Holiday rentals in Monterey

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Monterey

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

Guest favourite

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)

8–15 May

$169 SGD per night
Guest favourite

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

11–18 Sep

$506 SGD per night
Guest favourite

Flat 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!

14–21 Sep

$144 SGD per night

Popular amenities for Monterey holiday 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 holiday rentals in Monterey

Guest favourite

Flat in Sheffield

5.0 out of 5 average rating, 318 reviews

Hideaway with Spectacular Berkshire Views

18–25 Jun

$221 SGD per night
Guest favourite

Guest house in Stockbridge

4.96 out of 5 average rating, 171 reviews

Modern studio with views of the treetops

10–17 Jun

$228 SGD per night
Guest favourite

Home in Lee

5.0 out of 5 average rating, 224 reviews

Berkshire Mountain retreat with Urban eco-luxuries

19–26 Mar

$440 SGD per night
Guest favourite

Guest suite in South Lee

4.92 out of 5 average rating, 189 reviews

Sunny Riverside Apartment

27 May – 3 Jun

$239 SGD per night
Guest favourite

Loft in Great Barrington

4.99 out of 5 average rating, 296 reviews

The Old Red Barn

5–12 Apr

$216 SGD per night
Guest favourite

Cottage in Hillsdale

4.94 out of 5 average rating, 171 reviews

Cozy Cottage Catamount, Berkshires Walk to Brewery

28 Feb – 7 Mar

$170 SGD per night
Guest favourite

Holiday home in Great Barrington

4.94 out of 5 average rating, 131 reviews

Home in Great Barrington. Steps from downtown!

25 Nov – 2 Dec

$357 SGD per night
Guest favourite

Cottage in Great Barrington

4.93 out of 5 average rating, 234 reviews

Artist Cottage

14–21 Dec

$271 SGD per night
Guest favourite

Cottage in Monterey

5.0 out of 5 average rating, 33 reviews

Beaver Lodge

8–15 Jan

$267 SGD per night
Guest favourite

Chalet in Monterey

4.97 out of 5 average rating, 72 reviews

Cozy French Country chalet

3–10 Dec

$289 SGD per night
Guest favourite

Home in Monterey

4.9 out of 5 average rating, 39 reviews

- Lake Front 4 Bdr w/ Fast Internet! -

8–15 Sep

$644 SGD per night
Guest favourite

Cottage in Monterey

5.0 out of 5 average rating, 18 reviews

Historic Berkshires Cottage with a View

23–30 Oct

$450 SGD per night

Quick stats about holiday 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

$27 SGD before taxes and fees

Destinations to explore