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Chester Vacation Rentals

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Check prices for these dates

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

Our top choices for Chester vacation rentals

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, (205 reviews)
"Great stay"
United States
Anthony
The price is ￥23,283
￥32,043 total
includes taxes & fees
Sep 7 - Sep 8
Postcard Cabins Blake Brook, Outdoor Collection by Marriott Bonvoy
A white two-story house with a front porch, surrounded by a well-maintained lawn and trees.

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

Private Studio/Bathroom Handicap Accessible Room in Single Family Home
Windham
The price is ￥9,844
￥20,854 total
includes taxes & fees
Sep 7 - Sep 8
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.

3. 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 ￥21,939
￥31,094 total
includes taxes & fees
Sep 7 - Sep 8
This one room camping cabin is a great alternative to a tent camp site.
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, (12 reviews)
"Nice stay. Nice property. Would stay again"
United States
John B.
The price is ￥18,595
￥37,131 total
includes taxes & fees
Sep 7 - Sep 8
Mini cozy quiet apartment
A black leather sofa with a colorful patterned throw blanket and two pillows.

5. 2-bedroom condo in welcoming Plaistow close to beaches, mountains, and Boston

2-bedroom condo in welcoming Plaistow close to beaches, mountains, and Boston
Plaistow
The price is ￥24,330
￥52,168 total
includes taxes & fees
Sep 7 - Sep 8
2-bedroom condo in welcoming Plaistow close to beaches, mountains, and Boston
A kitchen with wooden cabinets, a dining table, chairs, a ceiling fan, and a view through a glass door.

6. Riverfront 2BR | Home King Suite | Patio & Grill

Riverfront 2BR | Home King Suite | Patio & Grill
Epping
10.0 out of 10, Exceptional, (1 review)
"Beautiful home that actually feels bigger than the photos show. Great place to stay and would stay again"
United States
Kimberly W.
Riverfront 2BR | Home King Suite | Patio & Grill
A spacious living room with a white sofa, a coffee table, and a chandelier.

7. 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 ￥30,658
￥67,173 total
includes taxes & fees
Sep 8 - Sep 9
Marvelous 3-bedroom townhome with Heated floor Manchester
A stainless steel refrigerator with a water dispenser, wooden cabinets, a granite countertop, and a black trash can.

8. 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 ￥26,408
￥50,524 total
includes taxes & fees
Sep 7 - Sep 8
Charming quiet
A lakeside cabin with a view of a calm lake and autumn foliage.

9. 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 ￥21,251
￥23,057 total
includes taxes & fees
Sep 10 - Sep 11
The Cottages at Harvey Lake
A view through a window of a grassy yard with a dock and a green shed.

10. Lakefront Salmon Cottage

Lakefront Salmon Cottage
Northwood
9.8 out of 10, Exceptional, (18 reviews)
"Beautiful location. Owner is very nice and welcoming. Had a great relaxing stay."
United States
Brian T.
The price is ￥21,245
￥26,442 total
includes taxes & fees
Sep 10 - Sep 11
Lakefront Salmon Cottage
A room with a chandelier, a fireplace, a dining table, a sofa, and a chessboard.

11. The Amoskeag - Ash Street Inn

The Amoskeag - Ash Street Inn
Corey Square
The price is ￥26,095
￥43,557 total
includes taxes & fees
Sep 17 - Sep 18
The Amoskeag - Ash Street Inn
A room with a large window, curtains, a bed, and a view of a forest and open field.

12. Serene Pondside Retreat Surrounded by Nature

Serene Pondside Retreat Surrounded by Nature
Deerfield
The price is ￥25,173
￥104,455 total
includes taxes & fees
Sep 14 - Sep 15
Serene Pondside Retreat Surrounded by Nature
A living room with a brown leather sofa, a wooden coffee table, and a white door.

13. 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 ￥30,002
￥54,933 total
includes taxes & fees
Sep 9 - Sep 10
Relaxing Family friendly Apartment!!
A modern living room with a flat-screen TV displaying streaming services, a black coffee table with a plant and decorative items, and a view into the bedroom through an open door.

14. 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 ￥26,877
￥61,545 total
includes taxes & fees
Oct 6 - Oct 7
Fabulous 3-bedroom house in Manchester
A living room with a fireplace, a ceiling fan, a bookshelf, and a coffee bar.

15. 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 ￥28,752
￥69,859 total
includes taxes & fees
Sep 23 - Sep 24
Charming & Historic 2BR Oasis in Downtown Luxury
A small, orange cabin by a lake with a picnic table and a deck.

16. Lakefront Orange Cottage

Lakefront Orange Cottage
Northwood
9.0 out of 10, Wonderful, (12 reviews)
"The personal touch and welcome gift was lovely z"
United States
Joyce
The price is ￥25,913
￥28,116 total
includes taxes & fees
Sep 7 - Sep 8
Lakefront Orange Cottage
A bedroom with a bed, two bedside tables, a door, and curtains.

17. 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 ￥15,470
￥38,081 total
includes taxes & fees
Sep 8 - Sep 9
Downtown Amesbury! 15 Mins to Beach
A covered outdoor area with a wooden bench, a table, and a view of a lake.

18. Lakefront Pink Cottage

Lakefront Pink Cottage
Northwood
10.0 out of 10, Exceptional, (4 reviews)
"We had an enjoyable two night stay at the cabin. Our dog loved his first ever swim and we wanted to stay longer."
United States
Matty B.
The price is ￥27,200
￥33,752 total
includes taxes & fees
Sep 8 - Sep 9
Lakefront Pink Cottage
A covered porch with a glass table and chairs, a view of a lake, and a building in the background.

19. Lakefront Yellow Cottage

Lakefront Yellow Cottage
Northwood
9.6 out of 10, Exceptional, (7 reviews)
"Clean, friendly, a great place to stay. I kayaked in the lake and it was beautiful. Hope to stay again next summer!"
United States
Ravaioli N.
The price is ￥25,913
￥32,017 total
includes taxes & fees
Sep 7 - Sep 8
Lakefront Yellow Cottage
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.

20. 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 ￥46,253
￥123,427 total
includes taxes & fees
Sep 9 - Sep 10
Family Oasis
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

Sonesta ES Suites Andover Boston

Sonesta ES Suites Andover Boston

8/10 Good
"Staff was helpful and nice. Property cleanliness was not the best in the rooms."
Debbie 2-night trip
Posted 3 hours ago
Sonesta ES Suites Andover Boston

Find out more about Chester

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

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.