Chestertown Vacation Rentals from ￥23,200: Search Short-Term Rentals

Check prices for these dates

Tonight

Tomorrow

This weekend

Next weekend

Vacation Rentals in Chestertown

Beach nearby, sun loungers, beach towels

"The area was quiet and house was nice. Perfect for our needs."

"Had an amazing stay. The people at the front desk especially sylvia were so kind amd friendly. Everyone was so helpful. The cabins are so clean and well stocked. The grounds are beautiful too"

"Had a great time good location and plenty of room."

Luxury Cabin, 1 Bedroom, Lake View | Living area | 42-inch Smart TV with digital channels, DVD player, streaming services

"Absolutely wonderful place and super friendly staff "

￥39,931 total

includes taxes & fees

Jun 21 - Jun 22

"Property was extremely clean and Tom was so helpful since I booked. Would definitely stay here again."

"Had a great time and was perfect for our family! "

"My 3 kids and I absolutely loved the spot. The stream in the back of the house was unique and gorgeous, Diane was communicative and pleasant. Highly recommended"

"Very peaceful property with lovely views. We will definitely be back!"

￥34,121 total

includes taxes & fees

Jun 23 - Jun 24

"This was a great little getaway. Would definitely come back. "

￥39,594 total

includes taxes & fees

Jun 24 - Jun 25

"Wonderful"

"Beautiful house with so many things to do- enjoy the deck outside, walk to the lake, ping pong or pool in the basement, enjoy time with friends. We will definitely come back! "

￥127,794 total

includes taxes & fees

Jun 21 - Jun 22

"Beautiful, quiet lakefront cabin. My spouse, toddler, medium size dog, and I had everything we needed to enjoy our stay."

Fridge, microwave, stovetop, coffee/tea maker

"We throughly enjoyed our stay and would like to return in the future."

"Cute cozy cottage close to Gore mountain "

￥37,823 total

includes taxes & fees

Jun 21 - Jun 22

"Property was clean location is close to village of Lake George- couple local breweries near By- had a wonderful stay "

"We had a great stayBeautiful views from the houseClose to ski mountains/restaurants etc!"

"Don’t like the shower room . No shelf in the bathroom. The floor was not clean as well as the bathroom."

￥35,491 total

includes taxes & fees

Jun 25 - Jun 26

"Perfect place away from the strip, so clean and well taken care of. I'd live there forever honestly."

"Everything was perfect. The house is gorgeous and had everything we needed. Love the location too!"

Save an average of 15% on thousands of hotels when you're signed in

Sign in

Sign up, it's free

Find out more about Chestertown

Search for holiday rentals in Chestertown on Expedia! You can easily find your home rentals, villas, holiday apartments in Chestertown using one of the methods below:

View our selection of featured holiday rentals in Chestertown
Use the map to find apartments and other holiday homes in the Chestertown neighbourhood you prefer
Enter your travel dates to view the best deals on holiday rentals in Chestertown while they last

Look no further and take a look at our great range of rental properties in Chestertown!

Recent reviews of Chestertown properties

5/5 Excellent

Good stay

"No frills, but it was clean and comfortable. Very close to everything in Lake George. Huge, well-lit parking lot. Check in and checkout was easy, the attendant was very nice. Coffee available in lobby in the morning"

A verified traveler stayed at Howard Johnson by Wyndham Lake George

Posted 14 hours ago

5/5 Excellent

"The staff was warm and friendly. The room was clean. The toilet bowl is too, shallow! I’m a petite woman and my hand touched the water when I wiped myself. Men: Beware of the shallow bowl. The hotel needed a roof and some other damage managed. It rained but not in my room. I stumbled on a cracked and loose tile on the balcony. I loved the location, the lake view and beach access right outside of my door. I used the bbq grill and had a great dinner! I’d stay again!"

A verified traveler stayed at Lakefront Terrace Resort

Posted 2 days ago

5/5 Excellent

"Everything and everyone was great except for when we arrived there was a fireman's convention of some sort and they reserved their parking spots with cones and chairs. There were no spots letft whatsoever. Just felt the hotel should have seen this and said something. Otherwise staff was friendly and attentive. Room was clean and updated tho some of the furniture was old and scratched, missing paint. The room also needs a chair or couch of some sort. "

A verified traveler stayed at The Georgian Lakeside Resort

Posted 3 days ago

Baymont by Wyndham Queensbury / Lake George

5/5 Excellent

"I like the location. This was the second time staying at this hotel. The only issue I had was there was a bus load of people that came to stay at the hotel and there were quite a bit of teenagers in this group. They ran up and down the hallways and slammed the doors into the early morning hours causing sleep disruption. I called the front desk and no one responded. When I went to check out the next morning no one was at the front desk to report the chaos that happened the night before. Overall I would stay again. "

A verified traveler stayed at Baymont by Wyndham Queensbury / Lake George

Posted 4 days ago

Explore a world of travel with Expedia

All accommodation types in Chestertown

Inns in Chestertown

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?

Family Friendly - Pet Friendly : This vacation home near Chestertown is located on a lake and has a balcony, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

How many vacation rentals will I find in Chestertown?

With 60 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?

Friends Lake and Loon Lake are a couple of lovely local spots to get outside and enjoy nature. Hudson River and Loon Lake Beach 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.

Members save 10% or more on over 100,000 hotels worldwide when you’re signed in

Chestertown Vacation Rentals

Check prices for these dates

Vacation Rentals in Chestertown

Peaceful Lakeside Retreat with Private Beach

Lake George Escape - Campground

Waterfront Home on Lake George w/ Boat Dock!

Walk to Million Dollar Beach from this awesome Cottage!

Trout House Village Resort

Modern Lakeside Cabin - 2 Kayaks, 2 SUPS, perfect lake stay

Family Friendly - Pet Friendly

Waterfall Gorge-ous Home w 200+ feet of river frontage -10 mi to Lake George

Camp Lillian Gorgeous New Cabin with Mountain Views

ADORABLE NEW CABIN WITH AMAZING MOUNTAIN VIEWS

Bolton Landing Mountain House!

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

Ultimate couples getaway! Quiet and private Lakeside Cottage in the Adirondacks

Adirondack Mountains Cottage Near Gore Mountain!

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

Beautiful Log House In Bolton In Lake George Paradise! Dog friendly!

Ultimate Adirondack Getaway ~ Private Pool and Hot Tub!

The Elms Waterfront Cottages

Charming cottage with a full kitchen, porch, & gas grill - walk to the lake

New Lakeside Cottage 5 minutes from great hiking with large deck and lake view

Find out more about Chestertown

Recent reviews of Chestertown properties

Howard Johnson by Wyndham Lake George

The Queensbury Hotel

Lakefront Terrace Resort

The Georgian Lakeside Resort

Heritage of Lake George

Baymont by Wyndham Queensbury / Lake George

Courtyard by Marriott Lake George

La Quinta Inn & Suites by Wyndham Lake George

Best Western of Lake George

Explore a world of travel with Expedia

Frequently asked questions