Aerial summer view of colonial Chestertown on the Chesapeake Bay in Maryland USA

Chestertown Vacation Rentals

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Check prices for these dates

In two weeks
3 Jul - 5 Jul
In two months
14 Aug - 16 Aug
In three months
11 Sep - 13 Sep
In four months
9 Oct - 11 Oct

Our top choices for Chestertown vacation rentals

Smart TV

Authentic Log Cabin with Lake Views and Sauna

Authentic Log Cabin with Lake Views and Sauna
Chestertown
9.4 out of 10, Exceptional, (3 reviews)
"Very nice cabin with amenities. Thank you for a great stay."
United States
Joe F.
The price is AED 992
AED 1,260 total
includes taxes & fees
23 Jun - 24 Jun
Authentic Log Cabin with Lake Views and Sauna
Interior

Forest Lake Haven close to Lake George and Gore Mountain, 5 BR spacious and NEW

Forest Lake Haven close to Lake George and Gore Mountain, 5 BR spacious and NEW
Chestertown
10.0 out of 10, Exceptional, (2 reviews)
"Great stay- Gabriella was an excellent, attentive, and thorough host. The home clearly has been renovated in recent years and is well appointed with thoughtful details that help make it a comfortable spot for a group of skiers. I look forward to staying here again on a future trip to ski at Gore."
United States
Todd A.
The price is AED 2,365
AED 4,281 total
includes taxes & fees
13 Jul - 14 Jul
Forest Lake Haven close to Lake George and Gore Mountain, 5 BR spacious and NEW
Private kitchen

4 BR modern farmhouse with 173 ft of private lakefront on tranquil Loon Lake.

4 BR modern farmhouse with 173 ft of private lakefront on tranquil Loon Lake.
Chestertown
4 BR modern farmhouse with 173 ft of private lakefront on tranquil Loon Lake.
WiFi

Lake George Escape - Campground

Lake George Escape - Campground
2.0 star property
Diamond Point
8.4 out of 10, Very Good, (173 reviews)
"Place and space"
United States
Laser Brookes
The price is AED 681
AED 755 total
includes taxes & fees
22 Jun - 23 Jun
Lake George Escape - Campground
Apartment (0 Bedroom) | Interior

Schroon Lake Room < 1 Mi to Marina & Beach!

Schroon Lake Room < 1 Mi to Marina & Beach!
3.0 star property
Schroon Lake
The price is AED 404
AED 622 total
includes taxes & fees
21 Jun - 22 Jun
Schroon Lake Room < 1 Mi to Marina & Beach!
Cabin, 1 Bedroom, Non Smoking, Lake View | Egyptian cotton sheets, premium bedding, individually decorated

Trout House Village Resort

Trout House Village Resort
3.0 star property
Hague
9.6 out of 10, Exceptional, (24 reviews)
"It was a great place, clean rooms, nice environment, cabins, family friendly, right on lake"
United States
Matthew
The price is AED 550
AED 702 total
includes taxes & fees
23 Jun - 24 Jun
Trout House Village Resort
Sports facility

The Elms Waterfront Cottages

The Elms Waterfront Cottages
2.5 star property
Lake Luzerne
8.4 out of 10, Very Good, (16 reviews)
"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. "
United States
Amanda
The price is AED 1,388
AED 1,541 total
includes taxes & fees
21 Jun - 22 Jun
The Elms Waterfront Cottages
Terrace/patio

Lake George Water Front Cabin Spectacular Views

Lake George Water Front Cabin Spectacular Views
Ticonderoga
9.6 out of 10, Exceptional, (35 reviews)
"Super pretty views and a very quiet and tranquil stay :)"
United States
Mackenzie C.
The price is AED 2,145
AED 4,351 total
includes taxes & fees
23 Jun - 24 Jun
Lake George Water Front Cabin Spectacular Views
Interior

