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.
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 🏠 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!
Adirondack Chalet
A wonderful and peaceful Chalet at the foot of Gore Mountain with a private inground pool and wireless internet. Just a 25 minute to Lake George and only minutes from other Lakes such as Thirteenth Lake in North River and Minerva Lake. White water rafting is just a few minutes from us and the sweet hamlet of North Creek with its great restaurants, bars, Supermarket, liquor store, antique shops and pharmacy is a mile away. The Chalet is private, with a big deck and is open all year
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.
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. A lovely porch looking towards the pond and exterior 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!
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.
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.
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.
The Cozy Cabin 1/4th of a Mile to Gore Mountain!
Stay at the Cozy Cabin for your next winter adventure! Only 1/4th of a mile to the entrance of Gore this is the perfect spot for your next ski trip. A short drive to all that North Creek has to offer including several great restaurants and shops. High speed internet / Roku TV. Enjoy hanging out by the wood stove on a chilly winter night. Book the Cozy Cabin today and plan your next winter vacation!
The Treehouse
Experience the cozy, rustic charm of this classic A-frame cabin. Perched in a hemlock forest at the edge of the Pharaoh Lake Wilderness, the Treehouse is the perfect setting for an Adirondack getaway. Nature will greet you at the door while the comforts of home await inside. The Schroon Lake Village and various attractions, amenities and outdoor excursions are just a short drive away.
Popular amenities for Chester holiday rentals
Other great holiday rentals in Chester
Gore Mountain Retreat
Big Bear Lodge w/ Hot Tub and Sauna
A - Frame Cabin with Hot Tub | 6 min to Gore Ski
Hot Tub, Firepit, Gameroom
Adirondack A-Frame • Schroon Lake & Firepit
Fully Restored Barn ! The Alexander Barn
Cozy, peaceful cabin near all - Homestead Cabin
Amazing Adirondack Lodge/Cabin-Crystal Lake
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
- Whiteface Mountain Ski Resort
- Gore Mountain
- Middlebury College
- Saratoga Spa State Park
- Lake Flower
- 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
- Lincoln Peak Vineyard
- Branbury State Park
- Lake St. Catherine State Park
- Shepard Park