Search Cottages in Chester

  • 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
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Compare 19 Cottages in Chester with updated reviews, rates, and availability.

Quaint Dunbarton Waterfront Cottage

9.4 out of 10, Exceptional, (46)
"LOVELY AND PEACEFULVERY KIND HOST."
Quaint Dunbarton Waterfront Cottage

Waterfront Cottage, Quiet and Secluded, on Swains Lake

9.4 out of 10, Exceptional, (62)
"Lovely stay,everything amazing would highly recommend!"
Waterfront Cottage, Quiet and Secluded, on Swains Lake

Baboosic Lake - Wonderful Classic S. NH Vacation Cottage all to Yourself

9.6 out of 10, Exceptional, (18)
"Our kids said the beds were the most comfortable beds they'd ever slept on, with the coziest blankets. The cabin was warm, cozy, and homey. Host was very nice and communication was timely and helpful. Beautiful view on the lake. Close to all amenities, shopping, and grocery stores."
Baboosic Lake - Wonderful Classic S. NH Vacation Cottage all to Yourself

Welcome to the Lake

10.0 out of 10, Exceptional, (35)
"The lake is right outside the door, and the view from the living room is just beautiful! We were in the area for work and didn't have much time to enjoy it, but there is a gorgeous gazebo on the side and a fire pit on the patio out back - both looking directly our onto the lake. One small downside, the bedroom is quite small - but we did enjoy the view of the sunrise on the lake right from the bed.."
Welcome to the Lake

Little Pond, Big Fish, Swimming, Hiking, Kayaking on our Private Lake.

9.2 out of 10, Wonderful, (5)
"The cabin is in a very nice, quiet and peaceful area. The property was clean and inviting. Once we figured how to work the pellet heater we were set. We were very pleased with our stay. "
Little Pond, Big Fish, Swimming, Hiking, Kayaking on our Private Lake.

Staycation + Work From Home in one private setting

10.0 out of 10, Exceptional, (18)
"Very nice hosts brought me chicken broth- came with a cold"
Staycation + Work From Home in one private setting

The PondeRosa cottage at Cobbett's pond

10.0 out of 10, Exceptional, (19)
"Location worked perfect for us to be near family and friends "
The PondeRosa cottage at Cobbett's pond

Big Fish, Little Pond. Fire Pit Swimming, Hiking, Kayaking, and Fishing!

9.2 out of 10, Wonderful, (10)
"When we arrived we were immediately struck by how spotlessly clean the whole cabin was. And there were very thoughtful welcome packs too. The cabin has quaint cottage touches and the surround sounds from the woods were lovely. Very relaxing and comfortable environment. Full-sized washer and dryer came in handy. Don’t miss America’s Stonehenge just up the road. Would happily stay here again."
Big Fish, Little Pond. Fire Pit Swimming, Hiking, Kayaking, and Fishing!

Waterfront cottage on large, wooded lot with amazing swimming and fishing

10.0 out of 10, Exceptional, (20)
"My family and I had a wonderful stay. The host was exceptionally responsive, 10/10, to any and all questions before and during our week's stay, including addressing any concerns and always got back quickly and was highly accommodating. We arrived to a nice welcome gift basket, which set the tone for a wonderful stay. Check in couldn't have been easier. The cottage has plenty of seating inside, including a table-bar facing the windows overlooking the lake. We enjoyed the out-door shower...
Waterfront cottage on large, wooded lot with amazing swimming and fishing

Cozy 3 bedroom seasonal cottage with very short walk to private community beach

9.6 out of 10, Exceptional, (10)
"Good stay"
Cozy 3 bedroom seasonal cottage with very short walk to private community beach

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

3.0 star property
Peek-a-boo Lake Views & Yard: Windham Home

Enchanting Romantic Waterfront Cottage

10.0 out of 10, Exceptional, (10)
"Me and my family had a pleasant experience at Anna’s house we had everything we could have needed she went the extra mile to make sure she thought of everything. She answered me right away if I needed something. The house was so cute and well put together me and my husband stayed in the master bedroom and it had an adjustable bed which made it comfortable for how me and my husband sleep. It was so beautiful waking up in the morning to the view of the lake. We will definitely be staying with her...
Enchanting Romantic Waterfront Cottage

The Guest Cottage in Paradise.

