Holiday rentals near Cheshire Hollow Farm
We found 630 holiday rentals — enter your dates for availability
Select the perfect private holiday rental that's near Cheshire Hollow Farm. Holiday rentals offer the best amenities for your stay with friends, family or just your pet, such as a fireplace and a washer and dryer. You'll be sure to find a property to rent to meet everyone's needs, including options that are accessible or non-smoking.
Holiday rentals with weekly discounts - Cheshire Hollow Farm
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 Litchfield County Four Season Country Paradise
9.69.6 out of 10 rating
Exceptional
(40 reviews)
Litchfield County Four Season Country Paradise
Roxbury, CT
8% off
Price is NZ$13,906
NZ$13,906
NZ$1,987 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 Long Meadow Manor, skiing, game room, Apple picking and Lake nearby
1010 out of 10 rating
Exceptional
(14 reviews)
Long Meadow Manor, skiing, game room, Apple picking and Lake nearby
Bethlehem, CT
8% off
Price is NZ$7,829
NZ$7,829
NZ$1,118 per night
includes taxes & fees
Image gallery for Lakefront Cottage On Quiet Lake, Private Dock, Private Beach Area, Boat Use
9.69.6 out of 10 rating
Exceptional
(67 reviews)
Lakefront Cottage On Quiet Lake, Private Dock, Private Beach Area, Boat Use
Bethlehem, CT
8% off
Price is NZ$3,017
NZ$3,017
NZ$431 per night
includes taxes & fees
Image gallery for Waterfront modern summer oasis under 2 hours from NYC! Swim from our dock!
1010 out of 10 rating
Exceptional
(11 reviews)
Waterfront modern summer oasis under 2 hours from NYC! Swim from our dock!
Bethlehem, CT
7% off
Price is NZ$4,448
NZ$4,448
NZ$635 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 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 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 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 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 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 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 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 Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville
1010 out of 10 rating
Exceptional
(57 reviews)
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville
Canton, CT
8% off
Price is NZ$4,138
NZ$4,138
NZ$591 per night
includes taxes & fees
Image gallery for Cozy dog friendly updated house in quiet village adjacent to park
1010 out of 10 rating
Exceptional
(34 reviews)
Cozy dog friendly updated house in quiet village adjacent to park
Northford, CT
8% off
Price is NZ$4,873
NZ$4,873
NZ$696 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 Relax at Rudy's peaceful resting place...
1010 out of 10 rating
Exceptional
(5 reviews)
Relax at Rudy's peaceful resting place...
East Haven, CT
8% off
Price is NZ$3,338
NZ$3,338
NZ$477 per night
includes taxes & fees
Image gallery for Charming 2-bedroom house centrally located in Bristol
9.69.6 out of 10 rating
Exceptional
(12 reviews)
Charming 2-bedroom house centrally located in Bristol
Bristol, CT
8% off
Price is NZ$1,980
NZ$1,980
NZ$283 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 TWO BEDROOM APARTMENT ON FIRST FLOOR ON A DUPLEX
9.89.8 out of 10 rating
Exceptional
(19 reviews)
TWO BEDROOM APARTMENT ON FIRST FLOOR ON A DUPLEX
Bristol, CT
12% off
Price is NZ$2,106
NZ$2,106
NZ$301 per night
includes taxes & fees
Image gallery for Cozy Getaway w/lots of Natural Light :) 5 mins to adventures
8.08.0 out of 10 rating
Very good
(6 reviews)
Cozy Getaway w/lots of Natural Light :) 5 mins to adventures
Middletown, CT
8% off
Price is NZ$2,178
NZ$2,178
NZ$311 per night
includes taxes & fees
Image gallery for Cozy Escape - Wooster Square
8.48.4 out of 10 rating
Very good
(9 reviews)
Cozy Escape - Wooster Square
New Haven, CT
8% off
Price is NZ$2,884
NZ$2,884
NZ$412 per night
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Cheshire Hollow Farm
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)
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