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Holiday Rentals in Chester

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Our top choices for Chester holiday rentals

1. Serene Pondside Retreat Surrounded by Nature

Serene Pondside Retreat Surrounded by Nature
Deerfield
The price is €545
includes taxes & fees
8 Sept - 9 Sept
Serene Pondside Retreat Surrounded by Nature

2. Postcard Cabins Blake Brook, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Blake Brook, Outdoor Collection by Marriott Bonvoy
2.5 star property
Epsom
9.6 out of 10, Exceptional, (204 reviews)
"Great stay"
United States
Anthony
The price is €172
includes taxes & fees
30 Sept - 1 Oct
Postcard Cabins Blake Brook, Outdoor Collection by Marriott Bonvoy

3. Family Oasis

Family Oasis
Kalivas Union
10.0 out of 10, Exceptional, (2 reviews)
"The house was spotless, and the linens were fresh and clean. There were ample coffee-making appliances, which was a great touch. I especially appreciated the generous supply of towels and the excellent lighting throughout the space."
United States
Elisse D.
The price is €682
includes taxes & fees
1 Oct - 2 Oct
Family Oasis

4. Large 3 floor Townhome with Patio, Backyard and Sauna

Large 3 floor Townhome with Patio, Backyard and Sauna
Rimmon Heights
9.8 out of 10, Exceptional, (20 reviews)
"Great place for a church group to brainstorm and pray! Comfortable and relaxing."
United States
Jeremy S.
The price is €601
includes taxes & fees
6 Sept - 7 Sept
Large 3 floor Townhome with Patio, Backyard and Sauna

5. Relaxing Family friendly Apartment!!

Relaxing Family friendly Apartment!!
Rimmon Heights
9.6 out of 10, Exceptional, (21 reviews)
"Would definitely stay again! House was clean and had everything we needed and more!!We were a group of 6 and there was plenty of room for all! "
United States
Sarah W.
The price is €306
includes taxes & fees
9 Sept - 10 Sept
Relaxing Family friendly Apartment!!

6. Spacious, family friendly 3700 sq ft w/ great yard

Spacious, family friendly 3700 sq ft w/ great yard
Straw-Smyth
The price is €943
includes taxes & fees
2 Oct - 3 Oct
Spacious, family friendly 3700 sq ft w/ great yard

7. Near Shopping & Canobie Lake! Apartment w/ Grill

Near Shopping & Canobie Lake! Apartment w/ Grill
3.5 star property
Salem
The price is €197
includes taxes & fees
6 Sept - 7 Sept
Near Shopping & Canobie Lake! Apartment w/ Grill

8. The Cottages at Harvey Lake

The Cottages at Harvey Lake
3.0 star property
Northwood
8.8 out of 10, Excellent, (48 reviews)
"The view of the lake from the cabin was excellent. "
United States
Matt
The price is €127
includes taxes & fees
10 Sept - 11 Sept
The Cottages at Harvey Lake

9. The Amoskeag - Ash Street Inn

The Amoskeag - Ash Street Inn
Corey Square
The price is €251
includes taxes & fees
1 Oct - 2 Oct
The Amoskeag - Ash Street Inn

10. 4 Corners At Amesbury Downtown Pet Friendly

4 Corners At Amesbury Downtown Pet Friendly
Amesbury
10.0 out of 10, Exceptional, (9 reviews)
" Clean and tidy a lot of space very good people cant wait for our next stay"
United States
Donald
The price is €492
includes taxes & fees
2 Sept - 3 Sept
4 Corners At Amesbury Downtown Pet Friendly

11. Marvelous 3-bedroom townhome with Heated floor Manchester

Marvelous 3-bedroom townhome with Heated floor Manchester
Highlands
9.4 out of 10, Exceptional, (6 reviews)
"Location was close to stores and easy access to the highway. Everything was new and clean. Beds were very comfortable.Would be a great location for families coming for college graduation. Would stay here again "
United States
Kimberly D.
The price is €373
includes taxes & fees
8 Sept - 9 Sept
Marvelous 3-bedroom townhome with Heated floor Manchester

