Cheshire Vacation Rentals

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Nov 23 - Nov 24
Tomorrow
Nov 24 - Nov 25
Next weekend
Nov 28 - Nov 30
In two weeks
Dec 5 - Dec 7

Vacation Rentals in Cheshire

Fridge, microwave, oven, stovetop
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.

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

Cheshire
9.2 out of 10, Wonderful, (11)
"Needed a place to sleep for a couple of nights and this worked for us."
United States
James (Jim) L.
$145 nightly
The price is $163
Nov 24 - Nov 25
Total with taxes and fees
Quiet 2bd Townhome apt in the heart of Cheshire. Backyard.
Honeymoon Apartment, 3 Bedrooms, Kitchen | In-room dining
Luxury Furnished Apartments by Hyatus Downtown at Yale

Luxury Furnished Apartments by Hyatus Downtown at Yale

3.5 star property
The Hill
9.6 out of 10, Exceptional, (60)
"Loved our stay here. "
United States
Christina
Luxury Furnished Apartments by Hyatus Downtown at Yale
Iron/ironing board, WiFi, bed sheets
Lux Boutique Large Private LOFT Pratt St Hartford

Lux Boutique Large Private LOFT Pratt St Hartford

Downtown Hartford
8.4 out of 10, Very Good, (23)
"Very clean and spacious! Loved all the amenities. Room itself was a bit echoey, but nice and quiet."
United States
Kiara
$135 nightly
The price is $152
Dec 1 - Dec 2
Total with taxes and fees
Lux Boutique Large Private LOFT Pratt St Hartford
Microwave
Cozy apartment in charming Hartford with AC, WiFi

Cozy apartment in charming Hartford with AC, WiFi

Downtown Hartford
9.0 out of 10, Wonderful, (7)
"Very nice for one night"
United States
Jack
$135 nightly
The price is $152
Nov 24 - Nov 25
Total with taxes and fees
Cozy apartment in charming Hartford with AC, WiFi
4 bedrooms, iron/ironing board, free WiFi, bed sheets
Waterfront Cottage in Branford

Waterfront Cottage in Branford

branford
10.0 out of 10, Exceptional, (97)
"Such a beautiful home and amazing views! Stayed here with friends for a wedding and it was the most ideal. "
United States
Bradie S.
Waterfront Cottage in Branford
Dining
Waterfront Cabin w Firepit, Dock, Deck, BBQ. Direct Lake Access! Pet-friendly!

Waterfront Cabin w Firepit, Dock, Deck, BBQ. Direct Lake Access! Pet-friendly!

Northwest Harwinton
8.6 out of 10, Excellent, (27)
"Love the place.. very clean ..loved the neighbors.. got to catch up on well needed rest.. the neighbors on the right were wonderful than the owners came and they were also wonderful also"
United States
Andrea m.
Waterfront Cabin w Firepit, Dock, Deck, BBQ. Direct Lake Access! Pet-friendly!
Fridge, microwave, oven, stovetop
Private Apartment in Berlin

Private Apartment in Berlin

2.0 star property
Berlin
9.2 out of 10, Wonderful, (5)
"We visited over a holiday weekend. The house is clean and a good size for the 3 adults in our group and our dog. It is in walking distance to several stores and a park. We would stay again if we were in the area. "
United States
Stacy B.
$281 nightly
The price is $318
Nov 24 - Nov 25
Total with taxes and fees
Private Apartment in Berlin
On the beach, sun loungers, beach towels
Beach Front Arts & Crafts House With Gorgeous Views Of The Sound

Beach Front Arts & Crafts House With Gorgeous Views Of The Sound

Milford
10.0 out of 10, Exceptional, (132)
"Wonderful stay in a nice quiet neighborhood "
United States
Jacob M.
Beach Front Arts & Crafts House With Gorgeous Views Of The Sound
WiFi, bed sheets
Totally Private Cozy studio in awesome Hartford with WiFi, AC

Totally Private Cozy studio in awesome Hartford with WiFi, AC

Downtown Hartford
8.6 out of 10, Excellent, (11)
"Great!"
United States
Sahai S.
$135 nightly
The price is $152
Nov 26 - Nov 27
Total with taxes and fees
Totally Private Cozy studio in awesome Hartford with WiFi, AC
Interior
Stunning Apt W/ Parking and Gym | Downtown at Yale

Stunning Apt W/ Parking and Gym | Downtown at Yale

The Hill
10.0 out of 10, Exceptional, (46)
"High quality experience, walking distance to all we needed, clean and spacious. Excellent support and communication from the hosts, would stay again."
United Kingdom
Coco N.
Stunning Apt W/ Parking and Gym | Downtown at Yale
Exterior
New One Bedroom Apartment Centrally Located in Southbury

New One Bedroom Apartment Centrally Located in Southbury

Southbury
9.8 out of 10, Exceptional, (18)
"Perfect sized apartment for a short stay - very convenient to my destination"
United States
S
$115 nightly
The price is $129
Nov 24 - Nov 25
Total with taxes and fees
New One Bedroom Apartment Centrally Located in Southbury
Beach nearby, beach towels
Gorgeous 4BR Beach House with Private Beach Access.

