Vacation rentals in Chester

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Top-rated vacation rentals in Chester

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Top guest favorite

A spacious bed with a wooden frame is adorned with soft linens and decorative pillows. Flanking the bed are two nightstands with lamps, providing ambient light. Natural light filters through a window covered with blinds, enhancing the serene atmosphere of the room.

Guest suite in Pottersville

4.99 out of 5 average rating, 146 reviews

Private Spacious Suite near Peaks, Lakes & WOL-BI

Come be rejuvenated at our spacious & peaceful Loft Suite located @ the south end of Schroon Lake in Pottersville,NY. 25 mins to Gore Mt & 30 mins 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!!

Guest favorite

A quiet outdoor setting features two plastic chairs placed near a gathering of firewood, which is arranged beside a babbling creek. Lush greenery surrounds the area, creating a natural backdrop that enhances the peaceful atmosphere.

Home in Wevertown

4.97 out of 5 average rating, 147 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.

Top guest favorite

The exterior of a vibrant red barn is shown, featuring a decorative quilt square on the wall. The sky is painted in shades of purple and pink, with clouds softly contrasting the structure. Lush green grass surrounds the base, contributing to the serene environment.

Barn in Chestertown

4.96 out of 5 average rating, 230 reviews

Cozy Red Barn Retreat | Hot Tub, Large Lawn

Relax in this cozy red barn! Rustic charm meets modern luxury. 1 min off I‑87 1 min to Schroon River 2 mins to Loon Lake 5 mins to Brant Lake 25 mins to Gore Mtn + Lake George Near tons of hikes, lakes & swimming holes +close to town! Unwind in the hot tub, cook in the full kitchen, and gather by the fire pit. Features: dining area, big shower, private bedroom, loft w/ 2 sofa beds, desk, big lawn, BBQ, ski chair swing + LVL 2 EV charger. Fast Wi-Fi • Self check-in • Please read house rules

Top guest favorite

A spacious living area features a cozy sofa and wooden furniture, complemented by a glass coffee table. Natural light illuminates the room through large windows, while soft drapes provide privacy. A warm wooden ceiling enhances the inviting ambiance.

Home in Chestertown

4.95 out of 5 average rating, 242 reviews

Adirondack Lake House

Adirondack beauty all year! Fully furnished home has lovely great room, fireplace , two bedrooms, one bath, basement family room, large deck, outdoor fire pit, screened porch with lake glimpse, limited air conditioning, rights to private lake, kayaks, canoes, w/d, fire pit with wood, in quiet wooded setting. Central location. This is NOT a lakefront property. It comes with lake access and is located across the street from the lake. Please see complete listing for accurate information.

Superhost

A spacious deck features a hot tub surrounded by lush greenery. Two comfortable seating areas, including two round chairs and a side table, offer a relaxing space. The backyard reveals a picturesque lawn, creating a serene outdoor atmosphere for enjoyment.

Home in Chestertown

4.91 out of 5 average rating, 106 reviews

Adirondack 🏠 near Gore Mt, North Creek, Loon lake.

Welcome to Loon Run Lodge that is located in the Adirondack mountains of upstate New York, ready to be your place to relax and enjoy skiing, snowshoeing, cross country skiing, snowmobiling, hiking, horseback riding, kayaking, boating, and swimming. This property only 15 min from Gore Mountain ski resort, few minutes to Adirondack Snowmobile Tour, loon lake beach, Loon Lake Marina, local restaurants and stores. Only 20 min to Lake George, Bolton Landing and 25 min to Lake George Village.

Top guest favorite

A studio apartment with a sloped ceiling features a cozy sleeping area with a patterned quilted bedspread. A kitchenette is visible in the background, with wooden cabinets and a white refrigerator. A small dining area with two chairs is situated near the window, allowing for natural light.

Loft in North Creek

5 out of 5 average rating, 121 reviews

Gore Mountain Studio Retreat

Relax and refresh in our studio apartment after an exhilarating day on the slopes, whitewater rafting on the Hudson, or a less vigorous pursuit. This cozy hideaway, nestled in timber, feels a little like sleeping in a tree house. Located on a quiet and peaceful road with views of Gore Mountain and the Hudson River, it is 5 minutes to the base of Gore Mountain Ski Area and 3 minutes to downtown North Creek with restaurants and shopping. Your Adirondack adventure starts and ends here!

