Vacation rentals in Chester

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Top-rated vacation rentals in Chester

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Guest favorite

Home in Wevertown

4.98 out of 5 average rating, 129 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.

Guest favorite

Rental unit in Chestertown

4.81 out of 5 average rating, 113 reviews

Lily Pad North at Loon Lake near Gore Mountain

**COVID-19 Update ** We have implemented enhance cleaning procedures including the use of disinfectants on high touch surfaces. We recently replaced all linens with commercial linens to withstand hot water washing and drying at high temps. We also provide anti-viral and anti-bacterial cleaners in each property. We request that all visitors follow NYS and local Covid-19 guidelines. The Lily Pad North at Loon Lake in Chestertown, NY is nestled in the Adirondack Mountains of upstate New York and r

Guest favorite

Chalet in Warrensburg

4.99 out of 5 average rating, 101 reviews

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 favorite

Barn in Chestertown

4.95 out of 5 average rating, 176 reviews

Red Barn Guesthouse. Lawn & Patio. 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 & a large lawn with a BBQ, ski chair swing, & fire pit. LVL 2 EV. PLEASE READ HOUSE RULES BEFORE BOOKING

Guest favorite

Guest suite in Pottersville

4.99 out of 5 average rating, 123 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 beauty of the Adirondacks!

Guest favorite

Chalet in Chestertown

4.98 out of 5 average rating, 144 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.

Guest favorite

Home in Chestertown

4.92 out of 5 average rating, 154 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.

Guest favorite

Townhouse in North Creek

4.95 out of 5 average rating, 119 reviews

The Dowager Town Home

One bedroom fully furnished townhome sleeps 4 people, 1 bedroom (queen bed) w/ pullout leather (queen-sized) sofa in living room w/ a new, thicker memory foam mattress Propane fireplace & deck overlooking the Hudson River. Located on Main Street, an easy walk to restaurants and taverns, plus a community center and boutique stores. Free village shuttle winter weekends and holidays and off-street parking. AT&T cell tower service. Verizon booster and high-speed fiber.

Guest favorite

Loft in Brant Lake

4.96 out of 5 average rating, 206 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.

Guest favorite

Cabin in North Creek

4.98 out of 5 average rating, 168 reviews

Gore Mountain Log Cabin Getaway

8 minutes to Gore Mountain. Perfect getaway for couples, family vacay, small sporting group, or long time friends. Log cabin located 5 mins to food & shopping. Summer offers gondola rides & short drive to lakes, fishing, boating; beautiful porch for morning coffee & lovely views. Gore Mountain in winter for skiing & snowboarding. 24 hour buffer between bookings from when guests check out. 3 night minimum stay on holidays. A/C unit in main room.

Guest favorite

Cabin in North Creek

4.84 out of 5 average rating, 258 reviews

Blue A-Frame~Loft~Central ADK Location!

Escape and unwind to our cozy Blue A-frame in the Adirondacks, North Creek, NY. Rustic charm meets modern comfort: spacious rooms, a loft bedroom, fully equipped kitchen, and internet. Ideal for adventure lovers: minutes from Gore Mountain, Hudson River rafting, and trails. The house is also Pet-friendly. This cabin is the perfect base to explore Lake George and Schroon Lake’s beauty. Come and enjoy ADK right from our doorstep.

Guest favorite

Cottage in North Creek

4.89 out of 5 average rating, 237 reviews

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