Skip to content
27 stays

Stays in Monterey

Check travel restrictions before booking.
Please review and follow government travel guidelines.
Learn more
SUPERHOST
Entire chalet in Monterey
Cozy French Country chalet
6 guests2 bedrooms5 beds1 bath
WifiKitchenAir conditioningFree parking
Rating 4.92 out of 5;24 reviews
Price:GYD31,339 / night
SUPERHOST
Entire house in Monterey
Charming cottage w/ gorgeous views.
4 guests2 bedrooms2 beds2 baths
WifiKitchenAir conditioningFree parking
Rating 4.92 out of 5;213 reviews
Price:GYD34,055 / night
SUPERHOST
Entire house in Sandisfield
Family friendly farmhouse in the Berkshires w pool
10 guests5 bedrooms7 beds2 baths
WifiKitchenAir conditioningFree parking
Rating 5.0 out of 5;31 reviews
Price:GYD89,391 / night
SUPERHOST
Entire cabin in Red Hook
Modern Upstate cabin + hot pool near Rhinebeck NY.
6 guests2 bedrooms3 beds1.5 baths
WifiKitchenAir conditioningFree parking
Rating 4.95 out of 5;145 reviews
Price:GYD81,481 / night
SUPERHOST
Entire house in Northampton
The Farm House, with a hot tub!
6 guests3 bedrooms3 beds1 bath
WifiKitchenAir conditioningFree parking
Rating 4.92 out of 5;300 reviews
Price:GYD41,785 / night
SUPERHOST
Farm stay in West Simsbury
Flamig Farm Staycation
5 guests2 bedrooms4 beds1 bath
WifiKitchenAir conditioningFree parking
Rating 4.92 out of 5;194 reviews
Price:GYD28,205 / night
SUPERHOST
Entire house in Egremont
Bucolic Berkshires House
6 guests3 bedrooms4 beds2 baths
WifiKitchenFree parking
Rating 4.98 out of 5;40 reviews
Price:GYD51,187 / night
SUPERHOST
Entire bungalow in Pittsfield
The Lakehouse
6 guests2 bedrooms3 beds1 bath
WifiKitchenAir conditioningFree parking
Rating 4.86 out of 5;43 reviews
Price:GYD26,264 / night
SUPERHOST
Entire house in Hudson
Beautiful 2 bed apartment just off Warren Street
4 guests2 bedrooms2 beds1 bath
WifiKitchenAir conditioningFree parking
Rating 4.93 out of 5;85 reviews
Price:GYD41,785 / night
SUPERHOST
Entire house in Lenox
Heart of Lenox Walk to Town Cozy Cottage!
4 guests2 bedrooms3 beds1 bath
WifiKitchenAir conditioningFree parking
Rating 4.95 out of 5;97 reviews
Price:GYD69,789 / night
SUPERHOST
Entire house in Hudson
COUNTRY RETREAT WITH POOL, HUDSON, NY
6 guests4 bedrooms4 beds2.5 baths
WifiKitchenFree parking
Rating 4.94 out of 5;124 reviews
Price:GYD40,801 / night
Entire cabin in Becket
Waldtreff - quiet grand cabin
10 guests3 bedrooms6 beds4 baths
WifiKitchenFree parking
Rating 5.0 out of 5;146 reviews
Price:GYD52,231 / night
SUPERHOST
Entire house in Red Hook
Hudson Valley Hideaway
10 guests4 bedrooms5 beds3 baths
WifiKitchenAir conditioningFree parking
Rating 4.91 out of 5;70 reviews
Price:GYD88,793 / night
SUPERHOST
Entire apartment in New Lebanon
Sunny Duplex at the old boarding house
5 guests2 bedrooms4 beds1 bath
WifiKitchenAir conditioningFree parking
Rating 4.94 out of 5;104 reviews
Price:GYD23,966 / night
SUPERHOST
Entire apartment in Northampton
North Street Nest, sunny downtown apartment
5 guests2 bedrooms3 beds1.5 baths
WifiKitchenAir conditioningFree parking
Rating 5.0 out of 5;493 reviews
Price:GYD20,773 / night
Entire house in Becket
"The Robin's Nest" Lakefront home Robin Hood Lake
8 guests4 bedrooms5 beds2 baths
WifiKitchenAir conditioningFree parking
Rating 5.0 out of 5;9 reviews
Price:GYD73,124 / night
SUPERHOST
Entire house in Salisbury
Harmony House
12 guests6 bedrooms9 beds4 baths
WifiKitchenAir conditioningFree parking
Rating 5.0 out of 5;34 reviews
Price:GYD110,431 / night
SUPERHOST
Entire house in Salisbury
Great Falls Farmhouse
11 guests6 bedrooms7 beds4.5 baths
WifiKitchenAir conditioningFree parking
Rating 5.0 out of 5;20 reviews
Price:GYD177,586 / night
SUPERHOST
Entire house in Lenox
The Berkshire Quintessential Cape downtown Lenox
6 guests3 bedrooms4 beds2 baths
WifiKitchenAir conditioningFree parking
Rating 4.93 out of 5;104 reviews
Price:GYD95,061 / night
SUPERHOST
Entire house in Hyde Park
Private getaway
8 guests4 bedrooms4 beds4 baths
WifiKitchenAir conditioningFree parking
Rating 4.93 out of 5;30 reviews
Price:GYD70,886 / night
1 20 of 27 places to stay
Enter dates to see full pricing. Additional fees apply. Taxes may be added.