Chester Vacation Rentals

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Check prices for these dates

In two weeks
Jun 5 - Jun 7
In two months
Jul 17 - Jul 19
In three months
Aug 14 - Aug 16
In four months
Sep 11 - Sep 13

Our top choices for Chester vacation rentals

View from property

Postcard Cabins Blake Brook, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Blake Brook, Outdoor Collection by Marriott Bonvoy
2.0 star property
Epsom
9.6 out of 10, Exceptional, (151 reviews)
"Great stay "
United States
Edward
The price is ￥22,101
￥30,880 total
includes taxes & fees
Jun 2 - Jun 3
Postcard Cabins Blake Brook, Outdoor Collection by Marriott Bonvoy
Lake

The Cottages at Harvey Lake

The Cottages at Harvey Lake
3.0 star property
Northwood
8.8 out of 10, Excellent, (46 reviews)
"The view of the lake from the cabin was excellent. "
United States
Matt
The price is ￥27,640
￥29,989 total
includes taxes & fees
Jun 3 - Jun 4
The Cottages at Harvey Lake
Interior

Lakefront Salmon Cottage

Lakefront Salmon Cottage
Northwood
9.8 out of 10, Exceptional, (11 reviews)
"Awesome place for quite getaway."
United States
Jason L.
The price is ￥27,651
￥34,312 total
includes taxes & fees
Jun 3 - Jun 4
Lakefront Salmon Cottage
3 bedrooms, WiFi, bed sheets

Fabulous 3-bedroom house in Manchester

Fabulous 3-bedroom house in Manchester
Manchester
9.4 out of 10, Exceptional, (8 reviews)
"Place was nice. Super clean and host was very available for questions. "
United States
Frank C.
The price is ￥21,608
￥55,015 total
includes taxes & fees
May 27 - May 28
Fabulous 3-bedroom house in Manchester
Exterior

Lakefront Orange Cottage

Lakefront Orange Cottage
Northwood
9.0 out of 10, Wonderful, (11 reviews)
"The personal touch and welcome gift was lovely z"
United States
Joyce
The price is ￥24,379
￥26,450 total
includes taxes & fees
May 26 - May 27
Lakefront Orange Cottage
Fridge, microwave, oven, stovetop

Comfortable spacious house, easy access to all

Comfortable spacious house, easy access to all
Newburyport
9.0 out of 10, Wonderful, (14 reviews)
"A big, comfortable house. The owner was quick to answer the questions that I had and resolved everything nicely."
United States
William
The price is ￥36,920
￥64,505 total
includes taxes & fees
May 25 - May 26
Comfortable spacious house, easy access to all
Dining

Lakefront Pink Cottage

Lakefront Pink Cottage
Northwood
10.0 out of 10, Exceptional, (1 review)
"Cozy cottage on the lake, beautiful view of the sunrise from bed! Plus kayak and paddle boats to use on the lake!"
United States
Caitlin H.
The price is ￥27,651
￥34,312 total
includes taxes & fees
May 26 - May 27
Lakefront Pink Cottage
Dining

Lakefront Yellow Cottage

Lakefront Yellow Cottage
Northwood
10.0 out of 10, Exceptional, (5 reviews)
"Clean, friendly, a great place to stay. I kayaked in the lake and it was beautiful. Hope to stay again next summer!"
United States
Ravaioli N.
The price is ￥26,342
￥32,718 total
includes taxes & fees
May 26 - May 27
Lakefront Yellow Cottage
Exterior

Lakefront Purple Cottage

Lakefront Purple Cottage
Northwood
9.2 out of 10, Wonderful, (7 reviews)
"Quaint colorful just right ."
United States
Susan B.
The price is ￥26,342
￥32,718 total
includes taxes & fees
Jun 3 - Jun 4
Lakefront Purple Cottage
Cookware/dishes/utensils

Charming quiet

Charming quiet
Rimmon Heights
9.8 out of 10, Exceptional, (18 reviews)
"The apartment was easy to find and much bigger than we anticipated based on the photos! We were in town for a wedding and greatly appreciated the spacious guest rooms, double vanity in the bathroom, and open kitchen which made it easy for all of us to get ready. "
United States
Kelsey W.
The price is ￥26,846
￥49,983 total
includes taxes & fees
Jun 2 - Jun 3
Charming quiet
Interior

