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Cheshire Holiday Rentals

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Holiday Rentals in Cheshire

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 centre
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
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
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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
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.
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
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
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
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!
Exterior
Cozy & Chic Cabin by the Lake, with access to private Beach!
10.0 out of 10, Exceptional, (7)
"Absolutely loved my stay. The host was incredibly accommodating and went above and beyond to make sure we had everything we needed. The space was stylish, clean, and cozy, with thoughtful touches throughout. The location was perfect, close to all the attractions yet tucked away in a quiet neighborhood. Would highly recommend to anyone looking for a comfortable and enjoyable stay!"
The price is NZ$707
includes taxes & fees
15 May - 16 May
Cozy & Chic Cabin by the Lake, with access to private 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!
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
Interior
Beautiful, Spacious, Beachfront Home - Perfect for Entertaining Family & Friends
10.0 out of 10, Exceptional, (40)
"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
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!
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
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
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
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 NZ$442
includes taxes & fees
26 May - 27 May
2 Fl Loft, East Rock, YALE, SOM, New Haven, @ State St/Bishop St -Anchor Lodging
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 NZ$490
includes taxes & fees
2 Jun - 3 Jun
Wooster Square New Haven • 3 Bedrooms • Apizza • Yale • SOM • Downtown
Property grounds
Lake Front home, dock w/2 kayaks, firepit, grill, pedal boat. Lv2 EV charger
9.6 out of 10, Exceptional, (4)
"Super-clean and the kitchen cabinets and drawers were all labeled-a great convenience. The house is situated in a quiet and tranquil spot, perfect for unwinding and enjoying one’s companions. Not avlocation for people who need entertainment, but want tranquility and nature. Would be great if there could be access to the washer and dryer, especially when folks are in and out of the sweet lake. The owners are extremely king and helpful."
Lake Front home, dock w/2 kayaks, firepit, grill, pedal boat. Lv2 EV charger
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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 detail
New Haven Hotel
3.5 star property
8.8 out of 10, Excellent, (1240)
"Fine for older hotel. "
The price is NZ$304
includes taxes & fees
22 May - 23 May
New Haven Hotel
Exterior
Holiday Inn Cheshire - Southington, an IHG Hotel
3.0 star property
8.4 out of 10, Very good, (858)
"Good"
The price is NZ$222
includes taxes & fees
27 May - 28 May
Holiday Inn Cheshire - Southington, an IHG Hotel
Exterior
Cheshire Welcome Inn
2.5 star property
8.4 out of 10, Very good, (553)
"."
The price is NZ$208
includes taxes & fees
15 May - 16 May
Cheshire Welcome Inn
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.

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.