RESTORED HISTORIC ADIRONDACK BIRD CAMP NEAR GORE MT WITH LOVELY MOUNTAIN VIEWS

RESTORED HISTORIC ADIRONDACK BIRD CAMP NEAR GORE MT WITH LOVELY MOUNTAIN VIEWS
North River
9.2 out of 10, Wonderful, (67 reviews)
"Had a great stay. Camp had rustic feel and was off the beaten path. Would stay again."
United States
Marcia M.
The price is AED 643
AED 974 total
includes taxes & fees
21 Jun - 22 Jun
RESTORED HISTORIC ADIRONDACK BIRD CAMP NEAR GORE MT WITH LOVELY MOUNTAIN VIEWS
Property grounds

ADORABLE CABIN WITH AMAZING MOUNTAIN VIEWS CLOSE TO GORE MT

ADORABLE CABIN WITH AMAZING MOUNTAIN VIEWS CLOSE TO GORE MT
North River
10.0 out of 10, Exceptional, (99 reviews)
"Everything was perfect! Great weekend trip!"
United States
Anne W.
The price is AED 606
AED 881 total
includes taxes & fees
21 Jun - 22 Jun
ADORABLE CABIN WITH AMAZING MOUNTAIN VIEWS CLOSE TO GORE MT
Pool

PET FRIENDLY Adirondacks Log Cabin! Lake George, Saratoga, SPAC, Sacandaga

PET FRIENDLY Adirondacks Log Cabin! Lake George, Saratoga, SPAC, Sacandaga
Stony Creek
10.0 out of 10, Exceptional, (28 reviews)
"Great secluded cabin. "
United States
SUZANNE B.
The price is AED 592
AED 1,329 total
includes taxes & fees
21 Jun - 22 Jun
PET FRIENDLY Adirondacks Log Cabin! Lake George, Saratoga, SPAC, Sacandaga
Terrace/patio

Red Oak Cabin: Our cozy cabin is tucked away but still close to any adventure!

Red Oak Cabin: Our cozy cabin is tucked away but still close to any adventure!
Lake George
10.0 out of 10, Exceptional, (23 reviews)
"Stay was great!"
United States
Lieishea
The price is AED 1,074
AED 2,179 total
includes taxes & fees
24 Jun - 25 Jun
Red Oak Cabin: Our cozy cabin is tucked away but still close to any adventure!
Beach

True Adirondack living. 3-bedroom house in tranquil Diamond Point.

True Adirondack living. 3-bedroom house in tranquil Diamond Point.
Diamond Point
10.0 out of 10, Exceptional, (9 reviews)
"Fantastic stay. Clean and welcoming. Plenty of staples supplied which is always helpful. Will visit again."
United States
Brad S.
The price is AED 2,185
AED 3,702 total
includes taxes & fees
27 Jun - 28 Jun
True Adirondack living. 3-bedroom house in tranquil Diamond Point.
Dining

Luxury Cabin Sleeps 4 to 7 - mins to Lake George

Luxury Cabin Sleeps 4 to 7 - mins to Lake George
Lake Luzerne
10.0 out of 10, Exceptional, (8 reviews)
"Awesome visit, everything as described!"
United States
Adam H.
The price is AED 845
AED 2,111 total
includes taxes & fees
25 Jun - 26 Jun
Luxury Cabin Sleeps 4 to 7 - mins to Lake George
House (3 Bedrooms) | Interior

9 Mi to Lake George Village: Home in Queensbury

9 Mi to Lake George Village: Home in Queensbury
3.0 star property
Queensbury
The price is AED 518
AED 1,673 total
includes taxes & fees
22 Jun - 23 Jun
9 Mi to Lake George Village: Home in Queensbury
Interior

Lakefront Rustic 1930s dog friendly Cabin w/lg screened porch near Lake George

Lakefront Rustic 1930s dog friendly Cabin w/lg screened porch near Lake George
Fort Ann
10.0 out of 10, Exceptional, (33 reviews)
"We had a lovely time with our dogs in this peaceful cabin. The views are beautiful. The owners were very responsive and the cabin was equipped with everything we needed."
United States
Teresa M.
The price is AED 1,355
AED 2,251 total
includes taxes & fees
1 Jul - 2 Jul
Lakefront Rustic 1930s dog friendly Cabin w/lg screened porch near Lake George
House, 5 Bedrooms | Exterior

