden and hot tub. You'll be sure to find a property to rent for everyone's needs, including options that are accessible or non-smoking.
Holiday rentals with weekly discounts - Cheshire Golf Course
Showing deals for:10 Oct - 17 Oct
Image gallery for Sweetbrier Farm -- Gorgeous Views, Beautiful Home
1010 out of 10 rating
Exceptional
(28 reviews)
Sweetbrier Farm -- Gorgeous Views, Beautiful Home
Litchfield, CT
12% off
Price is NZ$10,388
NZ$10,388
NZ$1,484 per night
includes taxes & fees
Image gallery for New hot tub & outdoor TV! 3 bedroom apt dwntn Middletown, across from Wesleyan
1010 out of 10 rating
Exceptional
(5 reviews)
New hot tub & outdoor TV! 3 bedroom apt dwntn Middletown, across from Wesleyan
Middletown, CT
8% off
Price is NZ$4,191
NZ$4,191
NZ$599 per night
includes taxes & fees
Image gallery for Waterfront home- Sleeps 10 - private beach-epic pool
1010 out of 10 rating
Exceptional
(25 reviews)
Waterfront home- Sleeps 10 - private beach-epic pool
Branford, CT
5% off
Price is NZ$24,492
NZ$24,492
NZ$3,499 per night
includes taxes & fees
Image gallery for Waterfront Cottage in Branford
1010 out of 10 rating
Exceptional
(94 reviews)
Waterfront Cottage in Branford
Branford, CT
8% off
Price is NZ$12,235
NZ$12,235
NZ$1,748 per night
includes taxes & fees
Image gallery for Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub
1010 out of 10 rating
Exceptional
(133 reviews)
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub
Branford, CT
8% off
Price is NZ$3,535
NZ$3,535
NZ$505 per night
includes taxes & fees
Image gallery for Direct Waterfront Private Beach Escape
9.89.8 out of 10 rating
Exceptional
(13 reviews)
Direct Waterfront Private Beach Escape
East Haven, CT
15% off
Price is NZ$11,054
NZ$11,054
NZ$1,579 per night
includes taxes & fees
Image gallery for Lake Front Cottage #7!
9.69.6 out of 10 rating
Exceptional
(130 reviews)
Lake Front Cottage #7!
Middlefield, CT
7% off
Price is NZ$2,356
NZ$2,356
NZ$337 per night
includes taxes & fees
Image gallery for Beautiful Waterfront Beach House for Family Vacations
1010 out of 10 rating
Exceptional
(40 reviews)
Beautiful Waterfront Beach House for Family Vacations
Branford, CT
8% off
Price is NZ$7,998
NZ$7,998
NZ$1,143 per night
includes taxes & fees
Image gallery for Clear LI Sound waterview, Wedding pics, Yale&Beach
1010 out of 10 rating
Exceptional
(5 reviews)
Clear LI Sound waterview, Wedding pics, Yale&Beach
East Haven, CT
8% off
Price is NZ$5,217
NZ$5,217
NZ$745 per night
includes taxes & fees
Image gallery for Live the life! Stunning Private Studio Guest Suite in an Avon Mountain Mansion!
9.89.8 out of 10 rating
Exceptional
(10 reviews)
Live the life! Stunning Private Studio Guest Suite in an Avon Mountain Mansion!
Avon, CT
8% off
Price is NZ$3,937
NZ$3,937
NZ$562 per night
includes taxes & fees
Image gallery for Sleeping Giant Getaway w/ Swim Spa/Tonal/Peloton
1010 out of 10 rating
Exceptional
(10 reviews)
Sleeping Giant Getaway w/ Swim Spa/Tonal/Peloton
Hamden, CT
8% off
Price is NZ$9,387
NZ$9,387
NZ$1,341 per night
includes taxes & fees
Image gallery for Amazing Waterfront Home in Branford Private Beach🏖 Panoramic Water Views+Hot Tub
9.89.8 out of 10 rating
Exceptional
(63 reviews)
Amazing Waterfront Home in Branford Private Beach🏖 Panoramic Water Views+Hot Tub
Branford, CT
14% off
Price is NZ$13,081
NZ$13,081
NZ$1,869 per night
includes taxes & fees
Image gallery for NEW-Another Fun Downtown Location 1st floor
9.89.8 out of 10 rating
Exceptional
(18 reviews)
NEW-Another Fun Downtown Location 1st floor
Southington, CT
7% off
Price is NZ$2,156
NZ$2,156
NZ$308 per night
includes taxes & fees
Image gallery for Cozy Lakefront Bungalow w firepit/dock/kayaks
1010 out of 10 rating
Exceptional
(26 reviews)
Cozy Lakefront Bungalow w firepit/dock/kayaks
Plymouth, CT
8% off
Price is NZ$6,696
NZ$6,696
NZ$957 per night
includes taxes & fees
Image gallery for Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape
1010 out of 10 rating
Exceptional
(33 reviews)
Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape
Plymouth, CT
8% off
Price is NZ$5,399
NZ$5,399
NZ$771 per night
includes taxes & fees
Image gallery for Historic cottage 100 yards from private beach on private compound
9.89.8 out of 10 rating
Exceptional
(6 reviews)
Historic cottage 100 yards from private beach on private compound
Branford, CT
19% off
Price is NZ$4,727
NZ$4,727
NZ$675 per night
includes taxes & fees
Image gallery for BEACH BUM CARRIAGE HOUSE with kayaks - steps to beach, park, marinas & brewery!
