Photo by Elizabeth Massa Peroulakis

Search Vacation Homes in Monterey

Start date: Check-in selected.
To Date
End date: Check-out

    Change your mind

    Book hotels with free cancellation

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
31 Oct - 2 Nov
In two weeks
7 Nov - 9 Nov
In one month
21 Nov - 23 Nov
In two months
19 Dec - 21 Dec

Vacation Homes in Monterey

Outdoor dining
Dog Friendly A-Frame in the Berkshires! Hike/Ski Appalachian Tr. Walk to lake!
Dog Friendly A-Frame in the Berkshires! Hike/Ski Appalachian Tr. Walk to lake!
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 AED 536
AED 1,386 total
includes taxes & fees
28 Oct - 29 Oct
Dog Friendly A-Frame in the Berkshires! Hike/Ski Appalachian Tr. Walk to lake!
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 AED 588
AED 1,441 total
includes taxes & fees
27 Oct - 28 Oct
Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking
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 AED 735
AED 1,336 total
includes taxes & fees
27 Oct - 28 Oct
Big farmhouse in the foothills of the Berkshires
Fridge, microwave, oven, stovetop
Home in Great Barrington
Home in Great Barrington
9.8 out of 10, Exceptional, (24)
"Crisp and clean with a great location.Wonderful choice."
United States
Richard B.
The price is AED 698
AED 1,120 total
includes taxes & fees
23 Nov - 24 Nov
Home in Great Barrington
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 AED 638
AED 1,546 total
includes taxes & fees
26 Oct - 27 Oct
Near Tanglewood: Historic Summer Retreat
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 AED 724
AED 1,658 total
includes taxes & fees
11 Nov - 12 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 AED 988
AED 1,806 total
includes taxes & fees
26 Oct - 27 Oct
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
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 AED 698
AED 1,719 total
includes taxes & fees
30 Oct - 31 Oct
Sun Filled Lenox Retreat - Minutes to Tanglewood!
Fridge, microwave, oven, stovetop
Great Barrington Get Away
Great Barrington Get Away
9.4 out of 10, Exceptional, (24)
"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 AED 937
AED 1,764 total
includes taxes & fees
27 Oct - 28 Oct
Great Barrington Get Away
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 AED 1,102
AED 1,534 total
includes taxes & fees
26 Oct - 27 Oct
Bungalow in the Berkshires
Game room
Pet Friendly Riverfront Home in Great Barrington
Pet Friendly Riverfront Home in Great Barrington
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 AED 702
AED 900 total
includes taxes & fees
7 Nov - 8 Nov
Pet Friendly Riverfront Home in Great Barrington
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 AED 1,322
AED 2,232 total
includes taxes & fees
4 Nov - 5 Nov
Cozy. Clean. Free bagel shop.
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 AED 3,306
AED 5,460 total
includes taxes & fees
27 Oct - 28 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 AED 1,570
AED 2,944 total
includes taxes & fees
31 Oct - 1 Nov
Spacious 5-bedroom house in charming Lee with WiFi
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 AED 2,311
AED 5,174 total
includes taxes & fees
25 Oct - 26 Oct
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Microwave, oven, stovetop, dishwasher
Cozy. Clean. Free bagel shop. 3 Fireplaces.
Cozy. Clean. Free bagel shop. 3 Fireplaces.
The price is AED 1,249
AED 2,158 total
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Monterey Hotel Reviews

Berkshire Mountain Lodge

Berkshire Mountain Lodge

10/10 Excellent
"We loved this place. Quiet, very clean,attractive. Loved that it had a kitchen area. Second story, sliding glass doors overlooked the fall foliage in the back of the building. Very peaceful.."
Steven 4-night trip
Posted 2 days ago
Berkshire Mountain Lodge