Holiday rentals in Monterey

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Top-rated holiday rentals in Monterey

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

Guest favourite
Home in Lee
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)
5–12 Sep
$153 SGD per night
4.89 out of 5 average rating, 234 reviews
Guest favourite
Chalet in Otis
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
15–22 Nov
$471 SGD per night
4.94 out of 5 average rating, 345 reviews
Guest favourite
Treehouse in Tyringham
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.
13–20 May
$338 SGD per night
5.0 out of 5 average rating, 222 reviews

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
Loft in Great Barrington
The Old Red Barn
22–29 Apr
$183 SGD per night
4.99 out of 5 average rating, 295 reviews
Guest favourite
Guest house in Stockbridge
Modern studio with views of the treetops
10–17 Jun
$195 SGD per night
4.96 out of 5 average rating, 170 reviews
Guest favourite
Flat in Sandisfield
Sunny Berkshire Studio Apartment
27 May – 3 Jun
$152 SGD per night
4.92 out of 5 average rating, 227 reviews
Guest favourite
Guest house in Becket
Country Cabin
26 Apr – 3 May
$141 SGD per night
4.93 out of 5 average rating, 257 reviews
Guest favourite
Cottage in Great Barrington
Artist Cottage
10–17 Jun
$242 SGD per night
4.93 out of 5 average rating, 234 reviews
Guest favourite
Holiday home in Great Barrington
Home in Great Barrington. Steps from downtown!
30 Nov – 7 Dec
$256 SGD per night
4.94 out of 5 average rating, 129 reviews
Guest favourite
Cottage in Monterey
Beaver Lodge
31 Dec – 7 Jan
$235 SGD per night
5.0 out of 5 average rating, 33 reviews
Guest favourite
Chalet in Monterey
Cozy French Country chalet
13–20 Nov
$248 SGD per night
4.97 out of 5 average rating, 71 reviews
Guest favourite
Home in Monterey
- Lake Front 4 Bdr w/ Fast Internet! -
8–15 May
$430 SGD per night
4.89 out of 5 average rating, 38 reviews
Guest favourite
Home in Monterey
Hupi House - A Peaceful, Wooded, Lakeside Retreat
8–15 May
$331 SGD per night
4.95 out of 5 average rating, 20 reviews
Guest favourite
Cottage in Monterey
Historic Berkshires Cottage with a View
23–30 Oct
$387 SGD per night
5.0 out of 5 average rating, 18 reviews
Guest favourite
Home in Monterey
*Spring Discount* Hilltop Getaway w Magic View!
15–22 May
$274 SGD per night
4.88 out of 5 average rating, 93 reviews

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