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Search Holiday Rentals in Cheshire

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Top Holiday Rentals in Cheshire

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
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
10.0 out of 10, Exceptional, (79)
"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.
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
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
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!
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!
10.0 out of 10, Exceptional, (6)
"Marianna was super responsive and the house was adorable!"
The price is £373
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
10.0 out of 10, Exceptional, (39)
"Sometimes you stay somewhere and the actual accomodations don't live up to the pictures online. Not the case here. This property is every bit as nice and clean as the photos make it appear. The downstairs is a very spacious, open layout. From the kitchen you can see all the way to the front windows. The bedrooms are very comfortable. Upstairs bathroom is large. House was very clean and had everything we needed. Seriously, no one in our party had a single complaint. Didn't need to contact Mike...
Beautiful, Spacious, Beachfront Home - Perfect for Entertaining Family & Friends
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
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!
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
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 £368
includes taxes & fees
6 May - 7 May
New Haven Oasis: Steps to Yale & Fine Dining
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
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
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
9.8 out of 10, Exceptional, (36)
"We stayed here for three nights, it was very clean. We had everything we needed and I felt like it was a safe neighborhood. The beds are comfortable, on the firmer side but I still slept great. Our hosts were very quick to answer all questions we had."
The price is £267
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
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 £217
includes taxes & fees
8 May - 9 May
2 Fl Loft, East Rock, YALE, SOM, New Haven, @ State St/Bishop St -Anchor Lodging
Fun Downtown Location
9.8 out of 10, Exceptional, (46)
"We enjoyed our stay for the weekend. We had 2 adults and 2 teenagers. Everyone had room to spread out. There is a full flight of stairs to enter the house and a sunroom that would be nice to enjoy in better weather. Thank you for a nice stay!"
Fun Downtown Location
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 £109
includes taxes & fees
6 May - 7 May
Clean, Comfy and Spacious Bedroom
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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.

Cheshire Holiday Rental Travel Info

Other types of properties in Cheshire you may be interested in

New Haven Hotel
3.5 star property
8.8 out of 10, Excellent, (1230)
"Nice and clean hotel with friendly and helpful staff. "
The price is £146
includes taxes & fees
13 May - 14 May
New Haven Hotel
Holiday Inn Cheshire - Southington, an IHG Hotel
3.0 star property
8.4 out of 10, Very good, (855)
"Good"
The price is £111
includes taxes & fees
5 May - 6 May
Holiday Inn Cheshire - Southington, an IHG Hotel
Cheshire Welcome Inn
2.5 star property
8.4 out of 10, Very good, (552)
"."
The price is £90
includes taxes & fees
9 May - 10 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.

Everything you need to know about Cheshire holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Cheshire holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Cheshire holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Cheshire holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Cheshire. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Cheshire holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Cheshire holiday rentals we have selected for you start as low as £109 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Cheshire rentals

At Expedia, we put the best Cheshire holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Cheshire rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Cheshire holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Cheshire. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find a holiday rental in Cheshire?

Yes, there are holiday rentals in Cheshire close to Cheshire Hollow Farm, 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?

Amazing Waterfront, Private Sandy Beach 🏖Hot Tub, Gorgeous Sunsets: This holiday home rental outside of Cheshire is located on the beach, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 4 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 garden, a selection of games and 1 hot tub 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 Cheshire Hollow Farm and Barker Character, Comic and Cartoon Museum, 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.

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