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Vacation rentals in Monterey

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Top-rated vacation rentals in Monterey

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

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Chalet in Otis

4.94 out of 5 average rating, 376 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

Home in Lee

4.9 out of 5 average rating, 252 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)

Treehouse in Tyringham

5 out of 5 average rating, 264 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.

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.

Rental unit in Otis

4.84 out of 5 average rating, 102 reviews

Springtime 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.

Guesthouse in New Marlborough

4.9 out of 5 average rating, 195 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!

Cabin in Monterey

4.95 out of 5 average rating, 266 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.

Home in Monterey

4.92 out of 5 average rating, 128 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.

Cottage in Becket

4.95 out of 5 average rating, 266 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)

Guesthouse in Lenox

4.94 out of 5 average rating, 337 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.

Home in Great Barrington

4.97 out of 5 average rating, 238 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.

Home in New Marlborough

4.89 out of 5 average rating, 129 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.

Vacation rentals for every style

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Popular amenities for Monterey vacation rentals

Free parking on premises

Air conditioning

Stay near Monterey's top sights

Beartown State Forest36 locals recommend

Benedict Pond Loop20 locals recommend

Tyringham Cobble Park19 locals recommend

Appalachian Trail17 locals recommend

Roadside Store & Cafe16 locals recommend

Ashintully Gardens13 locals recommend

Other great vacation rentals in Monterey

Home in Becket

4.95 out of 5 average rating, 65 reviews

Nerd Preservation Sanctuary

Cottage in Great Barrington

4.92 out of 5 average rating, 62 reviews

Carriage house with Chef's Kitchen, close to town

Home in Monterey

4.96 out of 5 average rating, 26 reviews

Hupi House - A Peaceful, Wooded, Lakeside Retreat

Home in Sandisfield

5 out of 5 average rating, 29 reviews

Waterfront oasis in heart of Berkshires

Home in Great Barrington

4.99 out of 5 average rating, 84 reviews

Private Home in The Berkshires (New Hot Tub!)

Cabin in Sandisfield

4.99 out of 5 average rating, 92 reviews

Berkshires Cabin in Woods with Mountain Views

Home in Monterey

4.94 out of 5 average rating, 16 reviews

Fall Weekends At Epic Lake House w/ Fire Pit

Home in Great Barrington

4.99 out of 5 average rating, 91 reviews

Granite Ledge, Modern home in a unique setting

Quick stats about vacation rentals in Monterey

Total rentals
70 properties
Nightly prices starting at
$90 before taxes and fees
Total number of reviews
3.1K reviews
Family-friendly rentals
70 properties are a good fit for families
Pet-friendly rentals
40 properties allow pets
Rentals with dedicated workspaces
40 properties have a dedicated workspace

Frequently Asked Questions

Do cottage rentals in Monterey have free parking?
Absolutely! We offer over 10 cottage rentals with free parking in Monterey. Enjoy a tailored experience with all the comforts you desire.
Are there pet-friendly vacation rentals in Monterey?
Four-legged friends are welcome in Monterey. Choose from more than 40 vacation rentals for guests traveling with pets.
Are there vacation rentals with a dedicated workspace in Monterey?
Yes! Work meets play with ease at over 40 vacation rentals in Monterey featuring dedicated workspaces. Stay connected and productive in your home away from home.
Do cottage rentals in Monterey have wifi?
Absolutely! We offer over 10 cottage rentals with wifi in Monterey. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly vacation rentals in Monterey?
Monterey has more than 70 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
Do cottage rentals in Monterey have a kitchen?
Absolutely! We offer over 10 cottage rentals with a kitchen in Monterey. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Monterey have air conditioning?
Absolutely! We offer over 40 house rentals with air conditioning in Monterey. Enjoy a tailored experience with all the comforts you desire.
How much does it cost to stay in cottage rentals in Monterey?
Experience the best of Monterey with our cottage rentals, starting at about $120 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

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