Holiday Homes in Monterey

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Our top choices for Monterey holiday homes

Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Sherwood Forest
10.0 out of 10, Exceptional, (5 reviews)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is €325
includes taxes & fees
11 Jun - 12 Jun
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

Real Estate: Therapy - Lake, Laundry, Love it

Real Estate: Therapy - Lake, Laundry, Love it
Sherwood Forest
The price is €291
includes taxes & fees
17 Jun - 18 Jun
Real Estate: Therapy - Lake, Laundry, Love it

Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Sherwood Forest
9.8 out of 10, Exceptional, (15 reviews)
"Great place and welcoming stay!"
United States
Frank M.
The price is €337
includes taxes & fees
7 Jun - 8 Jun
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

Cozy Riverside Berkshires Retreat

Cozy Riverside Berkshires Retreat
Great Barrington
9.2 out of 10, Wonderful, (15 reviews)
"Close to a great bakery and near to a farm market and shopping mall. "
United States
Cristine C.
The price is €269
includes taxes & fees
8 Jun - 9 Jun
Cozy Riverside Berkshires Retreat

stylish Berkshires Retreat

stylish Berkshires Retreat
Lee
The price is €313
includes taxes & fees
8 Jun - 9 Jun
stylish Berkshires Retreat

Big farmhouse in the foothills of the Berkshires

Big farmhouse in the foothills of the Berkshires
Russell
10.0 out of 10, Exceptional, (147 reviews)
"The house is absolutely charming and cozy. It was very clean as well. "
United States
Amanda C.
The price is €316
includes taxes & fees
7 Jun - 8 Jun
Big farmhouse in the foothills of the Berkshires

Near Tanglewood: Historic Summer Retreat

Near Tanglewood: Historic Summer Retreat
New Lebanon
9.4 out of 10, Exceptional, (26 reviews)
"Very clean, fully stocked kitchen,great location "
United States
Karen H.
The price is €324
includes taxes & fees
10 Jun - 11 Jun
Near Tanglewood: Historic Summer Retreat

Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.

Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
Chatham
9.6 out of 10, Exceptional, (5 reviews)
"Mark was very communicative and helpful, answering all questions quickly and accurately"
United States
Jim S.
The price is €293
includes taxes & fees
14 Jun - 15 Jun
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.

Treetop Hideaway in Tyringham

Treetop Hideaway in Tyringham
Monterey
9.2 out of 10, Wonderful, (11 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 €502
includes taxes & fees
8 Jun - 9 Jun
Treetop Hideaway in Tyringham

Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (32 reviews)
"Everything was as advertised!"
United States
Jessica S.
The price is €301
includes taxes & fees
14 Jun - 15 Jun
Home in Great Barrington

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 €342
includes taxes & fees
10 Jun - 11 Jun
Historic Berkshires Home Near Tanglewood, Trails & Wineries

Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove
Sheffield
10.0 out of 10, Exceptional, (43 reviews)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
The price is €434
includes taxes & fees
8 Jun - 9 Jun
Cheerful 3-bedroom cottage with woodstove

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

NEW! Spacious 4BR Ski Getaway - Minutes to Jiminy & Bousquet
New Lebanon
8.0 out of 10, Very good, (1 review)
"This location is great as an overnight trip. It’s centralized between ski resorts, restaurants near Pittsfield, MA and local NY. "
United States
Luz A.
The price is €345
includes taxes & fees
7 Jun - 8 Jun
NEW! Spacious 4BR Ski Getaway - Minutes to Jiminy & Bousquet

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 €470
includes taxes & fees
8 Jun - 9 Jun
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

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 €789
includes taxes & fees
5 Jul - 6 Jul
Spacious 5-bedroom house in charming Lee with WiFi

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 €452
includes taxes & fees
11 Jun - 12 Jun
Cozy. Clean. Free bagel shop. 3 Fireplaces.

The Owl and Firefly – A Cabin for Families

The Owl and Firefly – A Cabin for Families
Otis
10.0 out of 10, Exceptional, (1 review)
"I wish I could give The Owl and Firefly ten stars instead of 5. It's truly such a special vacation place that’s bound to bring joy to any family who comes here! Incredibly beautiful and so carefully planned and equipped, with great attention and much generosity given to every single detail, it made us feel so comfortable and truly cared for in a way I've never felt before in a vacation rental. The photos are very accurate but everything is even better when you can stand in the middle of the...
United States
Karen C.
The Owl and Firefly – A Cabin for Families

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, (5 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 €1,185
includes taxes & fees
20 Jun - 21 Jun
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

Perfect Nature Haven In Great Barrington

Perfect Nature Haven In Great Barrington
Great Barrington
9.6 out of 10, Exceptional, (8 reviews)
"Their place was one of the cleanest rental cabins we have ever been, the house is in a great location with beautiful surroundings, the check in and check out was extremely easy for a family with little kids, loved the place and we hope to be back!"
United States
Ethel B.
Perfect Nature Haven In Great Barrington
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
11,291
Accommodation
399 Holiday Homes
Lowest Price
€63
Highest Price
€187