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Chester Vacation Rentals

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Our top choices for Chester vacation rentals

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.
The price is CA $219
CA $482 total
includes taxes & fees
Dec 8 - Dec 9
The Sweet Suite - just minutes from MHT and 93

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
The price is CA $178
CA $254 total
includes taxes & fees
Dec 7 - Dec 8
Postcard Cabins Blake Brook, Outdoor Collection by Marriott Bonvoy

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 CA $219
CA $286 total
includes taxes & fees
Nov 8 - Nov 9
This one room camping cabin is a great alternative to a tent camp site.

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)
The price is CA $82
CA $156 total
includes taxes & fees
Nov 15 - Nov 16
Private Studio/Bathroom Handicap Accessible Room in Single Family Home

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.
The price is CA $167
CA $354 total
includes taxes & fees
Nov 8 - Nov 9
Mini cozy quiet apartment

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.
The price is CA $275
CA $490 total
includes taxes & fees
Nov 8 - Nov 9
Marvelous 3-bedroom townhome with Heated floor Manchester

7. The Amoskeag - Ash Street Inn

The Amoskeag - Ash Street Inn
Corey Square
The price is CA $257
CA $406 total
includes taxes & fees
Nov 9 - Nov 10
The Amoskeag - Ash Street Inn

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.
The price is CA $235
CA $794 total
includes taxes & fees
Nov 16 - Nov 17
Riverfront 2BR | Home King Suite | Patio & Grill

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.
The price is CA $252
CA $925 total
includes taxes & fees
Nov 8 - Nov 9
Serene Pondside Retreat Surrounded by Nature

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)
The price is CA $189
CA $389 total
includes taxes & fees
Nov 8 - Nov 9
Heated Winter Stay • 3BR Home • Free Parking • Near Hospitals • 6

11. Family Oasis

Family Oasis
Kalivas Union
10.0 out of 10, Exceptional, (3 reviews)
"Very clean interior."
United States
Douglas
The price is CA $415
CA $1,132 total
includes taxes & fees
Nov 8 - Nov 9
Family Oasis

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.
The price is CA $237
CA $436 total
includes taxes & fees
Nov 8 - Nov 9
Charming quiet

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.
The price is CA $346
CA $747 total
includes taxes & fees
Nov 27 - Nov 28
Charming & Historic 2BR Oasis in Downtown Luxury

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.
The price is CA $314
CA $528 total
includes taxes & fees
Nov 8 - Nov 9
Enchanting, romantic and fun river getaway

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.
The price is CA $414
CA $925 total
includes taxes & fees
Nov 10 - Nov 11
Large 3 floor Townhome with Patio, Backyard and Sauna

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.
The price is CA $294
CA $503 total
includes taxes & fees
Nov 8 - Nov 9
Relaxing Family friendly Apartment!!

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.
The price is CA $252
CA $540 total
includes taxes & fees
Nov 10 - Nov 11
Bright & Cozy Entire Apartment - Your New England Hub

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
The price is CA $123
CA $134 total
includes taxes & fees
Dec 6 - Dec 7
1 Queen Bed | Newly Redesigned

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.
The price is CA $796
CA $1,503 total
includes taxes & fees
Nov 8 - Nov 9
Triple Family Unit Combined

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.
The price is CA $196
CA $269 total
includes taxes & fees
Nov 10 - Nov 11
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

Find out more about Chester

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Chester. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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.