Holiday rentals near Cheshire Hollow Farm
We found 638 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:15 Aug - 22 Aug
Image gallery for Sweetbrier Farm -- Gorgeous Views, Beautiful Home
1010 out of 10 rating
Exceptional
(27 reviews)
Sweetbrier Farm -- Gorgeous Views, Beautiful Home
Litchfield, CT
12% off
Price is NZ$9,759
NZ$9,759
NZ$1,394 per night
includes taxes & fees
Image gallery for Swiss Chalet amidst sixteen acres in Litchfield Hills surrounded by land trust
1010 out of 10 rating
Exceptional
(9 reviews)
Swiss Chalet amidst sixteen acres in Litchfield Hills surrounded by land trust
Watertown, CT
8% off
Price is NZ$16,969
NZ$16,969
NZ$2,424 per night
includes taxes & fees
Image gallery for Charming 3BR Hilltop House, Newly Remodeled with Arcade
1010 out of 10 rating
Exceptional
(19 reviews)
Charming 3BR Hilltop House, Newly Remodeled with Arcade
Terryville, CT
7% off
Price is NZ$2,726
NZ$2,726
NZ$389 per night
includes taxes & fees
Image gallery for 6-Acre Luxurious Country Home with Goddess Point Lookout
1010 out of 10 rating
Exceptional
(8 reviews)
6-Acre Luxurious Country Home with Goddess Point Lookout
Woodbury, CT
8% off
Price is NZ$9,781
NZ$9,781
NZ$1,397 per night
includes taxes & fees
Image gallery for 1770 Colonial 5 Bedrooms 4 1/2 Baths Sleeps 9
1010 out of 10 rating
Exceptional
(11 reviews)
1770 Colonial 5 Bedrooms 4 1/2 Baths Sleeps 9
Litchfield, CT
25% off
Price is NZ$5,401
NZ$5,401
NZ$772 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
(13 reviews)
Long Meadow Manor, skiing, game room, Apple picking and Lake nearby
Bethlehem, CT
8% off
Price is NZ$9,041
NZ$9,041
NZ$1,292 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
(5 reviews)
NEW! Charming Riverside Home-CT River Private, Spacious, Family & Pet Friendly
Rocky Hill, CT
7% off
Price is NZ$4,544
NZ$4,544
NZ$649 per night
includes taxes & fees
Image gallery for Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape
1010 out of 10 rating
Exceptional
(32 reviews)
Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape
Plymouth, CT
8% off
Price is NZ$6,764
NZ$6,764
NZ$966 per night
includes taxes & fees
Image gallery for Rivers Edge Unique Newly Renovated River Spa Free-Standing Air Jet Tub retreat
1010 out of 10 rating
Exceptional
(7 reviews)
Rivers Edge Unique Newly Renovated River Spa Free-Standing Air Jet Tub retreat
Guilford, CT
8% off
Price is NZ$8,913
NZ$8,913
NZ$1,273 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$9,630
NZ$9,630
NZ$1,376 per night
includes taxes & fees
Image gallery for Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown
1010 out of 10 rating
Exceptional
(17 reviews)
Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown
Higganum, CT
8% off
Price is NZ$3,014
NZ$3,014
NZ$431 per night
includes taxes & fees
Image gallery for Charming Country Loft in Roxbury—Private & Serene! Escape to Litchfield Hills!
1010 out of 10 rating
Exceptional
(22 reviews)
Charming Country Loft in Roxbury—Private & Serene! Escape to Litchfield Hills!
