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Compare 82 Cottages in Monterey with updated reviews, rates, and availability.

Perfect Vacation Get Away - Historical New Marlborough
Exterior
Perfect Vacation Get Away - Historical New Marlborough
9.6 out of 10, Exceptional, (49)
"This was our first stop on a long journey from VA to ME, traveling with 2 dogs. It was perfect, the dogs were safe with lots of freedom to roam. What a beautiful, peaceful village and sweet little cottage."
The price is AED 551
AED 994 total
includes taxes & fees
24 Jun - 25 Jun
Perfect Vacation Get Away - Historical New Marlborough
Private Island - Largest Fresh Water Reservoir in Mass....
Aerial view
Private Island - Largest Fresh Water Reservoir in Mass....
10.0 out of 10, Exceptional, (3)
"So grateful to Bill for such a wonderful stay! The cottage was so lovely and had everything you could need for a weekend on the lake. Will definitely be returning in the future 😊"
Private Island - Largest Fresh Water Reservoir in Mass....
Sunny Lakeside Artist's Cottage with Dock and Kayaks
Property grounds
Sunny Lakeside Artist's Cottage with Dock and Kayaks
Sunny Lakeside Artist's Cottage with Dock and Kayaks
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Cozy cottage with kettle pond lake 2 minutes away
Exterior
Cozy cottage with kettle pond lake 2 minutes away
Cozy cottage with kettle pond lake 2 minutes away
Quiet rustic cottage with shared lake access
Quiet rustic cottage with shared lake access
10.0 out of 10, Exceptional, (94)
"A very nice stay. Communication with the host was great. We kept bothering her with questions and she responded quickly. The place is really beautiful. We lit a fire each night and played some of the provided games and watched Netflix. It's an easy drive to Great Barrington to get groceries at the Berkshire coop. We also took advantage of our surroundings and hikes on the AT a little each day. Next time we'll use the host's canoe to explore Lake Buel. The only minor complaint I would have is...
Quiet rustic cottage with shared lake access
The Cottage at Highland Lake, year-round, waterfront with a boat dock
Main deck
The Cottage at Highland Lake, year-round, waterfront with a boat dock
10.0 out of 10, Exceptional, (3)
"happen to get beautiful weather while staying at the cottage at highland lake. so nice to wake up with a view, and then at sunset to enjoy the glass like water."
The Cottage at Highland Lake, year-round, waterfront with a boat dock
Fun Getaway Lakehouse in the Hudson Valley
Tiny house for glamping! Sleeps 2 and fire pit!
Fun Getaway Lakehouse in the Hudson Valley
10.0 out of 10, Exceptional, (8)
"This was an excellent stay in a perfect location to explore both the Hudson Valley and the Berkshires. Host communicated seamlessly, and house is precisely as described. Very spacious and furnished in a neutral tones, minimalist style. Would recommend."
Fun Getaway Lakehouse in the Hudson Valley
Monterey Haven < 1/2 Mi to Lake Garfield w/ Kayaks
Monterey Vacation Rental | 3BR | 1BA | 900 Sq Ft | Stairs Required
Monterey Haven < 1/2 Mi to Lake Garfield w/ Kayaks
10.0 out of 10, Exceptional, (2)
"Nestled among luxe lakefront properties, this tidy cabin was perfectly suited to relaxing in kayaks and family dinners. Near Great Barrington and lovely hikes. Exceeded all expectations for a last minute getaway."
Monterey Haven < 1/2 Mi to Lake Garfield w/ Kayaks
Cozy Berkshire cottage with fireplace.
Interior
Cozy Berkshire cottage with fireplace.
10.0 out of 10, Exceptional, (20)
"the property was very well maintain, the host put alot of very personal and special touches inside the house.i have stayed in alot of houses over the years, but this one the host made you feel right at home."
Cozy Berkshire cottage with fireplace.
Cozy Hudson Valley Lake Cottage :Kayaks Included, great swimming, near Hudson!
Relax on the large deck with lake views
Cozy Hudson Valley Lake Cottage :Kayaks Included, great swimming, near Hudson!
10.0 out of 10, Exceptional, (2)
"The house is very cozy with a well appointed kitchen and a beautiful view of the lake. We would like to go back some day. The host is very responsive and kind."
Cozy Hudson Valley Lake Cottage :Kayaks Included, great swimming, near Hudson!
Cozy Berkshires Cottage w/ 11 Private Acres!
Lee Vacation Rental | 1BR | 1BA | 1,300 Sq Ft | Steps Required
Cozy Berkshires Cottage w/ 11 Private Acres!
Cozy Berkshires Cottage w/ 11 Private Acres!
Beachwood Cottage
Property grounds
Beachwood Cottage
10.0 out of 10, Exceptional, (1)
"Second time staying at the property. Comfortable, low key cabin. Access to private beach a big plus. Near Lenox, Stockbridge and Tanglewood."
Beachwood Cottage
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
Property grounds
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
3.5 star property
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
Spacious Historic Home in the Berkshires!
Property grounds
Spacious Historic Home in the Berkshires!
3.0 star property
Spacious Historic Home in the Berkshires!
Beautiful Berkshires Cottage on Lake Buel
Great Barrington Vacation Rental | 3BR | 2.5BA | 2,000 Sq Ft | Steps Required
Beautiful Berkshires Cottage on Lake Buel
10.0 out of 10, Exceptional, (1)
"I’ve been visiting the Berkshires for decades and never stayed at a place with such an amazing view of Lake Buel! Sunrise right from my bed. The house was stocked with everything that was needed for an amazing weekend. Wonderful place to stay!"
Beautiful Berkshires Cottage on Lake Buel
Rustic Berkshires Cottage at Lake Buel w/ Kayaks!
New Marlborough Vacation Rental | 1BR | 1BA | 750 Sq Ft | Stairs Required
Rustic Berkshires Cottage at Lake Buel w/ Kayaks!
9.0 out of 10, Wonderful, (33)
"The lakefront area was scenic and peaceful. The proximity of the property to Great Barrington and Stockbridge was a surprise (we did not know the area). The owner provided materials and tips on local sights and hiking trails that we useful. The time of year we went (end of May) turned out to be somewhat buggy - causing me to use the outside fireplace to keep them at bay. Overall, a nice experience."
Rustic Berkshires Cottage at Lake Buel w/ Kayaks!
Waterfalls and Trails at 'the Mills At Green Hole'
Exterior
Waterfalls and Trails at 'the Mills At Green Hole'
3.5 star property
Waterfalls and Trails at 'the Mills At Green Hole'
Underhill Cottage
Interior
Underhill Cottage
Underhill Cottage
Picturesque Cottage with Sunroom on Ashmere Lake!
Hinsdale Vacation Rental | 3BR | 2BA | 1,340 Sq Ft | Stairs Required
Picturesque Cottage with Sunroom on Ashmere Lake!
9.6 out of 10, Exceptional, (17)
"It was perfect for me and my close friends. We enjoyed the lake each day and all remarked that the beds were very comfortable. Wish we could have stayed longer."
Picturesque Cottage with Sunroom on Ashmere Lake!
Spacious & Modern Ashley Falls Home on 1 Acre
Living area
Spacious & Modern Ashley Falls Home on 1 Acre
3.0 star property
Spacious & Modern Ashley Falls Home on 1 Acre
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See all available properties in Monterey
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.

