Vacation rentals with outdoor seating in Monterey

Find and book unique outdoor seating rentals on Airbnb

Top-rated outdoor seating rentals in Monterey

Guests agree: these outdoor seating rentals are highly rated for location, cleanliness, and more.

0 of 0 items showing

1 of 3 pages

Guest favorite

Chalet in Otis

4.95 out of 5 average rating, 382 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

Guest favorite

Home in Lee

4.9 out of 5 average rating, 253 reviews

Cozy Berkshires Cottage

Stay in a cozy Berkshires 1920's cottage! The bedroom occupies the entire second floor with peaceful views of the surrounding field and yard. The cottage is set back from the main road, easily accessible yet private. - Zoned air conditioning & heating makes every room comfortable year-round. - Close to Tanglewood, Jacob's Pillow, Outlet Mall, Kripalu, Turnpike. - Ideal for couples, solo adventurers, business travelers, and furry friends (pets). (Note: MA requires 11.7% tax added to charges)

Guest favorite

Rental unit in Copake Falls

4.92 out of 5 average rating, 300 reviews

Modern Copake Falls Getaway - 8 Mins to Catamount

Hudson Valley/Berkshires vacation rental! Located on a 13 acre former horse farm, full size apt (private entrance) features all new everything and sits in the Taconic Mtns. Has a separate bedroom, new bathroom, kitchenette with Nespresso Coffee Maker, dining and living room with a fireplace and a private bathroom. Property has a pond, stream, 360 views. Relax on property or adventure out. 8 min from Catamount, 7 min from Bash Bish Falls, tons to do locally! 7 min walk to nearest hiking trail!

Guest favorite

Home in Monterey

4.89 out of 5 average rating, 102 reviews

Hilltop Retreat w Magic View! Ski Butternut 15min

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.

Guest favorite

Rental unit in Otis

4.83 out of 5 average rating, 106 reviews

Fall Oasis in the Berkshires

Beautiful, centrally located home in Otis with seasonal water views of the reservoir! Just a few minutes drive from Otis ridge ski resort and the local lakeside beach for seasonal activities. This home is located next door to the only eat in Restaurant/Bar in town and even has a private trail that leads to this restaurant, Katies country store and boat Launch on the Otis reservoir! That same trail is also ride on snowmobile access for snowmobilers and enduro riders/mountain bikers and hikers.

Guest favorite

Cottage in Great Barrington

4.93 out of 5 average rating, 266 reviews

Artist Cottage

Enchanting, private, romantic, retro style, artsy, cottage & lodge building with fireplaces and outdoor hot tub and shower area in a quaint, quiet, neighborhood nested at the base of Flag Rock and near nature trails and downtown Great Barrington. Perfect for a romantic get-away. Open retro style kitchen with wood stove and TV is stocked with utensils and pans for cooking with gas oven and retro appliances. Upstairs bedroom with ensuite large bathroom with soaking tub and message chair.

Guest favorite

Guesthouse in New Marlborough

4.9 out of 5 average rating, 196 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!

Guest favorite

Cabin in Monterey

4.95 out of 5 average rating, 268 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 favorite

Home in Monterey

4.92 out of 5 average rating, 130 reviews

Perfect Berkshire getaway.Cozy cottage.Great wifi.

Family-friendly rustic modern getaway set on 4 acres in the beautiful Berkshires. Escape the city and work using our fiber internet, or just come relax and read a book by the fire. Spend time in the great outdoors skiing at Butternut, hiking at Bob's Way or taking in a cultural event at Tanglewood or Jacobs Pillow. 15 minutes to Great Barrington, Lee and Lenox. 5 minutes to Otis Ridge ski, 15 minutes to Butternut and 25 to Catamount there is always something to do.

Guest favorite

Farm stay in Pittsfield

4.99 out of 5 average rating, 171 reviews

Private 2nd-floor studio on a working produce farm

Charming 2nd-floor studio on a working produce farm in beautiful Berkshire County. Convenient to many local attractions such as Tanglewood, Bousquet Mountain ski resort, Naumkeag, local theater, museums, and much more. Visit our farm stand from late June through mid-October for fresh vegetables, baked goods, and our delicious corn on the cob! Spend time visiting with the farm's goats, horses and chickens, or just relax out on the balcony and take in the views.

Guest favorite

Cottage in Becket

4.94 out of 5 average rating, 269 reviews

BERKSHIRE COTTAGE NEAR CRYSTAL CLEAR LAKE.

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 favorite

Guesthouse in Lenox

4.94 out of 5 average rating, 341 reviews

The Granary at House on Golden Hill

The Granary is a 1735 carriage house situated on a historic Berkshires farmhouse compound. Featuring 20-foot cedar-lined ceilings, original wide-planked pine floor boards, and large windows and skylights, the Granary provides sweeping mountain views and an idyllic Berkshires experience. King-sized bedroom, eat-in kitchen, and bathroom with soaking tub and standing shower. Minutes to downtown Lenox, Tanglewood, and centrally located in the Berkshires.