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Holiday Homes in Monterey

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Check prices for these dates

Next weekend
24 Oct - 26 Oct
In two weeks
31 Oct - 2 Nov
In one month
14 Nov - 16 Nov
In two months
12 Dec - 14 Dec

Featured Holiday Homes in Monterey

Outdoor dining
Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access!
Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access!
10.0 out of 10, Exceptional, (3)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is NZ$697
includes taxes & fees
28 Oct - 29 Oct
Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access!
Smart TV, books
Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking
Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking
9.6 out of 10, Exceptional, (8)
"Very nice location with tons of privacy, yet not too far from things to do. Very easy for our dog to navigate the property as well."
United States
James D.
The price is NZ$687
includes taxes & fees
27 Oct - 28 Oct
Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking
Fridge, microwave, oven, stovetop
Home in Great Barrington
Home in Great Barrington
9.8 out of 10, Exceptional, (24)
"Enjoyed our stay!!!"
United States
Fred W.
The price is NZ$447
includes taxes & fees
10 Nov - 11 Nov
Home in Great Barrington
Property grounds
Big farmhouse in the foothills of the Berkshires
Big farmhouse in the foothills of the Berkshires
10.0 out of 10, Exceptional, (140)
"Lovely old farmhouse with authentic yet comfortable furnishings. Would recommend!"
United States
Jon O.
The price is NZ$641
includes taxes & fees
19 Oct - 20 Oct
Big farmhouse in the foothills of the Berkshires
Property grounds
Cheerful 3-bedroom cottage with woodstove
Cheerful 3-bedroom cottage with woodstove
10.0 out of 10, Exceptional, (39)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
The price is NZ$790
includes taxes & fees
9 Nov - 10 Nov
Cheerful 3-bedroom cottage with woodstove
Fridge, microwave, oven, stovetop
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
2.0 star property
7.8 out of 10, Good, (6)
"Very clean and spacious! We enjoyed our stay with our small pup!"
United States
Ann C.
The price is NZ$847
includes taxes & fees
20 Oct - 21 Oct
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Fridge, microwave, oven, stovetop
Near Tanglewood: Historic Summer Retreat
Near Tanglewood: Historic Summer Retreat
9.6 out of 10, Exceptional, (22)
"Very cozy and comfortable with everything we needed to make our stay enjoyable. The kitchen was well stocked, the bedrooms a good size with comfortable mattresses. The deck and the yard were lovely. This location is gem!"
United States
Patty W.
The price is NZ$726
includes taxes & fees
19 Oct - 20 Oct
Near Tanglewood: Historic Summer Retreat
Exterior
Bungalow in the Berkshires
Bungalow in the Berkshires
10.0 out of 10, Exceptional, (3)
"We had a lovely stay. Easy check in and communication was great. "
United States
Dale G.
The price is NZ$731
includes taxes & fees
19 Oct - 20 Oct
Bungalow in the Berkshires
Fridge, microwave, oven, stovetop
Sun Filled Lenox Retreat - Minutes to Tanglewood!
Sun Filled Lenox Retreat - Minutes to Tanglewood!
9.4 out of 10, Exceptional, (3)
"The house is in a great location and is very user friendly and well equipped. The only suggestion I would make is to put an air conditioner in the third bedroom. Overall, a lovely stay."
United States
Sarah D.
The price is NZ$819
includes taxes & fees
30 Oct - 31 Oct
Sun Filled Lenox Retreat - Minutes to Tanglewood!
Terrace/patio
Historic Berkshires Home Near Tanglewood, Trails & Wineries
Historic Berkshires Home Near Tanglewood, Trails & Wineries
9.0 out of 10, Wonderful, (19)
"It was great - just what we were looking for. "
United States
Kaye S.
The price is NZ$698
includes taxes & fees
20 Oct - 21 Oct
Historic Berkshires Home Near Tanglewood, Trails & Wineries
Fridge, microwave, oven, stovetop
Great Barrington Get Away
Great Barrington Get Away
9.4 out of 10, Exceptional, (23)
"The host was very communicative and responsive during our arrival and check out. The listing and everything was as it said we were very pleased with both the location of the home and the actual home itself and the property walking distance to town truly cannot say enough. Thank you for Your hospitality. Our family is very grateful. "
United States
Amy B.
The price is NZ$907
includes taxes & fees
2 Nov - 3 Nov
Great Barrington Get Away
Games room
Cozy Riverfront Escape in Great Barrington - "Whiskers on the Water"
Cozy Riverfront Escape in Great Barrington - "Whiskers on the Water"
9.0 out of 10, Wonderful, (2)
"Close to a great bakery and near to a farm market and shopping mall. "
United States
Cristine C.
The price is NZ$554
includes taxes & fees
20 Oct - 21 Oct
Cozy Riverfront Escape in Great Barrington - "Whiskers on the Water"
Smart TV, fireplace, books
Cozy. Clean. Free bagel shop.
Cozy. Clean. Free bagel shop.
10.0 out of 10, Exceptional, (10)
"The perfect location for a stay in Great Barrington. The house is so well done and very comfortable!"
United States
Carly F.
The price is NZ$1,159
includes taxes & fees
4 Nov - 5 Nov
Cozy. Clean. Free bagel shop.
Exterior
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
10.0 out of 10, Exceptional, (1)
"Everything was well taken care of, the hosts were extremely nice, and the area is perfect! The city is also different and really cute! Will come back for sure!"
United States
Roberta
The price is NZ$2,460
includes taxes & fees
20 Oct - 21 Oct
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Property grounds
Charming 3-bedroom Modern cottage with lakeside views
Charming 3-bedroom Modern cottage with lakeside views
2.0 star property
The price is NZ$2,588
includes taxes & fees
28 Oct - 29 Oct
Charming 3-bedroom Modern cottage with lakeside views
Terrace/patio
Spacious 5-bedroom house in charming Lee with WiFi
Spacious 5-bedroom house in charming Lee with WiFi
8.0 out of 10, Very good, (1)
"House was large, clean, and comfortable. "
United States
John Z.
The price is NZ$1,298
includes taxes & fees
25 Oct - 26 Oct
Spacious 5-bedroom house in charming Lee with WiFi
Fridge, microwave, stovetop, dishwasher
Berkshire House Stay
Berkshire House Stay
9.8 out of 10, Exceptional, (19)
"Incredible location and immaculate home created such a great long weekend for our family. The house has everything you’ll need, organized and spotless. The owner was on top of every detail and communicated immediately. "
United Kingdom
Michael F.
The price is NZ$1,466
includes taxes & fees
19 Oct - 20 Oct
Berkshire House Stay
Microwave, oven, stovetop, dishwasher
Cozy. Clean. Free bagel shop. 3 Fireplaces.
Cozy. Clean. Free bagel shop. 3 Fireplaces.
The price is NZ$1,159
includes taxes & fees
4 Nov - 5 Nov
Cozy. Clean. Free bagel shop. 3 Fireplaces.
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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