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Chester Vacation Rentals

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Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for Chester vacation rentals

A modern kitchen with white cabinetry, a wooden island, and a dining area with a table and chairs.

1. The Sweet Suite - just minutes from MHT and 93

The Sweet Suite - just minutes from MHT and 93
Londonderry
10.0 out of 10, Exceptional, (6 reviews)
"What a wonderful spot!! Perfect for my husband and I to relax, work and visit family Clean and updated Host family went out of their way to welcome us, check in with us and make our stay so comfortable!! Highly recommend!! "
United States
Pamela O.
$334 nightly
The price is $362
Nov 25 - Nov 26
Total with taxes and fees
The Sweet Suite - just minutes from MHT and 93
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, (243 reviews)
"Great property we loved the cabin the view was beautiful and the amenities were very nice addition."
United States
Corneal
$167 nightly
The price is $181
Dec 7 - Dec 8
Total with taxes and fees
Postcard Cabins Blake Brook, Outdoor Collection by Marriott Bonvoy
A backyard with a fire pit, wooden chairs, and string lights.

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
$186 nightly
The price is $202
Nov 7 - Nov 8
Total with taxes and fees
This one room camping cabin is a great alternative to a tent camp site.
A two-story house with a front porch, surrounded by a well-maintained lawn and trees.

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

Private Studio/Bathroom Handicap Accessible Room in Single Family Home
Windham
6.0 out of 10, (1 review)
$103 nightly
The price is $111
Nov 15 - Nov 16
Total with taxes and fees
Private Studio/Bathroom Handicap Accessible Room in Single Family Home
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, (13 reviews)
"Nice stay. Nice property. Would stay again"
United States
John B.
$224 nightly
The price is $243
Nov 8 - Nov 9
Total with taxes and fees
Mini cozy quiet apartment
A spacious living room with a white sofa, a coffee table, and a chandelier.

6. 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.
$319 nightly
The price is $346
Nov 8 - Nov 9
Total with taxes and fees
Marvelous 3-bedroom townhome with Heated floor Manchester
A room with a chandelier, a fireplace, a dining table, a sofa, and a chessboard.

7. The Amoskeag - Ash Street Inn

The Amoskeag - Ash Street Inn
Corey Square
$272 nightly
The price is $289
Nov 9 - Nov 10
Total with taxes and fees
The Amoskeag - Ash Street Inn
A kitchen with wooden cabinets, a dining table, chairs, a ceiling fan, and a view through a glass door.

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

Riverfront 2BR | Home King Suite | Patio & Grill
Epping
9.0 out of 10, Wonderful, (2 reviews)
"Beautiful home that actually feels bigger than the photos show. Great place to stay and would stay again"
United States
Kimberly W.
$520 nightly
The price is $564
Nov 7 - Nov 8
Total with taxes and fees
Riverfront 2BR | Home King Suite | Patio & Grill
A deck with outdoor furniture, a tray with glasses and a pitcher, and a view of a lake.

9. 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.
$591 nightly
The price is $641
Nov 8 - Nov 9
Total with taxes and fees
Serene Pondside Retreat Surrounded by Nature
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.

10. Heated Winter Stay • 3BR Home • Free Parking • Near Hospitals • 6

Heated Winter Stay • 3BR Home • Free Parking • Near Hospitals • 6
Manchester
10.0 out of 10, Exceptional, (1 review)
$253 nightly
The price is $275
Nov 8 - Nov 9
Total with taxes and fees
Heated Winter Stay • 3BR Home • Free Parking • Near Hospitals • 6
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.

11. Family Oasis

Family Oasis
Kalivas Union
10.0 out of 10, Exceptional, (3 reviews)
"Very clean interior."
United States
Douglas
$771 nightly
The price is $837
Nov 8 - Nov 9
Total with taxes and fees
Family Oasis
A stainless steel refrigerator with a water dispenser, wooden cabinets, a granite countertop, and a black trash can.

12. Charming quiet

Charming quiet
Rimmon Heights
9.4 out of 10, Exceptional, (19 reviews)
"Had everything we needed from snacks, to water! Great place to stay! "
United States
Sierra M.
$277 nightly
The price is $301
Nov 8 - Nov 9
Total with taxes and fees
Charming quiet
A living room with a fireplace, a ceiling fan, a bookshelf, and a coffee bar.

13. 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.
$487 nightly
The price is $529
Nov 27 - Nov 28
Total with taxes and fees
Charming & Historic 2BR Oasis in Downtown Luxury
A deck with outdoor seating and a grill, overlooking a lake with a forested hillside.

14. Enchanting, romantic and fun river getaway

Enchanting, romantic and fun river getaway
North End
10.0 out of 10, Exceptional, (36 reviews)
"Beautiful home, relaxing location, great amenities."
United States
Dan W.
$344 nightly
The price is $373
Nov 8 - Nov 9
Total with taxes and fees
Enchanting, romantic and fun river getaway
A modern kitchen with white cabinets, stainless steel appliances, a wooden ceiling, and a green accent wall.

15. 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.
$608 nightly
The price is $660
Nov 9 - Nov 10
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.

16. 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.
$388 nightly
The price is $421
Nov 8 - Nov 9
Total with taxes and fees
Relaxing Family friendly Apartment!!
A living room with a sofa, armchair, coffee table, lamp, and potted plant.

17. 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.
$332 nightly
The price is $371
Nov 7 - Nov 8
Total with taxes and fees
Bright & Cozy Entire Apartment - Your New England Hub
A hotel room with a bed, bedside table, lamp, and a view of the outside.

18. 1 Queen Bed | Newly Redesigned

1 Queen Bed | Newly Redesigned
Nashua
10.0 out of 10, Exceptional, (6 reviews)
"It always seems like every time I stay at Motel 6. It’s very quiet and peaceful. People at the front desk are very professional and know how to do their job I tell people about my stays all the time By the way, the bathroom is beautiful"
United States
Joseph
$88 nightly
The price is $95
Dec 6 - Dec 7
Total with taxes and fees
1 Queen Bed | Newly Redesigned
A living room with a dark brown leather sofa, a wooden coffee table, and a white door.

19. 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.
$988 nightly
The price is $1,072
Nov 8 - Nov 9
Total with taxes and fees
Triple Family Unit Combined
A modern bedroom with a bed, a TV, a ceiling fan, and a window with blinds.

20. Aariz Nest

Aariz Nest
Methuen
9.0 out of 10, Wonderful, (2 reviews)
"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.
$174 nightly
The price is $194
Nov 9 - Nov 10
Total with taxes and fees
Aariz Nest
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

DoubleTree by Hilton Boston - Andover

DoubleTree by Hilton Boston - Andover

10/10 Excellent
"Great hotel with delicious buffet breakfast and nice pool and jacuzzi"
Belenis 2-night trip
Posted 2 hours ago
DoubleTree by Hilton Boston - Andover

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 $181 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?

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.