Holiday rentals near Cheshire Golf Course
We found 667 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:31 Oct - 7 Nov
Image gallery for Historic Whitneyville Cottage
9.49.4 out of 10 rating
Exceptional
(16 reviews)
Historic Whitneyville Cottage
Hamden, CT
7% off
Price is AU$2,074
AU$2,074
AU$296 per night
includes taxes & fees
Image gallery for Spacious Modern Beach House, perfect for families and groups up to 12
1010 out of 10 rating
Exceptional
(11 reviews)
Spacious Modern Beach House, perfect for families and groups up to 12
Branford, CT
16% off
Price is AU$7,097
AU$7,097
AU$1,014 per night
includes taxes & fees
Image gallery for Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape
1010 out of 10 rating
Exceptional
(35 reviews)
Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape
Plymouth, CT
8% off
Price is AU$6,197
AU$6,197
AU$885 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
(6 reviews)
New hot tub & outdoor TV! 3 bedroom apt dwntn Middletown, across from Wesleyan
Middletown, CT
8% off
Price is AU$3,863
AU$3,863
AU$552 per night
includes taxes & fees
Image gallery for Swiss Chalet amidst sixteen acres in Litchfield Hills surrounded by land trust
9.69.6 out of 10 rating
Exceptional
(14 reviews)
Swiss Chalet amidst sixteen acres in Litchfield Hills surrounded by land trust
Watertown, CT
8% off
Price is AU$12,800
AU$12,800
AU$1,829 per night
includes taxes & fees
Image gallery for Beautiful Waterfront Beach House for Family Vacations
1010 out of 10 rating
Exceptional
(43 reviews)
Beautiful Waterfront Beach House for Family Vacations
Branford, CT
8% off
Price is AU$7,258
AU$7,258
AU$1,037 per night
includes taxes & fees
Image gallery for Waterfront Cottage in Branford
1010 out of 10 rating
Exceptional
(95 reviews)
Waterfront Cottage in Branford
Branford, CT
8% off
Price is AU$9,101
AU$9,101
AU$1,300 per night
includes taxes & fees
Image gallery for Dove Haven | Find your Peace
9.89.8 out of 10 rating
Exceptional
(10 reviews)
Dove Haven | Find your Peace
New Haven, CT
8% off
Price is AU$11,212
AU$11,212
AU$1,602 per night
includes taxes & fees
Image gallery for Daniel Boone meets Mid Century Modern Retreat
1010 out of 10 rating
Exceptional
(13 reviews)
Daniel Boone meets Mid Century Modern Retreat
Killingworth, CT
8% off
Price is AU$8,097
AU$8,097
AU$1,157 per night
includes taxes & fees
Image gallery for John Hollister home on the farm
1010 out of 10 rating
Exceptional
(8 reviews)
John Hollister home on the farm
Glastonbury, CT
16% off
Price is AU$4,059
AU$4,059
AU$580 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 AU$2,174
AU$2,174
AU$311 per night
includes taxes & fees
Image gallery for Direct Waterfront Private Beach Escape
9.89.8 out of 10 rating
Exceptional
(14 reviews)
Direct Waterfront Private Beach Escape
East Haven, CT
15% off
Price is AU$8,119
AU$8,119
AU$1,160 per night
includes taxes & fees
Image gallery for MODERN GUESTHOUSE IN PRIVATE SETTING
1010 out of 10 rating
Exceptional
(5 reviews)
MODERN GUESTHOUSE IN PRIVATE SETTING
Guilford, CT
8% off
Price is AU$3,139
AU$3,139
AU$448 per night
includes taxes & fees
Image gallery for Amazing 11 Bedroom 15 Bathroom Mansion Close to Beaches
9.29.2 out of 10 rating
Wonderful
(10 reviews)
Amazing 11 Bedroom 15 Bathroom Mansion Close to Beaches
Killingworth, CT
8% off
Price is AU$16,985
AU$16,985
AU$2,426 per night
includes taxes & fees
Image gallery for Stylish & Luxurious 3 BDR Home with Play Station
9.29.2 out of 10 rating
Wonderful
(15 reviews)
Stylish & Luxurious 3 BDR Home with Play Station
Bristol, CT
7% off
Price is AU$1,883
AU$1,883
AU$269 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 AU$4,820
AU$4,820
AU$689 per night
includes taxes & fees
Image gallery for StedleyCreek! One bed-room apartment in the Stoney Creek area of Branford, CT.
