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Cheshire Vacation Rentals

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Tonight
May 15 - May 16
Tomorrow
May 16 - May 17
This weekend
May 17 - May 19
Next weekend
May 24 - May 26

Vacation Rentals in Cheshire

Fridge, microwave, coffee/tea maker, cookware/dishes/utensils
New Haven Village Suites
3.0 star property
7.6 out of 10, Good, (1823)
"We got upgraded To a 2 bed room room and we were so happy. The room was spacious and beautiful and clean. Def will be going back and getting that room again. "
The price is ￥18,060
￥20,769 total
includes taxes & fees
Jun 10 - Jun 11
New Haven Village Suites
Property grounds
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub
10.0 out of 10, Exceptional, (110)
"I stayed at this amazing studio cottage with my girlfriend for 2 nights for her birthday. Our hosts, Liz and Adam were simply amazing. They allowed us an early check in and a late check out. Liz even brought out bicycles for us to use to tour around the neighborhood and ride along the shore line. Because it was my girlfriends birthday (or maybe they just do this), they had Prosecco and Orange Juice plus beer and cheese and other snacks for us when we arrived. The cottage is adorable, perfect...
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub
Business center
Luxury Furnished Apartments by Hyatus Downtown at Yale
3.5 star property
10.0 out of 10, Exceptional, (17)
"Everything was okay, the apartment was great, enough space for 3 people. During the nighttime no noise, silence, good for well sleeping and so on… 5 points!"
Luxury Furnished Apartments by Hyatus Downtown at Yale
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Private kitchen | Fridge, microwave, oven, stovetop
Beautiful cozy rooms near hospital and down town area
8.4 out of 10, Very Good, (9)
"My friends and I had a great time. Nice and spacious. Thanks for quick reaponces."
The price is ￥17,052
￥38,969 total
includes taxes & fees
May 16 - May 17
Beautiful cozy rooms near hospital and down town area
1 bedroom, iron/ironing board, WiFi, bed sheets
cozy 1 bedroom 3rd floor nice quiet and conveniently located next to everything.
cozy 1 bedroom 3rd floor nice quiet and conveniently located next to everything.
Property grounds
A TREETOPS Retreat! Upscale, Artsy 5 bedroom that sleeps 9-11, With POOL
10.0 out of 10, Exceptional, (15)
"By far the most unique architecture that we have ever stayed in. Every room is an adventure from its shape to the stunning artifacts from around the world. A gorgeous setting that was perfect for relaxing. Everything is first class-five star. So memorable that we are coming back next year."
A TREETOPS Retreat! Upscale, Artsy 5 bedroom that sleeps 9-11, With POOL
On the beach, beach towels
gorgeous victorian direct ocean front single family six bedroom, ten rooms
10.0 out of 10, Exceptional, (51)
"Wonderful host. Easy communication. Great house."
gorgeous victorian direct ocean front single family six bedroom, ten rooms
Pool
lakefront estate
3.8 out of 10, (8)
"Overall do not stay in this house! They are scamming people! They say they are military family yet took advantage of one!! Still owe me my refund and refuse to answer VRBO to give the okay to refund my money! This place was not clean it was very unsanitary and there were drug paraphernalia in the backyard! Towels wet and dirty on the bathroom floor and one of the bedrooms the sheets were dirty in the floor claimed that the house keeper cleaned it! The pool was disgusting!! I have videos pictures...
lakefront estate
Property grounds
Beautiful 4BR Beach House with Private Beach Access.
10.0 out of 10, Exceptional, (64)
"Small house a short walk from beach that well accommodated our party of five. Clean and comfortable, well laid out and equipped with everything you’d need."
Beautiful 4BR Beach House with Private Beach Access.
Property grounds
NEW Luxury 1bd apt w/all the amenities @ Yale, Wooster Sq, DT New Haven. Pets ok
9.0 out of 10, Wonderful, (2)
"What a great place! Location, location. Located on edge of Little Italy with great restaurants and bars. Our favorite was Zenellis. Less than 15 minute walk to downtown New Haven with lots of dining options. Take in the Trinity Bar nearby- great fun! Furniture was modest but adequate. Great kitchen."
The price is ￥23,122
￥49,126 total
includes taxes & fees
May 18 - May 19
NEW Luxury 1bd apt w/all the amenities @ Yale, Wooster Sq, DT New Haven. Pets ok
Terrace/patio
Grace Island. Private Island! Vacations, Getaways, Weddings & Special Events.
Grace Island. Private Island! Vacations, Getaways, Weddings & Special Events.
4 bedrooms, iron/ironing board, WiFi, bed sheets
Waterfront Cottage in Branford
10.0 out of 10, Exceptional, (80)
