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Chester Vacation Rentals

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Check prices for these dates

In two weeks
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

Our top choices for Chester vacation rentals

View from property

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, (222 reviews)
"Great stay"
United States
Anthony
The price is AED 496
AED 697 total
includes taxes & fees
5 Nov - 6 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 AED 721
AED 1,352 total
includes taxes & fees
13 Oct - 14 Oct
Marvelous 3-bedroom townhome with Heated floor Manchester
A room with a chandelier, a fireplace, a dining table, a sofa, and a chessboard.

3. The Amoskeag - Ash Street Inn

The Amoskeag - Ash Street Inn
Corey Square
The price is AED 613
AED 1,024 total
includes taxes & fees
8 Oct - 9 Oct
The Amoskeag - Ash Street Inn
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.

4. 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 AED 1,087
AED 2,913 total
includes taxes & fees
11 Oct - 12 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.

5. 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 AED 437
AED 972 total
includes taxes & fees
11 Oct - 12 Oct
Mini cozy quiet apartment
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 AED 711
AED 2,612 total
includes taxes & fees
26 Oct - 27 Oct
Serene Pondside Retreat Surrounded by Nature
A stainless steel refrigerator with a water dispenser, wooden cabinets, a granite countertop, and a black trash can.

7. 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 AED 621
AED 1,200 total
includes taxes & fees
11 Oct - 12 Oct
Charming quiet
A living room with a brown leather sofa, a wooden coffee table, and a white door.

8. 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 AED 705
AED 1,291 total
includes taxes & fees
18 Oct - 19 Oct
Relaxing Family friendly Apartment!!
A two-story house with a front porch, surrounded by a well-maintained lawn and trees.

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

Private Studio/Bathroom Handicap Accessible Room in Single Family Home
Windham
The price is AED 215
AED 472 total
includes taxes & fees
8 Oct - 9 Oct
Private Studio/Bathroom Handicap Accessible Room in Single Family Home
A small, rustic room with a single bed, a cabinet, and a shelf with various items.

10. 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 AED 516
AED 727 total
includes taxes & fees
8 Oct - 9 Oct
This one room camping cabin is a great alternative to a tent camp site.
A modern kitchen with white cabinets, stainless steel appliances, a wooden ceiling, and a green accent wall.

11. 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 AED 1,047
AED 2,467 total
includes taxes & fees
11 Oct - 12 Oct
Large 3 floor Townhome with Patio, Backyard and Sauna
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.

12. 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 AED 674
AED 1,501 total
includes taxes & fees
19 Oct - 20 Oct
Heated Winter Stay • 3BR Home • Pet-Friendly • Free Parking • Near Hospitals • 6
A living room with a sofa, armchair, coffee table, lamp, and potted plant.

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

Bright & Cozy Entire Apartment - Your New England Hub
Haverhill
9.8 out of 10, Exceptional, (7 reviews)
"It was a great place to stay."
United States
Lorraine B.
The price is AED 652
AED 1,491 total
includes taxes & fees
8 Oct - 9 Oct
Bright & Cozy Entire Apartment - Your New England Hub
A modern bedroom with a bed, a TV, a ceiling fan, and a window with blinds.

14. 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 AED 661
AED 1,079 total
includes taxes & fees
8 Oct - 9 Oct
Aariz Nest
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)
"Very clean and plenty of room for everyone. Hosts were quick to respond to our questions. "
United States
Nicole A.
The price is AED 992
AED 2,351 total
includes taxes & fees
11 Oct - 12 Oct
Family Friendly
A two-story red house with a front porch, a driveway, and a well-maintained garden with various shrubs and a circular lawn feature.

16. 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.
Spacious 2BR Apartment Near Bradford & Merrimack Valley Parking Included.
A living room with a dark brown leather sofa, a wooden coffee table, and a white door.

17. 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 AED 2,193
AED 4,256 total
includes taxes & fees
19 Oct - 20 Oct
Triple Family Unit Combined
A bedroom with a bed, two bedside tables, a door, and curtains.

18. 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 AED 551
AED 1,142 total
includes taxes & fees
8 Oct - 9 Oct
Downtown Amesbury! 15 Mins to Beach
A modern kitchen with wooden cabinets, stainless steel appliances, and a dining area with a table and chairs.

19. 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 AED 829
AED 2,095 total
includes taxes & fees
19 Oct - 20 Oct
Beautiful & Relaxing Nashua Home - Minutes from Downtown
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 AED 509
AED 1,043 total
includes taxes & fees
14 Oct - 15 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

Best Western Plus Executive Court Inn & Conference Center

Best Western Plus Executive Court Inn & Conference Center

10/10 Excellent
"It's the only motel I've stayed at with an arcade in the motel very cool"
Tim 1-night trip
Posted 13 hours ago
Best Western Plus Executive Court Inn & Conference Center

Frequently asked questions

Can I find a vacation rental in Chester?

Yes, we offer vacation rentals close to well known points of interest in Chester, or you can select a secluded option if you're looking for relaxation.

What are some of the best vacation home rentals in Chester?

Indoor Pool, 2 Miles From Ocean, 7,000 Square Foot Luxury Home: This vacation home rental outside of Chester is located in a rural location and has an indoor pool, a patio, and a barbecue grill 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 you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

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 vacation rentals like in Chester?

Vacation rentals are private properties you can book for several days or more in Chester. Vacation rentals feature extras such as hot tubs, fire pits, and patios to help you enjoy your stay. If you're concerned about cleanliness, vacation rentals can provide a sense of safety away from public hotel elevators and lobbies bustling with people while still allowing you a great travel experience. You'll also have more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is an attractive choice for family trips.