Holiday houses in Monterey

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Top-rated holiday rentals in Monterey

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite

Chalet in Otis

4.95 out of 5 average rating, 426 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, 306 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

Home in Monterey

4.9 out of 5 average rating, 109 reviews

Hilltop Retreat w Magic View! Lake Beach 1 mile

Please enjoy our little slice of paradise! Perched just up the hill from Lake Garfield, The Hupi House offers a truly magical view of the lake and mountains for miles beyond. Let breathtaking sunsets be your evening entertainment! Inside you will find a stocked kitchen, high-quality appliances and bedding, fast wifi, and wooded seclusion. Outside you will find swimming, kayaking, hiking, leaf-peeping, star-gazing, skiing...Minutes to Ski Butternut, Great Barrington, Jacob's Pillow, Tanglewood.

Top Guest favourite

Guesthouse in Cummington

5 out of 5 average rating, 112 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!

Top Guest favourite

Apartment in Sheffield

5 out of 5 average rating, 371 reviews

Hideaway with Spectacular Berkshire Views

Located on the border of Massachusetts and Connecticut with spectacular views of the Berkshire Hills and fifteen minutes drive from Great Barrington, MA, this apartment is located on a secluded seven-acre property. Owners live on the property. Above an artist studio this renovated one bedroom apartment with private entrance, full kitchen, fast internet is stylish, light and airy with a contemporary and eclectic decor. Please note During winter all-wheel drive vehicle is strongly advised.

Top Guest favourite

Home in Great Barrington

4.99 out of 5 average rating, 125 reviews

Granite Ledge, Modern home in a unique setting

Welcome to Great Barrington, the heartbeat of the Berkshires! This newly remodeled home that sits on 3.5 acres, is conveniently located 1 min from Butternutt Ski Mountain, and a 6 min drive from downtown main street Great Barrington. Convenient to restaurants, shops, farmers markets, art galleries, Tanglewood, Stockbridge, The Norman Rockwell Museum, Simon’s Rock, etc. Enjoy a vibrantly diverse restaurant scene and cultural events while still staying in a private setting.

Superhost

Home in Tyringham

4.83 out of 5 average rating, 120 reviews

Treetop Hideaway in Tyringham

For your upcoming stay, look no further than this airy, secluded log cabin overlooking the beautiful Tyringham Valley. On the first floor, you will find a great room with vaulted ceilings and a fireplace, as well as a master suite, second bedroom, half bath and recently renovated kitchen. The second floor includes two more bedrooms and a bathroom. The exterior offers a screen porch with hot tub, wraparound deck and 35+ acres of woods bordering conservation land in Monterey.

Guest favourite

Guesthouse in New Marlborough

4.91 out of 5 average rating, 202 reviews

COZY GUESTHOUSE MINUTES AWAY FROM HIKING!

Renovated 1880's one bedroom cozy guesthouse in beautiful Southfield, MA. Full kitchen stocked with all necessities. Comfortable & stylish with a luxury king size bed. Minutes away from Ski Butternut, Berkshire attractions & trails. Walking distance to breakfast and lunch at The Southfield Store or have dinner at nearby The Old Inn On The Green and Cantina 229. 10 minutes from Great Barrington. Enjoy leaf-peeping, hiking, waterfalls, apple picking, skiing, and much more!

Top Guest favourite

Cabin in Monterey

4.95 out of 5 average rating, 285 reviews

Amazing Berkshire Mountains Cabin

Our incredible 4 bedroom home is situated on 2 beautiful secluded acres in picture perfect Monterey - the ultimate 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.

Guest favourite

Cottage in Becket

4.95 out of 5 average rating, 284 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 Monterey

4.96 out of 5 average rating, 267 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.

Superhost

Home in New Marlborough

4.88 out of 5 average rating, 138 reviews

Lake House in the Berkshire (Access Dock & Canoe

Unwind and reset at a newly built house on Lake Buel. With access to a private community dock and provided canoe, you can take advantage of life on the water. Inside this newly built house, you will find brand new furnishings and newly updated features to make your stay comfortable. Just a quick five minute drive to Great Barrington, home to some of the best restaurants that the Berkshires have to offer.