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Check prices for these dates

Next weekend
2 May - 4 May
In two weeks
9 May - 11 May
In one month
23 May - 25 May
In two months
20 Jun - 22 Jun

Compare 419 Vacation Homes in Monterey with updated reviews, rates, and availability.

Berkshire Village Carriage House - Super Private!!
Fridge, microwave, oven, stovetop

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (243)
"Celebrate 34 anniversary great place. Better than a hotel. Love the place would stay again. Couldn’t figure out how to use Apple TV to watch Netflix. Just need a couple steak knives if you do take out or cook in. Had a great time. Thanks Ed"
The price is AED 551
AED 841 total
includes taxes & fees
3 May - 4 May
Berkshire Village Carriage House - Super Private!!
4Br/3bath Lakefront/Ski House in Berkshires. Fully fitted kitchen. Hi speed wifi
Exterior

4Br/3bath Lakefront/Ski House in Berkshires. Fully fitted kitchen. Hi speed wifi

10.0 out of 10, Exceptional, (150)
"Very cozy, very clean, really enjoyed our stay. Marshall was a great host"
4Br/3bath Lakefront/Ski House in Berkshires. Fully fitted kitchen. Hi speed wifi
Spectacular views and close to Great Barrington.
Smart TV, fireplace

Spectacular views and close to Great Barrington.

10.0 out of 10, Exceptional, (1)
"A beautiful place for our grown family to congregate. Easy commute to Tanglewood, a pool to keep us cool, and a wonderful kitchen to cook in. There are lots of other houses within view but not bothersome. Had a great stay here."
Spectacular views and close to Great Barrington.
Peace and quiet on the lake
Interior

Peace and quiet on the lake

9.6 out of 10, Exceptional, (214)
"I love this place! It's been beautifully remodeled and is very comfortable. I would love to visit when it's warmer, but it's very cozy in the snow. I can't wait to come back with my kids. "
Peace and quiet on the lake
Lakeside Oasis Just You, The Lake & The View!
Exterior

Lakeside Oasis Just You, The Lake & The View!

9.8 out of 10, Exceptional, (70)
"It's a really lovely home on a beautiful property, with all the amenities we could have possibly needed, and also perfectly peaceful. The host was so welcoming and responsive, which made it that much nicer, too. My only regret is that we couldn't stay longer, and I would definitely want to stay there again. "
Lakeside Oasis Just You, The Lake & The View!
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!
Exterior

COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!

9.6 out of 10, Exceptional, (25)
"Our family of 4 stayed here while skiing at Catamount - great proximity, exactly as pictured, clean, and perfect size. Host was responsive - would stay here again!"
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!
Heart of Lenox Walk to Town Cozy Cottage!
Fridge, microwave, oven, stovetop

Heart of Lenox Walk to Town Cozy Cottage!

10.0 out of 10, Exceptional, (70)
"Was as nice as the pictures. A plus for a very comfortable king sized bed! Right in town for walking to shops and restaurants. Thank you!"
Heart of Lenox Walk to Town Cozy Cottage!
The Race Mountain House
Pool

The Race Mountain House

2.0 star property
10.0 out of 10, Exceptional, (1)
"We loved everything about the house - it was in a great location and perfect for a weekend away with friends!"
The Race Mountain House
Cheerful 3-bedroom cottage with woodstove
Property grounds

Cheerful 3-bedroom cottage with woodstove

10.0 out of 10, Exceptional, (36)
"Cute house that was perfectly arranged for our family. Kitchen is well stocked with spices galore! We cooked at home every night. Went hiking in both NY, CT and MA - super easy to get to all locations, beautiful views of mountains all around. Will definitely come back to this house again with our family! "
The price is AED 687
AED 1,621 total
includes taxes & fees
13 May - 14 May
Cheerful 3-bedroom cottage with woodstove
Perfect Nature Haven In Great Barrington
Exterior

Perfect Nature Haven In Great Barrington

2.0 star property
10.0 out of 10, Exceptional, (2)
"We had a great time at the house. We had everything we needed. It was close to town. The space is very comfortable."
Perfect Nature Haven In Great Barrington
Berkshires sanctuary with outdoor living area & firepit. 8minutes to Tanglewood!
Property grounds

Berkshires sanctuary with outdoor living area & firepit. 8minutes to Tanglewood!

10.0 out of 10, Exceptional, (4)
"Elise was an excellent host and super easy to work with. The property was even bigger, nicer, and cleaner than we expected. Plenty of room for a family getaway. "
Berkshires sanctuary with outdoor living area & firepit. 8minutes to Tanglewood!
Hilltown Nest is a wonderful place for family and friends to gather.
Property grounds

Hilltown Nest is a wonderful place for family and friends to gather.

9.8 out of 10, Exceptional, (15)
"Sadly we were only here for a couple of nights, but this place was very nice. I manage vacation rentals myself and i was very impressed by the cleanliness of this place, especially considering the size of it. The house is great for a family with lots of room to spread out. Our grandkids enjoyed tinkling on the piano and playing in the backyard. Would definitely choose to stay here again!"
Hilltown Nest is a wonderful place for family and friends to gather.
Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!
Terrace/patio

Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!

