
Holiday rentals with lake access in Stockbridge
Find and book unique lake access rentals on Airbnb
Quick stats about holiday rentals with lake access in Stockbridge

Total holiday rentals
Explore 20 holiday rentals in Stockbridge

Nightly prices starting at
Stockbridge holiday rentals start at €175 per night before taxes and fees

Verified guest reviews
Over 830 verified reviews to help you choose

Family-friendly holiday rentals
20 properties offer extra space & child-friendly amenities

Wifi availability
20 of Stockbridge holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Stockbridge rentals

4.9 Average rating
Stockbridge stays are highly rated by guests – averaging 4.9 out of 5!

Nearby attractions
Stockbridge’s top spots include Norman Rockwell Museum, Naumkeag and Berkshire Botanical Garden
Top-rated rentals with lake access in Stockbridge
Guests agree: these rentals with lake access are highly rated for location, cleanliness and more.

Slate Cabin - Stylish Country Escape x Rhinebeck
This designer cabin blends natural materials and modern finishes. — sophisticated & cozy. Gaze at (or swim in!) the stunning spring-fed pond steps from the house. Lounge on the deck or enjoy coffee in the sunroom. The interiors feature three bedrooms, two full bathrooms, living room with chic and cozy furniture and wood burning fireplace, and fully appointed kitchen that's a joy to cook in. Entertain your family & friends at the table for 10 and continue out to the grounds, beverage in hand.

Berkshires Cottage by Lake. Year Round Adventures.
THE BERKSHIRES COTTAGE IN THE WOODS BY A SPRING FED LAKE HAS SOMETHING FOR EVERYONE....... SWIM, FISH, KAYAK, HIKE, SKI, JACOBS PILLOW DANCE FESTIVALS, TANGLEWOOD OUTDOOR CONCERTS, GOLF, DINE, SHOP LEE OUTLETS, DINE WITH ENTERTAINMENT, PLAYS, ANTIQUES, FIRE PITS, HANGING IN A HAMMOCK, FLOAT ON CRYSTAL CLEAR WATER, BBQ ON THE DECK, OR JUST DOING NOTHING AT ALL UNPLUG AND RECHARGE. ESCAPE & RELAX. (90 second walk through wooded path to lake) Pets Considered. $29. pet fee = approved Pet Agreement.

Magical Private Island Retreat in Pine Plains
Enjoy the serenity of Twin Island Lake, surrounded by tranquil water, lush mountains and nature. this incredible private island retreat is only 2 hours from NYC. Take a canoe across a lily pad dotted lake to your own private island paradise. You will never find a magical space like this so close! The entire island is yours to enjoy and has plenty of outdoor spaces including a propane grill, hammocks and plenty of seating areas. The inside a humble aesthetic with wood paneling and charm.

NEW! Berkshires Farmhouse w/ Firepit & Wood Stove
Welcome to our little slice of heaven upstate. Located just a 5-minute drive to the MA border, a stay at our home in Canaan, NY means access to the best of both Columbia County and the Berkshires. In the summer, enjoy the private Adams Point Beach on Queechy Lake and easy access to Tanglewood. In the winter, explore 4 different local ski resorts and curl up by the cozy wood stove. In between, enjoy the peaceful pond views and secluded location on a dirt road. We can't wait to welcome you!

Cabin in Woods w/ Lake Access & *private* Hot Tub!
Don't miss your opportunity for a spring adventure at this cozy, secluded cabin with its own private hot tub and lake access! Welcome to Cabin on Hillside, a peaceful haven from the stresses of daily life. Situated in the charming town of Copake Lake, you get all the fun of a quaint lakeside community with the solitude of a wooded retreat. Whether you are looking for outdoor adventures, trips into town, or a peaceful homestay, this cabin provides it all! Come visit! Your oasis awaits!

Berkshire Lakefront House with Amazing Views
Enjoy the culture of the Berkshires & Hudson - 15 min from Tanglewood, Norman Rockwell Museum, Shakespeare & Co, PS21, McHaydn Theatre, Mount Greylock, Jiminy Peak Resort, zipline parks, Bousquet & more. Restaurants & market within driving distance and a membership-only beach within a short walk or drive. Great lake views with wrap-around porch. The lake is family-friendly. We welcome couples, solo adventurers, and families. Sorry, no "Group Bookings" - book & pay via one account only.

Hip Stockbridge Cabin - A stroll to the lake
Welcome to our stylish glamping cabin! Relax in the spacious yard & sunny deck. Cozy fieldstone fireplace, vaulted ceilings & skylights. The cottage features gorgeous pine wood & fantastic interior design. Unwind in the reading nook, master bedroom with skylights, or put on your favorite vinyl. Kids will adore the sleeping loft. Just a 9-minute walk or 2-minute drive to the public beach (the beautiful Stockbridge Bowl). BBQ grill, outdoor fire pit . Tanglewood is just minutes away.

