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Cheshire Vacation Rentals

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Oct 22 - Oct 23
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Oct 24 - Oct 26
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Oct 31 - Nov 2

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.
9.4 out of 10, Exceptional, (9)
"Needed a place to sleep for a couple of nights and this worked for us."
United States
James (Jim) L.
$155 nightly
The price is $175
Oct 27 - Oct 28
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
9.6 out of 10, Exceptional, (59)
"Loved our stay here. "
United States
Christina
Luxury Furnished Apartments by Hyatus Downtown at Yale
Seasonal outdoor pool
Luxury Apartments by Hyatus at Pierpont
Luxury Apartments by Hyatus at Pierpont
4.0 star property
9.4 out of 10, Exceptional, (21)
"Excellent location downtown and close to yale. A lot of complimentary amenities and activities. Very nice size rooms. A nice residential feel for a weeks stay."
United States
Brian
Luxury Apartments by Hyatus at Pierpont
WiFi, bed sheets
Totally Private Cozy studio in awesome Hartford with WiFi, AC
Totally Private Cozy studio in awesome Hartford with WiFi, AC
8.6 out of 10, Excellent, (11)
"Great!"
United States
Sahai S.
$140 nightly
The price is $158
Oct 27 - Oct 28
Total with taxes and fees
Totally Private Cozy studio in awesome Hartford with WiFi, AC
Fridge, microwave, oven, stovetop
Private Apartment in Berlin
Private Apartment 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.
$282 nightly
The price is $320
Nov 17 - Nov 18
Total with taxes and fees
Private Apartment in Berlin
Interior
Conference Room Rental no sleeping arrangements
Conference Room Rental no sleeping arrangements
$823 nightly
The price is $931
Oct 24 - Oct 25
Total with taxes and fees
Conference Room Rental no sleeping arrangements
Fridge, microwave, oven, stovetop
XL Center 1-BR Condo|DWNTN Hartford|Easy Parking
XL Center 1-BR Condo|DWNTN Hartford|Easy Parking
9.0 out of 10, Wonderful, (2)
"The location is fabulous to the convention center is fabulous!"
United States
Anonymous traveler
$222 nightly
The price is $251
Oct 28 - Oct 29
Total with taxes and fees
XL Center 1-BR Condo|DWNTN Hartford|Easy Parking
Exterior
Charming Studio| Near Yale| Downtown New Haven
Charming Studio| Near Yale| Downtown New Haven
9.0 out of 10, Wonderful, (9)
"A great place to stay during reunions! Prime campus-adjacent location, an easy walk to all things on campus!"
United States
Jason K.
$211 nightly
The price is $211
Oct 27 - Oct 28
Total with taxes and fees
Charming Studio| Near Yale| Downtown New Haven
Terrace/patio
Grace Island. Private Island! Vacations, Getaways, Weddings & Special Events.
Grace Island. Private Island! Vacations, Getaways, Weddings & Special Events.
Grace Island. Private Island! Vacations, Getaways, Weddings & Special Events.
Iron/ironing board, WiFi, bed sheets
Lux Boutique Large Private LOFT Pratt St Hartford
Lux Boutique Large Private LOFT Pratt St Hartford
8.4 out of 10, Very Good, (21)
"Location was great. Lots of things to do and many nearby options for eating and drinks. View was disappointing—dark and one window facing a brick wall. Biggest complaint was neighbors and noise—first two nights there was loud music and parties until early morning hours."
United States
Mike and Jaime R.
$144 nightly
The price is $163
Oct 27 - Oct 28
Total with taxes and fees
Lux Boutique Large Private LOFT Pratt St Hartford
Fridge, microwave, oven, stovetop
New Cozy 2BR Stay New Haven Close to Yale
New Cozy 2BR Stay New Haven Close to Yale
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.
$244 nightly
The price is $254
Oct 26 - Oct 27
Total with taxes and fees
New Cozy 2BR Stay New Haven Close to Yale