12. Triple Family Unit Combined

Triple Family Unit Combined
Rimmon Heights
10.0 out of 10, Exceptional, (4 reviews)
"Great location! Lots of room!"
United States
Jessica C.
Triple Family Unit Combined

13. Charming quiet

Charming quiet
Rimmon Heights
9.8 out of 10, Exceptional, (18 reviews)
"Had everything we needed from snacks, to water! Great place to stay! "
United States
Sierra M.
The price is €283
includes taxes & fees
1 Oct - 2 Oct
Charming quiet

14. Heated Winter Stay • 3BR Home • Pet-Friendly • Free Parking • Near Hospitals • 6

Heated Winter Stay • 3BR Home • Pet-Friendly • Free Parking • Near Hospitals • 6
Manchester
10.0 out of 10, Exceptional, (1 review)
The price is €538
includes taxes & fees
2 Oct - 3 Oct
Heated Winter Stay • 3BR Home • Pet-Friendly • Free Parking • Near Hospitals • 6

15. North End Retreat

North End Retreat
North End
10.0 out of 10, Exceptional, (3 reviews)
"Fantastic location for our need, easy to navigate surrounding area, exactly as listed and the cleanest place I’ve ever stayed in. We will be back!!"
United States
Diane A.
The price is €543
includes taxes & fees
13 Sept - 14 Sept
North End Retreat

16. Fabulous 3-bedroom house in Manchester

Fabulous 3-bedroom house in Manchester
Manchester
9.4 out of 10, Exceptional, (13 reviews)
"Great place to stay. The rooms were clean and the host was very communicative and accommodating."
United States
gisselle f.
The price is €314
includes taxes & fees
9 Sept - 10 Sept
Fabulous 3-bedroom house in Manchester

17. Mini cozy quiet apartment

Mini cozy quiet apartment
Rimmon Heights
9.8 out of 10, Exceptional, (12 reviews)
"Nice stay. Nice property. Would stay again"
United States
John B.
The price is €212
includes taxes & fees
1 Oct - 2 Oct
Mini cozy quiet apartment

18. Modern, All New 3BR Near UMASS

Modern, All New 3BR Near UMASS
Lowell
9.6 out of 10, Exceptional, (19 reviews)
"Great location for trips to Boston and local university graduation"
United States
John Y.
Modern, All New 3BR Near UMASS

19. Charming & Historic 2BR Oasis in Downtown Luxury

Charming & Historic 2BR Oasis in Downtown Luxury
Downtown Manchester
10.0 out of 10, Exceptional, (31 reviews)
"Great apartment! Clean, comfortable and fantastic location. Would happily stay there again."
United States
Tracy S.
The price is €390
includes taxes & fees
23 Sept - 24 Sept
Charming & Historic 2BR Oasis in Downtown Luxury
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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Top Chester Hotel Reviews

Find out more about Chester

Everything you need to know about Chester 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 Chester 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 Chester holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Chester holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chester. 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 Chester 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 Chester holiday rentals we have selected for you start as low as €172 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Chester rentals

At Expedia, we put the best Chester 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 Chester 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 Chester 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 Chester. 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 Chester?

Yes, there are holiday rentals close to the most popular sights in Chester, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Chester has to offer?

2-bedroom lakeside retreat in beautiful Windham: This holiday home rental outside of Chester is on a lake, and equipped with air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include an electric kettle to make your meal-planning easier.

What can I see and do in Chester?

While exploring the area, visit family-friendly sights like Canobie Lake Park, or get outside and enjoy nature at Onway Lake. While here, Chester Public Library and Chester Town Hall are other places worth a visit.

What are holiday rentals like in Chester?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Chester. Holiday rentals offer extras such as hot tubs, fire pits and patios so you'll have a home away from home. If you're concerned about a clean environment, a holiday rental can provide a sense of seclusion away from public hotel lifts and busy reception areas while still allowing you the excitement and enjoyment of travel. You'll also have more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a popular option for a small group gathering.