Photo by Tai Bui

Cheshire Holiday Rentals

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Holiday Rentals in Cheshire

New Haven Village Suites

3.0 star property
7.6 out of 10, Good, (1984)
"It was good"
The price is NZ$200
includes taxes & fees
26 Dec - 27 Dec
New Haven Village Suites

Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub

10.0 out of 10, Exceptional, (127)
"Although I went went it is cold the view and location were excellant. I can definately see taking advantage of this place during the summer. The host was responsive and available. "
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub

Luxury Furnished Apartments by Hyatus Downtown at Yale

3.5 star property
9.8 out of 10, Exceptional, (37)
"Great location. Nice place. Noisy neighbors though"
Luxury Furnished Apartments by Hyatus Downtown at Yale

cozy 1 bedroom 3rd floor nice quiet and conveniently located next to everything.

The price is NZ$202
includes taxes & fees
26 Dec - 27 Dec
cozy 1 bedroom 3rd floor nice quiet and conveniently located next to everything.

Beautiful cozy rooms near hospital and down town area

7.8 out of 10, Good, (18)
"I will forever love coming here. The host was great, Parking was amazing, Rooms were so cleanly. "
The price is NZ$443
includes taxes & fees
6 Jan - 7 Jan 2025
Beautiful cozy rooms near hospital and down town area

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

10.0 out of 10, Exceptional, (24)
"The house is an architectural gem with plenty of space for the family. We enjoyed the fireplace in the evenings."
A TREETOPS Retreat! Sleeps 10-12, perfect for large gatherings. Seasonal POOL!

Gorgeous Victorian direct ocean front single family six bedroom, ten rooms

10.0 out of 10, Exceptional, (58)
"Great"
Gorgeous Victorian direct ocean front single family six bedroom, ten rooms

Waterfront Cottage in Branford

10.0 out of 10, Exceptional, (89)
"House is beautiful and the view even better. On the waters edge and very quiet grandkids were occupied and very happy "
Waterfront Cottage in Branford

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

Grace Island. Private Island! Vacations, Getaways, Weddings & Special Events.

Grace Island. Private Island! Vacations, Getaways, Weddings & Special Events.

Beachfront 3-bedroom vacation home just 14 minutes from Yale University

10.0 out of 10, Exceptional, (28)
"Very comfortable home. Perfect for our grown family. We enjoyed the relaxed atmosphere, the beach and water views right outside the back steps. We set up our umbrellas and chairs, had fun using the kyack and paddle board. It was a wonderful and relaxing time together! Looking forward to it again next year."
Beachfront 3-bedroom vacation home just 14 minutes from Yale University

The Dream Location for Your Perfect Vacation

9.8 out of 10, Exceptional, (16)
"beautiful quiet spot on the beach, great place to stay."
The Dream Location for Your Perfect Vacation

Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape

10.0 out of 10, Exceptional, (27)
"This was a great get away for Thanksgiving. The listing is very accurate and the house is very well equipped especially as far as the kitchen and supplies. The space is very well thought out as well. "
Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape

Beautiful 4BR Beach House with Private Beach Access.

9.8 out of 10, Exceptional, (69)
"our annual girls (5) trip took us to Branford, CT this year. It was awesome to have a private beach access even though we couldn’t get in the water, but it was great for strolls and shell collecting. Would definitely do better with a second bathroom, but we managed just fine. Overall, it’s a nice little place to stay for a getaway. My only issue is not with the hosts or place, but with one of the fees and the checkout process. However, it does not take away from our stay. "
Beautiful 4BR Beach House with Private Beach Access.

New Haven Gem w/ Private Pool, Walk to Beach!

9.6 out of 10, Exceptional, (4)
"In town for college visits we were able to stay and use the home as “base” giving everyone space - inside and out to decompress. Kitchen was great and outdoor space is lovely. Beautiful walk to Lighthouse Point Park!"
New Haven Gem w/ Private Pool, Walk to Beach!

Writer's Retreat & Explorer's Adventure, S of Rte. 1 Madison!

