Photo by Julie Miller

Search Chestertown Cottage Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
Aug 22 - Aug 24
In two weeks
Aug 29 - Aug 31
In one month
Sep 12 - Sep 14
In two months
Oct 10 - Oct 12

Cottages in Chestertown

The Loon-ey Bin - Loon themed cottage less than 10 miles to Lake George
Beach nearby

The Loon-ey Bin - Loon themed cottage less than 10 miles to Lake George

9.0 out of 10, Wonderful, (27)
"Quiet cabin/home in walking distance to the lake. If you are looking for a quiet getaway, this is the perfect cabin. Only 20 mins from downtown lake George. I plan on staying here again next year!! "
The Loon-ey Bin - Loon themed cottage less than 10 miles to Lake George
Lake Luzerne Cottage with Lake Rights 15 Min from Lake George
Exterior

Lake Luzerne Cottage with Lake Rights 15 Min from Lake George

9.0 out of 10, Wonderful, (33)
"Cozy little cottage in a great location. We really enjoyed the area and our stay. "
Lake Luzerne Cottage with Lake Rights 15 Min from Lake George
Beautiful cottage on quiet country road walking distance to charming North Creek
Exterior

Beautiful cottage on quiet country road walking distance to charming North Creek

9.8 out of 10, Exceptional, (43)
"Cute cozy cottage close to Gore mountain "
The price is ￥27,230
￥39,211 total
includes taxes & fees
Aug 18 - Aug 19
Beautiful cottage on quiet country road walking distance to charming North Creek
Charming cottage with a cozy, welcoming vibe
Interior

Charming cottage with a cozy, welcoming vibe

7.4 out of 10, Good, (13)
"Perfect place away from the strip, so clean and well taken care of. I'd live there forever honestly."
Charming cottage with a cozy, welcoming vibe
Athol Vacation Rental w/ Mountain Views!
Fridge, microwave, stovetop, dishwasher

Athol Vacation Rental w/ Mountain Views!

10.0 out of 10, Exceptional, (27)
"Beautiful facility, views, and a very quiet secluded place. The place was very clean and well supplied with amenities'."
Athol Vacation Rental w/ Mountain Views!
The Elms Waterfront Cottages
Condo | In-room dining

The Elms Waterfront Cottages

2.5 star property
8.4 out of 10, Very Good, (16)
"We were treated like royalty here at the Elms. The owner, Chandler and his staff, go above and beyond. What a beautiful escape. We will most definitely return. "
The price is ￥45,592
￥50,607 total
includes taxes & fees
Aug 24 - Aug 25
The Elms Waterfront Cottages
Huckleberry Cottage at Cozy Nook
Outdoor dining

Huckleberry Cottage at Cozy Nook

9.6 out of 10, Exceptional, (16)
"It was exactly what we needed to be able to go sight seeing and shopping at the nearby outlets"
Huckleberry Cottage at Cozy Nook
Adirondack Mountains Cottage Near Gore Mountain!
Fridge, microwave, stovetop, coffee/tea maker

Adirondack Mountains Cottage Near Gore Mountain!

9.8 out of 10, Exceptional, (114)
"Excellent place and nice view"
Adirondack Mountains Cottage Near Gore Mountain!
Beautiful lakeview cottage on Friends Lake
Terrace/patio

Beautiful lakeview cottage on Friends Lake

9.6 out of 10, Exceptional, (28)
"Very clean cabin, close to beach and lake. Host was very cordial. Expecting to return next summer."
Beautiful lakeview cottage on Friends Lake
Walk to Million Dollar Beach from this awesome Cottage!
Exterior

Walk to Million Dollar Beach from this awesome Cottage!

10.0 out of 10, Exceptional, (160)
"Had a great time good location and plenty of room."
Walk to Million Dollar Beach from this awesome Cottage!
Housekeeping Cottage - near Lake George & Adirondacks
Property grounds

Housekeeping Cottage - near Lake George & Adirondacks

10.0 out of 10, Exceptional, (37)
"We had a wonderful time at the cottage!! Loved the outdoor firepit that you could cook over, fantastic option. We will definitely be back! 😄"
Housekeeping Cottage - near Lake George & Adirondacks
Cozy Cottage at Lake George Campsites!
Game room

Cozy Cottage at Lake George Campsites!

6.8 out of 10, (3)
"Centrally located and a very close proximity to a lot of things like Walmart and Six Flags. Luckily the cottages were not near the highway because it’s pretty loud back there. The only negatives were that the stove didn’t work and the pool was kind of murky. Other than that, we loved our stay. "
Cozy Cottage at Lake George Campsites!
#4 Adirondack FamilyFriendly Waterfront on LoonLake. Boating,fishing,swimming!
On the beach

#4 Adirondack FamilyFriendly Waterfront on LoonLake. Boating,fishing,swimming!

