Chester Vacation Rentals

  • Plan, book, stay with confidence

    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
Apr 25 - Apr 27
In two weeks
May 2 - May 4
In one month
May 16 - May 18
In two months
Jun 13 - Jun 15

Browse Select Chester Vacation Homes

Peek-a-Boo Lake Views & Yard: Windham Home
Terrace/patio

Peek-a-Boo Lake Views & Yard: Windham Home

8.8 out of 10, Excellent, (3)
"Lovely home in sweet neighborhood. The host was responsive to my communications. Very positive experience. "
Peek-a-Boo Lake Views & Yard: Windham Home
Safe Peaceful Quite Bright Gorgeous Accessibility
Miscellaneous

Safe Peaceful Quite Bright Gorgeous Accessibility

The price is CA $313
CA $561 total
includes taxes & fees
Apr 18 - Apr 19
Safe Peaceful Quite Bright Gorgeous Accessibility
Waterfront Home w/ Private Dock
Interior

Waterfront Home w/ Private Dock

10.0 out of 10, Exceptional, (14)
"This is a great little get away location. The pond neighborhood is quiet and everything is well maintained. Squirrel friends to watch gather nuts and ducks to calm the soul. "
The price is CA $382
CA $596 total
includes taxes & fees
Apr 25 - Apr 26
Waterfront Home w/ Private Dock
Location, Location, Location
Fridge, microwave, oven, stovetop

Location, Location, Location

10.0 out of 10, Exceptional, (5)
"Nicely appointed, spacious, conveniently located."
Location, Location, Location
Lakefront Salem Retreat - Fish, Swim, Kayak & More
TV

Lakefront Salem Retreat - Fish, Swim, Kayak & More

8.8 out of 10, Excellent, (9)
"Overall, we were happy with our stay. We were there in the winter, so we didn't get to enjoy the lake. The house was great as a launch point between Boston and the mountains.The house is literally on the lake. Water touches the lake side of the house. When we were there, the lake was frozen and beautiful.The house was well stocked and perfectly ready for us. There's plenty of parking. It's an older house, so the ceilings can be low and the floors are sometimes uneven. But the main room is...
Lakefront Salem Retreat - Fish, Swim, Kayak & More
2-bedroom vacation home 30 minutes from Boston and NH beaches
Fridge, microwave, oven, stovetop

2-bedroom vacation home 30 minutes from Boston and NH beaches

9.6 out of 10, Exceptional, (7)
"The house is very conveniently located near the expressway and Boston airport. It was a quick drive (when traffic was light). The bedrooms are good sized and are upstairs which was nice if one of us was up earlier than the other. "
The price is CA $165
CA $424 total
includes taxes & fees
Apr 17 - Apr 18
2-bedroom vacation home 30 minutes from Boston and NH beaches
Beautiful & Relaxing Nashua Home - Minutes from Downtown
Smart TV, books

Beautiful & Relaxing Nashua Home - Minutes from Downtown

10.0 out of 10, Exceptional, (9)
"The place was as advertised. The location was convenient to everything. The host was very responsive. It was a nice stay."
The price is CA $364
CA $743 total
includes taxes & fees
Apr 21 - Apr 22
Beautiful & Relaxing Nashua Home - Minutes from Downtown
Warm house with pool table, large deck, AC, washer/dryer, & beautiful kitchen
Fridge, microwave, oven, stovetop

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

6.8 out of 10, (15)
"Property was great "
Warm house with pool table, large deck, AC, washer/dryer, & beautiful kitchen
Waterfront Cottage
Property grounds

Waterfront Cottage

9.6 out of 10, Exceptional, (35)
"The property was perfect for what we needed and we will definately be staying again."
Waterfront Cottage
Classic New England Bunkhouse- Home for the whole family!
Terrace/patio

Classic New England Bunkhouse- Home for the whole family!

10.0 out of 10, Exceptional, (2)
"Very good place to stay. Quiet community and lovely home. Clean and bright. Would stay again for a homecoming."
The price is CA $327
CA $532 total
includes taxes & fees
Apr 21 - Apr 22
Classic New England Bunkhouse- Home for the whole family!
Across From Tuscan Family Farmhouse
Fridge, microwave, oven, stovetop

Across From Tuscan Family Farmhouse

9.8 out of 10, Exceptional, (6)
"Wonderful location, easy access to shopping centers and restaurants. Comfortable house with great amenities"
The price is CA $1,485
CA $2,073 total
includes taxes & fees
Apr 21 - Apr 22
Across From Tuscan Family Farmhouse
Relaxing Hampton Beach Vacation Home
Exterior

Relaxing Hampton Beach Vacation Home

10.0 out of 10, Exceptional, (74)
"Quiet secluded sitting areas overlooking the marsh made this stay. "
Relaxing Hampton Beach Vacation Home
Enchanting Romantic Riverfront Cottage
Smart TV, fireplace, DVD player, books

Enchanting Romantic Riverfront Cottage

2.0 star property
9.8 out of 10, Exceptional, (7)
"I recently had the pleasure of staying at this property that truly exceeded all my expectations.From the moment we arrived, I was blown away by the beauty of the place—pictures simply didn’t do it justice! The setting was peaceful and quiet, providing the perfect escape from the hustle and bustle of everyday life.The property was well-equipped with everything we needed for a comfortable stay. It felt like a home away from home, and we were able to relax and enjoy our time without any worries. A...
The price is CA $402
CA $482 total
includes taxes & fees
May 15 - May 16
Enchanting Romantic Riverfront Cottage
Lakefront Retreat w/ Kayaks, Grill, Fire Pit!
Outdoor dining

Lakefront Retreat w/ Kayaks, Grill, Fire Pit!

