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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

4.95 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

Home in Lee

4.9 out of 5 average rating, 255 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)

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!

Treehouse in Tyringham

5 out of 5 average rating, 269 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, 103 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

4.83 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.

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.

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.

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.

Farm stay in Pittsfield

4.99 out of 5 average rating, 172 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.

Home in Great Barrington

4.97 out of 5 average rating, 241 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.

Vacation home in Great Barrington

4.95 out of 5 average rating, 189 reviews

Home in Great Barrington. Steps from downtown!

Central and Private! Just steps away from historic downtown Great Barrington and East Mountain Hiking trails. Enjoy sunset views with friends and family, before you walk into town for a night out! 10 minutes (2 miles) to Butternut Ski Area This brand new home features all new appliances and furniture. Enjoy luxury, charm, and privacy while you rest easy at The Maple.

Vacation rentals for every style

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Unique stays

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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 New Marlborough

4.92 out of 5 average rating, 24 reviews

Spacious Berkshires retreat

Home in Becket

4.95 out of 5 average rating, 65 reviews

Nerd Preservation Sanctuary

Home in Monterey

4.96 out of 5 average rating, 28 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

Cabin in Sandisfield

4.99 out of 5 average rating, 96 reviews

Berkshires Cabin in Woods with Mountain Views

Home in Monterey

5 out of 5 average rating, 3 reviews

Berkshire Ski House on Lake Garfield W/HT By GB

Home in Monterey

4.94 out of 5 average rating, 17 reviews

Ready to Ski Butternut, Sleeps 8!

Home in Great Barrington

4.99 out of 5 average rating, 96 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 house rentals in Monterey have wifi?
Absolutely! We offer over 50 house 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 house rentals in Monterey?
Experience the best of Monterey with our house rentals, starting at about $140 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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