Vacation rentals in Chestertown

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Top-rated vacation rentals in Chestertown

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Guest favourite

Home in Wevertown

4.98 out of 5 average rating, 123 reviews

A Cozy Creekside Getaway minutes from Gore Mtn.

This quiet getaway is perfect for the family or a small group of friends. This two bedroom, two full bath home is situated on a quiet dirt road right in the heart of the Adirondacks and is perfect for the outdoor enthusiast. It offers easy access to the High Peaks and is just 5 miles from both Gore Mtn. and The Revolution Rail. Opportunities such as hiking, mountain biking, kayaking, rafting and fishing are all within 15 minutes of our location. SEASONAL DISCOUNTS AVAILABLE! Please inquire.

Jun. 30 – Jul. 7

$214 CAD per night

Guest favourite

Guest suite in Pottersville

5.0 out of 5 average rating, 103 reviews

Private & Serene Suite Near Gore-Peaks-Lakes -WOL

Come & be rejuvenated at our spacious & inviting Loft Suite at the south end of Schroon Lake in Pottersville, NY. 25 mins to Gore Mt & 30 minutes to hiking the ADK High Peaks. Located on a quiet private road, 2 miles off Northway/87, perfect for a romantic couples retreat or a small family getaway. In any season, we are surrounded with an abundance of activities & local attractions to enjoy. Lake George is 25 min south, Lake Placid 1 hour north. Come explore the splendor of the Adirondacks!!

Aug. 27 – Sep. 3

$196 CAD per night

Guest favourite

Cabin in Warrensburg

5.0 out of 5 average rating, 286 reviews

Romantic Lake George Getaway~The Bluebirds Nest

*Cozy getaway nestled in the Adirondack Mountains, just 15 minutes to Lake George *Vintage Record Player, Farm Fresh Eggs and pollinator gardens *A dreamy escape into nature where you will wake up and feel like you are still dreaming *This is not just any five star stay step outside we have millions our night sky is breathtaking *We strive for our guests to have nothing less than a five star experience, as you can see by our reviews *Decorated for Christmas Nov 1st-January 15

Sep. 5 – 12

$215 CAD per night

Guest favourite

Home in Chestertown

4.93 out of 5 average rating, 141 reviews

The Stone Lodge on Blythewood Island in Loon Lake

Looking for an all-season getaway in the Adirondacks? Come enjoy our lake and mountain views at the historic Stone Lodge on Blythewood Island in Loon Lake in Chestertown, NY. Our family has lived on the Island for more than 60 years. We welcome you to join us! The Stone Lodge was brought back to its original ambiance 7 years ago, when the Monroe family made it a place where others could enjoy the beauty, sights and sounds of nature from a beautiful authentic Adirondack retreat.

May 8 – 15

$565 CAD per night

Guest favourite

Barn in Chestertown

4.97 out of 5 average rating, 148 reviews

Red Barn Guesthouse. Cozy & Cute. Hot Tub! LV2 EV

Relax in this cozy barn! With a little rustic flair the inside is loaded with luxurious amenities. 1min off I-87 1min Schroon River 2mins Loon Lake 5mins Brant Lake 25mins Gore Mountain 25mins Lake George Tons of nearby hikes! This is the perfect place to rest your head. Soak in the Hot Tub. There's a full kitchen, dining area, loft with 2 sofa beds, a private bedroom, desk, spa-like shower & an outdoor lawn, & seasonal fire pit. PLEASE READ HOUSE RULES BEFORE BOOKING

Jun. 26 – Jul. 3

$513 CAD per night

Guest favourite

Home in Warrensburg

4.91 out of 5 average rating, 118 reviews

Adirondack Bungalow getaway

Cozy stand-alone bungalow is perfect for a hiking getaway or an amazing week touring breweries and wineries in the Adirondacks. Features a beautiful decorative fenced yard, with seasonal patio and outdoor gas fire table. Enjoy evenings on the open air porch and walk out your back door to Hackensack Mountain's trailhead. Just minutes away from downtown Lake George attractions. Leave your hiking gear or winter ski equipment out of site in the mudroom/laundry room.