Gorgeous 4BR Beach House with Private Beach Access.

Pine Orchard
9.8 out of 10, Exceptional, (75)
"Nice property, thanks to the owners.Jackie"
United States
Jacqueline M.
Gorgeous 4BR Beach House with Private Beach Access.
Exterior
Charming Studio| Near Yale| Downtown New Haven

Charming Studio| Near Yale| Downtown New Haven

Downtown New Haven
9.0 out of 10, Wonderful, (10)
"A great place to stay during reunions! Prime campus-adjacent location, an easy walk to all things on campus!"
United States
Jason K.
$220 nightly
The price is $220
Nov 24 - Nov 25
Total with taxes and fees
Charming Studio| Near Yale| Downtown New Haven
Smart TV, fireplace, video games
New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.

New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.

Durham
10.0 out of 10, Exceptional, (24)
"As advertised. Enjoyed our stay. "
United States
Jeff C.
$780 nightly
The price is $884
Nov 24 - Nov 25
Total with taxes and fees
New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.
Outdoor pool, a heated pool
A TREETOPS Retreat! Sleeps 10-12, perfect for large gatherings. Seasonal POOL!

A TREETOPS Retreat! Sleeps 10-12, perfect for large gatherings. Seasonal POOL!

Guilford
10.0 out of 10, Exceptional, (37)
"This property had all we needed and more ! "
United States
Kathie R.
A TREETOPS Retreat! Sleeps 10-12, perfect for large gatherings. Seasonal POOL!
Dining
Thanksgiving By The Sea-Scenic Waterviews, Hot Tub & Private Beach

Thanksgiving By The Sea-Scenic Waterviews, Hot Tub & Private Beach

Branford
10.0 out of 10, Exceptional, (71)
"Great family get together where we all were very comfortable. "
United States
Leanne B.
Thanksgiving By The Sea-Scenic Waterviews, Hot Tub & Private Beach
Beach nearby
BEACH BUM CARRIAGE HOUSE with kayaks - steps to beach, park, marinas & brewery!

BEACH BUM CARRIAGE HOUSE with kayaks - steps to beach, park, marinas & brewery!

Branford Center
9.2 out of 10, Wonderful, (19)
"This Carriage House is exactly as described. Wonderful location and setting, just steps away from Branford Point. Hope to visit again soon! "
United States
Terri L.
BEACH BUM CARRIAGE HOUSE with kayaks - steps to beach, park, marinas & brewery!
Fridge, microwave, oven, stovetop
XL Center 1-BR Condo|DWNTN Hartford|Easy Parking

XL Center 1-BR Condo|DWNTN Hartford|Easy Parking

Downtown Hartford
9.0 out of 10, Wonderful, (2)
"The location is fabulous to the convention center is fabulous!"
United States
Anonymous traveler
$240 nightly
The price is $272
Nov 26 - Nov 27
Total with taxes and fees
XL Center 1-BR Condo|DWNTN Hartford|Easy Parking
Interior
Conference Room Rental no sleeping arrangements

Conference Room Rental no sleeping arrangements

Main Street Historic District
$814 nightly
The price is $922
Nov 24 - Nov 25
Total with taxes and fees
Conference Room Rental no sleeping arrangements
Fridge, microwave, oven, stovetop
All New 1BR with tons of Charm

All New 1BR with tons of Charm

Wallingford Center
9.8 out of 10, Exceptional, (6)
"I highly recommend this property!! We were in town for a wedding celebration, and it proved perfect. The property is completely updated, well-appointed and clean. The property is centrally located and close to restaurants, shops and grocery markets. Karl was a great host and communicated with us throughout our stay. I highly recommend!!"
United States
Francis S.
$271 nightly
The price is $288
Dec 8 - Dec 9
Total with taxes and fees
All New 1BR with tons of Charm
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

The Capitol Hotel

The Capitol Hotel

10/10 Excellent
"Clean rooms, convenient location, friendly staff and great price"
Daren 3-night trip
Posted 1 day ago
The Capitol Hotel

Find out more about Cheshire

Everything you need to know about Cheshire vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Cheshire vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Cheshire vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Cheshire vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Cheshire. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Cheshire in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Cheshire rentals

At Expedia, we put the best Cheshire vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Cheshire rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Cheshire vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Cheshire. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

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?

Clean, Bright & Private WHOLE HOUSE 4 YOU. Safe, Centrally Located, Garage: Visitors like this Cheshire vacation home rental. It offers a patio, a garden, and air-conditioning to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a stovetop, and a microwave, so you can cook with friends or family.

What’s there to see and do in Cheshire?

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