9.8 out of 10, Exceptional, (24)
"I can not say enough about our stay. Hunter was an amazing host and communication was quick, easy, and made the experience delightful!!! The house is bright and comfy and the view was stunning and relaxing. Every room was perfect from bedroom to living room to kitchen. We wanted for nothing. A quiet getaway to relax was what we were looking for and this was the perfect stay for that. We would love to come back again when we need downtime. This was one of our favorite VRBO rentals ever. Thank...
Writer's Retreat & Explorer's Adventure, S of Rte. 1 Madison!

Cozy & Chic Cabin by the Lake, with access to private Beach!

10.0 out of 10, Exceptional, (17)
"great chic house, very clean"
Cozy & Chic Cabin by the Lake, with access to private Beach!

Amazing Waterfront Home Private Beach 🏖+ Hot Tub

9.8 out of 10, Exceptional, (59)
"Overall the house was great. The beds were so so comfortable and the house has everything you need to cook and grill. Unfortunately weather wasn’t ideal but we still got to enjoy the hot tub and at least check out the private beach. The beach is across the street and it’s not too bad, just a lot of sharp shells so I’d rec wearing some sandals to and on the beach! The house is a lot bigger than we realized and beautiful views all around. Owner was great and responsive. The master was awesome and...
Amazing Waterfront Home Private Beach 🏖+ Hot Tub

Lake Front home, dock w/2 kayaks, firepit, grill, pedal boat. Lv2 EV charger

9.4 out of 10, Exceptional, (6)
"There was 7 family members all had sleeping quarters. We enjoyed the location. The lake was beautiful went out on kayaks and enjoyed walks around the neighborhood. Sat outside and played games and enjoyed the fire. Nice weekend was had by all "
Lake Front home, dock w/2 kayaks, firepit, grill, pedal boat. Lv2 EV charger

Life is Better at the Beach!

10.0 out of 10, Exceptional, (28)
"When I walked in I immediately noticed how spotless the place was. Every room looked exactly like the pictures that were listed. They had all of the essentials. We didn't need anything except food. The host and the people in the neighborhood were friendly. It was a comfortable and fun stay."
Life is Better at the Beach!
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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Other types of properties in Cheshire you may be interested in

Holiday Inn Cheshire - Southington, an IHG Hotel

3.0 star property
8.4 out of 10, Very good, (951)
"Staff was super nice"
The price is NZ$165
includes taxes & fees
5 Jan - 6 Jan 2025
Holiday Inn Cheshire - Southington, an IHG Hotel

Cheshire Welcome Inn

2.5 star property
8.4 out of 10, Very good, (635)
"It was nice room but they had heat entirely off when i arrived The room was like a refrigerator "
The price is NZ$189
includes taxes & fees
30 Dec - 31 Dec
Cheshire Welcome Inn

New Haven Hotel

3.5 star property
8.8 out of 10, Excellent, (1376)
"Nice clean n updated property in the middle of everything "
The price is NZ$223
includes taxes & fees
1 Jan - 2 Jan 2025
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 holiday rental in Cheshire?

Yes, there are holiday rentals in Cheshire close to Drazen Orchards, or you can select a more secluded option if you're looking for a relaxing stay. Our travellers 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 holiday rentals that Cheshire has to offer?

A TREETOPS Retreat! Sleeps 10-12, perfect for large gatherings. Seasonal POOL!: This holiday home rental outside of Cheshire is located in the city centre, and has an outdoor pool, a fireplace and a BBQ 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 that you can cook with friends or family. It offers a balcony, a garden and a selection of books so that you can immerse yourself in your holiday.

How many holiday rentals are there in Cheshire?

Expedia has 3 holiday 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 holiday rental in Cheshire like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Cheshire. Holiday rentals offer amenities like WiFi and washers and dryers so you'll feel just like you're staying in your own home. If you're concerned about a sanitised environment, holiday rentals can offer a sense of seclusion away from public hotel lifts and busy lobbies while still allowing you to travel. You'll also get more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular option for small groups.