Vacation rentals in Monterey

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Monterey

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

Guest favorite

Home in Lee

4.89 out of 5 average rating, 234 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)

May 8 – 15

G$26,215 GYD per night
Guest favorite

Chalet in Otis

4.94 out of 5 average rating, 346 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

Sep 11 – 18

G$78,584 GYD per night
Guest favorite

Apartment in Copake Falls

4.93 out of 5 average rating, 250 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!

Sep 14 – 21

G$22,386 GYD per night

Popular amenities for Monterey vacation rentals

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

Apartment in Sheffield

5.0 out of 5 average rating, 318 reviews

Hideaway with Spectacular Berkshire Views

Jun 18 – 25

G$34,487 GYD per night
Guest favorite

Guesthouse in Stockbridge

4.96 out of 5 average rating, 171 reviews

Modern studio with views of the treetops

Jun 10 – 17

G$35,573 GYD per night
Guest favorite

Home in Lee

5.0 out of 5 average rating, 224 reviews

Berkshire Mountain retreat with Urban eco-luxuries

Mar 19 – 26

G$68,412 GYD per night
Guest favorite

Guest suite in South Lee

4.92 out of 5 average rating, 189 reviews

Sunny Riverside Apartment

May 27 – Jun 3

G$37,211 GYD per night
Guest favorite

Loft in Great Barrington

4.99 out of 5 average rating, 296 reviews

The Old Red Barn

Apr 5 – 12

G$33,611 GYD per night
Guest favorite

Cottage in Hillsdale

4.94 out of 5 average rating, 171 reviews

Cozy Cottage Catamount, Berkshires Walk to Brewery

Feb 28 – Mar 7

G$26,477 GYD per night
Guest favorite

Vacation home in Great Barrington

4.94 out of 5 average rating, 131 reviews

Home in Great Barrington. Steps from downtown!

Nov 25 – Dec 2

G$55,419 GYD per night
Guest favorite

Cottage in Great Barrington

4.93 out of 5 average rating, 234 reviews

Artist Cottage

Dec 14 – 21

G$42,145 GYD per night
Guest favorite

Cottage in Monterey

5.0 out of 5 average rating, 33 reviews

Beaver Lodge

Jan 8 – 15

G$41,528 GYD per night
Guest favorite

Chalet in Monterey

4.97 out of 5 average rating, 72 reviews

Cozy French Country chalet

Dec 3 – 10

G$44,852 GYD per night
Guest favorite

Home in Monterey

4.9 out of 5 average rating, 39 reviews

- Lake Front 4 Bdr w/ Fast Internet! -

Sep 8 – 15

G$100,023 GYD per night
Guest favorite

Cottage in Monterey

5.0 out of 5 average rating, 18 reviews

Historic Berkshires Cottage with a View

Oct 23 – 30

G$69,989 GYD per night

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

2.5K reviews

Nightly prices starting at

G$4,189 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 $20 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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