10 Mi To Gore Mountain: Home In Adirondack Park 5 Bedroom Home

10 Mi To Gore Mountain: Home In Adirondack Park 5 Bedroom Home
3.0 star property
Olmstedville
The price is AED 816
AED 2,933 total
includes taxes & fees
22 Jun - 23 Jun
10 Mi To Gore Mountain: Home In Adirondack Park 5 Bedroom Home
Fridge, microwave, oven, stovetop

Secluded retreat. Great for families. Walk to Trout lake. High Speed Internet.

Secluded retreat. Great for families. Walk to Trout lake. High Speed Internet.
Diamond Point
9.8 out of 10, Exceptional, (59 reviews)
"We enjoyed our trip and the house was very comfortable and clean and well updated."
United States
Nuala D.
The price is AED 2,020
AED 3,494 total
includes taxes & fees
21 Jun - 22 Jun
Secluded retreat. Great for families. Walk to Trout lake. High Speed Internet.
2 bedrooms, bed sheets

Huge Windows Downtown 2Bd Apt w/ Main Strip Access

Huge Windows Downtown 2Bd Apt w/ Main Strip Access
Glens Falls
10.0 out of 10, Exceptional, (2 reviews)
"Great location with rustic touches and fully renovated"
United States
Brian H.
The price is AED 1,102
AED 1,969 total
includes taxes & fees
28 Jun - 29 Jun
Huge Windows Downtown 2Bd Apt w/ Main Strip Access
Interior

GORGEOUS FAMILY FRIENDLY VICTORIAN WITH ALL NATURAL CEDAR HOT TUB NEAR GORE MT

GORGEOUS FAMILY FRIENDLY VICTORIAN WITH ALL NATURAL CEDAR HOT TUB NEAR GORE MT
North Creek
10.0 out of 10, Exceptional, (31 reviews)
"Our 3rd time staying here and it's always wonderful!"
United States
Blair G.
The price is AED 1,286
AED 2,075 total
includes taxes & fees
25 Jun - 26 Jun
GORGEOUS FAMILY FRIENDLY VICTORIAN WITH ALL NATURAL CEDAR HOT TUB NEAR GORE MT
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 Chestertown Hotel Reviews

Howard Johnson by Wyndham Lake George

Howard Johnson by Wyndham Lake George

10/10 Excellent
"Was a good experience..no issues with room or check in"
John 1-night trip
Posted 2 hours ago
Howard Johnson by Wyndham Lake George

Frequently asked questions

Can I find vacation rentals in Chestertown?

Yes, we give you a choice of vacation rentals near well known points of interest in Chestertown, or you can choose a more remote option if you want a relaxing place to stay. Nature enthusiasts will enjoy the lakeside in Chestertown. Make sure you have time to check out the coffeehouses and forests during your trip.

What are some of the best vacation home rentals in Chestertown?

Adirondack Bungalow Getaway: This vacation home near Chestertown is located in the mountains and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave. Make the most of the garden in this rental home to help you unwind.

How many vacation rentals will I find in Chestertown?

With 61 Expedia vacation rentals, you're sure to find just the right place for your Chestertown stay.

What’s there to see and do in Chestertown?

Loon Lake Beach and Friends Lake are a couple of lovely local spots to get outside and enjoy nature. Loon Lake and Hudson River are other places to visit while you're in town.

What’s a vacation rental in Chestertown like?

Vacation rentals are private properties you can book for a couple of days or more in Chestertown. Vacation rentals provide amenities like kitchens and laundry facilities so you'll have everything you want. If you're concerned about a clean environment, a vacation rental can provide a sense of security away from shared hotel elevators and busy lobbies while still allowing you a great travel experience. You'll also have more space in a vacation rental than in a standard hotel, which makes a vacation rental a popular option for a small group gathering.