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 AU$9,583
AU$9,583
AU$1,369 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 AU$2,761
AU$2,761
AU$394 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 AU$3,830
AU$3,830
AU$547 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 AU$4,072
AU$4,072
AU$582 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 AU$12,440
AU$12,440
AU$1,777 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 AU$7,040
AU$7,040
AU$1,006 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$2,180
AU$2,180
AU$311 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$8,654
AU$8,654
AU$1,236 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$3,597
AU$3,597
AU$514 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 AU$6,144
AU$6,144
AU$878 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$2,007
AU$2,007
AU$287 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 AU$4,946
AU$4,946
AU$707 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 AU$3,782
AU$3,782
AU$540 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 AU$9,001
AU$9,001
AU$1,286 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
8% off
Price is AU$7,420
AU$7,420
AU$1,060 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 AU$6,954
AU$6,954
AU$993 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 AU$3,064
AU$3,064
AU$438 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 AU$2,055
AU$2,055
AU$294 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 AU$4,462
AU$4,462
AU$637 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 AU$2,027
AU$2,027
AU$290 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 AU$1,844
AU$1,844
AU$263 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 AU$3,054
AU$3,054
AU$436 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 AU$1,961
AU$1,961
AU$280 per night
includes taxes & fees
Image gallery for Cozy quite private location that makes you feel like home
9.89.8 out of 10 rating
Exceptional
(7 reviews)
Cozy quite private location that makes you feel like home
Waterbury, CT
8% off
Price is AU$1,617
AU$1,617
AU$231 per night
includes taxes & fees
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Find the best place to stay - Cheshire Hollow Farm
Showing deals for: 7 Oct - 10 Oct
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 current price is AU$1,537
AU$1,537
for 3 nights, 1 home
AU$512 per night
includes taxes & fees
The Queen of the Thimble Islands
Sleeps 15 · 8 bedrooms · 4+ bathrooms
1010 out of 10
Exceptionalexceptional
24 reviews(24 reviews)
The current price is AU$6,378
AU$6,378
for 3 nights, 1 home
AU$2,126 per night
includes taxes & fees
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)
The current price is AU$2,069
AU$2,069
for 3 nights, 1 home
AU$690 per night
includes taxes & fees
CT Private Home on Belden Island
Sleeps 8 · 4 bedrooms · 2 bathrooms
9.09.0 out of 10
Wonderfulwonderful
2 reviews(2 reviews)
The current price is AU$3,295
AU$3,295
for 3 nights, 1 home
AU$1,098 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$32,924
AU$32,924
for 3 nights, 1 home
AU$10,975 per night
includes taxes & fees
Direct Waterfront "The Palms" Beach House
Sleeps 12 · 5 bedrooms · 1+ bathroom
1010 out of 10
Exceptionalexceptional
9 reviews(9 reviews)
The current price is AU$3,250
AU$3,250
for 3 nights, 1 home
AU$1,083 per night
includes taxes & fees