Cozy lakehouse
Relax with family or friends at this sweet cottage on Center Lake in the Berkshires. This lakeside cottage is charming and rustic. Enjoy a beautiful day on the lake swimming, fishing off the dock and kayaking. Grill dinner on your private deck and watch the stars come out in the evening Or enjoy all that the Berkshires have to offer, Jacob’s Pillow (15 min), Berkshire Theater (20 min), Tanglewood (30 min). There are plenty of nearby hiking trails and charming towns to explore.

Amazing Berkshire Mountains Cabin
Our incredible 4-bedroom home is situated on 2 beautiful secluded acres in picture perfect Monterey - the quintessential Berkshire County getaway, with modern kitchen, screened porch, 2 fireplaces a fabulous outdoor hot tub and a beautiful brook on the property. Enjoy hiking the Appalachian Trail in nearby Beartown State Forest or kayaking and swimming in the incomparable Lake Garfield. We are a quick ride to Ski Butternut, Catamount, Tanglewood, Lenox and Great Barrington.

HOT TUB! Dog & Family Friendly in the Berkshires!
Secluded Berkshires Retreat! -Dog/s, Family Friendly cottage -Freshly painted & new floors for 2026! -Patio w/ Hot tub, fire pit, canoe use -Acre secluded lot -Historic Lee, Stockbridge, Lenox/Tanglewood, Norman Rockwell Museum w/in 30 min! -30 min Monument Mt. & Berkshires Scenic Railway -Appalachian Trail hiking -Wineries/Breweries -Outlets/Small Shops -Master w/Queen -2nd bed with 1 Twin/Full Bunk -Full size pull out couch

Designer Home, Hot Tub, Private Yard, & Projector
A cozy, charming retreat just minutes from downtown Hudson—perfect for couples, families, or small groups looking to relax, unwind, and explore the Hudson Valley. + Hot tub, firepit & BBQ + Mini movie theater w/ projector + Dedicated workspace w/ views + Fast WiFi + Smart TV + Stocked kitchen + Coffee setup + Professionally designed interiors + Quick drive to Warren Street + Nature trail to Oakdale Lake

Rabbit Run in the heart of Stockbridge Village
Old meets new in this lovely cottage, a short walk from the Red Lion Inn. Lots of light, comfortable, traditional furniture, beautiful, fenced-in backyard with mountain views. Kitchen updated with Smeg refrigerator, gas stove, granite counters, hardwood floors throughout. Hiking trails, park, and tennis courts within a 5-minute walk. Lake rights to Stockbridge Bowl, Weber grill, and Solo firepit.
Popular amenities for lake access rentals in Stockbridge
Lake access house rentals

Renovated historic home, walk to Hudson River!

Great Barrington, Cabin Sleeps 14, Walk To Town

Modern Barn on 12 acres w Sauna, FirePit+swimming

Beautiful family home, Hike, Fireplace, Sleeps 12

Lake House in the Berkshire (Access Dock & Canoe

Linny's | Private Dock | Lake Access | Firepit

Copake Lake Artist’s Cottage with Dock and Kayaks

Idyllic family retreat - spacious lake home,
Apartment rentals with lake access

Hudson River Beach House

Enjoy every season the Berkshires have to offer.

The MoCA-Cabana: 2 bd + Sauna

Hip Warren Street Apartment

Captain's Quarters at Mickey's Marina

Private Elegant 1BR Apt One Block to Warren St.

Gateway to the Berkshires

Zen River Studio
Lake access cottage rentals

Cozy Cottage in the Berkshires

Waterlily Lakehouse - Modern+Waterfront+Retreat

Oriole Cottage@Copake Lake: 4 Kayaks, 1 Canoe

Cozy Catskill Cottage

Quiet 2 BR cottage in the heart of the Berkshires

The lake house

Charming Lakeview Cottage in the Berkshires

Lemongrass Cottage!
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- Rentals with a washing machine and dryer Stockbridge
- Rentals with a patio Stockbridge
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- Rentals with a fireplace Stockbridge
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- House rentals Stockbridge
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- Pet-friendly rentals Stockbridge
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- Fitness-friendly rentals Stockbridge
- Rentals with beach access Stockbridge
- Rentals with a hot tub Stockbridge
- Family-friendly rentals Stockbridge
- Rentals with a firepit Stockbridge
- Rentals with lake access Berkshire County
- Rentals with lake access Massachusetts
- Rentals with lake access United States
- Hunter Mountain
- Six Flags New England
- Berkshire East Mountain Resort
- Jiminy Peak Mountain Resort
- Catamount Mountain Ski Resort
- Windham Mountain
- Butternut Ski Area and Tubing Center
- June Farms
- Taconic State Park
- Thacher State Park
- Bash Bish Falls State Park
- Zoom Flume
- Hunter Mountain Resort
- Kent Falls State Park
- Bousquet Mountain Ski Area
- Mohawk Mountain Ski Area
- Ski Sundown
- Millbrook Vineyards & Winery
- Hudson Chatham Winery
- Rensselaer Polytechnic Institute
- Naumkeag
- University of Massachusetts Amherst
- Norman Rockwell Museum
- MVP Arena





