Holiday Rentals in Chester

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Holiday Rentals in Chester

Luxurious Spa Suite with Jacuzzi, Outdoor Sauna, Plunge Pool and Steam-bath
10.0 out of 10, Exceptional, (40)
"Very relaxing and welcoming. We needed a weekend away to ourselves and the amenities here helped us be connected and relaxed. Great location with lots of amenities close by, and close to Portsmouth for dining and shopping. Thank you so much for having us!"
Luxurious Spa Suite with Jacuzzi, Outdoor Sauna, Plunge Pool and Steam-bath
Tidy 2-Bed w/ Parking!🚗Wine!🍷UNH👩🏻‍🎓
9.4 out of 10, Exceptional, (9)
"Great little apartment that slept all 5 of us. Cooked all our dinners for the weekend in the apartment. Was pleasantly surprised by a complimentary bottle of wine that was great! Travis was easy to contact and answered all our questions in a timely manner. Highly recommended"
Tidy 2-Bed w/ Parking!🚗Wine!🍷UNH👩🏻‍🎓
Luxury Home | Walk to Beach | Island Path Escape
10.0 out of 10, Exceptional, (16)
"Property layout was perfect with each room having its own bathroom. Very spacious and good amenities."
The price is €583
includes taxes & fees
8 May - 9 May
Luxury Home | Walk to Beach | Island Path Escape
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Quaint Dunbarton Waterfront Cottage
9.2 out of 10, Wonderful, (39)
"Nicole and Jason were incredible hosts. They were quick to respond, and were extremely helpful. The house was extremely clean, and we loved the open concept. One of our family members is in a wheelchair, and was able to get around the house with ease. The house was fully equipped with towels, blankets, bedding, dishes, and more. Overall, an exceptional experience."
Quaint Dunbarton Waterfront Cottage
Indoor Pool, 2 Miles From Ocean, 7,000 Square Foot Luxury Home
9.6 out of 10, Exceptional, (76)
"Everything was perfect. Only area for improvement is cleanliness in a few areas of the home: garage, main floor laundry room, pool bathroom shower. Host is very communicative and respectful. Would highly recommend for a large gathering of family and friends."
Indoor Pool, 2 Miles From Ocean, 7,000 Square Foot Luxury Home
Pet-Friendly 4-Bedroom Retreat with King Bed, Prime Downtown Location!
Pet-Friendly 4-Bedroom Retreat with King Bed, Prime Downtown Location!
Enchanting, romantic and fun river getaway
10.0 out of 10, Exceptional, (7)
"Couldn’t ask for more in this beautiful location right on the river. If you can imagine, living on the pages of a decorating magazine, this is it. Not only a beautiful home, but ANNA has thought of everything. The kitchen is loaded with more than the basics we would need to launch our visit. Not only that little things like even Band-Aids are in the bathroom. Since we visited in winter, we didn’t get to use the gas grill or the docks or any of the outdoor amenities, but we could see they were...
Enchanting, romantic and fun river getaway
Chic Salem NH Studio w Private Entrance/Bathroom
9.6 out of 10, Exceptional, (14)
"Everything was very neat and check-in was easy because the instructions from the owner were so clear. There was a tad bit of noise from either a neighbor or the owner (space is attached to a home and share a wall) one evening and a bit of an odd smell the whole time. Not bad but not pleasant either. Like long after you’ve cooked something and a scent remains but no longer smells like food or maybe like the smell of a puppy that’s just come in from outside. Nothing that should keep anyone away...
The price is €336
includes taxes & fees
2 Jun - 3 Jun
Chic Salem NH Studio w Private Entrance/Bathroom
4 BR Serene Home Nestled Amongst the Canopy of Majestic Trees
10.0 out of 10, Exceptional, (2)
"Wonder trip! Thank you. We were very comfortable!"
4 BR Serene Home Nestled Amongst the Canopy of Majestic Trees
Warm house with pool table, large deck, AC, washer/dryer, & beautiful kitchen
5.4 out of 10, (6)
"We enjoyed cooking and playing pool was nice for all of us to have our own space."
Warm house with pool table, large deck, AC, washer/dryer, & beautiful kitchen
Waterfront Cottage
10.0 out of 10, Exceptional, (13)
