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Cheshire Holiday Rentals

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May 3 - May 4
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May 4 - May 5
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May 3 - May 5

Holiday Rentals in Cheshire

Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub
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
Luxury Furnished Apartments by Hyatus Downtown at Yale
Business centre
Luxury Furnished Apartments by Hyatus Downtown at Yale
3.5 star property
10.0 out of 10, Exceptional, (16)
"Apartment is very clean. Property management is very helpful. We definitely will stay here again, when we visit New Haven next time. "
Luxury Furnished Apartments by Hyatus Downtown at Yale
Waterfront Cottage in Branford
4 bedrooms, iron/ironing board, WiFi, bed sheets
Waterfront Cottage in Branford
10.0 out of 10, Exceptional, (80)
"I mean, that view! Photos are accurate and Dave was a great, responsive host. Twelve thumbs up from our group!"
Waterfront Cottage in Branford
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Beautiful 4BR Beach House with Private Beach Access.
Property grounds
Beautiful 4BR Beach House with Private Beach Access.
10.0 out of 10, Exceptional, (63)
"Very comfortable house with comfortable beds. It was great to have 4 bedrooms."
Beautiful 4BR Beach House with Private Beach Access.
Direct Beachfront Property On Long Island Sound
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
Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape
Property grounds
Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape
10.0 out of 10, Exceptional, (17)
"Well appointed and modern. A great quiet spot for the family."
Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape
Writer's Retreat & Explorer's Adventure, S of Rte. 1 Madison!
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!
Cozy & Chic Cabin by the Lake, with access to private Beach!
Exterior
Cozy & Chic Cabin by the Lake, with access to private Beach!
10.0 out of 10, Exceptional, (6)
"Marianna was super responsive and the house was adorable!"
The price is HK$1,758
HK$3,573 total
includes taxes & fees
2 Jun - 3 Jun
Cozy & Chic Cabin by the Lake, with access to private Beach!
Beautiful, Spacious, Beachfront Home - Perfect for Entertaining Family & Friends
Interior
Beautiful, Spacious, Beachfront Home - Perfect for Entertaining Family & Friends
10.0 out of 10, Exceptional, (39)
"We stayed for a second Family Christmas in a row. Stacie and Mike were great again!"
Beautiful, Spacious, Beachfront Home - Perfect for Entertaining Family & Friends
Life is Better at the Beach!
Beach nearby, sun-loungers
Life is Better at the Beach!
10.0 out of 10, Exceptional, (23)
"Nice weekend with friends and young kids. The place is family friendly, clean and has a great atmosphere. Audrey and her husband were very communicative and welcoming! We loved our stay"
Life is Better at the Beach!
Private Island Compound with Large Cottage and Guest House
Aerial view
Private Island Compound with Large Cottage and Guest House
10.0 out of 10, Exceptional, (18)
"Beautiful property with a really cool history! Loved the water toys and little beach!"
Private Island Compound with Large Cottage and Guest House
Guilford Carriage House at Granite Lodge!
1 bedroom, desk, iron/ironing board, internet
Guilford Carriage House at Granite Lodge!
10.0 out of 10, Exceptional, (3)
"Gorgeous cottage, spotless, tastefully decorated, thoughtful personal touches, many windows looking into private woods, comfortable bed with beautiful bedding!"
Guilford Carriage House at Granite Lodge!
New Haven Oasis: Steps to Yale & Fine Dining
4 bedrooms, iron/ironing board, bed sheets
New Haven Oasis: Steps to Yale & Fine Dining
10.0 out of 10, Exceptional, (1)
"This place is amazing it’s great for a big group or even family lookin for somewhere to stay, even tho the parking spaces in the back was full and no space it was a great stay and will be booking again!!"
The price is HK$1,244
HK$3,531 total
includes taxes & fees
6 May - 7 May
New Haven Oasis: Steps to Yale & Fine Dining
The Dream Location for Your Perfect Vacation
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
Amazing Waterfront, Private Sandy Beach 🏖Hot Tub, Gorgeous Sunsets
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
Amazing Beachfront - Dog Friendly-sorry, no cats-Classic Beach House
Interior
Amazing Beachfront - Dog Friendly-sorry, no cats-Classic Beach House
9.8 out of 10, Exceptional, (39)
"The house was great with a perfect location"
Amazing Beachfront - Dog Friendly-sorry, no cats-Classic Beach House
Wooster Square New Haven • 3 Bedrooms • Apizza • Yale • SOM • Downtown
Property grounds
Wooster Square New Haven • 3 Bedrooms • Apizza • Yale • SOM • Downtown
9.8 out of 10, Exceptional, (36)
"nice place in New Haven"
The price is HK$1,149
HK$2,275 total
includes taxes & fees
1 Jun - 2 Jun
Wooster Square New Haven • 3 Bedrooms • Apizza • Yale • SOM • Downtown
2 Fl Loft, East Rock, YALE, SOM, New Haven, @ State St/Bishop St -Anchor Lodging
Interior
2 Fl Loft, East Rock, YALE, SOM, New Haven, @ State St/Bishop St -Anchor Lodging
9.8 out of 10, Exceptional, (59)
"Located close to everything you need and in a quiet location close to the Yale Campus.....one of our favorite places to stay when we are in town!"
The price is HK$1,071
HK$2,086 total
includes taxes & fees
5 May - 6 May
2 Fl Loft, East Rock, YALE, SOM, New Haven, @ State St/Bishop St -Anchor Lodging
Fun Downtown Location
Dining
Fun Downtown Location
9.8 out of 10, Exceptional, (46)
"Clean, comfortable, convenient. Gracious host."
Fun Downtown Location
Clean, Comfy and Spacious Bedroom
Fridge, microwave, oven, stovetop
Clean, Comfy and Spacious Bedroom
9.6 out of 10, Exceptional, (4)
"It was exactly what we needed. long hours volunteering so, a place to rest our head, clean up and fuel our bodies. great host"
The price is HK$766
HK$1,037 total
includes taxes & fees
9 May - 10 May
Clean, Comfy and Spacious Bedroom
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

