Chester Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Chester vacation rentals

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, (94)
"This was our second stay and it’s a 10/10 for a romantic getaway! "
United States
Caitlin
$149 nightly
The price is $162
Jan 4 - Jan 5, 2026
Total with taxes and fees
Postcard Cabins Blake Brook, Outdoor Collection by Marriott Bonvoy

Idyllic Small-Town Stay

Idyllic Small-Town Stay
Derry
10.0 out of 10, Exceptional, (8)
"Liked the stay, thank you"
United States
Ciria
$119 nightly
The price is $129
Dec 29 - Dec 30
Total with taxes and fees
Idyllic Small-Town Stay

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)
"Wonderful property!! The owner takes great care of her house and it was an amazing weekend!!"
United States
Porter R.
$2,113 nightly
The price is $2,293
Jan 1 - Jan 2, 2026
Total with taxes and fees
Indoor Pool, 2 Miles From Ocean, 7,000 Square Foot Luxury Home

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.
$239 nightly
The price is $260
Dec 25 - Dec 26
Total with taxes and fees
Comfortable Studio Close to Airport / Arena / Mall

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.
$305 nightly
The price is $331
Dec 29 - Dec 30
Total with taxes and fees
Fabulous 3-bedroom house in Manchester

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
$241 nightly
The price is $257
Jan 13 - Jan 14, 2026
Total with taxes and fees
Dtwn Amesbury! 15 mins to beach!

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.
$217 nightly
The price is $235
Dec 28 - Dec 29
Total with taxes and fees
Cute Mini Apt - SNHU Arena

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.
$373 nightly
The price is $405
Jan 12 - Jan 13, 2026
Total with taxes and fees
Historical Winter Stay | Circa 1805 | Pet-Friendly

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.
$210 nightly
The price is $224
Jan 4 - Jan 5, 2026
Total with taxes and fees
Lovely Downtown Oasis ~ Hospitals/Colleges/Beaches

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.
$349 nightly
The price is $390
Jan 5 - Jan 6, 2026
Total with taxes and fees
Bright & Cozy Entire Apartment - Your New England Hub

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)
$408 nightly
The price is $443
Jan 7 - Jan 8, 2026
Total with taxes and fees
3BR • Fire Pit • Near Hospitals & Arena • Sleeps 6+ • Full Kitchen & Parking

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.
$245 nightly
The price is $248
Jan 4 - Jan 5, 2026
Total with taxes and fees
Modern 1BD Near Downtown & Hgwy

Relaxing Family friendly Apartment!!

Relaxing Family friendly Apartment!!
Rimmon Heights
9.6 out of 10, Exceptional, (19)
"Nice place "
United States
ron m.
$324 nightly
The price is $352
Dec 29 - Dec 30
Total with taxes and fees
Relaxing Family friendly Apartment!!

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.
$275 nightly
The price is $298
Jan 5 - Jan 6, 2026
Total with taxes and fees
Garage, Fully Fenced Yard, Sleep 8, Walk to Downtown

Charming Apartment-Saint Anselm -SNHU

Charming Apartment-Saint Anselm -SNHU
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.
$298 nightly
The price is $323
Dec 29 - Dec 30
Total with taxes and fees
Charming Apartment-Saint Anselm -SNHU

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.
$257 nightly
The price is $260
Jan 1 - Jan 2, 2026
Total with taxes and fees
Cozy & Quiet Escape Near Shopping & Restaurants

Waterfront Home w/ Private Dock

Waterfront Home w/ Private Dock
Epsom
10.0 out of 10, Exceptional, (20)
"The home was very clean and so organized. It felt inviting and warm. It was so easy to check in. We used the passcode that was provided. The kitchen was stocked with everything you would need. We loved our stay and highly recommend for a relaxing getaway with a nice view of the pond."
United States
Kerry B.
$339 nightly
The price is $368
Dec 28 - Dec 29
Total with taxes and fees
Waterfront Home w/ Private Dock

Restful and spacious 3-bedroom house in Manchester

Restful and spacious 3-bedroom house in Manchester
2.0 star property
Bakersville
$356 nightly
The price is $386
Dec 28 - Dec 29
Total with taxes and fees
Restful and spacious 3-bedroom house in Manchester

Walk to Tuscan Village | Modern 3bd Farmhouse

Walk to Tuscan Village | Modern 3bd Farmhouse
Salem
9.6 out of 10, Exceptional, (15)
"The house was clean, the communication was prompt and overall we had a great stay! "
United States
Seth M.
$1,491 nightly
The price is $1,506
Dec 27 - Dec 28
Total with taxes and fees
Walk to Tuscan Village | Modern 3bd Farmhouse

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.
$254 nightly
The price is $276
Dec 25 - Dec 26
Total with taxes and fees
Charming 2-bedroom apartment in Manchester with AC, WiFi
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Chester Hotel Reviews

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 $129 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.

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 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.