Holiday houses in Chestertown

4.97 out of 5 average rating, 144 reviews

Home in Wevertown

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.

4.98 out of 5 average rating, 112 reviews

Chalet in Warrensburg

ADK River Rapture- Warrensburg/Lk George/Gore Mntn

Elegant 3BR/3BaR Waterfront home with river access minutes from Lake George & Gore Mountain...river, lake & ski fun abound! Wraparound deck & floor to ceiling windows offer stunning Hudson River and mountain views from all angles. Open concept main floor has cathedral ceiling, magnificent stone fireplace in Great Room, custom hardwood floors, new granite kitchen & 3 spacious upstair BR's. Master BR offers a private, en suite bath while 2 guest bedrooms share another full bath. Total tranquility!

Guest suite in Pottersville

4.99 out of 5 average rating, 139 reviews

Private Spacious Suite near Gore, Hiking & WOL-BI

Come be rejuvenated at our spacious & inviting Loft Suite located at 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, 25 min south, Lake Placid, 1 hour north. Come explore the splendor of the Adirondacks!

4.95 out of 5 average rating, 219 reviews

Barn in Chestertown

Cozy Red Barn Retreat | Hot Tub, Fire Pit, 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

4.95 out of 5 average rating, 234 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.

4.94 out of 5 average rating, 101 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.

Superhost

Cabin in Johnsburg

4.82 out of 5 average rating, 221 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.

4.98 out of 5 average rating, 160 reviews

Chalet in Chestertown

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.

4.97 out of 5 average rating, 122 reviews

Cabin in Johnsburg

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)

5 out of 5 average rating, 106 reviews

Apartment in Chestertown

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!

4.93 out of 5 average rating, 116 reviews

Apartment in Warrensburg

Cozy Adirondack Getaway

Enjoy easy access to everything from this perfectly located home base with a simple one-block walk to Hackensack Mountain's trailhead and just minutes away from downtown Lake George attractions. This sweet 2nd level apartment is perfect for a hiking getaway or an amazing week touring breweries and wineries in the Adirondacks. Walking distance to the nearest grocery stores, pharmacy and post office.

4.9 out of 5 average rating, 252 reviews

Cottage in North Creek

1920s Honeymoon Cottage ADK Enchanted Nites Airbnb

WHITE WATER RAFTING, HIKING, FISHING, KAYAKING, 1.5 miles from exit 26 w/ 24-hour store 5 lakes within 5 Miles. 25 minutes from Lake George 3.5 hours from Manhattan 2.5 hours from Montreal 1 hour from Lake Placid NY. Situated on 10 acres of land Drinking water flows from a 300' well, cold and fresh. Recharge relax and center yourself. A historical taste of the ADK Mountains

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Other great holiday rentals in Chestertown

4.98 out of 5 average rating, 90 reviews

Cabin in Schroon Lake

The Treehouse

JillianRating, 5 stars8 months ago

Our stay at The Treehouse was wonderful. My family was immediately comfortable and loved our stay! Comfy beds, plenty of towels and lots of hooks and towel bars. The outdoor space was beautifully relaxing.

5 out of 5 average rating, 33 reviews

The Hayes Homestead

JohnRating, 5 stars1 week ago

This is a great little spot, well-appointed for a family stay and was perfect for our travel needs with our small dog. Pet-friendly, safe, quiet, and lots of helpful extras around the house to make you feel right at home. We really enjoyed our stay here, and are only sad it wasn't longer! Would absolutely come back. Thank you!!

5 out of 5 average rating, 40 reviews

Blue Bay Retreat - Loon Lake Lakefront w/ Hot Tub

GregRating, 5 stars1 week ago

Our stay at Andrew's beautiful home on Loon Lake was AMAZING. This was a family getaway with grown children and there was no shortage of things to do. The space was clean, and Andrew's "book" of suggested things to do and see in the area was extremely organized and straightforward. Property and house we very well maintained, and you could feel the "touch of home" that was evident in the details. I would highly recommend this as a peaceful respite from the chaos and a great place to share with family or friends while still having ample space to connect with nature. Well done, Andrew!

4.9 out of 5 average rating, 50 reviews

Chalet in Chestertown

Loon Lake Luxury with kayaks and canoe

AndreaRating, 5 stars11 months ago

We enjoyed our stay so much at DyAnn’s place - such a peaceful lake house, perfect for a family. We have 3 young kids and there was more than enough space. We experienced some storms and lost power and internet - host was very attentive and helpful, as was the automatic switch generator. This was by far the most well-stocked rental we’ve ever had. Area is quiet, not much for shops/restaurants, but so centrally located to other areas that we didn’t mind at all. We stayed very busy! We had a fantastic vacation at Loon Lake!

Superhost

Cabin in Chestertown

4.85 out of 5 average rating, 34 reviews

Cozy up at Friends Lake, ski/board close by!

JackieRating, 5 stars10 months ago

This was a wonderful vacation experience on every level. The house was beautiful, very clean and so so cozy-- we immediately felt at home. Kerri and Dave were very kind and responsive hosts. All instructions were easy and clear, and they were very generous in the use of their extra amenities (beach toys, boats, towels, etc.). The area is gorgeous, with lots to do, from the lake beach to nearby amusement parks to local hikes. Our family had a wonderful time-- I highly recommend staying at Kerri's and Dave's!

5 out of 5 average rating, 90 reviews

Home in Adirondack

Winter Wonderland/ Summer Solitude

MarcusRating, 5 stars3 months ago

This is a wonderful house for a skiing or winter vacation, which is why we have been coming back for several years. The house has all the conveniences you need for a winter holiday, and Gore Mountain is just 30 minutes away. Margaret and Tony went out of their way to ensure that we were comfortable and could make the most of our stay.

Guesthouse in Chestertown

5 out of 5 average rating, 12 reviews

Forest Lake Haven close to Gore Mt and Lake George

NicoleRating, 5 stars3 months ago

Loved staying at Gabriella’s place. Conveniently located and easy to find. We were arriving late and Gabriella made sure that the walkway was free of ice and snow (there had been some snowfall earlier). Absolutely spotless!! Will def stay here again.