Holiday rentals in Chestertown

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Top-rated holiday rentals in Chestertown

Guests agree: these stays are highly rated for location, cleanliness and more.

Guest favourite

Home in Wevertown

4.98 out of 5 average rating, 122 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.

22–29 May

£121 per night
Guest favourite

Guest suite in Pottersville

5.0 out of 5 average rating, 101 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!!

25 Apr – 2 May

£91 per night
Guest favourite

Cabin in Warrensburg

5.0 out of 5 average rating, 285 reviews

Romantic Lake George Getaway~The Bluebirds Nest

*Romantic 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

13–20 Dec

£125 per night

Popular amenities for Chestertown holiday rentals

Stay near Chestertown's top sights

Main Street Ice Cream Parlor50 locals recommend
The Bullhouse33 locals recommend
Tops Friendly Markets28 locals recommend
Panther Mountain Inn8 locals recommend
Odd Duck21 locals recommend
Dynamite Hill Recreation Area20 locals recommend

Other great holiday rentals in Chestertown

Guest favourite

Flat in Chestertown

5.0 out of 5 average rating, 86 reviews

Rustic Adirondack Studio Apartment

23–30 Nov

£113 per night
Guest favourite

Barn in Chestertown

4.98 out of 5 average rating, 44 reviews

Adirondack Base Camp by Loon Lake and Gore Mt.!

15–22 Apr

£149 per night
Guest favourite

Cabin in Johnsburg

4.97 out of 5 average rating, 65 reviews

2 bdrm ADK cabin 10 mins to GORE MTN

16–23 Mar

£117 per night
Guest favourite

Holiday home in Chestertown

5.0 out of 5 average rating, 23 reviews

Green Mansions Vacation Condo, 2 bedroom & 2 bath

17–24 May

£126 per night
Guest favourite

Flat in Schroon Lake

4.93 out of 5 average rating, 95 reviews

ADK Stay

27 Dec – 3 Jan

£86 per night
Guest favourite

Guest house in Brant Lake

4.98 out of 5 average rating, 85 reviews

Arrowhead @ Brant Lake

10–17 Jul

£125 per night
Guest favourite

Home in Chestertown

4.95 out of 5 average rating, 65 reviews

Modern Cabin w/ Hot Tub-Minutes to Lakes & Skiing

16–23 Jan

£291 per night
Guest favourite

Cottage in Chestertown

4.92 out of 5 average rating, 13 reviews

Private, Loon Lake front cozy cabin on 3 Acres

9–16 Jan

£163 per night
Guest favourite

Cabin in Warrensburg

4.93 out of 5 average rating, 28 reviews

Bearpine Cottage

14–21 Mar

£146 per night
Guest favourite

Cabin in Warrensburg

4.99 out of 5 average rating, 68 reviews

Adirondack Cozy Cabins - Moose Cabin

18–25 May

£118 per night
Guest favourite

Home in Chestertown

4.92 out of 5 average rating, 66 reviews

North Pine Lodge @ Loon Lake, ADK adventure awaits

20–27 Nov

£429 per night
Guest favourite

Home in Chestertown

5.0 out of 5 average rating, 15 reviews

Blue Bay Retreat - Loon Lake Lakefront w/ Hot Tub

15–22 Dec

£564 per night

Quick stats about holiday rentals in Chestertown

Total rentals

10 properties

Popular amenities

Kitchen, Wifi and Pool

Wifi availability

10 properties include access to wifi

Family-friendly rentals

10 properties are a good fit for families

Total number of reviews

250 reviews

Nightly prices starting at

£71 before taxes and fees

Destinations to explore

  1. Airbnb
  2. United States
  3. New York
  4. Warren County
  5. Chestertown