"The house is beautiful! Clean and organized. We had everything we needed and the view is incredible. We enjoyed the deck very much. So relaxing. My daughter (the bride) and her friends enjoyed getting ready there in the morning. I can’t say enough good things about this house."
Waterfront Cottage in Branford
Fridge, microwave, oven, stovetop
Spacious Victorian Loft
8.4 out of 10, Very Good, (6)
"We liked the rental. It was spacious and we appreciated the complimentary coffee. The rental is also a more affordable option in New Haven and not too far away from downtown. It was easy to get in touch with the owner, but it would’ve been helpful if they provided us checkin information in a timely manner. If you’re a light sleeper this might not be the place for you. It’s located by a busy road. There were a lot of cars that were built to be as loud as possible revving their engines into...
The price is ￥14,998
￥29,512 total
includes taxes & fees
Jun 2 - Jun 3
Spacious Victorian Loft
3 bedrooms, desk, WiFi, bed sheets
Direct Beachfront Property On Long Island Sound
10.0 out of 10, Exceptional, (26)
"We had a wonderful time on the beach, in the ocean and just relaxing in the house. There were nice restaurants in the area to try and some fun day trips to take with the kids. We'd go back!"
Direct Beachfront Property On Long Island Sound
Property grounds
The Dream Location for Your Perfect Vacation
9.8 out of 10, Exceptional, (15)
"The cottage has the most wonderful views! We loved our stay!"
The Dream Location for Your Perfect Vacation
Property grounds
Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape
10.0 out of 10, Exceptional, (18)
"Well appointed and modern. A great quiet spot for the family."
Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape
Pool
New Haven Gem w/ Private Pool, Walk to Beach!
8.0 out of 10, Very Good, (1)
"The house has a lot of updates/renovations that help it stand out from other traditional New England homes. Very comfortable, fully equipped kitchen, amenities. The property manager was very helpful and great communication. We didn't have a chance to use the pool or hot tub but would've been a big bonus if we had. I'm giving a four star rating primarily because I think the price point is a little high, there was a fair amount of outside noise (near Tweed airport), and the neighborhood feels very...
New Haven Gem w/ Private Pool, Walk to Beach!
Fridge, microwave, oven, stovetop
Amazing Waterfront, Private Sandy Beach 🏖Hot Tub, Gorgeous Sunsets
9.8 out of 10, Exceptional, (55)
"Everything was perfect!! House is amazing for family/friends gathering. Spacious, clean and great views. The home was everything we needed to celebrate the holiday. Thank you to host for communication and special touches throughout the home. Highly recommend"
Amazing Waterfront, Private Sandy Beach 🏖Hot Tub, Gorgeous Sunsets
Smart TV, books, stereo
Writer's Retreat & Explorer's Adventure, S of Rte. 1 Madison!
10.0 out of 10, Exceptional, (16)
"My month-long stay was absolutely wonderful. Hunter was an amazing, proactive host. The weather wasn't cooperative in the beginning of my stay, but Hunter went above and beyond to make sure whatever issues arose were taken care of and I couldn't be happier to have made this choice. I will definitely be back!"
Writer's Retreat & Explorer's Adventure, S of Rte. 1 Madison!
Property grounds
Guest Cottage on Country Estate
9.2 out of 10, Wonderful, (33)
"My husband and son stayed here for 5 days. They had a fabulous time hiking in the state park nearby. Thanks for a great stay!"
Guest Cottage on Country Estate
Don't see what you're looking for?
See all available properties in Cheshire
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.

Other types of properties in Cheshire you may be interested in

Exterior
Holiday Inn Cheshire - Southington, an IHG Hotel
3.0 star property
8.4 out of 10, Very Good, (858)
"Good"
The price is ￥18,163
￥20,888 total
includes taxes & fees
May 27 - May 28
Holiday Inn Cheshire - Southington, an IHG Hotel
Exterior
Cheshire Welcome Inn
2.5 star property
8.4 out of 10, Very Good, (554)
"Nice new property "
The price is ￥17,029
￥19,584 total
includes taxes & fees
May 30 - May 31
Cheshire Welcome Inn
Exterior detail
New Haven Hotel
3.5 star property
8.8 out of 10, Excellent, (1233)
"All was great!!"
The price is ￥24,874
￥28,605 total
includes taxes & fees
May 22 - May 23
New Haven Hotel
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.

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?

Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub : You might want to consider this vacation home rental near Cheshire, which is located on the beach and has an outdoor pool, a balcony, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave. Kick off your shoes and enjoy yourself with a garden and a spa tub.

How many vacation rentals are there in Cheshire?

Expedia has 3 vacation rentals for your stay in Cheshire.

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.