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

Nov 3 – 10

R2,012 ZAR 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!

Feb 27 – Mar 6

R13,610 ZAR per night

Guest favorite

Guesthouse in Southbury

4.93 out of 5 average rating, 266 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).

Aug 6 – 13

R2,972 ZAR 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 20 – 27

R1,379 ZAR 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.

Aug 12 – 19

R1,675 ZAR per night

Guest favorite

Apartment in Middletown

4.98 out of 5 average rating, 147 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 3 – 10

R2,480 ZAR per night

Guest favorite

Cottage in Middlefield

4.93 out of 5 average rating, 229 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.

Jun 4 – 11

R3,308 ZAR 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.

Sep 23 – 30

R1,533 ZAR 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.

Feb 9 – 16

R2,271 ZAR per night

Guest favorite

Guest suite in Cheshire

4.94 out of 5 average rating, 32 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.

Sep 17 – 24

R1,748 ZAR 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 18 – 25

R3,251 ZAR per night

Guest favorite

Guest suite in Morris

4.99 out of 5 average rating, 340 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.

Jan 21 – 28

R1,798 ZAR 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

4.94 out of 5 average rating, 48 reviews

Meriden Metro| Cozy Studio|Pool and Gym

May 6 – 13

R1,969 ZAR per night

Guest favorite

Apartment in Waterbury

4.98 out of 5 average rating, 66 reviews

Everything you need! Apartment!

Mar 2 – 9

R2,212 ZAR per night

Guest favorite

Apartment in Middlebury

4.98 out of 5 average rating, 64 reviews

Cozy Apartment with Water View of Brook

Feb 4 – 11

R2,089 ZAR per night

Guest favorite

Guest suite in Northford

5.0 out of 5 average rating, 13 reviews

Private Bright Studio Retreat with kitchen

Jan 3 – 10

R1,745 ZAR per night

Guest favorite

Home in Southington

4.96 out of 5 average rating, 70 reviews

Connecticut Chalet - Private Pond, Firepit, Views!

Aug 21 – 28

R5,798 ZAR per night

Guest favorite

Guesthouse in Wallingford

5.0 out of 5 average rating, 70 reviews

The Garden Loft - A Charming Choate Stay

Sep 17 – 24

R4,458 ZAR per night

Guest favorite

Apartment in Wallingford

4.82 out of 5 average rating, 28 reviews

Central Town 1BR Furnished Apt - Prime Location

May 27 – Jun 3

R1,822 ZAR per night

Guest favorite

Apartment in New Britain

4.95 out of 5 average rating, 92 reviews

Spacious Cozy Guest Suite

Jan 17 – 24

R1,852 ZAR 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
R576 ZAR 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

Apartment in Meriden

Apartment in Waterbury

Apartment in Middlebury

Guest suite in Northford

Home in Southington

Guesthouse in Wallingford

Apartment in Wallingford

Apartment in New Britain

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