Cheshire Vacation Rentals

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Our top choices for Cheshire vacation rentals

Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.

Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
Cheshire
9.4 out of 10, Exceptional, (16 reviews)
"Needed a place to sleep for a couple of nights and this worked for us."
United States
James (Jim) L.
The price is ¥13,913
¥26,307 total
includes taxes & fees
Feb 18 - Feb 19
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.

#43- Modern Luxury Log Cabin Retreat | Fire Pit

#43- Modern Luxury Log Cabin Retreat | Fire Pit
Prospect
The price is ¥27,951
¥66,340 total
includes taxes & fees
Feb 19 - Feb 20
#43- Modern Luxury Log Cabin Retreat | Fire Pit

Quiet and cozy studio apartment on premier Cheshire street close to New Haven

Quiet and cozy studio apartment on premier Cheshire street close to New Haven
Cheshire
The price is ¥18,691
¥27,309 total
includes taxes & fees
Feb 19 - Feb 20
Quiet and cozy studio apartment on premier Cheshire street close to New Haven

New England Tiny Home Experience: Coffee & More!

New England Tiny Home Experience: Coffee & More!
3.0 star property
Main Street Historic District
The price is ¥25,765
¥52,145 total
includes taxes & fees
Feb 17 - Feb 18
New England Tiny Home Experience: Coffee & More!

Urban Oasis 3BR Parking Washer & Dryer Yale East Rock

Urban Oasis 3BR Parking Washer & Dryer Yale East Rock
East Rock
9.8 out of 10, Exceptional, (11 reviews)
"Thanks to the detailed information from the host check-in couldn’t have been easier. The home was clean and well-appointed. Great location with access to the Yale tram and local markets and restaurants. "
United States
Denyce D.
The price is ¥14,990
¥41,467 total
includes taxes & fees
Feb 12 - Feb 13
Urban Oasis 3BR Parking Washer & Dryer Yale East Rock

Family Stays: Middletown, CT

Family Stays: Middletown, CT
Middletown
10.0 out of 10, Exceptional, (20 reviews)
"A truly wonderful experience! The host and home were amazing and we’ll definitely be staying here again!"
United States
Harmony R.
The price is ¥17,957
¥34,860 total
includes taxes & fees
Feb 24 - Feb 25
Family Stays: Middletown, CT

Welcoming 1500 square foot 3-bedroom house completely remodeled in Southington

Welcoming 1500 square foot 3-bedroom house completely remodeled in Southington
Southington
10.0 out of 10, Exceptional, (2 reviews)
"We had a great, relaxing Thanksgiving holiday at this spacious Southington, CT home. It was the perfect spot to visit one of my daughters and be able to have my mother-in-law stay with us so we could cook and host Thanksgiving dinner. The house was well-stocked and supplied with everything we needed, and then some; which allowed us to have a stress-free holiday as if we were in our own home. We highly recommend this home and will keep it in mind for future extended stays in the area."
United States
Cindy M.
The price is ¥15,318
¥79,272 total
includes taxes & fees
Feb 14 - Feb 15
Welcoming 1500 square foot 3-bedroom house completely remodeled in Southington

#26 Beautifully Renovated 2 BR Home

#26 Beautifully Renovated 2 BR Home
Plainville
10.0 out of 10, Exceptional, (4 reviews)
"We thoroughly enjoyed our stay! The space was great for our family of 4. Would recommend!"
United States
LaTanya W.
The price is ¥21,705
¥41,825 total
includes taxes & fees
Feb 13 - Feb 14
#26 Beautifully Renovated 2 BR Home

DTWN I Near Yale I King Beds I Free Parking I Gym I Free Coffee I Pets Welcome!

DTWN I Near Yale I King Beds I Free Parking I Gym I Free Coffee I Pets Welcome!
Downtown New Haven
10.0 out of 10, Exceptional, (2 reviews)
"We loved this rental. The location is one you might not think is good BUT IT IS. I loved the location. Great coffee shop around the corner. Short walk to great restaurants and it was a safe location. I will stay here again. Also the two bedrooms with two bathrooms is rare and each bedroom with a king bed is super rare. I highly recommend this rental and Joshua was so great and helpful. "
United States
Sharla C.
The price is ¥17,957
¥52,896 total
includes taxes & fees
Feb 12 - Feb 13
DTWN I Near Yale I King Beds I Free Parking I Gym I Free Coffee I Pets Welcome!

Cozy Two Bedroom Stay In Downtown New Haven!

Cozy Two Bedroom Stay In Downtown New Haven!
Dwight
10.0 out of 10, Exceptional, (1 review)
"Exactly as advertised and had nice personal touches. Very close to attractions and very walkable. "
United States
Kimberly S.
The price is ¥17,005
¥42,289 total
includes taxes & fees
Feb 12 - Feb 13
Cozy Two Bedroom Stay In Downtown New Haven!

The Sun Filled Cozy Creamery

The Sun Filled Cozy Creamery
Plainville
8.8 out of 10, Excellent, (25 reviews)
"Very cozy and comfortable.The location was perfect for our stay in the area."
United States
Heather T.
The price is ¥11,087
¥39,531 total
includes taxes & fees
Feb 12 - Feb 13
The Sun Filled Cozy Creamery

Newly Remodeled with deck. Close to town center

Newly Remodeled with deck. Close to town center
Wallingford
10.0 out of 10, Exceptional, (2 reviews)
"The apartment was perfect - size, location, furnishings and price. Will definitely return when I visit friends and family."
United States
Karen F.
The price is ¥21,549
¥49,609 total
includes taxes & fees
Feb 12 - Feb 13
Newly Remodeled with deck. Close to town center

Private Apartment in Berlin

Private Apartment in Berlin
Berlin
9.2 out of 10, Wonderful, (5 reviews)
"Place was great, not to small and not to big. Beds were extremely comfortable. Berlin is a busy town but the house in tucked far enough away from it all. Great place and would gladly stay again! "
United States
Daniel L.
The price is ¥14,990
¥45,111 total
includes taxes & fees
Feb 12 - Feb 13
Private Apartment in Berlin

The Nest At Elm City Flats.

