Vacation rentals in Cheshire

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Top-rated vacation rentals in Cheshire

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Guest favorite

Guest suite in New Britain

4.92 out of 5 average rating, 131 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

Aug 13 – 20

ﺩ.ﺇ386 per night

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 16 – 23

ﺩ.ﺇ2,605 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 15 – 22

ﺩ.ﺇ264 per night

Guest favorite

Guest suite in Bethlehem

4.99 out of 5 average rating, 200 reviews

Breezy Crest private & restful w/antique charm

Escape to this charming and historic two-story 1841 suite, nestled in the quaint town of Bethlehem. The upstairs bedroom boasts original exposed beams and antique details, creating a cozy and inviting atmosphere. Wake up to the sunrise from the comfort of your bed and enjoy a warm fire in the backyard while listening to the peaceful sounds of nature. Conveniently located between Litchfield and Woodbury, and just 90 miles from NYC, you'll have easy access to shops, restaurants, and ski slopes.

Sep 6 – 13

ﺩ.ﺇ606 per night

Guest favorite

Guest suite in Wallingford

5.0 out of 5 average rating, 499 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 28 – Apr 4

ﺩ.ﺇ321 per night

Guest favorite

Home in New Haven

5.0 out of 5 average rating, 169 reviews

Historic New Haven Home

Our family owned New Haven vacation house is a renovated 1920s Tudor. It's located in a quiet, safe, & beautiful neighborhood, close to downtown and Yale. We've carefully preserved historic aspects we love (ie: art deco tile & leaded glass windows), and combined it with central a/c, USB ports, new appliances, gas fireplace, high speed wifi & more. You’re also welcome to use the small screened in porch, patio with chairs, and the yard. The entire house and driveway is yours when you rent.

Apr 24 – May 1

ﺩ.ﺇ562 per night

Guest favorite

Condo in Middletown

4.97 out of 5 average rating, 101 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

Nov 23 – 30

ﺩ.ﺇ442 per night

Guest favorite

Apartment in Southington

4.93 out of 5 average rating, 269 reviews

#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.

Aug 4 – 11

ﺩ.ﺇ455 per night

Guest favorite

Apartment in Wallingford

4.86 out of 5 average rating, 22 reviews

Sweet Sparkling Clean Boho 1 bedroom

One bedroom, 3rd story apartment, completely separate, with its own entrance. Comes with a single off street parking space. Centrally located in downtown Wallingford. Close to shops, restaurants and bars. Also within a couple of miles of the Toyota Oakdale Theatre. If you are looking for a place to come and party for the night, this is not a good space for you. This is a quiet building with the landlord on premise. We do welcome fur babies under 50 pounds.

Dec 31 – Jan 7

ﺩ.ﺇ293 per night

Guest favorite

Apartment in Brookfield

4.94 out of 5 average rating, 184 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 23 – 30

ﺩ.ﺇ437 per night

Guest favorite

Guest suite in Cheshire

4.94 out of 5 average rating, 31 reviews

Cozy & Private Studio Suite

Quiet and private in-law suite. Located close to the center of Cheshire, convenient to Route 10 and the Merritt Parkway. Near to grocery stores, great restaurants, and shopping centers. 15 minute drive to Toyota Oakdale Theater, 20 minute drive to Lake Compounce Amusement and Water Park, and 30 minute drive to Yale University, Museums, and downtown New Haven. Great place to stay while visiting your family or if you're in the area for business.

Jun 9 – 16

ﺩ.ﺇ337 per night

Guest favorite

Guest suite in Hamden

4.96 out of 5 average rating, 713 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.

Jun 14 – 21

ﺩ.ﺇ622 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

Brooksvale Park4 locals recommend

C.J. Sparrow3 locals recommend

Farmington Canal Heritage Trail14 locals recommend

Other great vacation rentals in Cheshire

Guest favorite

Apartment in Meriden

4.93 out of 5 average rating, 46 reviews

Meriden Metro| Cozy Studio|Pool and Gym

Apr 25 – May 2

ﺩ.ﺇ329 per night

Guest favorite

Guest suite in Wolcott

5.0 out of 5 average rating, 14 reviews

Modern cozy, pet friendly

Sep 6 – 13

ﺩ.ﺇ463 per night

Guest favorite

Apartment in Waterbury

4.98 out of 5 average rating, 66 reviews

Everything you need! Apartment!

Feb 26 – Mar 5

ﺩ.ﺇ427 per night

Guest favorite

Guest suite in Northford

5.0 out of 5 average rating, 12 reviews

Private Bright Studio Retreat with kitchen

Aug 8 – 15

ﺩ.ﺇ324 per night

Superhost

Apartment in Meriden

5.0 out of 5 average rating, 4 reviews

Hillside Retreat

Jun 1 – 8

ﺩ.ﺇ356 per night

Guest favorite

Apartment in Middlebury

4.98 out of 5 average rating, 64 reviews

Cozy Apartment with Water View of Brook

Mar 27 – Apr 3

ﺩ.ﺇ400 per night

Guest favorite

Guesthouse in Wallingford

5.0 out of 5 average rating, 70 reviews

The Garden Loft - A Charming Choate Stay

Dec 6 – 13

ﺩ.ﺇ853 per night

Guest favorite

Home in Southington

4.96 out of 5 average rating, 69 reviews

Connecticut Chalet - Private Pond, Firepit, Views!

Aug 21 – 28

ﺩ.ﺇ1,141 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
ﺩ.ﺇ110 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 air conditioning, over 10 homes with wifi, 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

Apartment in Meriden

Guest suite in Wolcott

Apartment in Waterbury

Guest suite in Northford

Apartment in Meriden

Apartment in Middlebury

Guesthouse in Wallingford

Home in Southington

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