
Places to stay near Crooked Lake
Book unique holiday rentals, homes and more on Airbnb
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 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.

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.

Cozy Retreat in the Trees
Time travel to 1958 in this architectural gem! This mid-century modern glass and wood cabin is 300 yards away from a charming small lake. The house is NOT on the lake itself, but it is surrounded by trees in a lovely secluded spot. The only heat is a wood stove... but there is a 4-person cedar barrel sauna in the woods that is electric. A classic 1952 Spartanette travel trailer serves as an extra bedroom. This is a true retreat for romance and adventure.

Romantic-Private-Western Tiny Cabin w/HOT TUB
Just 2.5 hours from NYC & Boston, escape to The Hitching Post — a romantic Western-inspired tiny home in Chatham, NY with a private hot tub, firepit, outdoor shower & rustic luxury throughout. Once the hideout of a legendary samurai cowboy, this one-of-a-kind retreat features a cozy queen bed nook, luxe bath & kitchenette. Just a 2-minute walk to Chatham’s restaurants, shops, brewery & theater. A perfect Hudson Valley getaway for couples. @artparkhomes

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.

Riverside Retreat on the Hudson - Modern Cottage
Welcome to the Riverside Retreat on the Hudson, a modern renovated cottage located directly on the Hudson River! Enjoy the beautiful panoramic views from the comfort of the house or in the Adirondack chairs on the patio. Secluded and serene, yet minutes away from downtown Catskill (5 minutes) and Hudson (15 minutes). Hunter and Windham are 30 minutes away for hiking and skiing! We are so excited to share this very special place with you!

Summer Mountain Retreat + Views, Fire Pit, Hot Tub
Escape to your modern mountain retreat—perfect for Summer getaways! Just 15 mins to Tanglewood, MASS MoCA & The Clark, and close to scenic hikes, waterfalls, farm stands, breweries, and charming small towns. Soak in the wood-fired hot tub, enjoy evenings around the Breeo fire pit, cook fresh seasonal meals, and unwind in peaceful privacy. With EV charging and a quiet workspace, it’s ideal for refreshing escapes or Summer adventures.

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
Condo rentals with Wi-Fi

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

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

Historic Gem, Fireplace,2BR/2BA,Capitol District

Spacious 3 bedroom apt in Lenox historic downtown

Downtown Adams Vintage Getaway

Jiminy Peak Apartment

Elegant, spacious studio apt in historic mansion

LAKEFRONT: Walk to Marina, Restaurants, Near Track
Family-friendly house rentals

Pawfect Family Retreat w/fenced-in yard & Dog Park

Cozy Hudson Valley Cabin, Fully Stocked w/ Wifi

Modern Barn on 12 acres w Sauna, FirePit+swimming

Cantabile life in the Berkshires

Chic Hudson Farmhouse w/ Fireplace & Porch

Eclectic Troy Retreat w/ Hot Tub & Sauna!

Private Waterfall Retreat on 10 acres

Blacksmith House - Charming Historic Getaway
Apartment rentals with air conditioning

Berkshire Mountain Top Chalet

Washington Parkside 1 Bedroom In 1800s Brownstone!

The Beer Diviner Brewery Apartment

Luxury downtown penthouse, near Franklin Plaza.

Mountain View Retreat~Sunny Hill Golf / Skiing

Above SpringRise

Close to MVP/Airport/SUNY; 45m-1Hr: Saratoga, LG!

A Lovely Historic Apartment
Other great holiday rentals near Crooked Lake

Artist Cottage

Peaceful Tiny House Escape by Hudson & Berkshires

A Bedroom in the woods with lovely views!

Schoolhouse Spa Retreat on a Vermont Farm

Creekside Couple's Retreat w/Hot tub, Sauna & More

Cozy Cottage with pool and walk to lake

Berkshire’s Blue Cabin

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
- Windham Mountain
- June Farms
- Stratton Mountain Resort
- Catamount Mountain Ski Resort
- Howe Caverns
- Butternut Ski Area and Tubing Center
- West Mountain Ski Resort
- Taconic State Park
- Thacher State Park
- Bash Bish Falls State Park
- Hunter Mountain Resort
- Bousquet Mountain Ski Area
- Hildene, The Lincoln Family Home
- Rensselaer Polytechnic Institute
- Hudson Chatham Winery
- Saratoga Spa State Park
- MVP Arena
- Naumkeag
- New York State Museum





