Chester Vacation Rentals

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Check prices for these dates

In two weeks
Jan 9 - Jan 11
In two months
Feb 20 - Feb 22
In three months
Mar 20 - Mar 22
In four months
Apr 17 - Apr 19

Our top choices for Chester vacation rentals

Standard Cabin, 1 Queen Bed | Exterior
Postcard Cabins Blake Brook, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Blake Brook, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Blake Brook, Outdoor Collection by Marriott Bonvoy
2.0 star property
Epsom
9.6 out of 10, Exceptional, (98)
"This was our second stay and it’s a 10/10 for a romantic getaway! "
United States
Caitlin
The price is ￥17,066
￥25,312 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Postcard Cabins Blake Brook, Outdoor Collection by Marriott Bonvoy
Outdoor dining
Idyllic Small-Town Stay

Idyllic Small-Town Stay

Idyllic Small-Town Stay
Derry
10.0 out of 10, Exceptional, (8)
"Liked the stay, thank you"
United States
Ciria
The price is ￥13,175
￥20,241 total
includes taxes & fees
Dec 30 - Dec 31
Idyllic Small-Town Stay
Private kitchen
Comfortable Studio Close to Airport / Arena / Mall

Comfortable Studio Close to Airport / Arena / Mall

Comfortable Studio Close to Airport / Arena / Mall
2.0 star property
Highlands
10.0 out of 10, Exceptional, (1)
"Great location. Close to the airport and SNHU arena. Plenty of shopping options within a mile. Apartment was nice and clean."
United States
Steven T.
The price is ￥12,400
￥40,634 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Comfortable Studio Close to Airport / Arena / Mall
Exterior
Indoor Pool, 2 Miles From Ocean, 7,000 Square Foot Luxury Home

Indoor Pool, 2 Miles From Ocean, 7,000 Square Foot Luxury Home

Indoor Pool, 2 Miles From Ocean, 7,000 Square Foot Luxury Home
North Hampton
9.6 out of 10, Exceptional, (99)
"Owner very responsive to questions. Beautiful house on 9 acres of land. Great outdoor spaces, fire pit, grills, pool and hot tub."
United States
Christine C.
The price is ￥234,855
￥358,954 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Indoor Pool, 2 Miles From Ocean, 7,000 Square Foot Luxury Home
Exterior
Dtwn Amesbury! 15 mins to beach!

Dtwn Amesbury! 15 mins to beach!

Dtwn Amesbury! 15 mins to beach!
Amesbury
10.0 out of 10, Exceptional, (1)
"Excellent communication with the owner before and throughout the stay. Apartment is just as advertised. "
United States
Jennifer
The price is ￥16,127
￥40,206 total
includes taxes & fees
Jan 13 - Jan 14, 2026
Dtwn Amesbury! 15 mins to beach!
3 bedrooms, WiFi, bed sheets
Fabulous 3-bedroom house in Manchester

Fabulous 3-bedroom house in Manchester

Fabulous 3-bedroom house in Manchester
2.0 star property
Manchester
9.4 out of 10, Exceptional, (3)
"Place was nice. Super clean and host was very available for questions. "
United States
Frank C.
The price is ￥18,788
￥51,813 total
includes taxes & fees
Jan 10 - Jan 11, 2026
Fabulous 3-bedroom house in Manchester
Fridge, microwave, oven, stovetop
Lovely Downtown Oasis ~ Hospitals/Colleges/Beaches

Lovely Downtown Oasis ~ Hospitals/Colleges/Beaches

Lovely Downtown Oasis ~ Hospitals/Colleges/Beaches
Amesbury
9.0 out of 10, Wonderful, (2)
"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 ￥14,561
￥35,079 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Lovely Downtown Oasis ~ Hospitals/Colleges/Beaches
Dining
Historical Winter Stay | Circa 1805 | Pet-Friendly

Historical Winter Stay | Circa 1805 | Pet-Friendly

Historical Winter Stay | Circa 1805 | Pet-Friendly
Epping
9.6 out of 10, Exceptional, (10)
"Nice houseGood for 3-4 adults (2 bedrooms) - we had 2 people Screened patio was awesome No washer/dryer"
United States
Neil P.
The price is ￥19,728
￥63,367 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Historical Winter Stay | Circa 1805 | Pet-Friendly
1 bedroom, free WiFi, bed sheets
Cute Mini Apt - SNHU Arena

Cute Mini Apt - SNHU Arena

Cute Mini Apt - SNHU Arena
Rimmon Heights
9.8 out of 10, Exceptional, (10)
"Nice stay. Nice property. Would stay again"
United States
John B.
The price is ￥18,632
￥36,865 total
includes taxes & fees
Dec 30 - Dec 31
Cute Mini Apt - SNHU Arena
Smart TV
3BR • Fire Pit • Near Hospitals & Arena • Sleeps 6+ • Full Kitchen & Parking

3BR • Fire Pit • Near Hospitals & Arena • Sleeps 6+ • Full Kitchen & Parking

3BR • Fire Pit • Near Hospitals & Arena • Sleeps 6+ • Full Kitchen & Parking
2.0 star property
Manchester
10.0 out of 10, Exceptional, (1)
The price is ￥18,788
￥69,820 total
includes taxes & fees
Jan 12 - Jan 13, 2026
3BR • Fire Pit • Near Hospitals & Arena • Sleeps 6+ • Full Kitchen & Parking
Fridge, microwave, dishwasher, coffee/tea maker
Modern 1BD Near Downtown & Hgwy

