Chester Holiday Rentals

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Holiday Rentals in Chester

Postcard Cabins Blake Brook, Outdoor Collection by Marriott Bonvoy

2.0 star property
Epsom
9.6 out of 10, Exceptional, (81)
"Everything was wonderful!!"
United States
Christina
The price is NZ$305
includes taxes & fees
19 Nov - 20 Nov
Postcard Cabins Blake Brook, Outdoor Collection by Marriott Bonvoy

Idyllic Small-Town Stay

Derry
10.0 out of 10, Exceptional, (4)
"Liked the stay, thank you"
United States
Ciria
The price is NZ$238
includes taxes & fees
20 Nov - 21 Nov
Idyllic Small-Town Stay

Downtown Amesbury! 15 Mins to Beach

Amesbury
10.0 out of 10, Exceptional, (1)
"Perfect place! Easy walk to downtown Amesbury. Quite neighborhood "
United States
Holly B.
The price is NZ$363
includes taxes & fees
19 Nov - 20 Nov
Downtown Amesbury! 15 Mins to Beach

Lovely Downtown Oasis ~ Hospitals/Colleges/Beaches

Amesbury
10.0 out of 10, Exceptional, (1)
"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 NZ$413
includes taxes & fees
23 Nov - 24 Nov
Lovely Downtown Oasis ~ Hospitals/Colleges/Beaches

Lovely 2 bedroom- kitchenette

2.0 star property
Andover
9.2 out of 10, Wonderful, (5)
"Very pretty area and the host was extremely pleasant and communicative "
United States
Allen B.
The price is NZ$849
includes taxes & fees
19 Nov - 20 Nov
Lovely 2 bedroom- kitchenette

Family-Friendly Townhouse on the Merrimack River

Methuen
9.6 out of 10, Exceptional, (14)
"A lovely home on a river. Close to wedding venue, which was wonderful. Very clean home, and owner was quick to respond and welcoming. "
United States
Danielle B.
The price is NZ$530
includes taxes & fees
19 Nov - 20 Nov
Family-Friendly Townhouse on the Merrimack River

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 NZ$439
includes taxes & fees
16 Dec - 17 Dec
Modern 1BD Near Downtown & Hgwy

Exeter Winter MTR | 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 NZ$716
includes taxes & fees
19 Nov - 20 Nov
Exeter Winter MTR | Circa 1805 | Pet-Friendly

Fabulous 3-bedroom house in Manchester

2.0 star property
Manchester
10.0 out of 10, Exceptional, (2)
"Place was nice. Super clean and host was very available for questions. "
United States
Frank C.
The price is NZ$474
includes taxes & fees
19 Dec - 20 Dec
Fabulous 3-bedroom house in Manchester

Cute Mini Apt - SNHU Arena

Rimmon Heights
9.8 out of 10, Exceptional, (8)
"Surprisingly spacious 3rd floor apartment! We had a little trouble getting inside, but Nancy was super nice, helpful, and very accommodating to us. Would definitely recommend!"
United States
Alli M.
The price is NZ$418
includes taxes & fees
19 Nov - 20 Nov
Cute Mini Apt - SNHU Arena

Cozy Apartment Close to Downtown

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 NZ$676
includes taxes & fees
19 Nov - 20 Nov
Cozy Apartment Close to Downtown

Comfortable Studio Close to Airport / Arena / Mall

2.0 star property
Manchester
The price is NZ$457
includes taxes & fees
19 Nov - 20 Nov
Comfortable Studio Close to Airport / Arena / Mall

Relaxing Family friendly Apartment!!

Rimmon Heights
9.6 out of 10, Exceptional, (18)
"In a terrific part of Manchester next to the best breakfast place in the city, just a short shot to downtown. And much nicer than expected."
United States
Timothy G.
The price is NZ$622
includes taxes & fees
19 Nov - 20 Nov
Relaxing Family friendly Apartment!!

Classic New England Bunkhouse- Home for the whole family!

Haverhill
9.8 out of 10, Exceptional, (9)
"Nice place, neat and clean, beautiful neighborhood!"
United States
Cathy H.
The price is NZ$626
includes taxes & fees
19 Nov - 20 Nov
Classic New England Bunkhouse- Home for the whole family!

Loon's Ledge Lakehouse

Northwood
Loon's Ledge Lakehouse

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.
Cozy & Quiet Escape Near Shopping & Restaurants

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

2.0 star property
Manchester
The price is NZ$785
includes taxes & fees
19 Nov - 20 Nov
3BR • Fire Pit • Near Hospitals & Arena • Sleeps 6+ • Full Kitchen & Parking

Marvelous 3-bedroom townhome with Heated floor Manchester

2.0 star property
Manchester
The price is NZ$652
includes taxes & fees
19 Dec - 20 Dec
Marvelous 3-bedroom townhome with Heated floor Manchester

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 NZ$402
includes taxes & fees
20 Nov - 21 Nov
Dtwn Amesbury! 15 mins to beach!

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.
The price is NZ$572
includes taxes & fees
19 Nov - 20 Nov
Charming Apartment-Saint Anselm -SNHU
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

Everything you need to know about Chester holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Chester holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Chester holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chester holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chester holiday rentals we have selected for you start as low as NZ$238 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Chester rentals

At Expedia, we put the best Chester holiday 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 holiday.

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 holiday rental in Chester?

Yes, there are holiday rentals close to the most popular sights in Chester, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Chester has to offer?

Indoor Pool, 2 Miles From Ocean, 7,000 Square Foot Luxury Home: This holiday home rental outside of Chester is located in a rural location, and has an indoor pool, a patio and a BBQ 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 that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

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 Lake Massabesic. While here, Chester Public Library and Chester Town Hall are other places worth a visit.

What are holiday rentals like in Chester?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Chester. Holiday rentals offer extras such as hot tubs, fire pits and patios so you'll have a home away from home. If you're concerned about a clean environment, a holiday rental can provide a sense of seclusion away from public hotel lifts and busy reception areas while still allowing you the excitement and enjoyment of travel. You'll also have more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a popular option for a small group gathering.