
Places to stay near Crooked Lake
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Top-rated holiday rentals near Crooked Lake
Guests agree: these stays are highly rated for location, cleanliness and more.

A beautiful cozy house with a Burden Lake View!
This is a cozy lake house that has a sunny warm porch with couches and tables . We have a phone charging station and games for guests to enjoy . You walk into a living room with a large TV and dining room . The kitchen is small but modern with a dishwasher , coffee pot , and dishes . There is a porch attached to the back of the kitchen overlooking the beautiful lake! Please note: There is no lake access. Full basement with washer and dryer and a sitting area with games and dart board. No pets

Cozy cottage with pool, walking distance to lake
Cozy cottage with pool, fire-pit, and a short walk to the lake. Enjoy a relaxing stay at our home exploring the lake and local eateries, or a fun family getaway at the pool. Just a short drive to your winter fun at Jiminy Peak for skiing, or Saratoga during track Season. Minutes to the Crooked Lake House for your wedding stays. Don't forget your four legged family members, while you're snowshoeing, or swimming at the lake. With WIFI and A/C you can tele-work, while sitting pool side this summer.

Mid-Century Glass Octagon in the Berkshires
This architectural gem with wrap-around glass windows welcomes guests with its uniquely-designed, informal interior set on 7 private woodland acres. Cozy up around the wood-burning fireplace with floor to ceiling windows as a backdrop, or sit on the expansive deck around the firepit gazing at the stars. Use as a home base for the wonderful cultural and outdoor activities in the area, or enjoy nature in luxury without ever leaving home. *Book midweek for discounted rates IG@midcenturyoctagon

Barn Stay at Shadowbrook Farm
Welcome to the Shadowbrook Farm Stay. Tucked in the hills of upstate New York, this 1700's Shaker barn has been restored into a beautiful guest house. It sits upon a two hundred acre working pasture raised meat farm. This barn was used to hold, and milk cows for two hundred and fifty years. Guests will have access to portions of the farm lands which are highlighted on the maps provided in the Farm Stay manual. If you follow the farm road, you are able to meet every farm animal on the property!

The Hygge Loft- mid-mod cabin on 70 forested acres
The Hygge Loft: a midcentury modern-designed cabin nestled among 70 acres of privately-owned forest with rivers & hiking trails. Enjoy sipping an espresso or wine while listening to vinyl records, cozied up by the wood-burning fireplace. Take a walk in the forest to the river or stargaze by the firepit on the private deck. Indulge in a luxurious bath or snuggle up in the ultra comfy king-size bed with views of treetops and sky all around. It’s the kind of place you’ll never want to leave!

The Lodge at June Farms
See more of us on Prime Video's tv show, June Farms... streaming now! This cabin is a stunning, rustic, open-floor-plan retreat. The screened-in front porch looks down onto our horse pasture. This cabin is our most romantic cabin on the property. Our gigantic rain shower in the bathroom has an 8'x5' wall mirror and a French door that opens out to the forest. If you are a cook, this cabin is a chef's dream. You might also like our stunning new cabin called The Farmhouse.

Boutique TINY home+private HOT TUB-walk to Main St
March-April midweek special: Bottle of prosecco, robes/slippers, s'mores. Boutique-luxe tiny home with private hot tub, firepit, and dreamy loft lounge. Plush queen bed, full kitchen, and curated charm throughout. A peaceful & private oasis, yet just a 2-min walk to Chatham’s Main St. lined with restaurants, brewery, shops & theater. The perfect upstate NY getaway for couples—hike, visit galleries, stroll to dinner, or unwind in your own private spa oasis @artparkhomes.

Creekside Couple's Retreat w/Hot tub, Sauna & More
Tucked by an enchanting creek, this newly built cabin is a serene haven where nature and comfort meet. Unwind together in the hot tub beneath the stars, relax in the wood fired sauna, or enjoy a fun evening in the game room. Let the soothing sounds of the creek lull you to sleep as you take in the beauty of the outdoors from every window. Explore nearby trails, quaint towns, and secret escapes. Pet-friendly, perfect for couples seeking a magical retreat in every season.

