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Chester Holiday Rentals

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Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Chester holiday rentals

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1. 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, (231 reviews)
"Great stay"
United States
Anthony
The price is HK$997
HK$1,422 total
includes taxes & fees
17 Nov - 18 Nov
Postcard Cabins Blake Brook, Outdoor Collection by Marriott Bonvoy
A spacious living room with a white sofa, a coffee table, and a chandelier.

2. Marvelous 3-bedroom townhome with Heated floor Manchester

Marvelous 3-bedroom townhome with Heated floor Manchester
Highlands
9.0 out of 10, Wonderful, (7 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$1,540
HK$2,846 total
includes taxes & fees
28 Oct - 29 Oct
Marvelous 3-bedroom townhome with Heated floor Manchester
A living room with a wooden floor, a grey sofa, a coffee table with a vase, and a flat-screen TV mounted on the wall.

3. Family Oasis

Family Oasis
Kalivas Union
10.0 out of 10, Exceptional, (3 reviews)
"Very clean interior."
United States
Douglas
The price is HK$2,323
HK$6,225 total
includes taxes & fees
22 Oct - 23 Oct
Family Oasis
A neatly made bed with a white duvet and several pillows, a grey rug, and a dark headboard in a room with a simple, clean design.

4. Mini cozy quiet apartment

Mini cozy quiet apartment
Rimmon Heights
9.8 out of 10, Exceptional, (13 reviews)
"Nice stay. Nice property. Would stay again"
United States
John B.
The price is HK$934
HK$2,061 total
includes taxes & fees
25 Oct - 26 Oct
Mini cozy quiet apartment
A stainless steel refrigerator with a water dispenser, wooden cabinets, a granite countertop, and a black trash can.

5. 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$1,326
HK$2,538 total
includes taxes & fees
25 Oct - 26 Oct
Charming quiet
A modern kitchen with a central island, bar stools, hanging pendant lights, and a stainless steel refrigerator.

6. Serene Pondside Retreat Surrounded by Nature

Serene Pondside Retreat Surrounded by Nature
Deerfield
10.0 out of 10, Exceptional, (1 review)
"Wonderful property - we stayed here to visit our nearby family and attend opening day of the Deerfield fair. The property is immaculately maintained and the host responsive. We’ll be back!"
United States
Bobbi S.
The price is HK$1,519
HK$5,582 total
includes taxes & fees
26 Oct - 27 Oct
Serene Pondside Retreat Surrounded by Nature
A kitchen with wooden cabinets, a microwave, an LG dishwasher, and a window with blinds.

7. Relaxing Family friendly Apartment!!

Relaxing Family friendly Apartment!!
Rimmon Heights
9.6 out of 10, Exceptional, (21 reviews)
"Very nice stay."
United States
Colleen H.
The price is HK$1,648
HK$2,929 total
includes taxes & fees
20 Oct - 21 Oct
Relaxing Family friendly Apartment!!
A room with a chandelier, a fireplace, a dining table, a sofa, and a chessboard.

8. The Amoskeag - Ash Street Inn

The Amoskeag - Ash Street Inn
Corey Square
The price is HK$1,311
HK$2,205 total
includes taxes & fees
21 Oct - 22 Oct
The Amoskeag - Ash Street Inn
A modern kitchen with white cabinets, stainless steel appliances, a wooden ceiling, and a green accent wall.

9. 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 house for our large family. "
United States
Kayla B.
The price is HK$2,238
HK$5,246 total
includes taxes & fees
20 Oct - 21 Oct
Large 3 floor Townhome with Patio, Backyard and Sauna
A two-story house with a front porch, surrounded by a well-maintained lawn and trees.

10. Private Studio/Bathroom Handicap Accessible Room in Single Family Home

Private Studio/Bathroom Handicap Accessible Room in Single Family Home
Windham
The price is HK$459
HK$1,009 total
includes taxes & fees
20 Oct - 21 Oct
Private Studio/Bathroom Handicap Accessible Room in Single Family Home
A living room with a flat-screen TV mounted on the wall, a dark wooden coffee table with a potted plant and decorative items, and a small side table with a lamp.

11. 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$1,391
HK$3,170 total
includes taxes & fees
2 Nov - 3 Nov
Heated Winter Stay • 3BR Home • Pet-Friendly • Free Parking • Near Hospitals • 6
A small, rustic room with a single bed, a cabinet, and a shelf with various items.

12. This one room camping cabin is a great alternative to a tent camp site.

This one room camping cabin is a great alternative to a tent camp site.
Epping
The price is HK$1,102
HK$1,553 total
includes taxes & fees
20 Oct - 21 Oct
This one room camping cabin is a great alternative to a tent camp site.
A living room with a dark brown leather sofa, a wooden coffee table, and a white door.

13. Triple Family Unit Combined

Triple Family Unit Combined
Rimmon Heights
10.0 out of 10, Exceptional, (6 reviews)
"Great location! Lots of room!"
United States
Jessica C.
The price is HK$4,458
HK$8,898 total
includes taxes & fees
28 Oct - 29 Oct
Triple Family Unit Combined
A living room with a sofa, armchair, coffee table, lamp, and potted plant.

