Cheshire Vacation Rentals

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Vacation Rentals in Cheshire

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

Apartment in 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
Dec 3 - Dec 4
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

Aparthotel in The Hill

3.5 star property
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

Apartment in 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 3 - Dec 4
Total with taxes and fees
Lux Boutique Large Private LOFT Pratt St Hartford
Microwave
Cozy apartment in charming Hartford with AC, WiFi

Apartment in Downtown Hartford

8.8 out of 10, Excellent, (8)
"Very nice for one night"
United States
Jack
$135 nightly
The price is $152
Dec 3 - Dec 4
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

Cottage in branford

10.0 out of 10, Exceptional, (98)
"Beautiful location "
United States
Anne d.
Waterfront Cottage in Branford
Fridge, microwave, oven, stovetop
Private Apartment in Berlin

Vacation Home in Berlin

2.0 star property
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.
$279 nightly
The price is $316
Dec 7 - Dec 8
Total with taxes and fees
Private Apartment in Berlin
TV
Clean, Bright & Private WHOLE HOUSE 4 YOU. Safe, Centrally Located, Garage

Vacation Home in New Britain

10.0 out of 10, Exceptional, (7)
"The space was clean and light, great finishes. The home felt comfortable and was easy to find. Thank you for a wonderful weekend. "
United States
Lara S.
$220 nightly
The price is $248
Dec 7 - Dec 8
Total with taxes and fees
Clean, Bright & Private WHOLE HOUSE 4 YOU. Safe, Centrally Located, Garage
On the beach, sun loungers, beach towels
Beach Front Arts & Crafts House With Gorgeous Views Of The Sound

Vacation Home in Milford

10.0 out of 10, Exceptional, (134)
"Wonderful stay in a nice quiet neighborhood "
United States
Jacob M.
Beach Front Arts & Crafts House With Gorgeous Views Of The Sound
Interior
Stunning Apt W/ Parking and Gym | Downtown at Yale

Apartment in 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
Beach nearby, beach towels
Gorgeous 4BR Beach House with Private Beach Access.

Vacation Home in Pine Orchard

9.8 out of 10, Exceptional, (76)
"Nice property, thanks to the owners.Jackie"
United States
Jacqueline M.
Gorgeous 4BR Beach House with Private Beach Access.
Dining
Coastal Holiday Retreat: Luxury Waterfront, Hot Tub & Private Beach

Vacation Home in Branford

10.0 out of 10, Exceptional, (71)
"We had a wonderful vacation!! The house was perfect, check in couldn’t have easier and the views couldn’t have been better. A perfect summer getaway."
United States
Mike S.
Coastal Holiday Retreat: Luxury Waterfront, Hot Tub & Private Beach
Dining
Waterfront Cabin w Firepit, Dock, Deck, BBQ. Direct Lake Access! Pet-friendly!

Cabin in 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!
Interior
Conference Room Rental no sleeping arrangements

Apartment in Main Street Historic District

$823 nightly
The price is $931
Dec 3 - Dec 4
Total with taxes and fees
Conference Room Rental no sleeping arrangements
Fridge, microwave, oven, stovetop
All New 1BR with tons of Charm

Apartment in 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
1 bedroom, iron/ironing board, WiFi, bed sheets
Downtown New Haven Escape

Apartment in Dwight

2.0 star property
8.0 out of 10, Very Good, (6)
"Great place to stay, a little tight for 2 people but good for a single. Well appointed and a great location in the city. Would definitely recommend a stay here."
United States
Michael H.
$215 nightly
The price is $222
Dec 3 - Dec 4
Total with taxes and fees
Downtown New Haven Escape
Exterior
Charming Studio| Near Yale| Downtown New Haven

Apartment in 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.
$210 nightly
The price is $210
Dec 3 - Dec 4
Total with taxes and fees
Charming Studio| Near Yale| Downtown New Haven
Fridge, microwave, oven, stovetop
New Cozy 2BR Stay New Haven Close to Yale

Apartment in East Rock

2.0 star property
7.4 out of 10, Good, (3)
"Place was great for family and having a washer and dryer was a big help. Place was super clean and comfortable "
United States
CHUCK C.
New Cozy 2BR Stay New Haven Close to Yale
1 bedroom, WiFi, bed sheets
Private Third-Floor Attic Apartment Full Kitchen • King Bed • Backyard Access

Apartment in West New Haven

2.0 star property
9.0 out of 10, Wonderful, (2)
"Great communication and easy check in, would recommend "
United States
Ethan R.
$115 nightly
The price is $129
Dec 3 - Dec 4
Total with taxes and fees
Private Third-Floor Attic Apartment Full Kitchen • King Bed • Backyard Access
Seasonal outdoor pool
Luxury Apartments by Hyatus at Pierpont

Aparthotel in The Hill

4.0 star property
9.4 out of 10, Exceptional, (22)
"This was by far the best stay I’ve had in New Haven the apartment was very clean had everything I needed to cook the bed was fabulous had the best sleep not to mention I got to watch the sunset laying down in the bed it was the highlife of my stay loved it I’ve never in my life got to experience laying down in the bed watching the sunset it was great and I’ve been around the world stayed at some great places but never that 💓💓 I will be booking another stay here very soon and the host was so...
United States
Holly
Luxury Apartments by Hyatus at Pierpont
Interior
Charming & Private 1-bed & 1 ba ,sleeps 2, on 1st floor of a 5 bed 3ba House,

Vacation Home in Shelton

9.0 out of 10, Wonderful, (2)
"The house was very clean. Rudolph and his son were very personable and welcoming. Very much enjoyed our stay."
United States
Alex C.
$174 nightly
The price is $197
Dec 3 - Dec 4
Total with taxes and fees
Charming & Private 1-bed & 1 ba ,sleeps 2, on 1st floor of a 5 bed 3ba House,
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

Hampton Inn & Suites Hartford/East Hartford

Hampton Inn & Suites Hartford/East Hartford

10/10 Excellent
"We have stayed at this hotel multiple times. It is a very convenient location, it is always kept very clean, and it is a very good value noting also the exceptional complimentary breakfast. This trip stood out in that the customer service provided at the front desk was above and beyond to make our stay even better. Donna at the front desk went out of her way to correct a booking problem with our room and her kindness and friendliness made us feel both welcome and appreciated as guests. She provided exceptional customer service that is uncommon to find nowadays and she did it cheerfully despite the challeges brought about by a holiday weekend."
lea 3-night trip
Posted 9 hours ago
Hampton Inn & Suites Hartford/East Hartford

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 $129 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?

Private Apartment in Berlin: Visitors like this Cheshire vacation home rental. It is equipped with a balcony, air-conditioning, and laundry facilities to help you feel comfortable during your stay. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

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.