Microwave, electric kettle, cookware/dishes/utensils, paper towels
Cozy 1bedroom Apt Loft Style in welcoming Hartford with WiFi, AC, Elevator
Cozy 1bedroom Apt Loft Style in welcoming Hartford with WiFi, AC, Elevator
9.6 out of 10, Exceptional, (4)
"Cozy, clean, comfortable. Location is excellent and accessible to restaurants and venues. Highly recommended. "
United States
Jason B.
$178 nightly
The price is $201
Nov 1 - Nov 2
Total with taxes and fees
Cozy 1bedroom Apt Loft Style in welcoming Hartford with WiFi, AC, Elevator
Dining
Exclusive Weekend Fall Sale here Waterfront Beach Home🏖️Hot Tub+Stunning Views
Exclusive Weekend Fall Sale here Waterfront Beach Home🏖️Hot Tub+Stunning Views
9.8 out of 10, Exceptional, (70)
"Great family get together where we all were very comfortable. "
United States
Leanne B.
Exclusive Weekend Fall Sale here Waterfront Beach Home🏖️Hot Tub+Stunning Views
Private kitchen
Fully Furnished Private Loft Style Charm Trumbull Elevator
Fully Furnished Private Loft Style Charm Trumbull Elevator
7.0 out of 10, Good, (2)
"Great place to stay. Lots of room compared to a hotel room and it's nice to have the kitchen area. We used the bonus spaces a lot and found the building to be very quiet from room to room. The noise from outside at night was mostly car noise and seemed pretty standard for being in a central location. Thank you!"
United States
Emily
$170 nightly
The price is $193
Oct 27 - Oct 28
Total with taxes and fees
Fully Furnished Private Loft Style Charm Trumbull Elevator
Interior
Stunning Apt W/ Parking and Gym | Downtown at Yale
Stunning Apt W/ Parking and Gym | Downtown at Yale
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
Fridge, microwave, oven, stovetop
Cozy Two Bedroom Stay In Downtown New Haven!
Cozy Two Bedroom Stay In Downtown New Haven!
10.0 out of 10, Exceptional, (1)
"Exactly as advertised and had nice personal touches. Very close to attractions and very walkable. "
United States
Kimberly S.
$312 nightly
The price is $322
Oct 26 - Oct 27
Total with taxes and fees
Cozy Two Bedroom Stay In Downtown New Haven!
Outdoor dining
DIRECT WATERFRONT with awesome views and near Yale
DIRECT WATERFRONT with awesome views and near Yale
10.0 out of 10, Exceptional, (2)
"Great place to stay! Easy for an overnight for a family wedding!"
United States
Phoebe T.
$406 nightly
The price is $459
Oct 30 - Oct 31
Total with taxes and fees
DIRECT WATERFRONT with awesome views and near Yale
Exterior
Angelica’s safe haven @ west haven
Angelica’s safe haven @ west haven
10.0 out of 10, Exceptional, (5)
"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
$297 nightly
The price is $336
Oct 24 - Oct 25
Total with taxes and fees
Angelica’s safe haven @ west haven
Property grounds
Rustic Charm Meets Modern Comfort 3-Bedroom Raised-Ranch Cottage in Wooded Area
Rustic Charm Meets Modern Comfort 3-Bedroom Raised-Ranch Cottage in Wooded Area
9.8 out of 10, Exceptional, (6)
"Everything was amazing "
United States
MELISSA G.
Rustic Charm Meets Modern Comfort 3-Bedroom Raised-Ranch Cottage in Wooded Area
Interior
Chic 1-bedroom apartment with WiFi, fitness room in cool New Haven
Chic 1-bedroom apartment with WiFi, fitness room in cool New Haven
$269 nightly
The price is $304
Oct 24 - Oct 25
Total with taxes and fees
Chic 1-bedroom apartment with WiFi, fitness room in cool New Haven
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

Best Western Executive Hotel Of New Haven - West Haven

Best Western Executive Hotel Of New Haven - West Haven

10/10 Excellent
"Very nice"
Mahmut 1-night trip
Posted 1 day ago
Best Western Executive Hotel Of New Haven - West Haven

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 $158 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.