Holiday Rentals in Chester

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Holiday Rentals in Chester

Cabin in Epsom

2.0 star property
9.6 out of 10, Exceptional, (81)
"Everything was wonderful!!"
United States
Christina
The price is €124
includes taxes & fees
4 Dec - 5 Dec
Postcard Cabins Blake Brook, Outdoor Collection by Marriott Bonvoy

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

Holiday Home in Derry

10.0 out of 10, Exceptional, (4)
"Liked the stay, thank you"
United States
Ciria
The price is €120
includes taxes & fees
1 Dec - 2 Dec
Idyllic Small-Town Stay

Holiday Home in Northwood

3.0 star property
8.8 out of 10, Excellent, (46)
"The cottage was great! It was very clean and comfy. The host had everything ready for us for a late check in. "
United States
Tonja
The Cottages at Harvey Lake

Holiday Home in Durham

10.0 out of 10, Exceptional, (62)
"Perfect, clean & comfy. Will travel here again "
United States
GAIL L.
Luxurious Spa Suite with Jacuzzi, Outdoor Sauna, Plunge Pool and Steam-bath

Holiday Home in Nashua

10.0 out of 10, Exceptional, (16)
"This was the perfect location for us for what we needed. Kind of in the middle of everything!"
United States
R Scott B.
The price is €404
includes taxes & fees
9 Dec - 10 Dec
Beautiful & Relaxing Nashua Home - Minutes from Downtown

Holiday Home in Nashua

7.4 out of 10, Good, (3)
"Had my crew of 4 stay there when we had a build close by. Host was very responsive, accommodating and communication was great. The house was nice and had everything we needed. I had no complaints from my crew. We were commuting to MA so don't have much to say about the area or town."
United States
Chris H.
Spacious 4-bedroom house in welcoming Nashua NH

Holiday Home in Greenland

6.6 out of 10, (26)
"This house was very accommodating. The pictures and description were accurate. The house was close to many of the attractions we wanted to see. The check in process was easy."
United States
Trish K.
Warm house with pool table, large deck, AC, washer/dryer, & beautiful kitchen

Holiday Home in Manchester

2.0 star property
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 €292
includes taxes & fees
1 Dec - 2 Dec
Fabulous 3-bedroom house in Manchester

Holiday Home in Haverhill

9.8 out of 10, Exceptional, (11)
"Nice place, neat and clean, beautiful neighborhood!"
United States
Cathy H.
The price is €313
includes taxes & fees
1 Dec - 2 Dec
Classic New England Bunkhouse- Home for the whole family!

Cottage in Northwood

9.8 out of 10, Exceptional, (11)
"Awesome place for quite getaway."
United States
Jason L.
Lakefront Salmon Cottage

Holiday Home in Salem

9.8 out of 10, Exceptional, (20)
"Plenty of space and everything we needed for a weekend getaway while attended a wedding in the area. "
United States
Michael C.
The price is €1,640
includes taxes & fees
14 Dec - 15 Dec
Charming 1825 Farmhouse Near Boston & Canobie Lake

Apartment in Salem

9.4 out of 10, Exceptional, (9)
"Was in a very convenient spot. Near the highway as well as a mall and lots of dining options. Great place to stay if you’re going to Boston or anywhere near Salem New Hampshire "
United States
Jeremy
The price is €413
includes taxes & fees
23 Dec - 24 Dec
Quaint Salem Gem Close to Shopping, Hiking ,Boston

Cottage in Dunbarton

9.4 out of 10, Exceptional, (57)
"Great time at this quite little getaway. It was a hidden gem!"
United States
Jennifer R.
Quaint Dunbarton Waterfront Cottage

Holiday Home in Salem

9.6 out of 10, Exceptional, (14)
"The house was clean, the communication was prompt and overall we had a great stay! "
United States
Seth M.
The price is €702
includes taxes & fees
30 Dec - 31 Dec
Walk to Tuscan Village | Modern 3bd Farmhouse

Cabin in Pittsfield

10.0 out of 10, Exceptional, (34)
"Even more beautiful than we were lead to hope for!Can’t wait to return with our entire family!"
United States
Mary Ann L.
Bower Cabin- Cabin in woods on a remote pond, Romantic getaway, Green living!

Apartment in Salem

10.0 out of 10, Exceptional, (2)
"As advertised and very clean."
United States
Michael T.
Cozy 1 bedroom basemant apt with private entrance and AC in the heart of Salem

Apartment in 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 €220
includes taxes & fees
16 Dec - 17 Dec
Modern 1BD Near Downtown & Hgwy

Holiday Home in Kalivas Union

10.0 out of 10, Exceptional, (1)
"Excellent recent reno - kept the original features and added updates. Rooms are larger than they appear in the pix. Only concern are the steep, narrow stairs."
United States
Steve R.
The price is €701
includes taxes & fees
9 Dec - 10 Dec
Family Oasis

Holiday Home in Nashua

9.8 out of 10, Exceptional, (26)
"Great place for a family. Family friendly and even had toys available for the kids. We had a good stay."
United States
Dee C.
Cozy home with hot tub minutes to downtown Nashua and Shops
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, apart-hotels, 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 €120 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.