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Chester Holiday Rentals

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Check prices for these dates

In two weeks
18 Sept - 20 Sept
In two months
30 Oct - 1 Nov
In three months
27 Nov - 29 Nov
In four months
25 Dec - 27 Dec

Our top choices for Chester holiday rentals

Exterior

1. Serene Pondside Retreat Surrounded by Nature

Serene Pondside Retreat Surrounded by Nature
Deerfield
The price is HK$974
HK$4,892 total
includes taxes & fees
8 Sept - 9 Sept
Serene Pondside Retreat Surrounded by Nature
View from property

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 HK$1,129
HK$1,565 total
includes taxes & fees
30 Sept - 1 Oct
Postcard Cabins Blake Brook, Outdoor Collection by Marriott Bonvoy
Living area

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 HK$2,320
HK$6,277 total
includes taxes & fees
9 Sept - 10 Sept
Family Oasis
Private kitchen

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 HK$2,277
HK$5,354 total
includes taxes & fees
6 Sept - 7 Sept
Large 3 floor Townhome with Patio, Backyard and Sauna
Living area

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 HK$1,505
HK$2,790 total
includes taxes & fees
9 Sept - 10 Sept
Relaxing Family friendly Apartment!!
Private kitchen

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

Spacious, family friendly 3700 sq ft w/ great yard
Straw-Smyth
The price is HK$5,244
HK$8,403 total
includes taxes & fees
2 Sept - 3 Sept
Spacious, family friendly 3700 sq ft w/ great yard
Front of property

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

Near Shopping & Canobie Lake! Apartment w/ Grill
3.5 star property
Salem
The price is HK$894
HK$1,791 total
includes taxes & fees
6 Sept - 7 Sept
Near Shopping & Canobie Lake! Apartment w/ Grill
Lake

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 HK$1,066
HK$1,157 total
includes taxes & fees
10 Sept - 11 Sept
The Cottages at Harvey Lake
Interior

9. The Amoskeag - Ash Street Inn

The Amoskeag - Ash Street Inn
Corey Square
The price is HK$1,356
HK$2,270 total
includes taxes & fees
6 Sept - 7 Sept
The Amoskeag - Ash Street Inn
Terrace/patio

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 HK$2,725
HK$5,376 total
includes taxes & fees
23 Sept - 24 Sept
4 Corners At Amesbury Downtown Pet Friendly
Living area

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 HK$1,538
HK$3,370 total
includes taxes & fees
8 Sept - 9 Sept
Marvelous 3-bedroom townhome with Heated floor Manchester
Living area

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.
The price is HK$4,115
HK$8,497 total
includes taxes & fees
9 Sept - 10 Sept
Triple Family Unit Combined
Private kitchen

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 HK$1,325
HK$2,569 total
includes taxes & fees
2 Sept - 3 Sept
Charming quiet
Interior

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 HK$1,672
HK$4,502 total
includes taxes & fees
15 Sept - 16 Sept
Heated Winter Stay • 3BR Home • Pet-Friendly • Free Parking • Near Hospitals • 6
Private kitchen

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 HK$1,960
HK$4,856 total
includes taxes & fees
13 Sept - 14 Sept
North End Retreat
Room

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 HK$1,129
HK$2,858 total
includes taxes & fees
8 Sept - 9 Sept
Fabulous 3-bedroom house in Manchester
Room

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 HK$933
HK$1,888 total
includes taxes & fees
2 Sept - 3 Sept
Mini cozy quiet apartment
Dining

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
Living area

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 HK$1,434
HK$3,538 total
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

Exeter Inn

Exeter Inn

10/10 Excellent
"Nice independent motel with great restaurant in the lobby. Clean rooms and helpful staff."
Brian 1-night trip
Posted 2 hours ago
Exeter Inn

Find out more about Chester

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

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

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

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.