14. Bright & Cozy Entire Apartment - Your New England Hub

Bright & Cozy Entire Apartment - Your New England Hub
Haverhill
9.8 out of 10, Exceptional, (8 reviews)
"It was a great place to stay."
United States
Lorraine B.
The price is HK$1,393
HK$3,187 total
includes taxes & fees
20 Oct - 21 Oct
Bright & Cozy Entire Apartment - Your New England Hub
A modern kitchen with wooden cabinets, a stainless steel refrigerator, and a dining area with a table and chairs.

15. Family Friendly

Family Friendly
Rimmon Heights
10.0 out of 10, Exceptional, (9 reviews)
"This was a great rental for us! The apartments were spotlessly clean, well-appointed, and all updated. The beds were surprisingly comfortable, and there were thoughtful touches everywhere. It is clear the owners think about the needs and comfort of their guests! The stairs are a bit steep but it was fine for our group. We would definitely rent this place again!"
United States
Stacy B.
The price is HK$2,119
HK$4,998 total
includes taxes & fees
25 Oct - 26 Oct
Family Friendly
A modern bedroom with a bed, a TV, a ceiling fan, and a window with blinds.

16. Aariz Nest

Aariz Nest
Methuen
10.0 out of 10, Exceptional, (1 review)
"Friendly and helpful hostess greeted me upon arrival. VRBO app was very useful for communication. Having a washer and dryer in the unit was great. The TV had Netflix, but I mostly screen casted from my iPad while was there (16 days). Had my own entrance and parking spot in the driveway. I really can't think of any negative outside of a broken handle on the microwave, which was no big deal. Recommended!"
United States
Mark S.
The price is HK$1,570
HK$2,507 total
includes taxes & fees
20 Oct - 21 Oct
Aariz Nest
A two-story red house with a front porch, a driveway, and a well-maintained garden with various shrubs and a circular lawn feature.

17. Spacious 2BR Apartment Near Bradford & Merrimack Valley Parking Included.

Spacious 2BR Apartment Near Bradford & Merrimack Valley Parking Included.
Haverhill
9.2 out of 10, Wonderful, (7 reviews)
"Family really enjoyed alot Thank you. "
United States
Andrew G.
The price is HK$1,334
HK$2,700 total
includes taxes & fees
26 Oct - 27 Oct
Spacious 2BR Apartment Near Bradford & Merrimack Valley Parking Included.
A modern kitchen with wooden cabinets, stainless steel appliances, and a dining area with a table and chairs.

18. Beautiful & Relaxing Nashua Home - Minutes from Downtown

Beautiful & Relaxing Nashua Home - Minutes from Downtown
Nashua
10.0 out of 10, Exceptional, (20 reviews)
"Great home that had everything we needed for our stay! Many great amenities close by. Amazing communication by host! "
United States
Kristina M.
The price is HK$1,771
HK$4,443 total
includes taxes & fees
21 Oct - 22 Oct
Beautiful & Relaxing Nashua Home - Minutes from Downtown
A bedroom with a bed, two bedside tables, a door, and curtains.

19. Downtown Amesbury! 15 Mins to Beach

Downtown Amesbury! 15 Mins to Beach
Amesbury
10.0 out of 10, Exceptional, (1 review)
"Perfect place! Easy walk to downtown Amesbury. Quite neighborhood "
United States
Holly B.
The price is HK$1,177
HK$2,440 total
includes taxes & fees
28 Oct - 29 Oct
Downtown Amesbury! 15 Mins to Beach
A kitchen with white cabinets, a granite countertop, a stove, a sink, and a refrigerator.

20. Lovely Downtown Oasis ~ Hospitals/Colleges/Beaches

Lovely Downtown Oasis ~ Hospitals/Colleges/Beaches
Amesbury
8.8 out of 10, Excellent, (3 reviews)
"Everything was as advertised. We needed a one night stay to break up our road trip. Check in was as easy as possible. Was clean and comfortable. Would use again if in the area."
United States
Nancy M.
The price is HK$1,088
HK$2,228 total
includes taxes & fees
21 Oct - 22 Oct
Lovely Downtown Oasis ~ Hospitals/Colleges/Beaches
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

Methuen Inn and Conference Center

Methuen Inn and Conference Center

10/10 Excellent
"Did a one stop night on our way out from Salem and flying out of Boston Logan. Room was clean, AC worked, room was clean, and had no problems with anything during our very short stay. Good value for a weekend room"
Robert 1-night trip
Posted 12 hours ago
Methuen Inn and Conference Center

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?

Indoor Pool, 2 Miles From Ocean, 7,000 Square Foot Luxury Home: This holiday home rental outside of Chester is located in a rural location, and has an indoor pool, a patio and a BBQ to put you at ease in your new surroundings. It has 9 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.

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.