9.89.8 out of 10 rating
Exceptional
(8 reviews)
BEACH BUM CARRIAGE HOUSE with kayaks - steps to beach, park, marinas & brewery!
Branford, CT
8% off
Price is NZ$3,678
NZ$3,678
NZ$525 per night
includes taxes & fees
Image gallery for 6-Acre Luxurious Country Home with Goddess Point Lookout
1010 out of 10 rating
Exceptional
(9 reviews)
6-Acre Luxurious Country Home with Goddess Point Lookout
Woodbury, CT
8% off
Price is NZ$9,839
NZ$9,839
NZ$1,406 per night
includes taxes & fees
Image gallery for Magnificent Riverfront home, completely private. BOOK 7 NIGHTS GET 10% OFF
9.89.8 out of 10 rating
Exceptional
(118 reviews)
Magnificent Riverfront home, completely private. BOOK 7 NIGHTS GET 10% OFF
Middle Haddam, CT
7% off
Price is NZ$8,248
NZ$8,248
NZ$1,178 per night
includes taxes & fees
Image gallery for Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
1010 out of 10 rating
Exceptional
(5 reviews)
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
Cheshire, CT
9% off
Price is NZ$2,220
NZ$2,220
NZ$317 per night
includes taxes & fees
Image gallery for Ranch style living at its best with country garden & patio!
9.89.8 out of 10 rating
Exceptional
(11 reviews)
Ranch style living at its best with country garden & patio!
North Haven, CT
8% off
Price is NZ$3,349
NZ$3,349
NZ$478 per night
includes taxes & fees
Image gallery for 4000+ SqFt Home. Amazing Views, Private, Close to Downtown and Yale Univeristy
1010 out of 10 rating
Exceptional
(31 reviews)
4000+ SqFt Home. Amazing Views, Private, Close to Downtown and Yale Univeristy
East Haven, CT
27% off
Price is NZ$8,486
NZ$8,486
NZ$1,212 per night
includes taxes & fees
Image gallery for Home away from home Hot Tub and Pool in Middletown home of Wesleyan university
1010 out of 10 rating
Exceptional
(7 reviews)
Home away from home Hot Tub and Pool in Middletown home of Wesleyan university
Middletown, CT
8% off
Price is NZ$7,735
NZ$7,735
NZ$1,105 per night
includes taxes & fees
Image gallery for Modern 4 Bedroom Beach House: Ideal for Families & Long Stays
9.89.8 out of 10 rating
Exceptional
(11 reviews)
Modern 4 Bedroom Beach House: Ideal for Families & Long Stays
West Haven, CT
9% off
Price is NZ$8,263
NZ$8,263
NZ$1,180 per night
includes taxes & fees
Find spaces that suit your style
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Chalet
Find the best place to stay - Cheshire Golf Course
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub
Sleeps 2 · 1 bedroom · 1 bathroom
1010 out of 10
Exceptionalexceptional
133 reviews(133 reviews)
The Queen of the Thimble Islands
Sleeps 15 · 8 bedrooms · 4+ bathrooms
1010 out of 10
Exceptionalexceptional
24 reviews(24 reviews)
Dog-Friendly Oceanfront Getaway - Walk to Dining - Private Beach Access
Sleeps 6 · 3 bedrooms · 1 bathroom
1010 out of 10
Exceptionalexceptional
7 reviews(7 reviews)
CT Private Home on Belden Island
Sleeps 8 · 4 bedrooms · 2 bathrooms
9.09.0 out of 10
Wonderfulwonderful
2 reviews(2 reviews)
Cute country cottage for getaway stay
Sleeps 3 · 1 bedroom · 1 bathroom
1010 out of 10
Exceptionalexceptional
192 reviews(192 reviews)
Gorgeous Victorian direct ocean front single family six bedroom, ten rooms
Sleeps 12 · 6 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
60 reviews(60 reviews)
Top rated rentals - Cheshire Golf Course
Early spring visit
1010 out of 10
Exceptionalexceptional
14 reviews(14 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