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Our top choices for Monterey holiday homes

9.6 out of 10, Exceptional, (10 reviews)
"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 HK$1,249
HK$3,076 total
includes taxes & fees
27 Jan - 28 Jan
Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine

Holiday Home in Great Barrington

Home in Great Barrington
9.8 out of 10, Exceptional, (26 reviews)
"Great stay in a cool, new space, totally walkable to Railroad St. I would definitely go back to GB and would try to stay here again. "
United States
Cameron M.
The price is HK$1,137
HK$1,950 total
includes taxes & fees
26 Jan - 27 Jan
Home in Great Barrington
10.0 out of 10, Exceptional, (143 reviews)
"Perfect spot for a family celebration!"
United States
Kerry P.
The price is HK$1,263
HK$2,481 total
includes taxes & fees
26 Jan - 27 Jan
Big farmhouse in the foothills of the Berkshires

Holiday Home in New Lebanon

Near Tanglewood: Historic Summer Retreat
9.4 out of 10, Exceptional, (26 reviews)
"Perfect cosy home to stay at for a Berkshire vacation. Easy to get to everything."
United States
Paul S.
The price is HK$913
HK$2,717 total
includes taxes & fees
1 Feb - 2 Feb
Near Tanglewood: Historic Summer Retreat
9.0 out of 10, Wonderful, (21 reviews)
"Great stay in the Berkshires for a wedding. Amanda was very accommodating and communicative. "
United States
Wendy D.
The price is HK$1,046
HK$2,892 total
includes taxes & fees
2 Feb - 3 Feb
Historic Berkshires Home Near Tanglewood, Trails & Wineries
9.6 out of 10, Exceptional, (4 reviews)
"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 HK$1,404
HK$3,589 total
includes taxes & fees
26 Jan - 27 Jan
Sun Filled Lenox Retreat - Minutes to Tanglewood!
7.8 out of 10, Good, (7 reviews)
"The space was well situated to our plans, food,lake and hiking and very clean but smelled sooo strongly of dogs that we limited our time inside."
United States
Liz V.
The price is HK$2,099
HK$3,851 total
includes taxes & fees
23 Jan - 24 Jan
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
10.0 out of 10, Exceptional, (3 reviews)
"Emma's property is adorable! Clean, well appointed with fresh flowers on the table to great us. Smooth and easy communication from start to finish. Really close to Tanglewood and all the activities Western Massachusetts has to offer."
United States
Cheryl F.
The price is HK$1,053
HK$2,090 total
includes taxes & fees
1 Feb - 2 Feb
Sweet Cozy Victorian in Housatonic. Close to everything.
10.0 out of 10, Exceptional, (33 reviews)
"A college friends' retreat was fantastic, in part due to the location, cleanliness and amenities in this 3 bedroom house. Furniture was comfortable and kitchen was stocked with everything we needed. "
United States
cathy c.
The price is HK$2,331
HK$5,069 total
includes taxes & fees
26 Jan - 27 Jan
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
10.0 out of 10, Exceptional, (1 review)
"Fantastic place to stay!"
United States
James
The price is HK$1,661
HK$2,123 total
includes taxes & fees
25 Jan - 26 Jan
Suite 3 - Quiet and private accommodations in a country setting.
2.0 star property
The price is HK$1,365
HK$2,376 total
includes taxes & fees
25 Jan - 26 Jan
Renovated house. Built in 1890s. No neighbors in sight.
The price is HK$1,669
HK$2,701 total
includes taxes & fees
16 Feb - 17 Feb
3-bedroom house in beautiful Berkshires, close to amenities!

Holiday Home in Great Barrington

Family Ski Getaway in the Berkshires
9.2 out of 10, Wonderful, (7 reviews)
"Close to a great bakery and near to a farm market and shopping mall. "
United States
Cristine C.
The price is HK$1,579
HK$2,321 total
includes taxes & fees
3 Feb - 4 Feb
Family Ski Getaway in the Berkshires
10.0 out of 10, Exceptional, (3 reviews)
"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 HK$4,414
HK$10,356 total
includes taxes & fees
29 Jan - 30 Jan
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

Holiday Home in Great Barrington

Great Barrington Get Away
9.4 out of 10, Exceptional, (26 reviews)
"Nice large kitchen and yard, walking distance to downtown, friendly neighborhood- we enjoyed our stay! "
United States
Deb W.
The price is HK$2,417
HK$4,302 total
includes taxes & fees
28 Jan - 29 Jan
Great Barrington Get Away
8.8 out of 10, Excellent, (3 reviews)
"House was clean and made our Thanksgiving great with it's size and amenities. "
United States
Khalil S.
The price is HK$3,704
HK$6,715 total
includes taxes & fees
12 Feb - 13 Feb
Spacious 5-bedroom house in charming Lee with WiFi

Holiday Home in Great Barrington

Cozy. Clean. Free bagel shop. 3 Fireplaces.
10.0 out of 10, Exceptional, (1 review)
"The host was very responsive and friendly. The house was well equipped and very comfortable. We did get breakfast at the Great Barrington Bagel Company and had a great breakfast. Highly recommend!"
United States
Mary R.
The price is HK$3,119
HK$5,173 total
includes taxes & fees
22 Feb - 23 Feb
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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Top Monterey Hotel Reviews

Find out more about Monterey

Monterey Vacation Homes information

Number of reviews
303
Accommodation
387 Vacation Homes
Lowest Price
HK$1,950
Highest Price
HK$10,356

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