Chester Holiday Rentals

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Holiday Rentals in Chester

Postcard Cabins Blake Brook

2.0 star property
9.6 out of 10, Exceptional, (50)
"Perfect place "
The price is AU$272
includes taxes & fees
1 Sept - 2 Sept
Postcard Cabins Blake Brook

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

9.6 out of 10, Exceptional, (95)
"My friends and I had a great time in Chelsi's property. It is the perfect home to host a reunion, sociable gatherings, and brought everyone together. The amenities were fantastic and we were never bored. Great location! "
Indoor Pool, 2 Miles From Ocean, 7,000 Square Foot Luxury Home

Classic New England Bunkhouse- Home for the whole family!

10.0 out of 10, Exceptional, (6)
"Very good place to stay. Quiet community and lovely home. Clean and bright. Would stay again for a homecoming."
The price is AU$547
includes taxes & fees
11 Sept - 12 Sept
Classic New England Bunkhouse- Home for the whole family!

Luxurious Spa Suite with Jacuzzi, Outdoor Sauna, Plunge Pool and Steam-bath

9.8 out of 10, Exceptional, (58)
"We had a great stay here. The property and accommodations were excellent. Clean, quiet, and as comfortable as we could ask for. It is in a great location close to the University of NH (great to drive and walk through) and Portsmouth. Highly recommend staying here!"
Luxurious Spa Suite with Jacuzzi, Outdoor Sauna, Plunge Pool and Steam-bath

Relax in Our Cozy Duplex: Private, Quiet, and Perfect for Every Season!

8.4 out of 10, Very good, (6)
"It was a really nice place. Even though it is shared, we had plenty of privacy. In fact, we stayed 3 days and never saw the roommate mentioned in the post. I recommend to anyone looking for a comfortable place to stay. "
Relax in Our Cozy Duplex: Private, Quiet, and Perfect for Every Season!

Warm house with pool table, large deck, AC, washer/dryer, & beautiful kitchen

6.4 out of 10, (21)
"Property was great "
Warm house with pool table, large deck, AC, washer/dryer, & beautiful kitchen

The Cottages at Harvey Lake

3.0 star property
8.8 out of 10, Excellent, (45)
"The view of the lake from the cabin was excellent. "
The price is AU$226
includes taxes & fees
4 Sept - 5 Sept
The Cottages at Harvey Lake

Lakefront Salmon Cottage

9.8 out of 10, Exceptional, (11)
"Owner greeted me with a mug to check if i had needs, which i appreciate. Ive extended my stay its so peaceful and quiet here. The owners are genuinely lovely people "
The price is AU$262
includes taxes & fees
10 Sept - 11 Sept
Lakefront Salmon Cottage

Idyllic Small-Town Stay

The price is AU$245
includes taxes & fees
8 Sept - 9 Sept
Idyllic Small-Town Stay

Safe Peaceful Quite Bright Gorgeous Accessibility

7.8 out of 10, Good, (14)
"In town for a few days hunting with friends. Place was nice and owner was nice. Had trouble with the door lock code a few times. Almost had reservation cancelled because the owner could “hear animals” which was actually us getting our turkey calls out for the following day. Very clean house and quiet neighborhood. Felt weird that the owner was in some sort of a hidden apt. though. "
Safe Peaceful Quite Bright Gorgeous Accessibility

Spacious 4-bedroom house in welcoming Nashua NH

6.0 out of 10, (1)
The price is AU$797
includes taxes & fees
10 Sept - 11 Sept
Spacious 4-bedroom house in welcoming Nashua NH

A room with a bathroom for rent in a two bedroom two bathroom condo

The price is AU$408
includes taxes & fees
9 Sept - 10 Sept
A room with a bathroom for rent in a two bedroom two bathroom condo

Welcome to the Lake

10.0 out of 10, Exceptional, (41)
"We enjoyed our stay at this beautiful lake house with great hosts. Would highly recommend for anyone looking for a New Hampshire getaway."
Welcome to the Lake

A spacious modern elegant 3 bedroom Ranch, Whole House located in South Nashua.

9.6 out of 10, Exceptional, (9)
"Great bedding, roomy, tons of kitchen supplies, fenced yard. Worked wonderfully for me. "
The price is AU$595
includes taxes & fees
8 Sept - 9 Sept
A spacious modern elegant 3 bedroom Ranch, Whole House located in South Nashua.

Sunset-Facing Cottage on Mendums Pond in Barrington, NH

10.0 out of 10, Exceptional, (54)
"Beautiful setting on a quiet lake with loons and herons. We loved the deck overlooking the lake, and the kayaks and canoe provided (be sure to bring your own life vests)! The water was lovely and warm during our end-of-June stay."
Sunset-Facing Cottage on Mendums Pond in Barrington, NH

Quaint Dunbarton Waterfront Cottage

9.2 out of 10, Wonderful, (50)
"This property was perfect for us. My wife and 2 sons had a fantastic time. We were in New Hampshire for my sons college graduation. It was perfect for us. We had a beautiful weekend on the lake. It could not have been better!! Thank you for the memories!!"
Quaint Dunbarton Waterfront Cottage

Lovely 2 bedroom- kitchenette

2.0 star property
9.2 out of 10, Wonderful, (5)
"It served our purpose well. I would use it again"
The price is AU$774
includes taxes & fees
24 Sept - 25 Sept
Lovely 2 bedroom- kitchenette

Charming 2-bedroom waterfront cottage in welcoming Barrington with deck and WiFi

2.0 star property
9.6 out of 10, Exceptional, (7)
"We had a great experience overall. The house was super cozy and the view was amazing. House has everything we needed and then some. Joan was also very helpful and responsive when we had a few questions. We will definitely be back again!"
Charming 2-bedroom waterfront cottage in welcoming Barrington with deck and WiFi

Quaint Salem Gem Close to Shopping, Hiking ,Boston

9.2 out of 10, Wonderful, (7)
"It was clean and the owners answered questions promptly. Lots of ammenities included that were helpful."
The price is AU$720
includes taxes & fees
10 Sept - 11 Sept
Quaint Salem Gem Close to Shopping, Hiking ,Boston

Rustic Lake front cottage nestled in the pines with a Golf Putting Green.

3.0 star property
8.4 out of 10, Very good, (7)
"My family stayed in this beautiful home for 6 nights and we couldn’t have loved it more. The description matched the place perfectly. There was plenty of sleeping space for 6 adults and the view from the back porch was unreal. There was plenty of water supplies which gave everyone an equal opportunity to be out in the water. Would definitely stay here again!"
Rustic Lake front cottage nestled in the pines with a Golf Putting Green.
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

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 favourite 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 depend 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 AU$226 per night. Entering your travel dates in the search wizard might find you 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?

The Cottages at Harvey Lake: This holiday home rental outside Chester is located on the waterfront, and has a terrace, a garden and a BBQ to put you at ease in your new surroundings. It has 6 bedrooms, as well as a kitchenette with a fridge, a stovetop and a microwave, so that you can cook with friends or family.

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.