9.4 out of 10, Exceptional, (9)
"We had a great stay, thank you! Everything was great as all accommodations were met and other than getting food from the local nearby grocery store and our own personal things, nothing more was needed. Everything went so smoothly, other than our two dogs being home sick and whining at times, which ended up entailing a 7 hour round trip back home to leave them there with a sitter as we felt it was too much for our little fur babies to endure being in a strange place without us and better to...
Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!
Exclusive Estate, Heated Yearround Outdoor Pool
Fridge, microwave, oven, stovetop

Exclusive Estate, Heated Yearround Outdoor Pool

9.6 out of 10, Exceptional, (19)
"Lovely horse farm in the woods but not too far from useful shops. We had a great experience."
Exclusive Estate, Heated Yearround Outdoor Pool
Quintessential 6-BR Berkshires Lodge
Exterior

Quintessential 6-BR Berkshires Lodge

10.0 out of 10, Exceptional, (11)
"The house was perfect for us. Spacious, clean, comfortable. Beds comfortable. Bathrooms really nice. The road in the development is dirt, a 4wd is needed as stated. It was muddy and rutty on arrival, then snow and ice , but do-able. Great house. Would recommend "
Quintessential 6-BR Berkshires Lodge
Near Tanglewood: Historic Summer Retreat
Fridge, microwave, oven, stovetop

Near Tanglewood: Historic Summer Retreat

9.4 out of 10, Exceptional, (20)
"Nice home, spacious, clean, close to Jiminy Peak mountain (15mins)"
Near Tanglewood: Historic Summer Retreat
Indoor Pool & Lofted Game Area | Sunroom w/ Sweeping Mountain Views | Wellspring
Exterior

Indoor Pool & Lofted Game Area | Sunroom w/ Sweeping Mountain Views | Wellspring

10.0 out of 10, Exceptional, (10)
"We all enjoyed our stay. The house and indoor pool were wonderful. There are plenty of comfortable places to sit and enjoy the gorgeous views. We loved the location which is both close to Lenox restaurants, as well as, the southern Berkshires for food markets and activities for kids. The property manager was attentive, and the owner was very responsive. We loved our week at this family friendly property and highly recommend it. "
Indoor Pool & Lofted Game Area | Sunroom w/ Sweeping Mountain Views | Wellspring
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
Dining

Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

10.0 out of 10, Exceptional, (121)
"Would definetely stay again.IF....LOL minor but not so minor.Need t.v. in master bedroom.Would not be a huge iinvestment.Cc"
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
The Great Escape Ski Cottage w/HOT TUB @ Great Barrington
Interior

The Great Escape Ski Cottage w/HOT TUB @ Great Barrington

10.0 out of 10, Exceptional, (46)
"What a wonderful property for our girls trip! The house is clean, there’s so much hangout space, and it’s so well supplied. "
The Great Escape Ski Cottage w/HOT TUB @ Great Barrington
Beautiful Lenox Home, 3 Mi to Shakespeare & Co!
Interior

Beautiful Lenox Home, 3 Mi to Shakespeare & Co!

9.6 out of 10, Exceptional, (42)
"Ben and I enjoyed a good long weekend at the correctly described Beautiful Lenox Home. Mary, your host, has thought of everything to help you feel comfortable and very quickly to adjust to your home away from home. It is very well located so that you can easily visit the many places of interest nearby. The rules for checking in and out were clear and simple. We are delighted give this a 5-star rating. David and Ben will return, for sure!"
Beautiful Lenox Home, 3 Mi to Shakespeare & Co!
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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Other property types in Monterey

The Ponds at Foxhollow
Property grounds

The Ponds at Foxhollow

3.0 star property
8.6 out of 10, Excellent, (120)
"Very comfortable property in a lovely setting "
The price is AED 824
AED 920 total
includes taxes & fees
9 May - 10 May
The Ponds at Foxhollow
Deluxe Queen Room with 2 Queen Beds
1 bedroom, WiFi, bed sheets

Deluxe Queen Room with 2 Queen Beds

2.0 star property
The price is AED 400
AED 529 total
includes taxes & fees
30 Apr - 1 May
Deluxe Queen Room with 2 Queen Beds
Elegant 19th Century New England Newly Renovated 1BR Vacation Rental
Terrace/patio

Elegant 19th Century New England Newly Renovated 1BR Vacation Rental

9.4 out of 10, Exceptional, (61)
"3 day holiday getaway, my husband and our 2 pups. A hike in nearby trails in the woods, enjoyed Lee downtown eateries and shops. Beautiful winter wonderland in the Berkshires. The guest rental was perfect!!! Warm, spacious, comfortable, perfect location. "
Elegant 19th Century New England Newly Renovated 1BR Vacation Rental
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.