Photo by Fun Travelog

Search Vacation Homes in Monterey

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

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

Next weekend
Dec 19 - Dec 21
In two weeks
Dec 26 - Dec 28
In one month
Jan 9 - Jan 11
In two months
Feb 6 - Feb 8

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.
$304 nightly
The price is $321
Dec 10 - Dec 11
Total with taxes and fees
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.
$338 nightly
The price is $377
Dec 10 - Dec 11
Total with taxes and fees
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.
$201 nightly
The price is $225
Dec 10 - Dec 11
Total with taxes and fees
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.
$344 nightly
The price is $364
Dec 10 - Dec 11
Total with taxes and fees
Big farmhouse in the foothills of the Berkshires
Exterior
Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking

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.
$351 nightly
The price is $392
Dec 15 - Dec 16
Total with taxes and fees
Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking
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.
$332 nightly
The price is $372
Dec 11 - Dec 12
Total with taxes and fees
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.
$406 nightly
The price is $454
Dec 10 - Dec 11
Total with taxes and fees
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.
$441 nightly
The price is $493
Dec 11 - Dec 12
Total with taxes and fees
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.
$217 nightly
The price is $242
Dec 11 - Dec 12
Total with taxes and fees
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.
$464 nightly
The price is $518
Dec 10 - Dec 11
Total with taxes and fees
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.
$482 nightly
The price is $540
Dec 10 - Dec 11
Total with taxes and fees
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
$1,189 nightly
The price is $1,328
Dec 10 - Dec 11
Total with taxes and fees
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)
$253 nightly
The price is $283
Dec 15 - Dec 16
Total with taxes and fees
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.
$764 nightly
The price is $853
Dec 10 - Dec 11
Total with taxes and fees
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
$1,314 nightly
The price is $1,487
Dec 12 - Dec 13
Total with taxes and fees
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.
$666 nightly
The price is $743
Dec 16 - Dec 17
Total with taxes and fees
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

$526 nightly
The price is $588
Dec 10 - Dec 11
Total with taxes and fees
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.
$989 nightly
The price is $1,105
Dec 20 - Dec 21
Total with taxes and fees
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.
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

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 1 day ago
Holiday Inn Express Hotel & Suites Great Barrington by IHG

Find out more about Monterey

Monterey Vacation Homes information

Number of reviews
333
Accommodation
387 Vacation Homes
Lowest Price
$225
Highest Price
$1,487

Explore a world of travel with Expedia