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Vacation rentals in Cheshire

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Top-rated vacation rentals in Cheshire

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

Guest favorite
Guest suite in Wallingford
Wintergreen Gardens Suite @ William Becroft House
LGBTQ friendly. Our 1915 Arts & Crafts bungalow's spacious in-law suite offers driveway parking, pvt. entrance, sunroom, king bedroom, en-suite bath, kitchenette w/fridge, micro, coffee maker, toaster. Relax in bed with 40" HDTV with Amazon Prime, HBO Max, Netflix, premium cable. Enjoy private gardens to sun, read a book or cup of coffee. Short drive to 4 Vineyards, Theater and the train station. Coming for a special event? Book an appointment at our salon, Jimmy James Salon. Ask for info.
Jun 24 – Jul 1
$73 per night
Guest favorite
Home in New Haven
Q River House - 2 bdrm, minutes from Yale/Downtown
Q River House: newly remodeled two bedroom home in the historic Fair Haven neighborhood, conveniently located minutes from downtown New Haven and Yale. Take in river views with your morning coffee on the front porch and relax on the large and private back deck. Enjoy one of the city’s many fine restaurants or cook for yourself in the fully appointed modern kitchen. This riverfront home has been lovingly decorated with attention to style and comfort, and features off-street driveway parking.
Jan 5 – 12
$160 per night
Guest favorite
Apartment in Southington
#4 *BRAND NEW*INCREDIBLE LOCATION *SUPERHOST*
You're looking at a new construction Mid-Century Modern inspired In-Law Apartment with private access located in a beautiful, quiet neighborhood right in central CT just 1 minute from I-84. Pet fee $25/night per animal The unit features a large backyard with a patio, fire pit and chairs for your enjoyment. Fires must be approved by host. NOTE: THIS AIRBNB IS ONLY SUITABLE FOR UP TO FOR 4 ADULTS AND 1 CHILD. PLEASE ASK ME IF YOU HAVE ANY QUESTIONS OR CONCERNS.
Apr 20 – 27
$89 per night

Popular amenities for Cheshire vacation rentals

Stay near Cheshire's top sights

Costco Wholesale14 locals recommend
Viron Rondo Osteria5 locals recommend
Blackie's Hot Dog Stand4 locals recommend
Brooksvale Park4 locals recommend
Farmington Canal Heritage Trail14 locals recommend
C.J. Sparrow3 locals recommend

Other great vacation rentals in Cheshire

Guest favorite
Guest suite in Morris
Lakeside Private Guest Suite
Jun 10 – 17
$86 per night
Guest favorite
Apartment in New Haven
Urban Sanctuary
Apr 29 – May 6
$105 per night
Guest favorite
Apartment in Waterbury
Everything you need! Apartment!
Apr 25 – May 2
$97 per night
Guest favorite
Home in Southington
Connecticut Chalet - Private Pond, Firepit, Views!
Jul 17 – 24
$368 per night
Guest favorite
Home in Waterbury
Amazing views of the Brass City
Mar 13 – 20
$106 per night
Guest favorite
Apartment in New Britain
Spacious Cozy Guest Suite
Sep 8 – 15
$85 per night
Guest favorite
Guesthouse in Wallingford
The Garden Loft - A Charming Choate Stay
Jul 29 – Aug 5
$201 per night
Guest favorite
Guest suite in Northford
Private Bright Studio Retreat with kitchen
Jul 17 – 24
$75 per night
Guest favorite
Apartment in Wallingford
Simple Studio: Near Choate & All CT Cities
Sep 7 – 14
$90 per night
Guest favorite
Apartment in Middlebury
Cozy Apartment with Water View of Brook
Jan 11 – 18
$93 per night
Superhost
Home in Wallingford
Classic 4Bd/2Ba Entire Family Friendly Home.
Aug 8 – 15
$383 per night
Guest favorite
Guest suite in Plymouth
Secluded | Cozy | Nature
May 23 – 30
$86 per night

Quick stats about vacation rentals in Cheshire

Total rentals

20 properties

Popular amenities

Gym, BBQ grill, and Laptop-friendly workspace

Wifi availability

20 properties include access to wifi

Rentals with dedicated workspaces

10 properties have a dedicated workspace

Total number of reviews

530 reviews

Nightly prices starting at

$30 before taxes and fees

Destinations to explore

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  3. Connecticut
  4. New Haven County
  5. Cheshire