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Vacation rentals in Cheshire

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Cheshire

Guests agree: these stays are highly rated for location, cleanliness, and more.

Private room in Hamden
A Restorative Stay in the Woods (at edge of town)
We're proud to have been designated AirBnb CT's New Host of the Year for 2021! Come visit our cozy 1st floor BR w/ HD TV, sound bar, WIFI, small desk & mini-fridge. A connected spa-like private bath features an oversized shower & claw foot soaking tub. It's an ideal retreat for writers, artists, & nature lovers. While kitchen and common areas of our home aren't shared, seasonal outdoor spaces are. We're known for our great morning coffee. Come stay with us and see! We welcome guests 21 and over.
$65 per night
Private room in Hamden
Budget meets Boho-Chic!
2021 CT New Hosts of the Year offer our funky budget stay: 240sf basement room w/ tiny full bath. Geared to single travelers who appreciate antiques, music and eclectic decor from around the world! Enjoy spacious sitting area with 32" HD TV, desk, fridge, microwave, fun art, musical instruments, Joe's vinyl collection, great morning coffee and exceptional hospitality. Seasonally, the porch and deck sitting spaces overlook beautiful gardens. Come share our piece of paradise in the woods!
$35 per night
Private room in Hamden
Cozy Private Bedroom by the Trail & Sleeping Giant
Enjoy our Sleeping Giant private bedroom for 2! Adjacent to Farmington Canal Heritage Trail, this location has the best of both nature and city life. Right by Sleeping Giant, Quinnipiac, New Haven. Our unique ranch-style house has a separate entry for the guest rooms, with dedicated front door access. *Mini Fridge *Coffee Maker *Microwave *Toaster Oven *Kettle *Iron *Parking Spaces *Spotless Bedroom & Bathroom. The property is OWNER OCCUPIED at all times.
$49 per night

Stay near Cheshire's top sights

Photo of Costco Wholesale
Costco Wholesale14 locals recommend
Photo of Viron Rondo Osteria
Viron Rondo Osteria5 locals recommend
Photo of Blackie's Hot Dog Stand
Blackie's Hot Dog Stand4 locals recommend
Photo of Brooksvale Park
Brooksvale Park4 locals recommend
Photo of Farmington Canal Heritage Trail
Farmington Canal Heritage Trail15 locals recommend
Photo of C.J. Sparrow
C.J. Sparrow3 locals recommend

Other great vacation rentals in Cheshire

Private room in Cheshire
Cheshire Home (Private Room 1 of 3)
$50 per night
Private room in Hamden
Private Mount Carmel Suite w/Private Bath by Trail
$69 per night
Private room in Waterbury
Welcome to our beautiful home.
$60 per night
Home in Cheshire
Pool House
$140 per night
Rental unit in Wallingford
Spacious in-law apartment steps from Choate
$100 per night
Private room in Hamden
Spacious, comfortable, convenient to QU and Yale
$51 per night
Guest suite in Hamden
Large Private Studio + Entrance + Bath
$93 per night
Private room in Berlin
Red Door Retreat West
$49 per night
Guest suite in Cheshire
Remodeled Studio w/ Beautiful Yard and Jacuzzi Tub
$89 per night
Guesthouse in Wallingford
The Garden Loft - A Charming Choate Stay
$190 per night
Private room in Hamden
Elephant Room @ Partridge Xing - Queen HDTV, desk
$40 per night
Townhouse in Southington
Modern Two Bedroom Condo
$151 per night
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  2. United States
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  4. New Haven County
  5. Cheshire