Vacation rentals near Cheshire Hollow Farm
We found 624 vacation rentals — enter your dates for availability
Choose the right private vacation rental within close proximity to Cheshire Hollow Farm. Vacation rentals provide the best amenities for your family, friends, or furry companion, such as WiFi and a pool. You're sure to find a rental to meet everyone's needs, including options that are accessible or non-smoking.
Vacation rentals with weekly discounts - Cheshire Hollow Farm
Showing deals for:Nov 7 - Nov 14
Image gallery for Historic Whitneyville Cottage
9.49.4 out of 10 rating
Exceptional
(16 reviews)
Historic Whitneyville Cottage
Hamden, CT
10% off
Price is CA $185
CA $185
CA $1,925 total
CA $1,925 total
includes taxes & fees
Image gallery for Lakefront Home, Close to Mt Southington!
1010 out of 10 rating
Exceptional
(19 reviews)
Lakefront Home, Close to Mt Southington!
Wolcott, CT
10% off
Price is CA $263
CA $263
CA $2,857 total
CA $2,857 total
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
10% off
Price is CA $191
CA $191
CA $1,931 total
CA $1,931 total
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
10% off
Price is CA $383
CA $383
CA $3,433 total
CA $3,433 total
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
10% off
Price is CA $1,245
CA $1,245
CA $11,339 total
CA $11,339 total
includes taxes & fees
Image gallery for Amazing Lakefront Property
9.89.8 out of 10 rating
Exceptional
(24 reviews)
Amazing Lakefront Property
Middlefield, CT
5% off
Price is CA $646
CA $646
CA $6,039 total
CA $6,039 total
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
10% off
Price is CA $618
CA $618
CA $5,588 total
CA $5,588 total
includes taxes & fees
Image gallery for Waterfront Cabin w Firepit, Dock, Deck, BBQ. Direct Lake Access! Pet-friendly!
8.88.8 out of 10 rating
Excellent
(20 reviews)
Waterfront Cabin w Firepit, Dock, Deck, BBQ. Direct Lake Access! Pet-friendly!
Harwinton, CT
5% off
Price is CA $218
CA $218
CA $2,292 total
CA $2,292 total
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
10% off
Price is CA $1,088
CA $1,088
CA $10,023 total
CA $10,023 total
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
(71 reviews)
Lakefront Cottage On Quiet Lake, Private Dock, Private Beach Area, Boat Use
Bethlehem, CT
10% off
Price is CA $284
CA $284
CA $2,476 total
CA $2,476 total
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
(12 reviews)
Waterfront modern summer oasis under 2 hours from NYC! Swim from our dock!
Bethlehem, CT
10% off
Price is CA $303
CA $303
CA $3,060 total
CA $3,060 total
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
10% off
Price is CA $864
CA $864
CA $7,746 total
CA $7,746 total
includes taxes & fees
Image gallery for Guest Cottage on Country Estate
9.29.2 out of 10 rating
Wonderful
(41 reviews)
Guest Cottage on Country Estate
Watertown, CT
5% off
Price is CA $226
CA $226
CA $2,231 total
CA $2,231 total
includes taxes & fees
Image gallery for Litchfield County Four Season Country Paradise
9.69.6 out of 10 rating
Exceptional
(46 reviews)
Litchfield County Four Season Country Paradise
Roxbury, CT
10% off
Price is CA $1,219
CA $1,219
CA $11,117 total
CA $11,117 total
includes taxes & fees
Image gallery for Charming 2-bedroom Lake Front Cottage with WiFi, AC in welcoming Harwinton
1010 out of 10 rating
Exceptional
(5 reviews)
Charming 2-bedroom Lake Front Cottage with WiFi, AC in welcoming Harwinton
Harwinton, CT
19% off
Price is CA $211
CA $211
CA $2,016 total
CA $2,016 total
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
10% off
Price is CA $1,616
CA $1,616
CA $14,979 total
CA $14,979 total
includes taxes & fees
Image gallery for Cozy 2 bedroom home located minutes from downtown
9.69.6 out of 10 rating
Exceptional
(29 reviews)
Cozy 2 bedroom home located minutes from downtown
New Haven, CT
10% off
Price is CA $210
CA $210
CA $1,864 total
CA $1,864 total
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
10% off
Price is CA $167
CA $167
CA $1,633 total
CA $1,633 total
includes taxes & fees
Image gallery for NEW-Another Fun Downtown Location 1st floor
9.89.8 out of 10 rating
Exceptional
(20 reviews)
NEW-Another Fun Downtown Location 1st floor
Southington, CT
19% off
Price is CA $139
CA $139
CA $1,393 total
CA $1,393 total
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
(22 reviews)
Beautiful brook-side log cabin on 3 private acres - 2 bed, 1.5 bath, entire home
Harwinton, CT
10% off
Price is CA $272
CA $272
CA $2,627 total
CA $2,627 total
includes taxes & fees
Image gallery for Charming Historic Owl House in Old Wethersfield
9.69.6 out of 10 rating
Exceptional
(14 reviews)
Charming Historic Owl House in Old Wethersfield
Wethersfield, CT
10% off
Price is CA $718
CA $718
CA $6,661 total
CA $6,661 total
includes taxes & fees
Image gallery for Guilford home -self check in, off-street parking
9.29.2 out of 10 rating
Wonderful
(9 reviews)
Guilford home -self check in, off-street parking
Guilford, CT
13% off
Price is CA $282
CA $282
CA $2,602 total
CA $2,602 total
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
10% off
Price is CA $357
CA $357
CA $3,224 total
CA $3,224 total
includes taxes & fees
Image gallery for Luxury Stay in an Expansive Historical Home
1010 out of 10 rating
Exceptional
(39 reviews)
Luxury Stay in an Expansive Historical Home
North Haven, CT
5% off
Price is CA $869
CA $869
CA $8,297 total
CA $8,297 total
includes taxes & fees
Find spaces that suit your style
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Find the best place to stay - Cheshire Hollow Farm
The Queen of the Thimble Islands
Sleeps 15 · 8 bedrooms · 4+ bathrooms
1010 out of 10
Exceptionalexceptional
27 reviews(27 reviews)
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub
Sleeps 2 · 1 bedroom · 1 bathroom
1010 out of 10
Exceptionalexceptional
136 reviews(136 reviews)
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)
CT Private Home on Belden Island
Sleeps 8 · 4 bedrooms · 2 bathrooms
9.09.0 out of 10
Wonderfulwonderful
2 reviews(2 reviews)
Grace Island. Private Island! Vacations, Getaways, Weddings & Special Events.
Sleeps 22 · 11 bedrooms · 5+ bathrooms
Cute country cottage for getaway stay
Sleeps 3 · 1 bedroom · 1 bathroom
1010 out of 10
Exceptionalexceptional
194 reviews(194 reviews)
Top rated rentals - Cheshire Hollow Farm
Heaven in New Haven.
1010 out of 10
Exceptionalexceptional
12 reviews(12 reviews)
Wonderful All Round
1010 out of 10
Exceptionalexceptional
35 reviews(35 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, yards and more
More for lessMore space, more privacy, more amenities — more value