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Search Vacation Homes in Monterey

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Check prices for these dates

In two weeks
26 Dec - 28 Dec
In two months
6 Feb - 8 Feb
In three months
6 Mar - 8 Mar
In four months
3 Apr - 5 Apr

Our top choices for Monterey vacation homes

Private kitchen
Home in the Woods

Vacation Home in Russell

10.0 out of 10, Exceptional, (3)
"We really enjoyed our stay at the Home in the Woods. We stayed for 1 night on the way to Amherst for a graduation. The home is very cozy and clean. Jessica was easy to communicate with and the check-in/check out process was simple. Highly recommend!"
United States
Travis H.
The price is AED 621
AED 1,176 total
includes taxes & fees
12 Dec - 13 Dec
Home in the Woods
Outdoor dining
Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!

Vacation Home in Sherwood Forest

10.0 out of 10, Exceptional, (5)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is AED 535
AED 1,386 total
includes taxes & fees
16 Dec - 17 Dec
Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!
Fridge, microwave, oven, stovetop
Home in Great Barrington

Vacation Home in Great Barrington

9.8 out of 10, Exceptional, (26)
"Enjoyed our stay!!!"
United States
Fred W.
The price is AED 479
AED 847 total
includes taxes & fees
15 Dec - 16 Dec
Home in Great Barrington
Property grounds
Big farmhouse in the foothills of the Berkshires

Vacation Home in Russell

10.0 out of 10, Exceptional, (143)
"Perfect spot for a family celebration!"
United States
Kerry P.
The price is AED 735
AED 1,335 total
includes taxes & fees
11 Dec - 12 Dec
Big farmhouse in the foothills of the Berkshires
Exterior
Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine

Vacation Home in Sherwood Forest

9.6 out of 10, Exceptional, (10)
"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
15 Dec - 16 Dec
Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine
Terrace/patio
Historic Berkshires Home Near Tanglewood, Trails & Wineries

Vacation Home in Lebanon Springs

8.8 out of 10, Excellent, (20)
"It was great - just what we were looking for. "
United States
Kaye S.
The price is AED 496
AED 1,366 total
includes taxes & fees
11 Dec - 12 Dec
Historic Berkshires Home Near Tanglewood, Trails & Wineries
Property grounds
Cheerful 3-bedroom cottage with woodstove

Vacation Home in Sheffield

10.0 out of 10, Exceptional, (41)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
The price is AED 724
AED 1,657 total
includes taxes & fees
14 Dec - 15 Dec
Cheerful 3-bedroom cottage with woodstove
Fridge, microwave, oven, stovetop
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

Vacation Home in Pittsfield

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 1,810 total
includes taxes & fees
11 Dec - 12 Dec
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Outdoor dining
Sweet Cozy Victorian in Housatonic. Close to everything.

Vacation Home in Housatonic

10.0 out of 10, Exceptional, (3)
"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 AED 496
AED 886 total
includes taxes & fees
18 Dec - 19 Dec
Sweet Cozy Victorian in Housatonic. Close to everything.
Fridge, microwave, oven, stovetop
Great Barrington Get Away

Vacation Home in Great Barrington

9.4 out of 10, Exceptional, (25)
"We stayed here for Memorial Day weekend and had a wonderful trip. Close to the downtown shops, and all the supplies a family needs staying in a home. Thanks for the great stay!"
United States
Elizabeth G.
The price is AED 1,047
AED 1,904 total
includes taxes & fees
17 Dec - 18 Dec
Great Barrington Get Away
Exterior
Perfect House In Hillsdale, Brings Friends & Fam

Vacation Home in Hillsdale

8.4 out of 10, Very Good, (5)
"As a group of 10 friends, this house was everything we could have wanted. 5 bedrooms, a very large living room, and a dining table to fit all of us at once. Very close to Catamount, Hy’s Fried, Roe Jan brewery and more. Very clean for such an old house. "
United States
Stefanie K.
The price is AED 683
AED 1,971 total
includes taxes & fees
11 Dec - 12 Dec
Perfect House In Hillsdale, Brings Friends & Fam
Exterior
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

Vacation Home in Great Barrington

10.0 out of 10, Exceptional, (2)
"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 2,079
AED 4,878 total
includes taxes & fees
18 Dec - 19 Dec
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Game room
Pet Friendly Riverfront Home in Great Barrington

Vacation Home in Great Barrington

9.4 out of 10, Exceptional, (6)
The price is AED 744
AED 1,093 total
includes taxes & fees
15 Dec - 16 Dec
Pet Friendly Riverfront Home in Great Barrington
Property grounds
Walk into town, soak up sun on enclosed porch & steps away from nature trails!

Vacation Home in Stockbridge

10.0 out of 10, Exceptional, (29)
"Great stay in a well appointed house close to trails, Stockbridge center, and a quick car trip to Lenox, Great Barrington, Tanglewood, Jacobs Pillow, and Shakespeare & Co. we enjoyed the morning walks, coffee at the Lost Lamb, drinks at the Red Lion Inn, dance at Jacob’s Pillow, music at Tanglewood, ice cream at High Lawn Farm, and just that Berkshire vibe! "
United States
Phillip F.
The price is AED 1,686
AED 3,134 total
includes taxes & fees
11 Dec - 12 Dec
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Property grounds
Charming 3-bedroom Modern cottage with lakeside views

Vacation Home in Hartland

2.0 star property
The price is AED 3,305
AED 5,459 total
includes taxes & fees
22 Dec - 23 Dec
Charming 3-bedroom Modern cottage with lakeside views
Terrace/patio
Spacious 5-bedroom house in charming Lee with WiFi

Vacation Home in Lee

8.0 out of 10, Very Good, (1)
"House was large, clean, and comfortable. "
United States
John Z.
The price is AED 1,561
AED 2,900 total
includes taxes & fees
17 Dec - 18 Dec
Spacious 5-bedroom house in charming Lee with WiFi
Microwave, oven, stovetop, dishwasher
Cozy. Clean. Free bagel shop. 3 Fireplaces.

Vacation Home in Great Barrington

The price is AED 1,249
AED 2,158 total
includes taxes & fees
11 Dec - 12 Dec
Cozy. Clean. Free bagel shop. 3 Fireplaces.
Fridge, microwave, oven, stovetop
Berkshire House Stay

Vacation Home in Lee

10.0 out of 10, Exceptional, (21)
"Wonderful stay, beautiful, well equipped and clean property. Highly recommend for an adult famiky getaway "
United States
jennifer r.
The price is AED 2,262
AED 4,057 total
includes taxes & fees
20 Dec - 21 Dec
Berkshire House Stay
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

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG

10/10 Excellent
"Great hospitality "
regina maria 1-night trip
Posted 2 days ago
Holiday Inn Express Hotel & Suites Great Barrington by IHG