Holiday Homes in Monterey

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Our top choices for Monterey holiday homes

Berkshires Cottage! Dog friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

Berkshires Cottage! Dog friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Sherwood Forest
9.8 out of 10, Exceptional, (14 reviews)
"Nicole was very attentive and very quick to respond to any question we had. Her cottage was perfect for a quiet getaway, just what everybody needs!"
United States
Matthew F.
The price is AU$540
includes taxes & fees
15 Mar - 16 Mar
Berkshires Cottage! Dog friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

Big farmhouse in the foothills of the Berkshires

Big farmhouse in the foothills of the Berkshires
Russell
10.0 out of 10, Exceptional, (143 reviews)
"Perfect spot for a family celebration!"
United States
Kerry P.
The price is AU$474
includes taxes & fees
26 Mar - 27 Mar
Big farmhouse in the foothills of the Berkshires

Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (28 reviews)
"The house was pristine, bright, with everything we needed. We hope to come back again to enjoy the area. "
United States
maureen k.
The price is AU$387
includes taxes & fees
15 Mar - 16 Mar
Home in Great Barrington

Cozy Riverside Berkshires Retreat

Cozy Riverside Berkshires Retreat
Great Barrington
9.0 out of 10, Wonderful, (12 reviews)
"Close to a great bakery and near to a farm market and shopping mall. "
United States
Cristine C.
The price is AU$414
includes taxes & fees
22 Mar - 23 Mar
Cozy Riverside Berkshires Retreat

Near Tanglewood: Historic Summer Retreat

Near Tanglewood: Historic Summer Retreat
New Lebanon
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 AU$542
includes taxes & fees
19 Mar - 20 Mar
Near Tanglewood: Historic Summer Retreat

3-bedroom house in beautiful Berkshires, close to amenities!

3-bedroom house in beautiful Berkshires, close to amenities!
Pittsfield
The price is AU$479
includes taxes & fees
23 Mar - 24 Mar
3-bedroom house in beautiful Berkshires, close to amenities!

Walk into town, soak up sun on enclosed porch & steps away from nature trails!

Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Stockbridge
10.0 out of 10, Exceptional, (34 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 AU$770
includes taxes & fees
15 Mar - 16 Mar
Walk into town, soak up sun on enclosed porch & steps away from nature trails!

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!
Pittsfield
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 AU$688
includes taxes & fees
15 Mar - 16 Mar
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

Historic Berkshires Home Near Tanglewood, Trails & Wineries

Historic Berkshires Home Near Tanglewood, Trails & Wineries
Lebanon Springs
9.0 out of 10, Wonderful, (21 reviews)
"Comfy beds, clean, great big deck with a view. "
United States
Corinne T.
The price is AU$524
includes taxes & fees
22 Mar - 23 Mar
Historic Berkshires Home Near Tanglewood, Trails & Wineries

Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Great Barrington
10.0 out of 10, Exceptional, (4 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 AU$1,825
includes taxes & fees
15 Mar - 16 Mar
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

Luxury Barn Retreat — All-Season Escape Awaits!

Luxury Barn Retreat — All-Season Escape Awaits!
East Chatham
10.0 out of 10, Exceptional, (2 reviews)
"Accommodations were even better than we expected. The rooms were very clean, and there are unique (and sometimes whimsical, other times thought-provoking) decorations/pictures throughout the barn. The kitchen was basically a chef’s kitchen- all appliances were top notch. The backyard was spacious, and even contained a (non-working) pay phone booth! My wife loved the swinging two-seat chair on the porch! "
United States
Timothy S.
The price is AU$875
includes taxes & fees
16 Mar - 17 Mar
Luxury Barn Retreat — All-Season Escape Awaits!

Sun Filled Lenox Retreat - Minutes to Tanglewood!

Sun Filled Lenox Retreat - Minutes to Tanglewood!
Lee
9.6 out of 10, Exceptional, (4 reviews)
"Very charming, comfortable, and clean. It was in a great location and only minutes away from a lot of sightseeing locations. House management was very accommodating and friendly. I would stay here again."
United States
Paulo I.
The price is AU$625
includes taxes & fees
19 Mar - 20 Mar
Sun Filled Lenox Retreat - Minutes to Tanglewood!

Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove
Sheffield
10.0 out of 10, Exceptional, (42 reviews)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
The price is AU$702
includes taxes & fees
29 Mar - 30 Mar
Cheerful 3-bedroom cottage with woodstove

Treetop Hideaway in Tyringham

Treetop Hideaway in Tyringham
Monterey
9.0 out of 10, Wonderful, (10 reviews)
"This was the perfect location for our mom and daughters weekend! Spacious comfortable. Our only regret was that we didn’t stay longer!"
United States
Sarah B.
The price is AU$777
includes taxes & fees
17 Mar - 18 Mar
Treetop Hideaway in Tyringham

Spacious 5-bedroom house in charming Lee with WiFi

Spacious 5-bedroom house in charming Lee with WiFi
Lee
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 AU$1,009
includes taxes & fees
22 Mar - 23 Mar
Spacious 5-bedroom house in charming Lee with WiFi

Secluded Sophistication in the Berkshires - 49 Acres of Quiet Luxury in Becket.

Secluded Sophistication in the Berkshires - 49 Acres of Quiet Luxury in Becket.
Becket
10.0 out of 10, Exceptional, (1 review)
"Beautiful home, attentive host. Location is as peaceful as can be. "
United States
Rick M.
The price is AU$888
includes taxes & fees
17 Mar - 18 Mar
Secluded Sophistication in the Berkshires - 49 Acres of Quiet Luxury in Becket.

NEW! Spacious 4BR Ski Getaway - Minutes to Jiminy & Bousquet

NEW! Spacious 4BR Ski Getaway - Minutes to Jiminy & Bousquet
New Lebanon
The price is AU$463
includes taxes & fees
17 Mar - 18 Mar
NEW! Spacious 4BR Ski Getaway - Minutes to Jiminy & Bousquet

Renovated house. Built in 1890s. No neighbors in sight.

Renovated house. Built in 1890s. No neighbors in sight.
Chatham
8.0 out of 10, Very good, (1 review)
"Mark was very communicative and helpful, answering all questions quickly and accurately"
United States
Jim S.
The price is AU$431
includes taxes & fees
29 Mar - 30 Mar
Renovated house. Built in 1890s. No neighbors in sight.

Cozy. Clean. Free bagel shop. 3 Fireplaces.

Cozy. Clean. Free bagel shop. 3 Fireplaces.
Great Barrington
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 AU$916
includes taxes & fees
6 Apr - 7 Apr
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

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Monterey Holiday Homes information

Number of reviews
345
Accommodation
387 Holiday Homes
Lowest Price
AU$387
Highest Price
AU$1,825