The Nest At Elm City Flats.
West New Haven
9.6 out of 10, Exceptional, (7 reviews)
"We had a great stay at this apartment. You do have to go up three flight of stairs but thankfully we were able to climb them. "
United States
Joan S.
The price is ¥13,913
¥36,495 total
includes taxes & fees
Feb 12 - Feb 13
The Nest At Elm City Flats.

Luxe Living! Apt 1 Mi to West Haven Medical Center

Luxe Living! Apt 1 Mi to West Haven Medical Center
3.0 star property
West Haven
The price is ¥21,393
¥55,905 total
includes taxes & fees
Feb 12 - Feb 13
Luxe Living! Apt 1 Mi to West Haven Medical Center

Angelica’s safe haven @ west haven

Angelica’s safe haven @ west haven
West Haven
10.0 out of 10, Exceptional, (6 reviews)
"Quiet place with spacious living room perfect for movie nights. Also just a 10-minute drive from the beach and multiple dining options. Host was very accommodating and communicative. Would stay here again."
United States
Veronica
The price is ¥22,642
¥53,169 total
includes taxes & fees
Feb 12 - Feb 13
Angelica’s safe haven @ west haven

#24 *Serenity* A Lakefront Cottage Retreat

#24 *Serenity* A Lakefront Cottage Retreat
Middletown
9.8 out of 10, Exceptional, (21 reviews)
"We had a wonderful stay at this property! The house itself was beautiful—spacious, clean, and incredibly comfortable. The setting was just as impressive, offering peaceful views and a great atmosphere to relax and unwind. Everything was exactly as described, if not better. We would absolutely stay here again and highly recommend it to anyone looking for a serene and well-appointed home base for our stay. "
United States
Nichole N.
The price is ¥22,798
¥51,670 total
includes taxes & fees
Feb 22 - Feb 23
#24 *Serenity* A Lakefront Cottage Retreat

All New 1BR with tons of Charm

All New 1BR with tons of Charm
Wallingford Center
9.8 out of 10, Exceptional, (8 reviews)
"Charming, unique, and very comfortable. Would surely stay again. "
United States
David S.
The price is ¥17,957
¥45,010 total
includes taxes & fees
Feb 17 - Feb 18
All New 1BR with tons of Charm

Cozy 1-bedroom apartment in lovely Oxford

Cozy 1-bedroom apartment in lovely Oxford
Oxford
10.0 out of 10, Exceptional, (1 review)
"I made a late reservation, and my host, Jackie, was always accommodating, welcoming, and in regular communication with me. The amenities were just what I needed, right down to the coffee pod and snack selection! The apartment is well laid out, as if I were walking into my own home, convenient to shopping and friends.Thank you, Jackie!"
United States
LIsa G.
The price is ¥17,489
¥25,031 total
includes taxes & fees
Feb 12 - Feb 13
Cozy 1-bedroom apartment in lovely Oxford

Cozy 1bedroom Apt Loft Style in welcoming Hartford with WiFi, AC, Elevator

Cozy 1bedroom Apt Loft Style in welcoming Hartford with WiFi, AC, Elevator
Downtown Hartford
9.6 out of 10, Exceptional, (5 reviews)
"Great location. Clean property"
United States
Sue R.
The price is ¥16,396
¥30,957 total
includes taxes & fees
Feb 12 - Feb 13
Cozy 1bedroom Apt Loft Style in welcoming Hartford with WiFi, AC, Elevator
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Cheshire Hotel Reviews

Find out more about Cheshire

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Frequently asked questions

Can I find a vacation rental in Cheshire?

Yes, we have vacation rentals in Cheshire close to Barker Character, Comic and Cartoon Museum, or you can select a more remote option if you'd like a relaxing place to stay. Our travelers say Cheshire has a good selection of restaurants. Make sure you have time to check out the waterfalls and shopping during your trip.

What are some of the best vacation home rentals in Cheshire?

A spacious TREETOPS Reunion/ Retreat/Event venue! Sleeps 10-12. Seasonal POOL!: Visitors like this Cheshire vacation home rental. It is located in the city center and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a balcony, a garden, and a selection of books so you can immerse yourself in your vacation.

What’s there to see and do in Cheshire?

Family-friendly attractions include Barker Character, Comic and Cartoon Museum and Cheshire Hollow Farm, whereas Roaring Brook Park and Bartlem Park are a couple of great spots to enjoy the outdoors. While here, Maplecroft Plaza Shopping Center and Drazen Orchards are other places worth a visit.

What’s a vacation rental in Cheshire like?

Vacation rentals are private properties you can book for a few weeks or just a few days in Cheshire. Vacation rentals feature amenities like kitchens and laundry facilities so you'll have all the conveniences of home. If you're concerned about a clean environment, vacation rentals can offer a sense of security away from public hotel elevators and busy lobbies while still allowing you the experience of travel. You'll also have more space in a vacation rental than in a hotel, which is another reason why a vacation rental is an attractive option for family trips or small group gatherings.