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.

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Guest favorite

Home in North Haven

5.0 out of 5 average rating, 123 reviews

Luxury Stay in Expansive Historical Home

The Bassett House, originally built in 1802, this large historic farmhouse was elegantly remolded in 2018. North Haven, CT is centrally located and just minutes from Yale, Quinnipiac, UNH, and SCSU as well as shopping, the best restaurants, hiking trails state parks and beaches, and many local attractions including various vineyards. If you’re planning a business trip or a gathering for family or friends, then our home can provide you with an exceptional level of comfort during your time in CT!

Mar 23 – 30

G$147,850 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!

Sep 10 – 17

G$14,984 GYD per night

Guest favorite

Guesthouse in Glastonbury

4.96 out of 5 average rating, 133 reviews

Unique luxurious private building in historic area

Unique private space for sophisticated adult(s). Located just 7 miles from downtown Hartford, 1 mile from Route 2 & 84/91 interchange. Guests may relax in this completely renovated historic Barn, with covered parking, away from street view. Enjoy this luxurious space and the private gym which includes treadmill, eliptical, bike, free weights, boxing bags, and yoga space. Upstairs, walk the catwalk between spacious bedroom and full sized Office / Loft over looking historic Main Street.

Jul 19 – 26

G$28,140 GYD per night

Guest favorite

Guest suite in Wallingford

5.0 out of 5 average rating, 502 reviews

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.

Mar 27 – Apr 3

G$18,199 GYD per night

Guest favorite

Condo in Middletown

4.97 out of 5 average rating, 105 reviews

Entire place to yourself Cromwell/Middletown Line

Welcome to Cromwell / Middletown line, open space condo has living room with smart TV, Wi-Fi and sofa bed connected with dining room with four seats, the kichen is well stocked with all the amenities you need, 24 hours keyless access to the apartment, free parking, swimming pool. Washer / dryer unit on - site paid through a prepaid card. Condo is located near I 91 and Route 9 ramps and just minutes from shopping, restaurants and more, 5 min drive to Wesleyan University, Middlesex Hospital

Feb 21 – 28

G$25,062 GYD per night

Guest favorite

Apartment in Middletown

4.98 out of 5 average rating, 150 reviews

Apartment Near Wesleyan, Downtown, Wedding Venues!

Welcome! We are sure you will enjoy your stay in this centrally located first-floor apartment, which sleeps 5-6 guests! You'll feel at home in this cozy 2-bedroom unit, stocked with everything you would need during your stay. Walking distance away from Main Street and Wesleyan, you'll be able to explore all Middletown and the surrounding area has to offer. Two porches, a fenced-in backyard, and a firepit are all available for your use! Pets are welcome! Any questions? Message us!

Sep 12 – 19

G$26,948 GYD per night

Guest favorite

Home in Bristol

4.93 out of 5 average rating, 115 reviews

Cozy Family Home - Kid & Pet Friendly

3 bedroom house on a quiet street. 5mins down the road from ESPN and Lake Compounce. Kid friendly. Pet friendly. Workspace available. 1 bedroom w/ king bed. 1 bedroom w/ queen bed. 1 bedroom w/ 2 twin beds. Fully finished basement with 60inch TV, kids toys and fitness equipment/stationary bike. Deck and below deck hang out space. Though we aren’t living here full time, it’s still the place we call home, and we will use it when it’s not booked. Long stays welcome.

Dec 13 – 20

G$28,919 GYD per night

Guest favorite

Cottage in Middlefield

4.93 out of 5 average rating, 230 reviews

Lake Beseck cottage

Very comfortable 1 bedroom cottage 200 yards from the lake. Large bathroom with shower, heated floors and laundry. Full kitchen, living room with sofa and TV and wifi. Bedroom has a long double Tempurpedic bed. Finished porch with dining table/ chairs and a desk/work area. Microwave, coffee maker, toaster, toaster oven, Patio with gas grill, popcorn air popper, rice and vegetable steamer. WIFI printer. Pack and play upon request. Washer and dryer, hair dryer.

Apr 5 – 12

G$35,938 GYD per night

Guest favorite

Apartment in Brookfield

4.94 out of 5 average rating, 186 reviews

Peaceful apartment on 3.5 acres w/ Artist studio.

Welcome to our cozy apartment! This fully enclosed apartment is attached to our main house on a beautiful 3.5-acre property in Brookfield. Enjoy a kitchen, comfortable living and bedroom area, and a clean bathroom. Guests have access to a shared 32 ft, 10 ft deep pool, artist studio, pool table,, garden, fire space, and outdoor seating. We provide a guidebook for your convenience. Book now and experience a perfect blend of comfort, creativity, and relaxation.