Contemporary Cabin in Catskill Mountains
Our luxurious cabin is more than just an Airbnb; it's a personal sanctuary designed with your comfort and tranquility in mind. Nestled on 1.5 acres of Catskill Mountain beauty, this idyllic retreat offers everything you need for a relaxing getaway or extended stay. Enjoy the modern amenities, cozy furnishings, and breathtaking views that make our cabin a truly special place. View more pictures at @the_reve_cabin Ready to escape the ordinary? Book your stay today.

Lake House in Averill Park, NY
Our lake house is on Glass Lake in Averill Park, NY. In case you want to venture off, it is close to Saratoga (race season!), the Berkshires MA, Albany NY, and Vermont. Incredibly private with spacious property. Our lake house is great for families with kids and couples, and handicap accessible. It is great for any season (leaves, skiing, fishing, swimming). Kayaks, row boat.....and the lake!! Booking guest must be at least 25 years old.

Cozy, bright 3-bedroom Cottage with fireplace.
Cozy, spacious brook-side cottage with 3 bedrooms, 2 baths, fully-equipped kitchen, fireplace, and serene, 382-acre country setting. Colorful artwork, designer furnishings, and well-appointed kitchen and bathrooms will make you feel welcome and at home. Historic charm of Bennington ten minutes away. NYC (182 miles); Boston (118); Mt. Snow (32); Prospect Mountain (13). Close to MASS MoCA (22), Tanglewood (49) and Manchester outlets (32).

Dog Friendly Farm
Welcome to The June Arthur Farm! This beautiful spot has a long agricultural history. It hasn't been in production for the past 40 years but we're slowly bringing it back to life. It's once again producing good, happy, Hudson Valley food: eggs, fruit, lamb, and beef. We hope you'll come visit us. Note for the skiers out there: We're 20 minutes from Jiminy Peak!
Popular amenities for holiday rentals near Crooked Lake
Apartment rentals with wifi

2BR w/ Parking + deck - Near Downtown & MVP Arena

Jiminy's GEM: ski-in/ski-out 3br/3ba condo at base

Spacious 3 bedroom apt in Lenox historic downtown

Jiminy Peak Apartment

Gorgeous Waterfront - Close to track & Saratoga

Elegant, spacious studio apt in historic mansion

Jiminy Peak Country Inn 1 Bedroom Suite

Jiminy Peak Country Inn - ski in/out condo MT view
Family-friendly house rentals

Escape to Lakefront Leisure—Amazing views!

Scandinavian Cottage/Mountain Views/Fire pit

The Vermont Farmhouse|Hiking|Dog Trails|Village

Cozy Hudson Valley Cabin, Fully Stocked w/ Wifi

Modern Ski-Home With Views Near Hunter & Windham

Chic Hudson Farmhouse w/ Fireplace & Porch

19th c. Barn in The Berkshires

Rustic Swedish Barn/Featured in Airbnb Magazine
Apartment rentals with air conditioning

Berkshire Mountain Top Chalet

1 bdrm apt in Athens on the Hudson

Washington Parkside 1 Bedroom In 1800s Brownstone!

Susie's Climax Creations

The Beer Diviner Brewery Apartment

COLD SPRING

Hudson River Beach House

See MoCA from your mansion+Sauna!
Other great holiday rentals near Crooked Lake

Artist Cottage

Luxury Barn Retreat — All-Season Escape Awaits!

Dog Friendly Studio

Cozy Modern Sugar House with spectacular views.

Schoolhouse Spa Retreat on a Vermont Farm

Cozy Retreat in the Trees

Cozy Cottage with pool and walk to lake

Guest Suite in Old Chatham Hunt Country
Destinations to explore
- Hunter Mountain
- Stratton Mountain
- Saratoga Race Course
- Berkshire East Mountain Resort
- Jiminy Peak Mountain Resort
- Stratton Mountain Resort
- Catamount Mountain Ski Resort
- Windham Mountain
- Howe Caverns
- Butternut Ski Area and Tubing Center
- Mount Snow Ski Resort
- Thacher State Park
- West Mountain Ski Resort
- Hunter Mountain Resort
- Bash Bish Falls State Park
- Bousquet Mountain Ski Area
- Zoom Flume
- Saratoga Spa State Park
- Taconic State Park
- Norman Rockwell Museum
- June Farms
- Hildene, The Lincoln Family Home
- Naumkeag
- National Museum of Racing and Hall of Fame