Modern 1BD Near Downtown & Hgwy

Modern 1BD Near Downtown & Hgwy
North Andover
10.0 out of 10, Exceptional, (1)
"What a cozy little spot? It was as described, our host was very accommodating and communicative, and its a good location, a nice neighborhood close to town as well as highways. We very much enjoyed our stay and will look to stay again when we're in the area"
United States
Chris H.
The price is ￥21,813
￥38,881 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Modern 1BD Near Downtown & Hgwy
Fridge, microwave, oven, stovetop
Garage, Fully Fenced Yard, Sleep 8, Walk to Downtown

Garage, Fully Fenced Yard, Sleep 8, Walk to Downtown

Garage, Fully Fenced Yard, Sleep 8, Walk to Downtown
Nashua
10.0 out of 10, Exceptional, (7)
"We enjoyed our stay with our 3y and 5y - the house and neighborhood were safe, clean, and easy. We had a great stay!"
United States
Meghan L.
The price is ￥19,023
￥46,633 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Garage, Fully Fenced Yard, Sleep 8, Walk to Downtown
Exterior
Cozy & Quiet Escape Near Shopping & Restaurants

Cozy & Quiet Escape Near Shopping & Restaurants

Cozy & Quiet Escape Near Shopping & Restaurants
2.0 star property
Salem
7.4 out of 10, Good, (3)
"My husband and I stayed 3 nights. The space was clean and well stocked. Good central location. Good communication with host."
United States
Dorothy D.
The price is ￥23,504
￥40,683 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Cozy & Quiet Escape Near Shopping & Restaurants
Smart TV, computer monitors
Bright & Cozy Entire Apartment - Your New England Hub

Bright & Cozy Entire Apartment - Your New England Hub

Bright & Cozy Entire Apartment - Your New England Hub
Haverhill
9.8 out of 10, Exceptional, (6)
"Check in was easy! Nice apartment that has been updated. It was great for my family while we were in the area visiting multiple locations."
United States
Erin W.
The price is ￥32,880
￥66,984 total
includes taxes & fees
Dec 30 - Dec 31
Bright & Cozy Entire Apartment - Your New England Hub
Cookware/dishes/utensils
Charming quiet

Charming quiet

Charming quiet
Rimmon Heights
10.0 out of 10, Exceptional, (14)
"This property exceeded our expectations. It was clean, lots of sunshine, good lighting, and well equiped with air conditioners in each room and the kitchen had everything we needed. Definitely a home away from home."
Canada
Kim B.
The price is ￥26,460
￥50,623 total
includes taxes & fees
Dec 30 - Dec 31
Charming quiet
3 bedrooms, iron/ironing board, free WiFi, bed sheets
Relaxing Family friendly Apartment!!

Relaxing Family friendly Apartment!!

Relaxing Family friendly Apartment!!
Rimmon Heights
9.6 out of 10, Exceptional, (19)
"Nice place "
United States
ron m.
The price is ￥30,061
￥55,042 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Relaxing Family friendly Apartment!!
Living area
Charming 2-bedroom apartment in Manchester with AC, WiFi

Charming 2-bedroom apartment in Manchester with AC, WiFi

Charming 2-bedroom apartment in Manchester with AC, WiFi
North End
7.0 out of 10, Good, (2)
"Good location with easy parking. Be aware that the steps up to the apartment are definitely winding and narrow. "
United States
Alan G.
The price is ￥22,703
￥43,151 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Charming 2-bedroom apartment in Manchester with AC, WiFi
Dining
Very spacious, clean, and comfortable first floor unit. Close to major highway!

Very spacious, clean, and comfortable first floor unit. Close to major highway!

Very spacious, clean, and comfortable first floor unit. Close to major highway!
2.0 star property
Wolfe Park
8.8 out of 10, Excellent, (9)
"We had a pleasant visit and stay"
United States
Desiree H.
The price is ￥23,486
￥46,378 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Very spacious, clean, and comfortable first floor unit. Close to major highway!
Beach nearby
Island Path Escape | 3BR Monthly | Views | Fireplace

Island Path Escape | 3BR Monthly | Views | Fireplace

Island Path Escape | 3BR Monthly | Views | Fireplace
Hampton Beach
10.0 out of 10, Exceptional, (29)
"Wonderful place! Will stay again "
United States
Melba K.
The price is ￥30,531
￥84,432 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Island Path Escape | 3BR Monthly | Views | Fireplace
Oven, stovetop, dishwasher
Restful and spacious 3-bedroom house in Manchester

Restful and spacious 3-bedroom house in Manchester

Restful and spacious 3-bedroom house in Manchester
2.0 star property
Bakersville
The price is ￥40,708
￥60,647 total
includes taxes & fees
Jan 3 - Jan 4, 2026
Restful and spacious 3-bedroom house in Manchester
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

La Quinta Inn & Suites by Wyndham Salem NH

La Quinta Inn & Suites by Wyndham Salem NH

10/10 Excellent
"I love the smell of the room when you first walk in they take pride in cleaning the rooms and will be coming back but they really should have Netflix in all their rooms would be perfect "
Kevon 3-night trip
Posted 1 day ago
La Quinta Inn & Suites by Wyndham Salem NH

Find out more about Chester

Search for holiday rentals in Chester on Expedia! You can easily find your home rentals, villas, holiday apartments in Chester using one of the methods below:

  • View our selection of featured holiday rentals in Chester
  • Use the map to find apartments and other holiday homes in the Chester neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Chester while they last

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?

The Cottages at Harvey Lake: This vacation home rental outside of Chester is located on the waterfront and has a terrace, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave.

What can I see and do in Chester?

While exploring the area, visit family-friendly sights like Stonyfield Farm, or get outside and enjoy nature at Lake Massabesic. 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.