House holiday rentals in Monterey
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Top-rated house rentals in Monterey
Guests agree: these houses are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for house rentals in Monterey
House rentals with a pool
Home in Hudson
4.93 out of 5 average rating, 227 reviewsCasa Luna Country Retreat with Pool, Hudson, NY
13–20 Sep
Home in Ghent
4.87 out of 5 average rating, 270 reviewsModern Barn on 12 acres w Sauna, FirePit+swimming
4–11 Dec
Home in Sheffield
4.85 out of 5 average rating, 114 reviewsRace Mountain House
8–15 Jul
Home in Rhinebeck
4.96 out of 5 average rating, 164 reviewsOn The Hill in Rhinebeck
20–27 Dec
Home in Pine Plains
4.95 out of 5 average rating, 131 reviewsStylish, Secluded Getaway with Pool & Fireplace
22–29 Sep
Home in Catskill
4.93 out of 5 average rating, 164 reviewsThe Grandview | Catskill, NY
16–23 Sep
Home in Staatsburg
4.98 out of 5 average rating, 105 reviewsHilltop Escape ~ 25 acre private retreat
18–25 Apr
Home in Sheffield
4.94 out of 5 average rating, 16 reviewsPrivate Berkshire County Retreat
10–17 Jun
Weekly house rentals
Home in Stockbridge
4.95 out of 5 average rating, 103 reviewsSun-filled, Charming Stockbridge Classic- In Town!
29 Mar – 5 Apr
Home in Dalton
4.88 out of 5 average rating, 113 reviewsThe Yellow House
29 Nov – 6 Dec
Home in Becket
4.86 out of 5 average rating, 287 reviewsReal Estate:Therapy - Lake, Laundry, Love it
11–18 Nov
Home in Colebrook
4.99 out of 5 average rating, 202 reviewsNorbrook Farm ~ Rustic farmhouse w/ pond & trails
1–8 Apr
Home in Becket
4.94 out of 5 average rating, 36 reviewsNerd Preservation Sanctuary
16–23 Dec
Home in Monterey
4.91 out of 5 average rating, 11 reviews3bd Near Lake w Kayaks & Shared Tennis Court !
18–25 May
Home in Otis
4.83 out of 5 average rating, 59 reviewsSpringtime Oasis in the Berkshires!
19–26 Jun
Home in New Marlborough
4.87 out of 5 average rating, 15 reviewsSpacious Berkshires retreat
1–8 Jun
Private house rentals
Home in Tyringham
4.85 out of 5 average rating, 68 reviewsTreetop Hideaway in Tyringham
2–9 Nov
Home in Great Barrington
5.0 out of 5 average rating, 67 reviewsGranite Ledge, Modern home in a unique setting
27 Nov – 4 Dec
Home in Sandisfield
5.0 out of 5 average rating, 19 reviewsWaterfront oasis in heart of Berkshires
16–23 Mar
Home in Stockbridge
4.94 out of 5 average rating, 90 reviewsBright Stockbridge country home, near everything!
10–17 Dec
Home in Monterey
4.85 out of 5 average rating, 20 reviewsCanary House: sunny, cheerful summer cottage
12–19 Dec
Home in Otis
5.0 out of 5 average rating, 23 reviews4 Bedroom Farmhouse close enough/far enough
27 Nov – 4 Dec
Home in New Marlborough
5.0 out of 5 average rating, 18 reviewsGrand View
16–23 Jan
Home in Becket
5.0 out of 5 average rating, 3 reviewsLakeside 3-BR Berkshires Residence
15–22 Jan
Quick stats about house rentals in Monterey
Total rentals
50 properties
Rentals with dedicated workspaces
30 properties have a dedicated workspace
Pet-friendly rentals
30 properties allow pets
Family-friendly rentals
50 properties are a good fit for families
Total number of reviews
1.8T reviews
Nightly prices starting at
₹11,677 before taxes and fees
Destinations to explore
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