Roxbury, CT
12% off
Price is NZ$2,553
NZ$2,553
NZ$365 per night
includes taxes & fees
Image gallery for Beautiful brook-side log cabin on 3 private acres - 2 bed, 1.5 bath, entire home
1010 out of 10 rating
Exceptional
(17 reviews)
Beautiful brook-side log cabin on 3 private acres - 2 bed, 1.5 bath, entire home
Harwinton, CT
7% off
Price is NZ$3,232
NZ$3,232
NZ$462 per night
includes taxes & fees
Image gallery for Historic Whitneyville Cottage
9.69.6 out of 10 rating
Exceptional
(14 reviews)
Historic Whitneyville Cottage
Hamden, CT
7% off
Price is NZ$2,333
NZ$2,333
NZ$333 per night
includes taxes & fees
Image gallery for Cozy Getaway w/lots of Natural Light :) 5 mins to adventures
9.29.2 out of 10 rating
Wonderful
(5 reviews)
Cozy Getaway w/lots of Natural Light :) 5 mins to adventures
Middletown, CT
8% off
Price is NZ$2,200
NZ$2,200
NZ$314 per night
includes taxes & fees
Image gallery for Cozy Escape - Wooster Square
8.08.0 out of 10 rating
Very good
(8 reviews)
Cozy Escape - Wooster Square
New Haven, CT
9% off
Price is NZ$3,264
NZ$3,264
NZ$466 per night
includes taxes & fees
Image gallery for Romantic Botanical Glamping with pool, gardens & smoked dinner for 2 available.
1010 out of 10 rating
Exceptional
(16 reviews)
Romantic Botanical Glamping with pool, gardens & smoked dinner for 2 available.
Southbury, CT
8% off
Price is NZ$2,873
NZ$2,873
NZ$410 per night
includes taxes & fees
Image gallery for The Green Lily Suite
1010 out of 10 rating
Exceptional
(6 reviews)
The Green Lily Suite
New Haven, CT
14% off
Price is NZ$1,737
NZ$1,737
NZ$248 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$3,371
NZ$3,371
NZ$482 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
(56 reviews)
Gorgeous River Views! On Rails to Trails and just steps to quaint Collinsville
Canton, CT
8% off
Price is NZ$4,180
NZ$4,180
NZ$597 per night
includes taxes & fees
Image gallery for River Overlook - Check the view from your deck!
1010 out of 10 rating
Exceptional
(15 reviews)
River Overlook - Check the view from your deck!
Canton, CT
8% off
Price is NZ$2,466
NZ$2,466
NZ$352 per night
includes taxes & fees
Image gallery for Lovely Family sized 3 bedroom Colonial home, close to restaurant.
8.68.6 out of 10 rating
Excellent
(11 reviews)
Lovely Family sized 3 bedroom Colonial home, close to restaurant.
Middletown, CT
8% off
Price is NZ$3,511
NZ$3,511
NZ$502 per night
includes taxes & fees
Image gallery for The Overlook near South Farms in Litchfield County is Hospitality, integrated.
9.29.2 out of 10 rating
Wonderful
(5 reviews)
The Overlook near South Farms in Litchfield County is Hospitality, integrated.
Morris, CT
8% off
Price is NZ$2,851
NZ$2,851
NZ$407 per night
includes taxes & fees
Image gallery for Cozy BoHo pet & family friendly near downtown & hospitals
8.68.6 out of 10 rating
Excellent
(8 reviews)
Cozy BoHo pet & family friendly near downtown & hospitals
Hartford, CT
7% off
Price is NZ$1,782
NZ$1,782
NZ$255 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
129 reviews(129 reviews)
The Queen of the Thimble Islands
Sleeps 15 · 8 bedrooms · 4+ bathrooms
1010 out of 10
Exceptionalexceptional
22 reviews(22 reviews)
Cute country cottage for getaway stay
Sleeps 3 · 1 bedroom · 1 bathroom
1010 out of 10
Exceptionalexceptional
181 reviews(181 reviews)
CT Private Home on Belden Island
Sleeps 8 · 4 bedrooms · 2 bathrooms
8.08.0 out of 10
Very goodvery good
1 review(1 review)
NEW Luxury 1bd apt w/all the amenities @ Yale, Wooster Sq, DT New Haven. Pets ok
Sleeps 2 · 1 bedroom · 1 bathroom
9.89.8 out of 10
Exceptionalexceptional
6 reviews(6 reviews)
Gorgeous Victorian direct ocean front single family six bedroom, ten rooms
Sleeps 12 · 6 bedrooms · 2 bathrooms
1010 out of 10
Exceptionalexceptional
59 reviews(59 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