10.0 out of 10, Exceptional, (18)
"The Paradise Guest Cottage was a lovely 1 mo stay for me since I enjoy being on fresh water. From watching the morning sun dance on the water to looking down from the deck at the fish swimming below, every view of the lake was beautiful. And because the trees shaded the deck from noon on, there was almost always a nice cool cross breeze through the cottage. Otherwise, the A/Cs were very effective. Laid back in this clean, well kept cottage, complete kitchen, W&D, comfortable bed, with no...
The Guest Cottage in Paradise.

Enjoy being serenaded by loons at this rustic Northwood lake view cottage!

10.0 out of 10, Exceptional, (3)
"very peaceful nice people"
Enjoy being serenaded by loons at this rustic Northwood lake view cottage!

Riverfront New Hampshire Cottage w/ Boat Dock

3.0 star property
Riverfront New Hampshire Cottage w/ Boat Dock

Southern New Hampshire lakefront

Southern New Hampshire lakefront

Lakefront Salem Retreat - Fish, Swim, Kayak & More

3.0 star property
Lakefront Salem Retreat - Fish, Swim, Kayak & More

Lakefront Retreat w/ Kayaks, Grill, Fire Pit!

3.0 star property
Lakefront Retreat w/ Kayaks, Grill, Fire Pit!

Sunsets and Breezes! Short walk to beach and Boardwalk! The best of Hampton!

10.0 out of 10, Exceptional, (2)
"Excellent getaway! The cottage was very cozy and beautifully decorated. The owners were always available and the location was perfect! We hope to stay there again on our next vacation!"
Sunsets and Breezes! Short walk to beach and Boardwalk! The best of Hampton!

Walk to Beach: Water-view Seabrook Sanctuary

3.0 star property
Walk to Beach: Water-view Seabrook Sanctuary
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

Other property types in Chester

Postcard Cabins Blake Brook

2.0 star property
9.8 out of 10, Exceptional, (7)
"The getaway cabins are now a preference in comparison to regular hotel rooms. They were cozy & it was a nice getaway from the regular routine. I recommend anyone to give the cabins a try they are amazing"
The price is SAR 506
SAR 549 total
includes taxes & fees
26 Mar - 27 Mar
Postcard Cabins Blake Brook

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

9.6 out of 10, Exceptional, (84)
"This is a charming 400-year-old farmhouse that has been well-loved and is perfect for hosting large get togethers. While it has been updated over the years, most of the original layout remains intact. There are lots of rules, but none are unreasonable, and there is a lot to know simply because it is a very large, historic home. This house feels warm and welcoming. It has tons of windows offering lots of light and lovely views from every room. There are six bedrooms upstairs, and the room off the...
The price is SAR 5,626
SAR 8,598 total
includes taxes & fees
16 Mar - 17 Mar
Indoor Pool, 2 Miles From Ocean, 7,000 Square Foot Luxury Home

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

10.0 out of 10, Exceptional, (2)
"Lovely home in sweet neighborhood. The host was responsive to my communications. Very positive experience. "
Peek-a-Boo Lake Views & Yard: Windham Home
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.

Frequently asked questions

Why book your cottage in Chester with Expedia?
Expedia has some wonderful cottages in Chester, so start packing for a memorable stay on nature’s doorstep. If you’re on a budget, click on how much you’d like to spend and the star rating of your property. Or, try out our filters to search for cottages with a kitchen or a pool. We’ll help you find the right place whatever your escape looks like.
How can I find cheap cottages in Chester?
Expedia is here to help you track down cheap cottages in Chester. To book a terrific stay in a couple of clicks, try out our convenient filter tool to refine your search by star rating, amenities and budget.