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.

Guest favorite

Guest suite in New Britain

4.92 out of 5 average rating, 130 reviews

Clean, Quiet and Safe w/Amenities to spare!

This newly renovated in-law apartment (basement) has a private entrance and Ring security protection in the quaint, quiet neighborhood bordering Berlin/New Britain. Come relax, enjoy biking trails, local restaurants and public parks. Renovated with attention to detail, this place has all the comforts of home. Includes two flat screen TVs in bedroom and living room with Fire sticks (cable/movies), two fireplaces and granite vanity & breakfast bar. Working professionals get 10% off long term stays

Jul 2 – 9

G$20,493 GYD per night
Guest favorite

Guesthouse in Southbury

4.93 out of 5 average rating, 265 reviews

Charming Guest Cottage with Modern Amenities

Private Guest House set on 5+ Acres, along with Historic Colonial Home. Bright and sunny and over looks pool and gardens (seasonal). Efficiency with Kitchen featuring 2 burner stove, Microwave, Under Counter Fridge/Freezer/Ice Maker, Dishwasher, Granite Counters. . Dining Area, Great Room w/ soaring ceilings, French Doors to private patio, hardwood floors. Loft with full-sized bed, and sofa can be a to Queen Size Sleeper. Full bath with extra-large shower. Dog friendly (approval needed).

Apr 4 – 11

G$32,436 GYD per night
Guest favorite

Guest suite in Watertown

4.91 out of 5 average rating, 162 reviews

Lrg Studio Apartment - walk to Taft

Welcome to my downstairs space! This clean open concept space is ready for your long term or overnight stay. This studio space is the lower level of a raised ranch house. I live upstairs with my dog and share laundry with airbnb guests. The space has a private entrance through the garage, private bath, and kitchen area in a quiet neighborhood. Walking distance to Taft and convenient to Rts 8 & 84. Off street pkg. Whether you are interested in two nights or two months, you are welcome here!

Aug 17 – 24

G$15,054 GYD 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
C.J. Sparrow3 locals recommend
Farmington Canal Heritage Trail14 locals recommend

Other great vacation rentals in Cheshire

Guest favorite

Home in Southington

4.95 out of 5 average rating, 62 reviews

Connecticut Chalet - Private Pond, Firepit, Views!

Aug 26 – Sep 2

G$87,584 GYD per night
Guest favorite

Guesthouse in Wallingford

5.0 out of 5 average rating, 65 reviews

The Garden Loft - A Charming Choate Stay

Oct 28 – Nov 4

G$48,657 GYD per night
Guest favorite

Home in Southington

4.97 out of 5 average rating, 37 reviews

Large 1st floor of duplex in town center

Apr 12 – 19

G$27,523 GYD per night
Guest favorite

Guest suite in Northford

5.0 out of 5 average rating, 10 reviews

Private Bright Studio Retreat with kitchen

Jun 20 – 27

G$17,752 GYD per night
Guest favorite

Guest suite in Plymouth

5.0 out of 5 average rating, 20 reviews

Secluded | Cozy | Nature

Jul 4 – 11

G$20,626 GYD per night
Guest favorite

Apartment in New Britain

4.96 out of 5 average rating, 80 reviews

Spacious Cozy Guest Suite

Oct 14 – 21

G$20,214 GYD per night
Superhost

Home in Wallingford

4.91 out of 5 average rating, 23 reviews

Spacious 4Bd/2Ba Family Friendly Home. Sleeps 10

Jan 2 – 9

G$84,476 GYD per night
Guest favorite

Guest suite in Durham

4.83 out of 5 average rating, 18 reviews

Spacious Studio in quiet neighborhood.

Jul 24 – 31

G$22,904 GYD per night
Guest favorite

Home in Southington

5.0 out of 5 average rating, 6 reviews

A+ location*Classy Clean Fully Remodeled*Sleeps 6*

Dec 9 – 16

G$76,263 GYD per night
Guest favorite

Apartment in Bristol

4.98 out of 5 average rating, 48 reviews

2 Bedroom Apartment Near Bristol Center

Mar 5 – 12

G$28,491 GYD per night
Superhost

Home in Watertown

4.89 out of 5 average rating, 36 reviews

Tiny Home Away From Home - Complete Privacy, Peace

Apr 29 – May 6

G$27,497 GYD per night
Guest favorite

Home in Waterbury

4.9 out of 5 average rating, 31 reviews

Come and enjoy the BURY's of CT!

May 31 – Jun 7

G$39,169 GYD 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

G$6,283 GYD before taxes and fees

Frequently Asked Questions

  • Do house rentals in Cheshire have air conditioning?

    Absolutely! We offer over 10 house rentals with air conditioning in Cheshire. Enjoy a tailored experience with all the comforts you desire.

  • What are the most popular amenities for House Rentals in Cheshire?

    Enhance your stay in our House Rentals with the most popular amenities: over 10 homes with wifi, over 10 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • Are there vacation rentals with a dedicated workspace in Cheshire?

    Yes! Work meets play with ease at over 10 vacation rentals in Cheshire featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • How much does it cost to stay in house rentals in Cheshire?

    Experience the best of Cheshire with our house rentals, starting at about $30 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

Destinations to explore

  1. Airbnb
  2. United States
  3. Connecticut
  4. New Haven County
  5. Cheshire