Vacation rentals in Monterey

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Top-rated vacation rentals in Monterey

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Guest favorite

Home in Lee

4.89 out of 5 average rating, 235 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)

Sep 24 – Oct 1

G$25,988 GYD per night

Guest favorite

Chalet in Otis

4.94 out of 5 average rating, 349 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

Oct 23 – 30

G$84,193 GYD per night

Guest favorite

Cabin in Monterey

4.93 out of 5 average rating, 186 reviews

Exotic Mountain Retreat in the Berkshires

Early & Late Checkout Available! Only 15 minutes from Butternut Ski mountain and the charming town of Great Barrington. We always try to accommodate for your enjoyment so we ask you to respect our policies and the tranquility of our neighbors. Please limit your stay to no more than 15 guests. Any Large House parties will not be permitted. Kindly bring your outside activities inside by 10:00 PM in respect of our community and neighbors. No street parking is allowed. No Charge for wood.Thank you!

May 6 – 13

G$217,729 GYD per night

Guest favorite

Loft in Great Barrington

4.99 out of 5 average rating, 296 reviews

The Old Red Barn

Renovated studio in barn built circa 1830, centrally located to all activities in the Berkshires. Bright and sunny space with views of fields and spectacular sunsets. Open upstairs loft bedroom with pine floors, catherial ceiling, exposed beams, full kitchen , bathroom and washer and dryer. The Berkshires are beautiful in the fall , come stay ! 5 minute drive to town. Walk to the Green River , hike the trails. We provide all basic household supplies. We invite all to enjoy our old red barn.

May 17 – 24

G$31,341 GYD per night

Guest favorite

Apartment in Copake Falls

4.93 out of 5 average rating, 256 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!

Oct 15 – 22

G$17,897 GYD per night

Guest favorite

Treehouse in Tyringham

5.0 out of 5 average rating, 226 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.

Oct 4 – 11

G$64,890 GYD per night

Guest favorite

Guesthouse in Becket

4.93 out of 5 average rating, 258 reviews

Country Cabin

Lovely private country setting. Listen to owls and coyotes at night, birds during the day. When it rains you can enjoy the sound on the metal roof. I only accept advance reservations of 2 nights or more. (You may reserve a single night booking within 5 days of the request.) The space is for 2 adults but I allow for flexibility, so don't hesitate to ask. Seasonal/weekend rates may apply. I live on the property with my partner and the cabin would not otherwise be on the real estate market.

Jan 25 – Feb 1

G$25,383 GYD per night

Guest favorite

Guest suite in South Lee

4.92 out of 5 average rating, 190 reviews

Sunny Riverside Apartment

The Berkshires are a perfect spot for a getaway week or weekend. You will enjoy this cozy 2-story apartment, easily accessible to all that the region has to offer. The apartment has a fully equipped kitchen, dining space, living area, and two bedrooms, overlooking the Housatonic River. Every town in South County is 5-15 minutes drive, and in 50 minutes you could be at The Clark Museum or Mass MOCA in North County. Several ski areas are nearby, and Kripalu is just an easy 10 minute drive.

Mar 24 – 31

G$26,830 GYD per night

Guest favorite

Guesthouse in New Marlborough

4.91 out of 5 average rating, 179 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!

Jul 13 – 20

G$33,189 GYD per night

Guest favorite

Cabin in Monterey

4.95 out of 5 average rating, 250 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.

Jun 5 – 12

G$71,806 GYD per night

Guest favorite

Home in Monterey

4.93 out of 5 average rating, 116 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.