Other property types in Monterey

Cabin w/3 Acres, Tennis+BBall Courts by 4 Ski Mtns
Sandisfield Vacation Rental | 4BR | 3BA | 1,978 Sq Ft | Stairs Required
Cabin w/3 Acres, Tennis+BBall Courts by 4 Ski Mtns
9.8 out of 10, Exceptional, (32)
"We loved our time, very cozy cabin"
Cabin w/3 Acres, Tennis+BBall Courts by 4 Ski Mtns
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
The Lake-we provide kayaks and a canoe!
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
9.6 out of 10, Exceptional, (195)
"We’ve stayed at the cabin with our dog four times and always enjoy our peaceful stay. It’s cozy, clean and private. Also, the Sherwood Shoppe - just down the road - is a wonderful place for breakfast, homemade chili and much more."
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
Pristine Home In Becket Woods
Pristine Home In Becket Woods
10.0 out of 10, Exceptional, (8)
"I really loved my stay at this beautiful property surrounded by nature and peacefulness in the Berkshire mountains. The owners were great too with communication and making things easy for check in and check out. Highly recommend this place!"
Pristine Home In Becket Woods
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.

Recent reviews of Monterey hotels
Expedia verified reviews

The Black Swan Lee - Lenox, Ascend Hotel Collection

The Black Swan Lee - Lenox, Ascend Hotel Collection

5/5 Excellent
"Loved the lake in the back !!!"
A verified traveler stayed at The Black Swan Lee - Lenox, Ascend Hotel Collection
Posted 2 days ago
The Black Swan Lee - Lenox, Ascend Hotel Collection