A lake surrounded by autumn-colored trees reflecting on the water.

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Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Monterey vacation homes

A spacious living area with a large sofa, a kitchen island with bar stools, a wooden staircase, and a television displaying a movie.

1. Real Estate: Therapy - Lake, Laundry, Love it

Real Estate: Therapy - Lake, Laundry, Love it
Sherwood Forest
8.0 out of 10, Very good, (1 review)
"Very good trip overall. Great location. Just a few things needed to make it over the top!"
United States
William C B.
The price is ￥7,914
￥45,435 total
includes taxes & fees
Sep 27 - Sep 28
Real Estate: Therapy - Lake, Laundry, Love it
A spacious cabin with large windows, a gray sofa, and a wooden ceiling.

2. Treetop Hideaway in Tyringham

Treetop Hideaway in Tyringham
Monterey
9.2 out of 10, Wonderful, (11 reviews)
"We had coordinated an early check-in, but when we arrived, the house hadn’t been cleaned yet which was a miscommunication. I reached out to Catherine and she promptly responded and got the cleaners RIGHT over. The house was spotless and in wonderful condition for the rest of our stay, and it was dealt with very quickly and wonderfully. Would definitely stay again. The house was great for our girls trip. Also the beds are very comfortable!! "
United States
Samantha G.
The price is ￥45,423
￥92,345 total
includes taxes & fees
Sep 28 - Sep 29
Treetop Hideaway in Tyringham
A hot tub with a string of lights above it, set against a dark night sky.

3. 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, (16 reviews)
"Great place and welcoming stay!"
United States
Frank M.
The price is ￥25,355
￥62,264 total
includes taxes & fees
Sep 29 - Sep 30
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
A cozy attic bedroom with a sloped ceiling, wooden beams, a large window with a view of trees, a bed, a desk, and a kitchenette.

4. 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, (9 reviews)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is ￥23,076
￥59,188 total
includes taxes & fees
Sep 28 - Sep 29
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
A modern kitchen with a central island, wooden beams, and a view to the outdoors.

5. Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (39 reviews)
"Perfect location to walk into town - clean, light, airy and neat space. Enjoyable visit!"
United States
HEATHER G.
The price is ￥33,553
￥53,036 total
includes taxes & fees
Oct 25 - Oct 26
Home in Great Barrington
A staircase leading to a second floor, a living room with a sofa, and a kitchen area.

6. Riverside Retreat in the Berkshires

Riverside Retreat in the Berkshires
Great Barrington
9.6 out of 10, Exceptional, (27 reviews)
"If you like cuddly cats, book it! A quick night stay while in town for a wedding and Studly was a perfect host… and Marissa :)Easy location, was nice to watch the fish jump and bald eagle hunt for his breakfast as we enjoyed our coffee on the step."
United States
Kelly B.
The price is ￥31,884
￥49,860 total
includes taxes & fees
Sep 29 - Sep 30
Riverside Retreat in the Berkshires
An outdoor seating area with wicker furniture and a glass table, surrounded by lush greenery.

7. Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove
Sheffield
10.0 out of 10, Exceptional, (45 reviews)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
The price is ￥29,486
￥69,531 total
includes taxes & fees
Oct 12 - Oct 13
Cheerful 3-bedroom cottage with woodstove
A kitchen with white shelves containing various kitchenware, a kettle, and a window with a view of trees and a building outside.

8. Sweet Cozy Victorian in Housatonic. Close to everything.

Sweet Cozy Victorian in Housatonic. Close to everything.
Housatonic
9.8 out of 10, Exceptional, (12 reviews)
"The host did a great job of prepping the place and being welcoming to us. It was clean and thoughtfully designed. So happy we found this spot!"
United States
Peter S.
The price is ￥31,654
￥55,159 total
includes taxes & fees
Oct 11 - Oct 12
Sweet Cozy Victorian in Housatonic. Close to everything.
A bedroom with a brick fireplace, wooden beams, a bed with white bedding, and a wall-mounted picture.

9. Cozy. Clean. Free bagel shop. 3 Fireplaces.

Cozy. Clean. Free bagel shop. 3 Fireplaces.
Great Barrington
10.0 out of 10, Exceptional, (3 reviews)
"Great spot. As advertised and perfect."
United States
Mark M.
The price is ￥67,898
￥117,033 total
includes taxes & fees
Sep 29 - Sep 30
Cozy. Clean. Free bagel shop. 3 Fireplaces.
A house with a porch, a garden with pink flowers, and a stone wall along the road.

10. Big farmhouse in the foothills of the Berkshires

Big farmhouse in the foothills of the Berkshires
Russell
10.0 out of 10, Exceptional, (152 reviews)
"Great location"
United States
Will G.
The price is ￥29,916
￥55,754 total
includes taxes & fees
Oct 7 - Oct 8
Big farmhouse in the foothills of the Berkshires
A two-story house with a front porch, surrounded by a garden with various plants and rocks.

