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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

A two-story house with a deck, surrounded by a forest and a river.

1. Serene Pondside Retreat Surrounded by Nature

Serene Pondside Retreat Surrounded by Nature
Deerfield
$585 nightly
The price is $635
Sep 8 - Sep 9
Total with taxes and fees
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
$184 nightly
The price is $200
Sep 30 - Oct 1
Total with taxes and fees
Postcard Cabins Blake Brook, Outdoor Collection by Marriott Bonvoy
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, (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.
$737 nightly
The price is $800
Sep 1 - Sep 2
Total with taxes and fees
Family Oasis
A modern kitchen with white cabinets, stainless steel appliances, a wooden ceiling, and a green accent wall.

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.
$635 nightly
The price is $689
Sep 6 - Sep 7
Total with taxes and fees
Large 3 floor Townhome with Patio, Backyard and Sauna
A living room with a brown leather sofa, a wooden coffee table, and a white door.

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.
$328 nightly
The price is $356
Sep 9 - Sep 10
Total with taxes and fees
Relaxing Family friendly Apartment!!
A modern kitchen with stainless steel appliances, wooden cabinets, and a central island with two bar stools.

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

Spacious, family friendly 3700 sq ft w/ great yard
Straw-Smyth
$988 nightly
The price is $1,072
Sep 1 - Sep 2
Total with taxes and fees
Spacious, family friendly 3700 sq ft w/ great yard
A house with a front porch, a large tree in front, and a grassy yard.

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

Near Shopping & Canobie Lake! Apartment w/ Grill
3.5 star property
Salem
$211 nightly
The price is $229
Sep 6 - Sep 7
Total with taxes and fees
Near Shopping & Canobie Lake! Apartment w/ Grill
A lakeside cabin with a view of a calm lake and autumn foliage.

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
$136 nightly
The price is $148
Sep 10 - Sep 11
Total with taxes and fees
The Cottages at Harvey Lake
A room with a chandelier, a fireplace, a dining table, a sofa, and a chessboard.

9. The Amoskeag - Ash Street Inn

The Amoskeag - Ash Street Inn
Corey Square
$272 nightly
The price is $290
Sep 16 - Sep 17
Total with taxes and fees
The Amoskeag - Ash Street Inn
A round outdoor table with a built-in fire feature, surrounded by wicker furniture and a white deck railing.

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
$436 nightly
The price is $470
Sep 1 - Sep 2
Total with taxes and fees
4 Corners At Amesbury Downtown Pet Friendly
A spacious living room with a white sofa, a coffee table, and a chandelier.

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.
$396 nightly
The price is $430
Sep 8 - Sep 9
Total with taxes and fees
Marvelous 3-bedroom townhome with Heated floor Manchester
A living room with a dark brown leather sofa, a wooden coffee table, and a white door.

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.
$999 nightly
The price is $1,084
Sep 9 - Sep 10
Total with taxes and fees
Triple Family Unit Combined
A stainless steel refrigerator with a water dispenser, wooden cabinets, a granite countertop, and a black trash can.

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.
$302 nightly
The price is $328
Sep 1 - Sep 2
Total with taxes and fees
Charming quiet
A living room with a flat-screen TV mounted on the wall, a dark wooden coffee table with a potted plant, a remote control, and decorative items.

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)
$529 nightly
The price is $574
Sep 14 - Sep 15
Total with taxes and fees
Heated Winter Stay • 3BR Home • Pet-Friendly • Free Parking • Near Hospitals • 6
A modern kitchen with wooden cabinets, stainless steel appliances, a built-in oven, and a window with blinds.

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.
$571 nightly
The price is $620
Sep 13 - Sep 14
Total with taxes and fees
North End Retreat
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.

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.
$337 nightly
The price is $366
Sep 14 - Sep 15
Total with taxes and fees
Fabulous 3-bedroom house in Manchester
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.

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.
$222 nightly
The price is $241
Sep 1 - Sep 2
Total with taxes and fees
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.
$321 nightly
The price is $342
Sep 1 - Sep 2
Total with taxes and fees
Modern, All New 3BR Near UMASS
A living room with a fireplace, a ceiling fan, a bookshelf, and a coffee bar.

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.
$416 nightly
The price is $451
Sep 23 - Sep 24
Total with taxes and fees
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

Hampton Village Inn

Hampton Village Inn

8/10 Good
"Nice place we’re helpful close to beach and Resturant"
JOE 2-night trip
Posted less than an hour ago
Hampton Village Inn

Find out more about Chester

Everything you need to know about Chester vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Chester vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Chester vacation 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 low season months. For more hustle and bustle, you may prefer to visit Chester in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $200 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Chester rentals

At Expedia, we put the best Chester vacation 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 vacation.

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.

Explore a world of travel with Expedia

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?

2-bedroom lakeside retreat in beautiful Windham: This vacation 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 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.