Jan 3 – 10

G$24,523 GYD per night

Guest favorite

Guest suite in Hamden

4.96 out of 5 average rating, 716 reviews

Large Private Studio + Entrance + Bath

Large beautiful secluded studio with a private entry and private bath. Includes comfy queen size bed, futon sofa bed, free wifi, large TV with tons of movies, eat-in table, microwave, mini-fridge, Keurig, closet w/ iron, and your own dedicated room temperature controls. Located in a beautiful, safe, and quiet neighborhood, the studio is attached to a split level house and located in the back on the lower level. It overlooks beautiful woodlands.

Jul 5 – 12

G$35,323 GYD per night

Guest favorite

Guest suite in Morris

4.99 out of 5 average rating, 344 reviews

Lakeside Private Guest Suite

Feel like you're in your own studio apartment in the spacious, bright lower level of our home! Walk out to your own private lounging/dining area. Separate entrance and parking space. Enjoy the serenity of Camp Columbia state park, as it is our extended backyard. Tip: The sunsets are beautiful! 2 hours from NYC, 30-45 minutes to local skiing and just 10 minutes to Washington Depot.

Apr 5 – 12

G$19,422 GYD per night

Guest favorite

Home in Cheshire

5.0 out of 5 average rating, 118 reviews

Pool House

The Pool House is a one bedroom that is fully furnished with all the amenities you would need. There is a queen size bed and a sofa in the living room that pulls out to a full size bed. Fully equipped kitchen, dinning room and living room area. Washer and dryer. Heated pool with large patio and deck. Outdoor refrigerator and gas grill.

Nov 14 – 21

G$30,102 GYD per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Cheshire vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Cheshire's top sights

Costco Wholesale14 locals recommend

Viron Rondo Osteria5 locals recommend

Blackie's Hot Dog Stand4 locals recommend

Farmington Canal Heritage Trail14 locals recommend

Brooksvale Park4 locals recommend

C.J. Sparrow3 locals recommend

Other great vacation rentals in Cheshire

Guest favorite

Guesthouse in Southbury

4.93 out of 5 average rating, 266 reviews

Charming Guest Cottage with Modern Amenities

Sep 19 – 26

G$32,285 GYD per night

Guest favorite

Guest suite in Bethlehem

4.99 out of 5 average rating, 205 reviews

Breezy Crest private & restful w/antique charm

Jul 25 – Aug 1

G$37,239 GYD per night

Guest favorite

Apartment in Southington

4.93 out of 5 average rating, 270 reviews

#4 *BRAND NEW*INCREDIBLE LOCATION *SUPERHOST*

Dec 23 – 30

G$29,365 GYD per night

Guest favorite

Apartment in Meriden

4.91 out of 5 average rating, 58 reviews

Meriden Metro| Cozy Studio|Pool and Gym

May 13 – 20

G$20,260 GYD per night

Guest favorite

Guest suite in Cheshire

4.95 out of 5 average rating, 37 reviews

Cozy & Private Studio Suite

Aug 13 – 20

G$20,983 GYD per night

Guest favorite

Guest suite in Wolcott

4.88 out of 5 average rating, 16 reviews

Modern cozy, pet friendly

Sep 24 – Oct 1

G$26,282 GYD per night

Guest favorite

Apartment in Wallingford

4.88 out of 5 average rating, 24 reviews

Sweet Sparkling Clean Boho 1 bedroom

Feb 3 – 10

G$18,410 GYD per night

Guest favorite

Guesthouse in Wallingford

5.0 out of 5 average rating, 72 reviews

The Garden Loft - A Charming Choate Stay

Dec 2 – 9

G$48,430 GYD per night

Show all

Quick stats about vacation rentals in Cheshire

Total rentals
20 properties
Wifi availability
20 properties include access to wifi
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Family-friendly rentals
10 properties are a good fit for families
Total number of reviews
550 reviews
Nightly prices starting at
G$6,254 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.
Are there family-friendly vacation rentals in Cheshire?
Cheshire has more than 10 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
Do house rentals in Cheshire have wifi?
Absolutely! We offer over 10 house rentals with wifi in Cheshire. Enjoy a tailored experience with all the comforts you desire.

Vacation rentals in Cheshire

Top-rated vacation rentals in Cheshire

Vacation rentals for every style

Hotels

Unique stays

Homes

Popular amenities for Cheshire vacation rentals

Stay near Cheshire's top sights

Other great vacation rentals in Cheshire

Guesthouse in Southbury

Guest suite in Bethlehem

Apartment in Southington

Apartment in Meriden

Guest suite in Cheshire

Guest suite in Wolcott

Apartment in Wallingford

Guesthouse in Wallingford

Quick stats about vacation rentals in Cheshire

Total rentals

Wifi availability

Rentals with dedicated workspaces

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Frequently Asked Questions

Do house rentals in Cheshire have air conditioning?

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

Are there vacation rentals with a dedicated workspace in Cheshire?

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

Are there family-friendly vacation rentals in Cheshire?

Do house rentals in Cheshire have wifi?

Destinations to explore