Holiday rentals in Big Pond

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Top-rated holiday rentals in Big Pond

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Guest favourite

Chalet in Otis

4.95 out of 5 average rating, 423 reviews

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

Top guest favourite

Treehouse in Tyringham

4.99 out of 5 average rating, 305 reviews

Gingerbread House Tower in the Berkshire Hills

Escape to this newly renovated, off-beat retreat for a magical stay. Part of Tyringham’s Gingerbread House located on the Santarella Estate in the Berkshires, Western Mass. This one-of-a-kind loft with tower bedchamber offers guests a fairytale experience. The open concept living space filled with plants brings the outdoors inside and offers ample room to relax. If looking for activity, guests can spend the day on the grounds, walking nearby trails, or exploring the many nearby Berkshire towns.

Guest favourite

Cottage in Becket

4.93 out of 5 average rating, 226 reviews

The Yellow • 1,750ft² (170m²), 2-level cottage • Open concept with 180° view from living room 'gorgeous with amazing views' • 3 bedrooms (all queen size beds), 2 full baths • Fully equipped kitchen • Private dock & firepit • Canoe & 2 kayaks • Two smart TVs & 4 Google smart speakers • 1 Gigabit Wi-Fi • Workspace with laptop stand upstairs • Additional full size bed upstairs • Additional queen size sofa bed downstairs • Additional twin trundle downstairs • Washer and dryer with laundry detergent

Superhost

Home in Otis

4.94 out of 5 average rating, 147 reviews

Berkshires hideaway! Hikes & serenity near lake

Welcome to your light-filled home in the Berkshires. With a two-level wraparound deck & open floorplan, you can enjoy your time together, away from the world. Big spaces and cozy spots throughout. Perfect for families (with a swingset!) or getaways with friends. Otis Reservoir, MA's biggest lake, is nearby. Audubon preserve behind the house. Great, private home base for hiking, summer music/dance/theatre, trips to Kripalu or MassMOCA, skiing... or for going nowhere at all. Dogs OK! (note: fee)

Top guest favourite

Guest house in Cummington

5 out of 5 average rating, 109 reviews

Clark Cottage

Enjoy a peaceful stay in this cozy, creative space. Set on 10 acres of gardens and woods, this cottage is perfectly located to explore Western Massachusetts - with places like MASS MoCA, Shelburne Falls, Tanglewood and Northampton all within a 30min to 1 hour drive. Upstairs is a queen bed and full bath, while downstairs features a functional kitchen, work desk, grand windows, and a living space with full sleeper sofa. We live in the main house on property but respect your privacy-see photos!

Superhost

Home in Becket

4.93 out of 5 average rating, 155 reviews

Lake front retreat - Stylish Berkshire home

Absolute privacy! Escape to this beautifully renovated mid-century home w/ 4 bedrooms on Long Bow Lake. Featuring stylish wood floors & modern design, the cozy dining room boasts a gas fireplace. This family-friendly retreat offers exclusive lake frontage complete w/ a dock & 4 kayaks for endless fun! Enjoy serene moments on the screened porch, fire up the Weber grill, or challenge each other to ping pong. Located just 20 mins from Downtown Lee, outlets, hikes, & Otis Ridge skiing

Top guest favourite

Flat in Otis

4.95 out of 5 average rating, 107 reviews

Enjoy every season the Berkshires have to offer.

Come enjoy the Berkshires any season you choose. We are close to local ski areas, with have access to snow shoeing, ice fishing and many more winter activities. Also located within minutes of the many cultural attractions the Berkshires have to offer, Jacob's Pillow, Shakespeare & Company, and Tanglewood. Enjoy the beautiful fall foliage on our small private pond. You can bring your kayak or canoe to enjoy the wildlife that abounds or catch & release in our pond.

Guest favourite

Cottage in Becket

4.95 out of 5 average rating, 283 reviews

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(will consider pets.)(90 second walk through wooded path to lake)

Guest favourite

Home in Otis

4.97 out of 5 average rating, 115 reviews

Direct Lakefront Home on Otis Reservoir Giant Yard

Year round retreat directly on Otis Reservoir offering 62’ of lake frontage on MA largest and fully recreational lake. Enjoy the lake views right from our docks, Solo Stove firepit, expansive deck, main floor or bedrooms. The house sits 100 yards back from the lake leaving a large lawn for outdoor activities. Updated and renovated in 2021! Many local snowmobile trails and ski resorts too! Heated garage and 2nd driveway for larger trucks/trailer or RV's.

Guest favourite

Home in Great Barrington

4.96 out of 5 average rating, 266 reviews

Jaw dropping mountain & lake views

Curl up with a good book by the fire and gaze out at the dreamy picturesque mountain and lake views..... Or ski, swim, hike and enjoy so much more that the Berkshires has to offer in this centrally located Southern Berkshire county home. Private mountain top adventure awaits.. Centrally located in Southern Berkshire County: 10 minutes from Butternut ski, 20 minutes to Great Barrington, 25 minutes Stockbridge & Lenox and 2 ½ hours from NYC and Boston.

Top guest favourite

Home in Otis

4.95 out of 5 average rating, 165 reviews

Idyllic family retreat - spacious lake home,

This recently renovated waterfront home is perfectly situated close to many Berkshire attractions for an ideal getaway. Lake views are stunning year around. The fire-pit at shore offers a unique outdoor gathering option. Warm and welcoming interior with three levels of living for families and friends (up to 8 people). Area offers family-friendly hiking. Enjoy the whimsical decor and mid-century style furnishings. Cook in the well-equipped kitchen.

Superhost

Cabin in Otis

4.88 out of 5 average rating, 57 reviews

Enjoy 43 Acres on Two Ponds!

Welcome to Mamacha, a winter wonderland on 43 acres of protected land with marked trails, massive boulders, breathtaking views and perfect for hiking, snowshoeing (we have 5 pairs for your use!), snowmobiling (our cabin is within a network of trails!), and skiing! We’re 20 minutes from Butternut (also has snow tubing!) in Great Barrington and 10 minutes from Otis Ridge (night skiing!). We hope you love it as much as we do.