Guest favorite

A charming cabin exterior is surrounded by greenery, featuring a welcoming front porch with screened windows. Red Adirondack chairs are positioned nearby, alongside a wooden picnic table. A fire pit is visible in the yard, indicating a space for outdoor gatherings.

Cabin in Johnsburg

4.83 out of 5 average rating, 224 reviews

Butternut Adirondack Cabin.

Private stylish cabin. Expanded and newly Renovated. AC WiFi. Fireplace. Heating System. Full Kitchen, and bathroom with shower. Roku. In ground Pool shared by 5 other cabins. All new Furniture and new Queen Bed. Mill Creek neighbors the property for Trout fishing. Minutes to great skiing at Gore Mt. Minutes to Lake George and minutes to other Lakes, and Whitewater rafting and hiking. Guests to bring their own soaps and towels. $75 Per Pet Fee must bring pet covers for couches & bed.

Guest favorite

The modern chalet-style home is set among tall trees, featuring a spacious wrap-around deck with outdoor seating. The peaked roof adds a distinct character, while large windows allow natural light to flood the interior. The sandy ground surrounds the lower level, enhancing the natural setting.

Chalet in Chestertown

4.98 out of 5 average rating, 163 reviews

Chalet on Loon Lake (Gore Mt. 20 min.)

Located on beautiful Loon Lake, this modern chalet style home, with private beach and dock, features an open floor plan with 4 bedrooms, 2 full baths and loft. The house is fully furnished and has all the creature comforts. Outdoor amenities include a wrap-around deck and outdoor dining furniture. Enjoy boating, fishing, hiking, skiing and snowmobiling. Located just 30 minutes from Lake George and 20 minutes from Gore Mountain and the North Creek Ski Bowl and cross county trail system.

Top guest favorite

A bright living room features large windows framed with red-checkered curtains, allowing natural light to fill the space. A cozy couch and a coffee table are placed near a gas fireplace, while a wooden ceiling adds warmth to the design. A view of snow-covered outdoor surroundings is visible through the glass doors.

Cabin in Johnsburg

4.97 out of 5 average rating, 130 reviews

2 bdrm ADK cabin 10 mins to GORE MTN

The "Mellow Moose" cabin is a quiet and peaceful retreat in the woods. Spend the day exploring the region or simply relax in nature. Afternoons are great for reading a book as the sun shines through the large living room windows. Relax on the screened in front porch for a quiet evening and a drink. Or enjoy a campfire and watch the sunset through the trees. Use this as your home base for a ski trip or take a trip to Schroon lake, Brant lake or Lake George. (Roughly 30mins)

Top guest favorite

A cozy bedroom is presented with a wooden accent wall featuring decorative elements. A spacious bed is dressed in soft linens, complemented by pillows in varying textures. Soft lighting creates a warm ambiance, while a small bedside arrangement of flowers adds a natural touch.

Chalet in North Creek

5 out of 5 average rating, 110 reviews

Private Chalet w/ Adventures in the Adirondacks!

Welcome to Oven Mountain Chalets!! Located within minutes of Gore Mountain, Town of North Creek, and Scenic Hiking Trails. Comfortably sleeps Four (1 Queen and 2 Twin); Screened in balcony; AC unit; Fully equipped/stocked kitchen to cook your favorite meals! Lots of amenities provided. Spacious bathroom with deep tub/shower providing luxurious towels/linens. Chalet located on 10 acres of nature's gift of wildlife sounds, views, star glitter nights.

Top guest favorite

A spacious log cabin exterior is surrounded by greenery. The deck features a red umbrella and an American flag is displayed on the stone-walled front. A gravel driveway leads to the cabin, which includes a two-car garage and large windows allowing natural light inside.

Apartment in Chestertown

5 out of 5 average rating, 114 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!

Superhost

A rustic chalet is nestled among tall trees, surrounded by vibrant foliage. The structure features large windows and a wraparound deck. A figure is seen on the balcony, appreciating the natural surroundings during autumn.

Chalet in North Creek

4.77 out of 5 average rating, 163 reviews

Gore Mountain Chalet - Moments From Adventure! (Sk

Escape to Gore Mountain Chalet - your rustic retreat in the Adirondacks! Nestled on 10 private acres with a serene pond view, our cozy home offers a wraparound deck, indoor brick fireplace, fully stocked kitchen, and high-speed fiber internet. Enjoy the comforts of Wi-Fi, Roku TV, charcoal grill, washer/dryer, and ample parking—all just minutes from North Creek, skiing, hiking, rail biking, and rafting.