Holiday Inn Cheshire - Southington, an IHG Hotel
Exterior
Holiday Inn Cheshire - Southington, an IHG Hotel
3.0 star property
8.4 out of 10, Very good, (855)
"Good"
The price is HK$943
HK$1,085 total
includes taxes & fees
5 May - 6 May
Holiday Inn Cheshire - Southington, an IHG Hotel
Cheshire Welcome Inn
Exterior
Cheshire Welcome Inn
2.5 star property
8.4 out of 10, Very good, (552)
"."
The price is HK$852
HK$980 total
includes taxes & fees
8 May - 9 May
Cheshire Welcome Inn
Best Western Hartford Hotel & Suites
Lobby
Best Western Hartford Hotel & Suites
2.5 star property
8.0 out of 10, Very good, (1002)
"The staff was exceptional"
The price is HK$790
HK$909 total
includes taxes & fees
20 May - 21 May
Best Western Hartford Hotel & Suites
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.

Search for holiday rentals in Cheshire on Expedia! You can easily find your home rentals, villas, holiday apartments in Cheshire using one of the methods below:

  • View our selection of featured holiday rentals in Cheshire
  • Use the map to find apartments and other holiday homes in the Cheshire neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Cheshire while they last

Look no further and take a look at our great range of rental properties in Cheshire!

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.

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.

Recent reviews of Cheshire properties
Expedia verified reviews

DoubleTree by Hilton Hartford Downtown

DoubleTree by Hilton Hartford Downtown

5/5 Excellent
"Very convenient stay for the evening since we had concert tickets at the XL center. You can go into the XL center from inside the hotel. Room was clean and bed was cozy. "
A verified traveller stayed at DoubleTree by Hilton Hartford Downtown
Posted 1 day ago
DoubleTree by Hilton Hartford Downtown