The Amoskeag - Ash Street Inn

The Amoskeag - Ash Street Inn
Corey Square
The price is ￥33,231
￥51,912 total
includes taxes & fees
May 25 - May 26
The Amoskeag - Ash Street Inn
Indoor pool, a heated pool

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

Indoor Pool, 2 Miles From Ocean, 7,000 Square Foot Luxury Home
North Hampton
9.6 out of 10, Exceptional, (108 reviews)
"Plenty of room for the whole family. The pool was a big hit with everyone and the theater was perfect for football and karaoke "
United States
Celeste F.
Indoor Pool, 2 Miles From Ocean, 7,000 Square Foot Luxury Home
Smart TV

Relaxing Family friendly Apartment!!

Relaxing Family friendly Apartment!!
Rimmon Heights
9.6 out of 10, Exceptional, (20 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.
The price is ￥30,499
￥55,844 total
includes taxes & fees
Jun 2 - Jun 3
Relaxing Family friendly Apartment!!
Fridge, microwave, oven, stovetop

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, (19 reviews)
"Great place for a church group to brainstorm and pray! Comfortable and relaxing."
United States
Jeremy S.
Large 3 floor Townhome with Patio, Backyard and Sauna
Outdoor dining

Idyllic Small-Town Stay

Idyllic Small-Town Stay
Derry
10.0 out of 10, Exceptional, (15 reviews)
"Excellent place to stay, very clean and well furnished. "
United States
Thomas
The price is ￥24,645
￥40,197 total
includes taxes & fees
Jun 22 - Jun 23
Idyllic Small-Town Stay
Interior

Large Private Guest House with Lake Views

Large Private Guest House with Lake Views
Salem
10.0 out of 10, Exceptional, (2 reviews)
"The owner was flexible and communicative when we had a hiccup at check in, and everything was as expected!"
United States
Kaleigh M.
The price is ￥46,861
￥63,944 total
includes taxes & fees
Jun 17 - Jun 18
Large Private Guest House with Lake Views
Cookware/dishes/utensils

North End Relaxing Family

North End Relaxing Family
North End
9.4 out of 10, Exceptional, (6 reviews)
"Excellent space for large gatherings, very clean, and very comfortable beds."
United States
Nathan L.
The price is ￥77,115
￥171,135 total
includes taxes & fees
May 24 - May 25
North End Relaxing Family
Fridge, microwave, oven, stovetop

North End Retreat

North End Retreat
North End
10.0 out of 10, Exceptional, (2 reviews)
"Fantastic location for our need, easy to navigate surrounding area, exactly as listed and the cleanest place I’ve ever stayed in. We will be back!!"
United States
Diane A.
The price is ￥39,713
￥98,414 total
includes taxes & fees
May 25 - May 26
North End Retreat
Dining

Stylish Apartment Near Downtown & Major Highways

Stylish Apartment Near Downtown & Major Highways
North Andover
9.6 out of 10, Exceptional, (15 reviews)
"Great spot to stay in. Would stay again!"
United States
Lorenzo H.
The price is ￥99,742
￥165,450 total
includes taxes & fees
Jun 8 - Jun 9
Stylish Apartment Near Downtown & Major Highways
Microwave, oven, stovetop, dishwasher

Spacious, family friendly 3700 sq ft w/ great yard

Spacious, family friendly 3700 sq ft w/ great yard
Straw-Smyth
The price is ￥106,271
￥168,907 total
includes taxes & fees
May 26 - May 27
Spacious, family friendly 3700 sq ft w/ great yard
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

Motel 6 Nashua, NH - South

Motel 6 Nashua, NH - South

6/10 Okay
"Room 240 toilet needs servicing ..."
Tyrell 2-night trip
Posted 1 hour ago
Motel 6 Nashua, NH - South

Find out more about Chester

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Look no further and take a look at our great range of rental properties in Chester!

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?

Enchanting Romantic Riverfront Cottage: This vacation home rental outside of Chester offers a fireplace, a balcony, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a stovetop, a microwave, and a coffee maker. It offers a garden, a hot tub, and a selection of books so you can immerse yourself in your vacation.

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 Town Hall and Chester Public Library 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.