11. 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, (40 reviews)
"The house was lovely - my sisters and I had a wonderful time. Everything was warm and welcoming - it felt like home! We hope to make it an annual visit :)"
United States
Anonymous traveler
The price is ￥72,804
￥135,419 total
includes taxes & fees
Sep 28 - Sep 29
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
A modern kitchen with white cabinets, a stainless steel microwave, a stove, and a refrigerator.

12. NEW RENO - Chalet-style farm loft near Tanglewood

NEW RENO - Chalet-style farm loft near Tanglewood
New Lebanon
8.6 out of 10, Excellent, (7 reviews)
"Awesome location went for a solo trip w the purpose of spending time alone in nature with myself and god got exactly that calm quiet beautiful scenic area great room and service would book again"
United States
Varun M.
The price is ￥11,079
￥32,920 total
includes taxes & fees
Sep 27 - Sep 28
NEW RENO - Chalet-style farm loft near Tanglewood
A wooden cabin interior with a bench, a rug, and a hanging plant.

13. Peaceful and cozy 1 bed 1 bath in quaint Winchester

Peaceful and cozy 1 bed 1 bath in quaint Winchester
Winchester
10.0 out of 10, Exceptional, (2 reviews)
"Great place and wonderful host."
United States
Thomas C.
The price is ￥19,657
￥35,505 total
includes taxes & fees
Oct 4 - Oct 5
Peaceful and cozy 1 bed 1 bath in quaint Winchester
A spacious bedroom with a four-poster bed, a large window, and a view of the outdoors.

14. Stylish Mid-century Modern Berkshires Cape

Stylish Mid-century Modern Berkshires Cape
Lee
10.0 out of 10, Exceptional, (6 reviews)
"Besides, it being in a great location, the home is absolutely lovely!"
United States
H B.
Stylish Mid-century Modern Berkshires Cape
A spacious living room with a sectional sofa, a coffee table, and a dining area with a table and chairs. There is a large window providing a view of the outdoors.

15. 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, (7 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 ￥89,558
￥200,285 total
includes taxes & fees
Oct 4 - Oct 5
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
A bedroom with a bed, bedside lamp, and a window with curtains.

16. Ellie’s Overlook, best view in the Berkshires!

Ellie’s Overlook, best view in the Berkshires!
Richmond
The price is ￥49,855
￥109,384 total
includes taxes & fees
Oct 21 - Oct 22
Ellie’s Overlook, best view in the Berkshires!
A spacious living room with a dining area, a kitchen, and a large window.

17. 1800s Carriage house in Berkshires / Hudson Valley

1800s Carriage house in Berkshires / Hudson Valley
New Lebanon
7.0 out of 10, Good, (2 reviews)
"Lovely location with a view of the mountains from the deck.Both bedrooms- a master bedroom and a kids room are air conditioned. (The living room and kitchen are cooled with overhead fan)"
United States
Leslie H.
The price is ￥14,244
￥36,263 total
includes taxes & fees
Sep 28 - Sep 29
1800s Carriage house in Berkshires / Hudson Valley
A camping setup with a metal chair and a table by a river in a forest.

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

Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
Chatham
10.0 out of 10, Exceptional, (15 reviews)
"Super lovely house and host was helpful and communicative. Absolutely recommend if you are looking for a place in this area!"
United States
Jess S.
The price is ￥31,490
￥53,785 total
includes taxes & fees
Oct 7 - Oct 8
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
A white two-story house with a porch, surrounded by trees and a hill.

19. 1789 Shaker Farmhouse in Berkshires/Hudson Valley

1789 Shaker Farmhouse in Berkshires/Hudson Valley
Canaan
10.0 out of 10, Exceptional, (5 reviews)
"We had a wonderful stay. The house was spacious and the owner was readily available for all questions. It’s a really nice location. "
United States
Christine C.
The price is ￥31,337
￥74,323 total
includes taxes & fees
Oct 5 - Oct 6
1789 Shaker Farmhouse in Berkshires/Hudson Valley
A spacious room with a wooden ceiling, large windows, and a chandelier.

20. Luxury Barn Retreat — All-Season Escape Awaits!

Luxury Barn Retreat — All-Season Escape Awaits!
East Chatham
10.0 out of 10, Exceptional, (3 reviews)
"Peaceful weekend spot"
United States
Michael T.
The price is ￥65,342
￥113,742 total
includes taxes & fees
Sep 28 - Sep 29
Luxury Barn Retreat — All-Season Escape Awaits!
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

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

10/10 Excellent
"Great location to Tanglewood, 11 min ride. Clean room, comfy beds, great shower. Loved the pool and hot tub. Breakfast was just okay. We went down 20 minutes before breakfast was to be closed and not much there to be had. I had to ask for a bagel and no waffles."
Wendy 1-night trip
Posted 1 hour ago
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Find out more about Monterey

Monterey Vacation Homes information

Number of reviews
372
Accommodation
378 Vacation Homes
Lowest Price
￥32,920
Highest Price
￥200,285