"Wonderful cottage in a quiet neighborhood on a nice little lake. It is a great setting and was perfect for us to decompress after spending holiday festivities with family. Greg was great to work with and provided all the communication needed to be prepared for the cottage. We are looking to book again due to the proximity to the coast, shopping and restaurants!"
Waterfront Cottage
Waterfront Cottage, Quiet and Secluded, on Swains Lake
9.4 out of 10, Exceptional, (53)
"Loved the cottage, it was peaceful and relaxing. We will be back again"
Waterfront Cottage, Quiet and Secluded, on Swains Lake
A spacious modern elegant 3 bedroom Ranch, Whole House located in South Nashua.
The price is €355
includes taxes & fees
15 May - 16 May
A spacious modern elegant 3 bedroom Ranch, Whole House located in South Nashua.
Modern 2/1 Centrally Located Salem, NH
10.0 out of 10, Exceptional, (2)
"Close to everything including 93. Quiet. Kitchen well stocked."
The price is €360
includes taxes & fees
26 May - 27 May
Modern 2/1 Centrally Located Salem, NH
Charming Carriage House on Historic Scenic Farm
8.8 out of 10, Excellent, (5)
"Cute house on a beautiful farm. Perfect location while visiting daughter at UNH. Very comfortable and had everything we needed. Will definitely be back!"
Charming Carriage House on Historic Scenic Farm
Classic New England Bunkhouse- Home for the whole family!
The price is €364
includes taxes & fees
5 May - 6 May
Classic New England Bunkhouse- Home for the whole family!
Cozy country tiny house
8.0 out of 10, Very good, (1)
"Quiet and cozy.. great for a get away weekend"
Cozy country tiny house
Pet-Friendly Merrimack Home w/ Grill: 8 Mi to Mall
3.0 out of 10, (2)
"This house is listed as a 3 bed 2 bath house. The three bedrooms are very small but you can get by for a day or two. The beds were in rough shape and not very comfortable. The queen (I think it was a queen but seemed smaller) has a frame but the box spring is just on the floor. The bathroom upstairs is very narrow. The second bath downstairs is not one you’d want to use. There is a ton of old trash and clothes scattered all over the basement. Overall it seems like whoever bought this house...
Pet-Friendly Merrimack Home w/ Grill: 8 Mi to Mall
**10 mins to Beach | Portsmouth | Maine | Hampton**
10.0 out of 10, Exceptional, (3)
"Accommodations were as expected. Unit was clean."
The price is €345
includes taxes & fees
5 May - 6 May
**10 mins to Beach | Portsmouth | Maine | Hampton**
Comfortable spacious house, easy access to all
9.0 out of 10, Wonderful, (9)
"Staying in Newburyport was a great location for our family of 4 to visit friends and family in New England! We went kayaking on Plum island, toured Newburyport, Kittery Maine, Quincy Market in Boston etc. The property was adequate for us, nice to have laundry, space for us to have meals. The negative was that the property was not very clean, lots of dust and unfinished details. The place needs some upkeep!"
The price is €443
includes taxes & fees
4 Jun - 5 Jun
Comfortable spacious house, easy access to all
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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.

Other types of properties in Chester you may be interested in

Country Inn & Suites by Radisson, Manchester Airport, NH
3.0 star property
8.0 out of 10, Very good, (1007)
"Breakfast was good. Staff friendly. Dogs allowed"
The price is €113
includes taxes & fees
12 May - 13 May
Country Inn & Suites by Radisson, Manchester Airport, NH
DoubleTree by Hilton Manchester Downtown
4.0 star property
9.0 out of 10, Wonderful, (1004)
"The hotel was beautiful, staff was great. "
The price is €128
includes taxes & fees
26 May - 27 May
DoubleTree by Hilton Manchester Downtown
Park View Inn - Salem
2.0 star property
8.8 out of 10, Excellent, (1007)
"Good Place "
The price is €101
includes taxes & fees
5 May - 6 May
Park View Inn - Salem
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.

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 €336 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 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 Pawtuckaway State Park. Chester Village Cemetery and Zorvino Vineyards are a couple of places you'll find in the wider area.

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.

Recent reviews of Chester properties
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