Sep 15 – 22

G$38,093 GYD per night

Guest favorite

Apartment in Sandisfield

4.92 out of 5 average rating, 227 reviews

Sunny Berkshire Studio Apartment

Sunny many windowed studio apartment attached at west end of the main house. Self contained with kitchen and bathroom. Plus addition sleeping area (attached bedroom). Studio and bedroom have full size beds Studio also has narrow twin futon. 1 mile long gravel road for a "walk out the door and go" wake up morning hike. State forest is across from house, along Bosworth Road and along Rt 57. Long Term Guests welcome. $5/guest after 2. PET FEE: $25/stay

Feb 26 – Mar 5

G$24,094 GYD per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Monterey vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Monterey's top sights

Ashintully Gardens13 locals recommend

Lake Garfield Beach7 locals recommend

Les Trois Emme Vineyard & Winery7 locals recommend

Roadside Store & Cafe16 locals recommend

Benedict Pond Loop20 locals recommend

Bidwell House Museum11 locals recommend

Other great vacation rentals in Monterey

Guest favorite

Guest suite in Austerlitz

4.86 out of 5 average rating, 137 reviews

Rustic-Modern Studio - Near Hudson, Chatham, & GB

Sep 18 – 25

G$18,425 GYD per night

Guest favorite

Guesthouse in Stockbridge

4.96 out of 5 average rating, 175 reviews

Modern studio with views of the treetops

May 8 – 15

G$34,501 GYD per night

Superhost

Apartment in Lee

4.78 out of 5 average rating, 106 reviews

Cozy Berkshire Cottage Style Apartment

Oct 31 – Nov 7

G$24,467 GYD per night

Guest favorite

Apartment in Sheffield

4.92 out of 5 average rating, 122 reviews

Private Berkshire Barn Apartment

Nov 19 – 26

G$30,682 GYD per night

Guest favorite

Home in New Marlborough

4.89 out of 5 average rating, 122 reviews

Lake House in the Berkshire (Access Dock & Canoe

Sep 8 – 15

G$67,266 GYD per night

Guest favorite

Cottage in Becket

4.94 out of 5 average rating, 237 reviews

BERKSHIRE COTTAGE NEAR CRYSTAL CLEAR LAKE.

Jan 15 – 22

G$39,169 GYD per night

Guest favorite

Apartment in Sheffield

5.0 out of 5 average rating, 319 reviews

Hideaway with Spectacular Berkshire Views

Dec 24 – 31

G$34,522 GYD per night

Guest favorite

Guesthouse in Lenox

4.95 out of 5 average rating, 279 reviews

The Granary at House on Golden Hill

Sep 2 – 9

G$33,330 GYD per night

Show all

Quick stats about vacation rentals in Monterey

Total rentals
70 properties
Rentals with dedicated workspaces
40 properties have a dedicated workspace
Pet-friendly rentals
30 properties allow pets
Family-friendly rentals
60 properties are a good fit for families
Total number of reviews
2.6K reviews
Nightly prices starting at
G$12,512 GYD before taxes and fees

Frequently Asked Questions

Do house rentals in Monterey have free parking?
Absolutely! We offer over 50 house 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 30 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 60 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
Do house rentals in Monterey have a kitchen?
Absolutely! We offer over 50 house 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.

Vacation rentals in Monterey

Top-rated vacation rentals in Monterey

Vacation rentals for every style

Houses

Hotels

Unique stays

Popular amenities for Monterey vacation rentals

Stay near Monterey's top sights

Other great vacation rentals in Monterey

Guest suite in Austerlitz

Guesthouse in Stockbridge

Apartment in Lee

Apartment in Sheffield

Home in New Marlborough

Cottage in Becket

Apartment in Sheffield

Guesthouse in Lenox

Quick stats about vacation rentals in Monterey

Total rentals

Rentals with dedicated workspaces

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Frequently Asked Questions

Do house rentals in Monterey have free parking?

Are there pet-friendly vacation rentals in Monterey?

Are there vacation rentals with a dedicated workspace in Monterey?

Do house rentals in Monterey have wifi?

Are there family-friendly vacation rentals in Monterey?

Do house rentals in Monterey have a kitchen?

Do house rentals in Monterey have air conditioning?

How much does it cost to stay in house rentals in Monterey?

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