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Our top choices for Monterey vacation 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 ¥22,844
¥58,945 total
includes taxes & fees
May 12 - May 13
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

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, (14 reviews)
"Very nice cabin, responsive host."
United States
Nick R.
The price is ¥27,889
¥65,105 total
includes taxes & fees
Jun 1 - Jun 2
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, (14 reviews)
"Great location and nice size house for a family of 5. We had a couple hiccups but the host responded quickly and handled things promptly. "
United States
Jennifer L.
The price is ¥31,728
¥49,616 total
includes taxes & fees
May 12 - May 13
Cozy Riverside 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, (146 reviews)
"The house is absolutely charming and cozy. It was very clean as well. "
United States
Amanda C.
The price is ¥31,336
¥56,970 total
includes taxes & fees
May 12 - May 13
Big farmhouse in the foothills of the Berkshires

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 ¥37,133
¥78,755 total
includes taxes & fees
May 12 - May 13
Cheerful 3-bedroom cottage with woodstove

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 ¥42,163
¥77,198 total
includes taxes & fees
May 12 - May 13
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

Real Estate: Therapy - Lake, Laundry, Love it

Real Estate: Therapy - Lake, Laundry, Love it
Sherwood Forest
The price is ¥9,025
¥46,660 total
includes taxes & fees
May 27 - May 28
Real Estate: Therapy - Lake, Laundry, Love it

Modern Victorian Walk to Main Street

Modern Victorian Walk to Main Street
Great Barrington
10.0 out of 10, Exceptional, (27 reviews)
"The house and location both perfect for a girls weekend away! "
United States
karen b.
The price is ¥46,221
¥119,010 total
includes taxes & fees
May 12 - May 13
Modern Victorian Walk to Main Street

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, (37 reviews)
"Charming house in a wonderful setting in the Berkshires. "
United States
Mark Cristen J.
The price is ¥56,248
¥113,757 total
includes taxes & fees
May 12 - May 13
Walk into town, soak up sun on enclosed porch & steps away from nature trails!

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 ¥88,697
¥208,108 total
includes taxes & fees
May 12 - May 13
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

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 ¥42,930
¥88,933 total
includes taxes & fees
May 12 - May 13
Treetop Hideaway in Tyringham

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, (4 reviews)
"Mark was very accommodating and always available immediately if I had a question. The place was very clean and comfortable. Perfect location. We would love to come back in the summer when we can use the fire pit and the creek in the back. "
United States
Jessica V.
The price is ¥28,986
¥50,539 total
includes taxes & fees
May 18 - May 19
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.

Private 4BR Mtn Retreat Fiber WiFi, Spacious & Trails Dogs OK

Private 4BR Mtn Retreat Fiber WiFi, Spacious & Trails Dogs OK
Hillsdale
10.0 out of 10, Exceptional, (128 reviews)
"This home has beautiful views. It is quiet and clean with all of the amenities we needed. We had a lovely stay."
United States
Anne S.
The price is ¥41,599
¥72,387 total
includes taxes & fees
May 17 - May 18
Private 4BR Mtn Retreat Fiber WiFi, Spacious & Trails Dogs OK

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 ¥47,004
¥83,305 total
includes taxes & fees
May 12 - May 13
Cozy. Clean. Free bagel shop. 3 Fireplaces.

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 ¥74,031
¥133,096 total
includes taxes & fees
May 17 - May 18
Spacious 5-bedroom house in charming Lee with WiFi
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 Vacation Homes information

Number of reviews
436
Accommodation
399 Vacation Homes
Lowest Price
¥46,660
Highest Price
¥208,108