9.6 out of 10, Exceptional, (16)
"The views were absolutely amazing! We will definitely be back."
#4 Adirondack FamilyFriendly Waterfront on LoonLake. Boating,fishing,swimming!
Tree-lined dog-friendly cottage with wrap-around deck, grill, & gas fireplace
Outdoor dining

Tree-lined dog-friendly cottage with wrap-around deck, grill, & gas fireplace

7.6 out of 10, Good, (5)
"The humble cabin was all that we needed. Near town, simple, a bit outdated"
Tree-lined dog-friendly cottage with wrap-around deck, grill, & gas fireplace
Dog friendly lakefront home w/fireplace near Lk George. Telecommuters welcome!
Exterior

Dog friendly lakefront home w/fireplace near Lk George. Telecommuters welcome!

10.0 out of 10, Exceptional, (18)
"The house is tranquil, clean and well-equipped. My son and I were very comfortable, wish we could have been there more than 1 night. "
Dog friendly lakefront home w/fireplace near Lk George. Telecommuters welcome!
Secluded, romantic cottage with stunning views of the Hudson River
Property grounds

Secluded, romantic cottage with stunning views of the Hudson River

9.0 out of 10, Wonderful, (4)
"Lovely little getaway yet close to everything. We enjoyed this retreat after lots of family time!"
Secluded, romantic cottage with stunning views of the Hudson River
A beautiful lake view cabin on Friends Lake
Property grounds

A beautiful lake view cabin on Friends Lake

9.6 out of 10, Exceptional, (51)
"Another wonderful relaxing stay. So happy to have spent another week here. And same as last year every thing went smoothly and we had a great time exploring and visiting with family. Thank you Amanda for another great stay!"
A beautiful lake view cabin on Friends Lake
Cozy Cottage at Lake George Campsites!
Game room

Cozy Cottage at Lake George Campsites!

4.0 out of 10, (2)
"Property is beautiful BUT beware the cabins are much smaller than they appear in the photos. The upstairs with the 2 beds is just a crawl space with beds. Not suitable for young kids or anyone tall lol. The steps leading up to that space is dangerous. Make sure to buy the linen package, i didnt even know it exsisted until we arrived and it was to late to purchase. Beware of the slippery floors as well, my kids took many spills on them. The bunkbeds are also in closet NOT room. "
Cozy Cottage at Lake George Campsites!
Hand-Crafted Cottage near Gore Mountain and Minerva Lake
TV, fireplace, books

Hand-Crafted Cottage near Gore Mountain and Minerva Lake

10.0 out of 10, Exceptional, (210)
"Great stay and exactly as described. Loved the wood stove and cozy living room, lots of space for the kids upstairs. On a very quiet road."
Hand-Crafted Cottage near Gore Mountain and Minerva Lake
Bolton Landing Cottage w/ Deck, Walk to Beach!
Beach nearby

Bolton Landing Cottage w/ Deck, Walk to Beach!

9.8 out of 10, Exceptional, (30)
"Everything was exactly as it was supposed to be. Great place, very clean, perfect location. Loved the whole week there."
Bolton Landing Cottage w/ Deck, Walk to Beach!
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chestertown Hotel Reviews

La Quinta Inn & Suites by Wyndham Lake George

La Quinta Inn & Suites by Wyndham Lake George

10/10 Excellent
"Our stay was very enjoyable. Check in went smoothly. The room was clean, roomy and comfortable. The pool and breakfast was awesome. Great place to stay!"
Lisa 2-night trip
Posted 18 hours ago
La Quinta Inn & Suites by Wyndham Lake George

Frequently asked questions

How much do cottages in Chestertown cost?
Prices for cottages in Chestertown range between ￥27,230 and ￥45,592 per night. Whatever your budget, you're sure to find the perfect place to immerse yourself in nature. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many cottages are there in Chestertown?
You can choose from 165 cottages in Chestertown. No matter if you're traveling with the little ones or planning a weekend break with close friends, Expedia can help you find the ideal property to reconnect with nature.
Are there any family-friendly cottages in Chestertown?
If you want to slow the pace down a notch in Chestertown, make a booking for the crew at Sunset Mountain Lodge. With a 3-star rating and conveniences like a playground and WiFi, you'll have no trouble settling in at this family-friendly cottage. After checking in and kicking back together in your cozy digs, it's time to head out and discover the local sights. Natural Stone Bridge and Caves and Loon Lake Beach are top family-friendly attractions in Chestertown.