Jan. 4 – 11

$167 CAD per night

Guest favourite

Loft in Brant Lake

4.96 out of 5 average rating, 192 reviews

Cozy Adirondack Efficiency

Located 18 miles from Gore Mountain, 2 miles from Brant Lake and 1.5 miles from the Schroon River, this cozy Adirondack efficiency allows guests to experience all that the North Country has to offer with the comfort of modern amenities. Ample space for parking makes this efficiency ideal for those pulling snowmobiles, boats, and jet skis. The efficiency is located on the second story of an unoccupied building--guests will have the entire space to themselves.

Jul. 8 – 15

$164 CAD per night

Guest favourite

Guesthouse in Bolton

4.97 out of 5 average rating, 178 reviews

Romantic Getaway-Close to Bolton downtown

Unwind and recharge at this spacious, beautiful bungalow.. Take a 10 min stroll to downtown Bolton Landing! This cottage was lovingly finished with a beautiful gas fireplace, quartz countertops in the fully equipped kitchen, and barn wood accents for a luxurious yet rustic feel. Enjoy a cocktail while playing darts, ring toss and card games in the tiki hut. Bolton downtown shops, and restaurants are only a 2 min drive. Lake George village 20 min away.

Nov. 1 – 8

$245 CAD per night

Guest favourite

Apartment in Chestertown

4.83 out of 5 average rating, 105 reviews

Lily Pad North at Loon Lake near Gore Mountain

Lily Pad North is nestled in the Adirondack Mountains of upstate NY. This two bedroom unit is super clean and a great place to relax. The property is rural, yet centrally located to 5 lakes, skiing at Gore Mountain, and famous Lake George Village, with easy highway access only five minutes away. Sleeps 5 adults plus 1 infant. If you have a smaller or larger group, please inquire about the availability of a 4 bedroom unit or the adjacent 7 bedroom house.

Feb. 11 – 18

$199 CAD per night

Guest favourite

Home in Brant Lake

4.92 out of 5 average rating, 138 reviews

RiverSong-Brant Lake riverfront cabin with a view

Secluded 1.5 bedroom riverfront home with private beach/river access, firepit, screened porch, large patio deck * Barbeque grill * disc-golf basket * 8 person picnic table *Roku tv *Games etc... Kayak/Canoe rental available. Ideal for couples and small families, can accommodate up to 4 sleeping indoors. Lots of grass to tent under the stars! 2 min from Interstate 87 5 min to Brant Lake 10 min to Schroon Lake 15 min to Lake George 20 min to Gore Mt

May 28 – Jun. 4

$231 CAD per night

Guest favourite

Cabin in Schroon

4.96 out of 5 average rating, 168 reviews

Little Bearfoot Lodge

This cosy Little Lodge is located minutes from Schroon Lake, where one can find boating, fishing, water skiing, and a beautiful beach to just swim and hang out and take in the tremendous scenery. We are located Close to Snowmobile 1 trail on Hoffman. Also, we are minutes from Gore. Mountain Ski Area. So, get ready to leave the rat race and come and enjoy beautiful Schroon Lake and more importantly to stay at the Little Bearfoot Lodge.

Jun. 2 – 9

$226 CAD per night

Guest favourite

Apartment in Chestertown

5.0 out of 5 average rating, 86 reviews

Rustic Adirondack Studio Apartment

Come and enjoy the Adirondacks for an overnight stay or a couple of days. Enjoy our lakefront with access to swimming, kayaking and paddle boarding or just kick back at the dock and enjoy your coffee or other beverage. We are located on Loon Lake outside of Chestertown, NY. Access to many hiking trails is only a short drive away. So come visit and enjoy yourself. We look forward to meeting you!

Oct. 10 – 17

$194 CAD per night