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Chester Vacation Rentals

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Check prices for these dates

In two weeks
Aug 21 - Aug 23
In two months
Oct 2 - Oct 4
In three months
Oct 30 - Nov 1
In four months
Nov 27 - Nov 29

Our top choices for Chester vacation rentals

Living area

1. Sleek and Tidy Luxurious guest suite with private entrance

Sleek and Tidy Luxurious guest suite with private entrance
Nashua
$288 nightly
The price is $313
Aug 9 - Aug 10
Total with taxes and fees
Sleek and Tidy Luxurious guest suite with private entrance
1 bedroom, iron/ironing board, WiFi, bed sheets

2. Aariz Nest

Aariz Nest
Methuen
$263 nightly
The price is $294
Aug 9 - Aug 10
Total with taxes and fees
Aariz Nest
View from property

3. 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, (181 reviews)
"Beautiful place love it all!!!"
United States
Emelin
$175 nightly
The price is $190
Sep 8 - Sep 9
Total with taxes and fees
Postcard Cabins Blake Brook, Outdoor Collection by Marriott Bonvoy
1 bedroom, WiFi (free), bed sheets

4. 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.
$219 nightly
The price is $238
Aug 9 - Aug 10
Total with taxes and fees
Mini cozy quiet apartment
Pool

5. Large Private Guest House with Lake Views

Large Private Guest House with Lake Views
Salem
10.0 out of 10, Exceptional, (3 reviews)
"Great communication, check in/out was very easy."
United States
Kathy M.
$373 nightly
The price is $405
Aug 9 - Aug 10
Total with taxes and fees
Large Private Guest House with Lake Views
Smart TV

6. 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.
$729 nightly
The price is $791
Aug 10 - Aug 11
Total with taxes and fees
Family Oasis
Lake

7. The Cottages at Harvey Lake

The Cottages at Harvey Lake
3.0 star property
Northwood
8.8 out of 10, Excellent, (47 reviews)
"The view of the lake from the cabin was excellent. "
United States
Matt
$148 nightly
The price is $161
Sep 8 - Sep 9
Total with taxes and fees
The Cottages at Harvey Lake
Smart TV

8. 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.
$324 nightly
The price is $352
Aug 9 - Aug 10
Total with taxes and fees
Relaxing Family friendly Apartment!!
Pool

9. Peaceful Lake Front Cottage in Southern NH

Peaceful Lake Front Cottage in Southern NH
Salem
10.0 out of 10, Exceptional, (2 reviews)
"Excellent tranquil spot"
United States
James A.
$574 nightly
The price is $623
Aug 12 - Aug 13
Total with taxes and fees
Peaceful Lake Front Cottage in Southern NH
Coffee/tea maker, fridge, microwave, oven

10. 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.
$721 nightly
The price is $782
Aug 9 - Aug 10
Total with taxes and fees
Large 3 floor Townhome with Patio, Backyard and Sauna
3 bedrooms, WiFi, bed sheets

11. 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.
$324 nightly
The price is $351
Aug 18 - Aug 19
Total with taxes and fees
Fabulous 3-bedroom house in Manchester
Smart TV

12. 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.
$401 nightly
The price is $435
Sep 7 - Sep 8
Total with taxes and fees
Marvelous 3-bedroom townhome with Heated floor Manchester
Interior

13. The Amoskeag - Ash Street Inn

The Amoskeag - Ash Street Inn
Corey Square
$270 nightly
The price is $287
Aug 9 - Aug 10
Total with taxes and fees
The Amoskeag - Ash Street Inn
Cookware/dishes/utensils

14. 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.
$301 nightly
The price is $327
Aug 16 - Aug 17
Total with taxes and fees
Charming quiet
Interior

15. 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)
$504 nightly
The price is $547
Aug 18 - Aug 19
Total with taxes and fees
Heated Winter Stay • 3BR Home • Pet-Friendly • Free Parking • Near Hospitals • 6
Private kitchen

16. Comfortable Studio Close to Airport / Arena / Mall

Comfortable Studio Close to Airport / Arena / Mall
Highlands
10.0 out of 10, Exceptional, (1 review)
"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.
$315 nightly
The price is $341
Sep 7 - Sep 8
Total with taxes and fees
Comfortable Studio Close to Airport / Arena / Mall
Living area

17. Triple Family Unit Combined

Triple Family Unit Combined
Rimmon Heights
10.0 out of 10, Exceptional, (3 reviews)
"Great location! Lots of room!"
United States
Jessica C.
$1,000 nightly
The price is $1,085
Aug 16 - Aug 17
Total with taxes and fees
Triple Family Unit Combined
Smart TV, books, computer monitors

18. Bright & Cozy Entire Apartment - Your New England Hub

Bright & Cozy Entire Apartment - Your New England Hub
Haverhill
9.8 out of 10, Exceptional, (7 reviews)
"It was a great place to stay."
United States
Lorraine B.
$350 nightly
The price is $391
Aug 18 - Aug 19
Total with taxes and fees
Bright & Cozy Entire Apartment - Your New England Hub
Exterior

19. Spacious 2BR Apartment Near Bradford & Merrimack Valley Parking Included.

Spacious 2BR Apartment Near Bradford & Merrimack Valley Parking Included.
Haverhill
10.0 out of 10, Exceptional, (5 reviews)
"Family really enjoyed alot Thank you. "
United States
Andrew G.
$308 nightly
The price is $344
Aug 31 - Sep 1
Total with taxes and fees
Spacious 2BR Apartment Near Bradford & Merrimack Valley Parking Included.
Exterior

20. Lakefront Orange Cottage

Lakefront Orange Cottage
Northwood
9.0 out of 10, Wonderful, (12 reviews)
"The personal touch and welcome gift was lovely z"
United States
Joyce
$166 nightly
The price is $180
Aug 19 - Aug 20
Total with taxes and fees
Lakefront Orange Cottage
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 Manchester Downtown

DoubleTree by Hilton Manchester Downtown

8/10 Good
"I expect certain things when staying at a well regarded chain hotel - one of those is free internet usage. It's been 20 years since I have had to pay for Boingo or the like but here we are having to sign up for Hilton Honors membership to access the wi-fi. Sorry; way too many emails as it is, boys! Parking was not free although when making the reservation I was under the impression it was. It was discounted so for that, thanks. No complimentary breakfast? Come ON! I know the price of eggs were supposed to go down day one and of course they didn't but there wasn't much special on offer besides eggs, toast, cereals...all nice but for 10.99? I have stayed at far cheaper hotels that were less grasping. The room was clean and linens and towels crisp; it was quiet at night and perfect climate control for the room temperature. Friendly staff. So except for the above griping about the Hilton snatching at every last dime from their guests I give this hotel a Good, but not Excellent rating."
Kelley 1-night trip
Posted 2 hours ago
DoubleTree by Hilton Manchester Downtown

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 $183 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.