Holiday rentals in Chester
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Top-rated holiday rentals in Chester
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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.
Modern Cabin w/ Hot Tub-Minutes to Lakes & Skiing
Welcome to Jackson's Lodge! Looking for an Adirondack escape for your family and friends in any season? Nestled in a private, 4 acre park like setting in the Southeast ADKs, this cozy mid century modern cabin will show you what upstate NY living is all about. After exploring the best the ADKs have to offer, come soak in the hot tub, unwind in the cedar screened-in porch, or pull up a chair to the natural stone fire pit. Roast some 'smores, take in the night sky, and let your stress melt away!
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)
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.
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.
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!
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.
Water's Edge at Beaver Pond
Like being on a boathouse, this unique custom cottage/camp embraces the spirit of Adirondack lakehouse living... with a breathtaking view from every room! Perched on the shore of private Beaver Pond, this pristine lake offers great recreational activities (canoe/ kayak/ paddleboard/ swimming/ fishing). Inside the cottage, this home is designed with every detail carefully selected, and all modern amenities included! Cozy, comfortable and well-appointed... a perfect vacation location!
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.
Luxe Logs - your perfect Adirondack Getaway!
Sparkling Clean Luxe Log cabin, set in a beautiful location on 3 private acres in Adirondack Park. This is the ultimate wilderness experience, offering all your modern amenities. Whether you want to stargaze, hike, enjoy cross-country or downhill skiing, white water raft, horseback ride or simply just enjoy the crisp fresh air and the outdoors - Luxe Logs is the ultimate escape from the city life, located less than 4 h away from Manhattan and only 3 min from Gore Ski Mountain
Twilight Cabin
382 Back To Sodom Rd. WiFi, family-friendly activities and the beach. You’ll love my place because of the high ceilings, the location, the coziness, and the views. Built by a local craftsman with logs from our area and local river stone for the fireplace. Cabin is completely modernized. Lovely porch and lights along the Pond. Minutes to all outdoor activities. Pet fee $75 per pet per stay must be paid at time of booking. Must bring dog blankets and pick up after the dog.
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 holiday rentals
Other great holiday rentals in Chester
Gore Mountain Retreat
Adirondack Owl's Nest Guest House
Big Bear Lodge w/ Hot Tub and Sauna
A - Frame Cabin with Hot Tub | 6 min to Gore Ski
Hot Tub, Firepit, Gameroom
House in the Adirondacks, 15 min from Gore!
Fully Restored Barn ! The Alexander Barn
Cozy, peaceful cabin near all - Homestead Cabin
Frequently Asked Questions
What are the best places to stay in Chester?
Stays in and around Chester’s downtown or in nearby residential areas offer convenient access to shops and local walks. Some rural accommodations provide quieter, scenic settings.
What are the best things to do in Chester with kids?
Kids can enjoy playgrounds at local parks, family-friendly trails, and occasional visits to ice cream shops. Seasonal farms with activities like fruit picking also draw families during harvest seasons.
What are some of the best things to do in Chester?
You can explore the downtown area’s shops and cafés, visit local parks, or walk along suggested rail trails. Community events, especially in summer and autumn, also draw visitors.
How is the weather in Chester?
Chester experiences cold winters from 10–35°F (-12–2°C), and warm, humid summers with highs of 80–82°F (27–28°C). Rain falls year-round, so packing a jacket is helpful in any season.
When is the best time to visit Chester?
Late spring and early autumn are often recommended for milder weather, with temperatures around 57–72°F (14–22°C) and vibrant scenery. Summer brings community events and outdoor activities, while winter has a quieter pace and occasional snowfall.
What are the best places to visit in Chester?
Explore Chester's historic downtown area, locally owned shops, and parks with open green spaces. The town features art galleries and seasonal farm markets reflecting the community’s rural roots.
What are some hiking trails in Chester?
Chester has local paths through woodlands, along streams, and around rural landscapes that invite gentle walks. Nature lovers often explore nearby parks or public lands with quiet outdoor routes.
What are some family activities we can do in Chester?
Families often explore local parks, visit community playgrounds, or walk the nearby trails. Seasonal farms and ice cream stands are also popular with kids and adults alike.
What are some of the best day trip ideas from Chester?
Consider exploring nearby orchards, scenic state parks, or local museums in surrounding towns. Outdoor adventure areas and historic villages are frequently suggested for enriching day trips.
Are there any pet friendly accommodations available in Chester?
Many vacation rentals and some local stays welcome pets, especially in residential neighborhoods around Chester. Parks and outdoor spaces nearby make it easy to explore the area with your companion animal.
What are some local tips for visiting Chester?
Chester has a small-town atmosphere, so exploring local shops and markets can be rewarding. Locals often enjoy the town’s walking trails, and attending seasonal events is a way to connect with the community.
What is Chester known for?
Chester is known for its small-town character, historic architecture, and community events rooted in agricultural traditions. Residents and visitors enjoy local festivals and gatherings throughout the year.
What are the best hidden gems to explore in Chester?
Discover tucked-away art galleries, handcrafted goods at local shops, and seasonal farm stands in Chester. Quiet parks and small businesses are often suggested for those seeking authentic local experiences.
What are the best foods to try in Chester?
Local menus highlight casual American fare, including burgers, pizza, and homemade desserts. Seasonal farm stands and ice cream shops are also popular, especially in warmer months.
What should I bring for a trip to Chester?
Pack for changing seasons—summers reach up to 82°F (28°C), while winters can dip to 10°F (-12°C), so layers and a warm coat are helpful. Comfortable walking shoes are useful for exploring parks, and a rain jacket is practical throughout the year.
What is the nightlife in Chester like?
Chester has a relaxed evening atmosphere, with locally owned restaurants, pubs, and occasional live music. Nightlife is low-key, often centered on dining and conversation.
What are the most popular events or festivals in Chester?
Chester has seasonal celebrations such as summer carnivals, autumn harvest festivals, and community parades on holiday weekends. Outdoor concerts and farmers markets are frequently suggested in the warmer months.
Are there family friendly vacation rentals in Chester?
Many vacation rentals in Chester are suited for families, with options that have spacious layouts, kitchens, and yard space. Staying near parks or trails can add convenience for active families.
Destinations to explore
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- Lake George
- Saratoga Race Course
- The Wild Center
- Six Flags Great Escape Lodge & Indoor Water park
- West Mountain Ski Resort
- Fort Ticonderoga
- Middlebury College
- Lake Flower
- Saratoga Spa State Park
- Gore Mountain
- Adirondack Extreme Adventure Course
- National Museum of Racing and Hall of Fame
- Lake Placid Olympic Jumping Complex K-120 Meter Jump Tower
- Trout Lake
- Congress Park
- Adirondack Animal Land
- Willard Mountain
- Branbury State Park
- Lincoln Peak Vineyard
- Shepard Park
- Lake St. Catherine State Park
- Button Bay State Park