9.6 out of 10, Exceptional, (10)
"We went in November for a small family retreat and did expect to nor did we swim or kayak. But being on the lake, sitting on the dock and small beach was a magical way to see so many many stars in the sky. It was steps to walk into Pawtuckaway park and go in a hike. We made it to the fire tower!"
Lakefront Retreat w/ Kayaks, Grill, Fire Pit!
Linden Tree: Walk to Hallmark Holiday Downtown, Gas Fireplace, Spacious, Fast WiFi, Smart TV
Beach nearby

Linden Tree: Walk to Hallmark Holiday Downtown, Gas Fireplace, Spacious, Fast WiFi, Smart TV

7.8 out of 10, Good, (14)
"Clean, nice, centrally located. Appox 0.8 mile walk to shops."
Linden Tree: Walk to Hallmark Holiday Downtown, Gas Fireplace, Spacious, Fast WiFi, Smart TV
Charming 4-bedroom unit with 2 full bathrooms in serene Methuen Ma
Interior

Charming 4-bedroom unit with 2 full bathrooms in serene Methuen Ma

10.0 out of 10, Exceptional, (1)
"Lovely home and FANTASTIC customer service. Quick response for any requests. I asked about a coffee pot and he brought a brand new pot. It snowed and without being asked he came and shoveled and salted the walk and driveway. I will happily visit again. "
Charming 4-bedroom unit with 2 full bathrooms in serene Methuen Ma
Entire House, Sleep 11, Garage, Fully Fenced Backyard
Fridge, microwave, oven, stovetop

Entire House, Sleep 11, Garage, Fully Fenced Backyard

10.0 out of 10, Exceptional, (2)
"Our family of 7 enjoyed the space this house offered. Lei was very quick in responding to questions. The neighborhood was very peaceful and quiet. My kids really enjoyed the Pine St. Eatery for breakfast and it's right around the corner from this house."
Entire House, Sleep 11, Garage, Fully Fenced Backyard
The Cottages at Harvey Lake
Lake

The Cottages at Harvey Lake

3.0 star property
8.6 out of 10, Excellent, (39)
"This fit the bill for an unplanned birthday overnight. Everything went smoothly and was as described. We regret our stay was too short to enjoy some of the amenities but we hope to return."
The price is CA $222
CA $241 total
includes taxes & fees
May 4 - May 5
The Cottages at Harvey Lake
Modern Home-Near Beach/w lg Stylish Patio & HotTub, Fire Tables & Outdoor Dining
Terrace/patio

Modern Home-Near Beach/w lg Stylish Patio & HotTub, Fire Tables & Outdoor Dining

10.0 out of 10, Exceptional, (3)
"This is a beautiful home. Close to all the action in Hampton Beach. KC and the Sunshine Band was playing at the Casino Ballroom it was a great show!!! Ruthie was a wonderful host and kept in touch throughout our 10 day stay. We will definitely stay here again next year with friends. Thank you Ruthie for everything ;)"
Modern Home-Near Beach/w lg Stylish Patio & HotTub, Fire Tables & Outdoor Dining
Riverfront New Hampshire Cottage w/ Boat Dock
Miscellaneous

Riverfront New Hampshire Cottage w/ Boat Dock

8.6 out of 10, Excellent, (7)
"Nice I like and can back "
Riverfront New Hampshire Cottage w/ Boat Dock
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.
Don't see what you're looking for?
See all available properties in Chester
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Other property types in Chester

Postcard Cabins Blake Brook
Exterior

Postcard Cabins Blake Brook

2.0 star property
10.0 out of 10, Exceptional, (13)
"This place is amazing. It was so quiet that I found myself whispering. Our dog loved it and she’s usually stressed out on trips. My only regret is only booking one night. "
The price is CA $188
CA $256 total
includes taxes & fees
Apr 17 - Apr 18
Postcard Cabins Blake Brook
Indoor Pool, 2 Miles From Ocean, 7,000 Square Foot Luxury Home
Indoor pool, a heated pool

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

9.6 out of 10, Exceptional, (86)
"I gave this weekend to my family as a Christmas gift. Each year we go away together as my gift to them. This home was a perfect spot for our group. Adults could enjoy games in the spacious kitchen while children enjoyed the theater or karaoke in the other end of the spacious house. The indoor pool was fabulous and many memories were made over the weekend. Highly recommend for your family adventures."
Indoor Pool, 2 Miles From Ocean, 7,000 Square Foot Luxury Home
Cozy 3 bedroom in a friendly neighborhood close to I-93!
Fridge, microwave, oven, stovetop

Cozy 3 bedroom in a friendly neighborhood close to I-93!

10.0 out of 10, Exceptional, (2)
"This was a great stay. The cleanest property I have ever stayed at bar none! Centrally located. Comfortable beds and thoughtful touches throughout. Definitely would stay again! "
Cozy 3 bedroom in a friendly neighborhood close to I-93!
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.