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

Chestertown Vacation Rentals

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Our top choices for Chestertown vacation rentals

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 CA $378
CA $477 total
includes taxes & fees
Jun 23 - Jun 24
Authentic Log Cabin with Lake Views and Sauna

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 CA $901
CA $1,631 total
includes taxes & fees
Jul 13 - Jul 14
Forest Lake Haven close to Lake George and Gore Mountain, 5 BR spacious and NEW

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
The price is CA $630
CA $1,275 total
includes taxes & fees
Jul 17 - Jul 18
4 BR modern farmhouse with 173 ft of private lakefront on tranquil Loon Lake.

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 CA $234
CA $260 total
includes taxes & fees
Jun 25 - Jun 26
Lake George Escape - Campground

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 CA $85
CA $159 total
includes taxes & fees
Jun 18 - Jun 19
Schroon Lake Room < 1 Mi to Marina & Beach!

Trout House Village Resort

Trout House Village Resort
3.0 star property
Hague
9.8 out of 10, Exceptional, (23 reviews)
"It was a great place, clean rooms, nice environment, cabins, family friendly, right on lake"
United States
Matthew
The price is CA $209
CA $267 total
includes taxes & fees
Jun 22 - Jun 23
Trout House Village Resort

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 CA $529
CA $587 total
includes taxes & fees
Jun 18 - Jun 19
The Elms Waterfront Cottages

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 CA $817
CA $1,657 total
includes taxes & fees
Jun 29 - Jun 30
Lake George Water Front Cabin Spectacular Views

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 CA $245
CA $371 total
includes taxes & fees
Jun 18 - Jun 19
RESTORED HISTORIC ADIRONDACK BIRD CAMP NEAR GORE MT WITH LOVELY MOUNTAIN VIEWS

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 CA $231
CA $337 total
includes taxes & fees
Jun 23 - Jun 24
ADORABLE CABIN WITH AMAZING MOUNTAIN VIEWS CLOSE TO GORE MT

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 CA $251
CA $538 total
includes taxes & fees
Jun 18 - Jun 19
PET FRIENDLY Adirondacks Log Cabin! Lake George, Saratoga, SPAC, Sacandaga

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 CA $409
CA $827 total
includes taxes & fees
Jun 24 - Jun 25
Red Oak Cabin: Our cozy cabin is tucked away but still close to any adventure!

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 CA $833
CA $1,410 total
includes taxes & fees
Jun 18 - Jun 19
True Adirondack living. 3-bedroom house in tranquil Diamond Point.

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 CA $350
CA $835 total
includes taxes & fees
Jun 21 - Jun 22
Luxury Cabin Sleeps 4 to 7 - mins to Lake George

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 CA $197
CA $638 total
includes taxes & fees
Jun 22 - Jun 23
9 Mi to Lake George Village: Home in Queensbury

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 CA $516
CA $868 total
includes taxes & fees
Jul 1 - Jul 2
Lakefront Rustic 1930s dog friendly Cabin w/lg screened porch near Lake George

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 CA $327
CA $1,141 total
includes taxes & fees
Jun 21 - Jun 22
10 Mi To Gore Mountain: Home In Adirondack Park 5 Bedroom Home

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 CA $693
CA $1,233 total
includes taxes & fees
Jun 24 - Jun 25
Secluded retreat. Great for families. Walk to Trout lake. High Speed Internet.

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 CA $420
CA $752 total
includes taxes & fees
Jun 18 - Jun 19
Huge Windows Downtown 2Bd Apt w/ Main Strip Access

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 CA $490
CA $786 total
includes taxes & fees
Jun 18 - Jun 19
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

Find out more about Chestertown

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Chestertown. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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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.