Vacation rentals in Chester

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Top-rated vacation rentals in Chester

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Top guest favorite
The cottage exterior is framed by greenery, with a serene view of the lake reflecting the sunset colors. Mountains are visible in the distance, enhancing the tranquil setting. Water gently laps at the shore, creating a peaceful atmosphere.
Cottage in Adirondack
4.98 out of 5 average rating, 115 reviews

Lakeside with direct water access & amazing views

La Bella Loona - A beautiful 1 bd cottage located directly on Schroon lake. Amazing mountain and lake views from every window. 50' of direct water access with small sandy beach, outdoor firepit and grill, and multiple hang out spots. The cottage is newly built and furnished, has an indoor fireplace, central AC, fully stocked kitchen, and screened in room overlooking the lake. There are 2 kayaks available for use. Be assured everything is provided to make your stay as comfortable as possible.

Guest favorite
A cabin with large windows is framed by a wooden deck, surrounded by trees. Two red chairs are positioned near a stone fire pit, with logs arranged for a fire. A grassy area provides a natural setting, inviting outdoor relaxation.
Cabin in Johnsburg
4.97 out of 5 average rating, 154 reviews

2 bdrm ADK cabin 10 mins to GORE MTN

The "Mellow Moose" cabin is a quiet and peaceful retreat tucked in the woods. Spend the day exploring the region or just simply relaxing 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 a way to explore Schroon lake, Brant lake or Lake George. (Roughly 30mins)

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, 259 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 quaint cabin is surrounded by lush greenery and vibrant flowers. A stone fireplace completes the exterior, with a cozy seating area of red Adirondack chairs visible in front. Natural landscaping enhances the inviting setting in this serene outdoor space.
Cabin in Johnsburg
4.76 out of 5 average rating, 241 reviews

Adirondack Green Cabin #2

We have AC and WiFi. Wood burning fireplace and firepit and normal heat. Inground Pool shared by 5 other cabins. Private Firepit. Good for couples, adventurers, business travelers, families, big groups because we have 6 total cabins on the property and can accommodate 50 people. Just minutes to all outdoor activities and our area is a 4 season destination. Onetime $75 per pet per stay must be paid at time of booking. Must bring dog blankets. $30 per person extra per night after 4 guests.

Guest favorite
A hot tub is situated on a wooden deck overlooking a winter landscape. Snow-covered trees surround the area, with a serene ambiance created by the falling snowflakes. Steam rises gently from the water, inviting relaxation amid the tranquil scene.
Home in Chestertown
4.92 out of 5 average rating, 120 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
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, 264 reviews

Cozy Red Barn Retreat | Hot Tub, Grill, Lawn, EV+

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, primary bedroom, loft w/ 2 sofa beds, desk, big lawn, grill, ski chair + LVL 2 EV charger. Fast Wi-Fi • Self check-in • Please read house rules!

Top guest favorite
Guest suite in Pottersville
4.99 out of 5 average rating, 167 reviews

Private Spacious Suite near Lakes, Peaks & WOL-BI

Surround yourself with peace & tranquility in our spacious suite located at the south end of Schroon Lake. 25 mins to ski Gore & 30 mins to hike in the ADK High Peaks. Located on a quiet private road, 2 miles off Northway/I-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!

Top 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, 171 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 cozy great room is furnished with a spacious gray sectional sofa, two white chairs, and a round black coffee table. A large TV is mounted on the wooden wall, complemented by a decorative shelf filled with books. Natural light enters through multiple windows, accentuating the wood paneling.
Cabin in North Creek
4.98 out of 5 average rating, 114 reviews

Lux Cabin in the ADK w/fireplace mins to Gore Mnt.

Come enjoy this wonderful "Lil Log Cabin" with luxuries and privacy for an unforgettable Adirondack escape. With Wifi throughout the 4-acre estate, indoor/outdoor music and 65" 4k TV in the main room. Simply cozy up with a great book by the fire or roast marshmallows after a day of limitless outdoor adventures. With multiple destinations in every direction, we are centrally located near hiking paths, ski mountains, lake George's lively entertainment, Bolton Landing and so much more.

Top guest favorite
A spacious bedroom features soft lighting and light-colored decor, creating a calming environment. A cozy outdoor space showcases a fire pit surrounded by chairs, set against a wooden fence. An inviting living area includes a unique hanging chair and beautifully arranged floral accents.
Cabin in Warrensburg
5 out of 5 average rating, 138 reviews

Romantic Getaway at Firefly Mountain

💫 A place made for two… Escape to your own private romantic hideaway in the Adirondacks, tucked among whispering pines and star-filled skies. This cozy cabin was designed for couples who want to slow down, reconnect, and enjoy simple magic together — firelight, quiet mornings, long talks, and late-night stargazing. Pour a glass of wine, curl up together next to the fireplace , and let the world disappear for a while. This is not just any 5 ⭐️stay step outside we have Millions !!

Top 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, 163 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 skiing (both alpine & nordic), hiking, mountain biking, kayaking, rafting and fishing are all within 15 minutes of our location.

Guest favorite
Cabin in Wevertown
4.9 out of 5 average rating, 100 reviews

Riverview Cabin- Minutes to Gore Mt!

Welcome to The Hudson Hideaway, the perfect all season Adirondack Getaway. Relax and unwind at this unique and cozy cabin with a view of the Hudson River. Bring your fishing poles and tubes to fully enjoy the river in your own backyard! 0nly 10 minutes to Gore Mountain/North Creek and 25 minutes to Lake George. We are centrally located to a vast array of year round Adirondack adventures, including Rev Rail, hiking , skiing, snowshoeing, kayaking, and whitewater rafting.

Popular amenities for Chester vacation rentals

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