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Holiday Homes in Monterey

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Featured Holiday Homes in Monterey and around

Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access!

10.0 out of 10, Exceptional, (3)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
The price is €351
includes taxes & fees
28 Oct - 29 Oct
Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access!

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (260)
"We enjoyed our stay. Excellent location to explore Western Mass!"
The price is €201
includes taxes & fees
3 Nov - 4 Nov
Berkshire Village Carriage House - Super Private!!

Charming 3-bedroom Modern cottage with lakeside views

2.0 star property
Charming 3-bedroom Modern cottage with lakeside views

Big farmhouse in the foothills of the Berkshires

10.0 out of 10, Exceptional, (140)
"Lovely old farmhouse with authentic yet comfortable furnishings. Would recommend!"
The price is €314
includes taxes & fees
9 Oct - 10 Oct
Big farmhouse in the foothills of the Berkshires

Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking

9.6 out of 10, Exceptional, (8)
"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."
Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking

Sun Filled Lenox Retreat - Minutes to Tanglewood!

9.4 out of 10, Exceptional, (3)
"The house is in a great location and is very user friendly and well equipped. The only suggestion I would make is to put an air conditioner in the third bedroom. Overall, a lovely stay."
The price is €439
includes taxes & fees
9 Oct - 10 Oct
Sun Filled Lenox Retreat - Minutes to Tanglewood!

Bungalow in the Berkshires

10.0 out of 10, Exceptional, (3)
"Great location, very clean and well appointed with everyth"
The price is €423
includes taxes & fees
8 Nov - 9 Nov
Bungalow in the Berkshires

Home in Great Barrington

9.8 out of 10, Exceptional, (23)
"Enjoyed our stay!!!"
The price is €250
includes taxes & fees
22 Oct - 23 Oct
Home in Great Barrington

3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

2.0 star property
8.0 out of 10, Very good, (5)
"Very clean and spacious! We enjoyed our stay with our small pup!"
The price is €466
includes taxes & fees
8 Nov - 9 Nov
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

Cheerful 3-bedroom cottage with woodstove

10.0 out of 10, Exceptional, (39)
"The property was centrally located for skiing, and was a comfortable stay."
The price is €433
includes taxes & fees
13 Oct - 14 Oct
Cheerful 3-bedroom cottage with woodstove

NEW RENO Historic Creamery in Berkshires w/hot tub

10.0 out of 10, Exceptional, (4)
"Beautifully decorated farmhouse in a great location to enjoy the Berkshires. "
The price is €412
includes taxes & fees
9 Oct - 10 Oct
NEW RENO Historic Creamery in Berkshires w/hot tub

Cozy Riverfront Escape in Great Barrington - "Whiskers on the Water"

10.0 out of 10, Exceptional, (1)
"The host was exceptional and so kind. The location was in close proximity to 3 quaint New England small towns whose downtowns had many restaurants and local shops to enjoy-Great Barrington (GB Eats for breakfast), Stockbridge (best shopping) and Lenox (exceptional dinner at Frankie’s Italian). The house looked updated on the outside but inside looked like early 1900s with a hint of Victorian influence. My only caution is for anyone with mobility issues as all 3 bedrooms and the only (very small)...
The price is €279
includes taxes & fees
2 Nov - 3 Nov
Cozy Riverfront Escape in Great Barrington - "Whiskers on the Water"

Near Tanglewood: Historic Summer Retreat

9.6 out of 10, Exceptional, (22)
"Very cozy and comfortable with everything we needed to make our stay enjoyable. The kitchen was well stocked, the bedrooms a good size with comfortable mattresses. The deck and the yard were lovely. This location is gem!"
The price is €359
includes taxes & fees
9 Oct - 10 Oct
Near Tanglewood: Historic Summer Retreat

Cozy. Clean. Free bagel shop.

10.0 out of 10, Exceptional, (10)
"The perfect location for a stay in Great Barrington. The house is so well done and very comfortable!"
Cozy. Clean. Free bagel shop.

Great Barrington Get Away

9.4 out of 10, Exceptional, (23)
"The host was very communicative and responsive during our arrival and check out. The listing and everything was as it said we were very pleased with both the location of the home and the actual home itself and the property walking distance to town truly cannot say enough. Thank you for Your hospitality. Our family is very grateful. "
The price is €473
includes taxes & fees
22 Oct - 23 Oct
Great Barrington Get Away

Experience Timeless Elegance in The Edith Wharton Room!

Experience Timeless Elegance in The Edith Wharton Room!

Spacious 5-bedroom house in charming Lee with WiFi

The price is €713
includes taxes & fees
15 Oct - 16 Oct
Spacious 5-bedroom house in charming Lee with WiFi

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

10.0 out of 10, Exceptional, (1)
"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!"
The price is €1,239
includes taxes & fees
22 Oct - 23 Oct
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

Cozy. Clean. Free bagel shop. 3 Fireplaces.

Cozy. Clean. Free bagel shop. 3 Fireplaces.

Elegant Carriage House room with a queen bed and private patio.

Elegant Carriage House room with a queen bed and private patio.
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

Find out more about Monterey

Find out more about Monterey

Monterey Holiday Homes information

Number of reviews
531
Accommodation
443 Holiday Homes
Lowest Price
€201
Highest Price
€1,239

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