1010 out of 10 rating
Exceptional
(10 reviews)
StedleyCreek! One bed-room apartment in the Stoney Creek area of Branford, CT.
Branford, CT
7% off
Price is AU$2,556
AU$2,556
AU$365 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 AU$8,739
AU$8,739
AU$1,248 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 AU$2,010
AU$2,010
AU$287 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 AU$3,629
AU$3,629
AU$518 per night
includes taxes & fees
Image gallery for Large Waterfront Modern Beach House
1010 out of 10 rating
Exceptional
(20 reviews)
Large Waterfront Modern Beach House
East Haven, CT
8% off
Price is AU$9,101
AU$9,101
AU$1,300 per night
includes taxes & fees
Image gallery for NEW! Charming Riverside Home-CT River Private, Spacious, Family & Pet Friendly
1010 out of 10 rating
Exceptional
(6 reviews)
NEW! Charming Riverside Home-CT River Private, Spacious, Family & Pet Friendly
Rocky Hill, CT
8% off
Price is AU$4,155
AU$4,155
AU$594 per night
includes taxes & fees
Image gallery for Family Stays: Middletown, CT
1010 out of 10 rating
Exceptional
(9 reviews)
Family Stays: Middletown, CT
Middletown, CT
8% off
Price is AU$1,754
AU$1,754
AU$251 per night
includes taxes & fees
Image gallery for Cozy Lakefront Bungalow w firepit/dock/kayaks
1010 out of 10 rating
Exceptional
(29 reviews)
Cozy Lakefront Bungalow w firepit/dock/kayaks
Plymouth, CT
8% off
Price is AU$6,197
AU$6,197
AU$885 per night
includes taxes & fees
Find spaces that suit your style
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Condo/Apartment
Cabin
Cottage
Villa
Chalet
Find the best place to stay - Cheshire Golf Course
Showing deals for: 31 Oct - 3 Nov
Dog-Friendly Oceanfront Getaway - Walk to Dining - Private Beach Access
Sleeps 6 · 3 bedrooms · 1 bathroom
1010 out of 10
Exceptionalexceptional
5 reviews(5 reviews)
The current price is AU$2,131
AU$2,131
for 3 nights, 1 home
AU$710 per night
includes taxes & fees
Grace Island. Private Island! Vacations, Getaways, Weddings & Special Events.
Sleeps 22 · 11 bedrooms · 5+ bathrooms
The current price is AU$33,391
AU$33,391
for 3 nights, 1 home
AU$11,130 per night
includes taxes & fees
Direct waterfront cottage on private sandy beach
Sleeps 6 · 2 bedrooms · 1 bathroom
1010 out of 10
Exceptionalexceptional
5 reviews(5 reviews)
The current price is AU$1,857
AU$1,857
for 3 nights, 1 cottage
AU$619 per night
includes taxes & fees
Direct Waterfront Private Beach Escape
Sleeps 9 · 4 bedrooms · 1+ bathroom
9.89.8 out of 10
Exceptionalexceptional
14 reviews(14 reviews)
The current price is AU$4,118
AU$4,118
for 3 nights, 1 home
AU$1,373 per night
includes taxes & fees
Beautiful Waterfront Beach House for Family Vacations
Sleeps 6 · 3 bedrooms · 1+ bathroom
1010 out of 10
Exceptionalexceptional
43 reviews(43 reviews)
The current price is AU$3,659
AU$3,659
for 3 nights, 1 home
AU$1,220 per night
includes taxes & fees
4000+ SqFt Home. Amazing Views, Private, Close to Downtown and Yale Univeristy
Sleeps 10 · 5 bedrooms · 3 bathrooms
1010 out of 10
Exceptionalexceptional
33 reviews(33 reviews)
The current price is AU$4,671
AU$4,671
for 3 nights, 1 home
AU$1,557 per night
includes taxes & fees
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