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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, (2003)
"The room layout, amenities and cleanliness were excellent. Think about adding a continental breakfast."
The price is AU$160
includes taxes & fees
24 Feb - 25 Feb
New Haven Village Suites

Luxury Furnished Apartments by Hyatus Downtown at Yale

3.5 star property
9.8 out of 10, Exceptional, (38)
"Great location. Nice place. Noisy neighbors though"
Luxury Furnished Apartments by Hyatus Downtown at Yale

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

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

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

10.0 out of 10, Exceptional, (59)
"Our family ranged in ages from 13 to 96. We were 12 people for a couple days and then 10. We all had a marvelous time and my mom just can’t stop talking about how beautiful the view and the antique furniture was. It was difficult for that many people only having two bathrooms, but we made it work. We did run out of hot water so we learned to scatter showers when possible. The view is amazing and the location was wonderful for us. I can’t say enough, how accommodating our hostess was. We told her...
Gorgeous Victorian direct ocean front single family six bedroom, ten rooms

Blue Back Bungalow

2.0 star property
9.8 out of 10, Exceptional, (9)
"Thank you so much for the amazing stay!!!! The place is beautiful, very clean and cosy! True Jem of West Hartford! We were here for my nieces wedding and felt very comfortable! Thank you for the wonderful TV set, amazing furniture, blow dryer and decorations! Everything in the house set up well and with love."
The price is AU$541
includes taxes & fees
18 Feb - 19 Feb
Blue Back Bungalow

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

10.0 out of 10, Exceptional, (116)
"The Arts and Crafts home was more beautiful than the pictures reflected! We loved all of the details in the woodwork, hidden little corners, tons of space to spread out and wonderful places to gather together. Having recently sold our "family home" we were thrilled to find this home in which to have a mini- family reunion. The kitchen was incredibly well-stocked- from serving platters to garlic powder to paper towels...We had everything we needed. The gas fireplace created a beautiful focal...
Beach Front Arts & Crafts House With Gorgeous Views Of The Sound

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!

Comfortable & Modern Living Near Yale University and New Haven Hospital

10.0 out of 10, Exceptional, (1)
The price is AU$284
includes taxes & fees
18 Feb - 19 Feb
Comfortable & Modern Living Near Yale University and New Haven Hospital

Lux Boutique Large Private LOFT Pratt St Hartford

9.2 out of 10, Wonderful, (11)
"We came for the night and the location was perfect. In walking distance to bars and restaurants. Clean, easy, no complaints. If there is a game/event at the XL Center then you should know that on-street parking may be difficult. This isn't a problem, just something to be aware of."
The price is AU$306
includes taxes & fees
18 Feb - 19 Feb
Lux Boutique Large Private LOFT Pratt St Hartford

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.

Amazing Lakefront Property

9.8 out of 10, Exceptional, (24)
"Absolutely beautiful house! Super clean! Superb setting! Very comfortable! Amazing view! Many amenities! Host very responsive and kind! The property manager quickly responded to our needs. My family and friends loved the spectacular experience and would definitely comeback! "
Amazing Lakefront Property

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

10.0 out of 10, Exceptional, (128)
"having previously rented VRBO properties in Palm Springs, West Palm Beach & Ft. Lauderdale I can confirm this property is exceptional. The studio has 1st tier amenities, waterfront location & in addition the hosts provided most welcoming foods and snacks, an overall wonderful experienceJimBrooklyn, NY"
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub

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

10.0 out of 10, Exceptional, (22)
"Mariana is a wonderful host. She communicates well and is very efficient in responding to any questions or inquiries you may have.The cabin is very clean, and has just about everything you would need. We really enjoyed using the fireplace! 10/10 recommend. "
Cozy & Chic Cabin by the Lake, with access to private Beach!

󰀄 Modern Boho Dream Home 󰀄 Completely Renovated

󰀄 Modern Boho Dream Home 󰀄 Completely Renovated

Cozy BoHo pet & family friendly near downtown & hospitals

8.4 out of 10, Very good, (7)
"We stayed 4 nights for our family trip. The home was sparkling clean and we found all we need. I love boho styled rooms. No issues with neighbors. All kind of TV subscription available. Overall very positive experience. Thank you!"
The price is AU$441
includes taxes & fees
18 Feb - 19 Feb
Cozy BoHo pet & family friendly near downtown & hospitals

Tranquil 3-bedroom house with additional full-size sofa bed in Hartford

The price is AU$602
includes taxes & fees
10 Mar - 11 Mar
Tranquil 3-bedroom house with additional full-size sofa bed in Hartford

Luxury Apartments by Hyatus at Pierpont

4.0 star property
9.4 out of 10, Exceptional, (13)
"Great. Would prefer to anyone"
Luxury Apartments by Hyatus at Pierpont

Lake house cozy to relax with a family. 6 bedroom very spacious house.

Lake house cozy to relax with a family. 6 bedroom very spacious house.

Beautiful, Spacious, Beachfront Home - Perfect for Entertaining Family & Friends

10.0 out of 10, Exceptional, (46)
"The house was beautiful and a perfect place for our family to be at while visiting our daughter who is a student at Yale. We saw the sunrise over the ocean from our bedroom window. Wish we found this sooner!"
Beautiful, Spacious, Beachfront Home - Perfect for Entertaining Family & Friends

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. "
Beautiful cozy rooms near hospital and down town area
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 by IHG

3.0 star property
8.4 out of 10, Very good, (1003)
"The staff was friendly and helpful. We would stay again. It was quiet and clean. "
The price is AU$163
includes taxes & fees
23 Feb - 24 Feb
Holiday Inn Cheshire - Southington by IHG

New Haven Hotel

3.5 star property
8.8 out of 10, Excellent, (1459)
"Great location close to Yale. Property was clean, room was comfortable and free adjacent parking was nice."
The price is AU$214
includes taxes & fees
13 Mar - 14 Mar
New Haven Hotel

Cambria Hotel New Haven University Area

3.0 star property
8.8 out of 10, Excellent, (631)
"Very classy hotel and very clean "
The price is AU$199
includes taxes & fees
16 Mar - 17 Mar
Cambria Hotel New Haven University Area
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 Barker Character, Comic and Cartoon Museum, 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.