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Compare 78 Cottages in Richmond with updated reviews, rates, and availability.

Beachwood Cottage
Property grounds
Beachwood Cottage
10.0 out of 10, Exceptional, (3)
"We had a great week at this cottage and Daryl was a responsive and helpful host. Our kids are already asking to return next year."
Beachwood Cottage
Charming historic cottage on scenic road to Mt. Greylock
Summer
Charming historic cottage on scenic road to Mt. Greylock
10.0 out of 10, Exceptional, (101)
"We spent three nights in the Stone Schoolhouse, hiking, visiting The Clarke, and enjoying a lovely evening concert at Tanglewood. Convenient location for seeing the Berkshires, unique quarters and friendly hosts. Highly recommend!"
Charming historic cottage on scenic road to Mt. Greylock
Quiet rustic cottage with shared lake access
Quiet rustic cottage with shared lake access
10.0 out of 10, Exceptional, (98)
"Great property, just as it looked in the images."
Quiet rustic cottage with shared lake access
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, (11)
"Beautiful house with amazing views. Very clean, all brand new. Great location. We would rent it again. Had an amazing Labor Day weekend. Thank you!"
Fun Getaway Lakehouse in the Hudson Valley
Cozy Berkshire cottage with fireplace.
Interior
Cozy Berkshire cottage with fireplace.
10.0 out of 10, Exceptional, (21)
"Cozy is in the description and it is very apt. Very comfortable, great location. Easy to get to anywhere in the Berkshires. Plenty of parking. We didn't get a chance to hike the trails behind the cottage but will next time!"
Cozy Berkshire cottage with fireplace.
Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly!
Aerial view
Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly!
8.4 out of 10, Very Good, (5)
"We had a lovely two weeks at the Pfeifer cottage. Everything was as promised. The location was quiet, but easy access to Great Barrington and Tanglewood. Two of our grandkids visited and they were in love with the spiral staircase! We way come back again someday."
Pine View Cottage, Berkshires Getaway Lake Buel w/ lake rights. Pet friendly!
Cozy cottage with pool, walking distance to lake
Dining
Cozy cottage with pool, walking distance to lake
10.0 out of 10, Exceptional, (12)
"This was our second year in a row here! We already booked for next summer! Peaceful and calm. The pool is fantastic."
Cozy cottage with pool, walking distance to lake
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, (3)
"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
Morgan House on Crooked Lake
Private kitchen
Morgan House on Crooked Lake
10.0 out of 10, Exceptional, (6)
"Beautiful home on water. Perfect place to have family gatherings! Looking forward to another visit. Best area for pizza, too! ( Kay’s)"
Morgan House on Crooked Lake
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, (5)
"Very clean, cute house right on the lake. We enjoyed our time there. "
Cozy Hudson Valley Lake Cottage :Kayaks Included, great swimming, near Hudson!
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
Property grounds
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
3.0 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, (35)
"Quiet apot even when boaters were using the lake. Had a couple of issues that were addressed quickly."
Rustic Berkshires Cottage at Lake Buel w/ Kayaks!
A Charming Cottage - Secluded in Nature and Relaxing
Exterior
A Charming Cottage - Secluded in Nature and Relaxing
10.0 out of 10, Exceptional, (2)
"I’ve been dreaming of a NYC getaway for years and fell in love with this home!!! I love the cozy feeling of being in such magical woods with such a beautiful lake nearby. Having access to the teepee was so special and added even more character. The beds are soooo comfortable I can’t wait to go back!!!"
A Charming Cottage - Secluded in Nature and Relaxing
Waterfalls and Trails at 'the Mills At Green Hole'
Exterior
Waterfalls and Trails at 'the Mills At Green Hole'
3.0 star property
Waterfalls and Trails at 'the Mills At Green Hole'
Underhill Cottage
Interior
Underhill Cottage
Underhill Cottage
Cottage in the Clouds With Mountain Views
Fully stocked kitchen. Two skylights provide plenty of natural light
Cottage in the Clouds With Mountain Views
9.4 out of 10, Exceptional, (3)
"A nice place to relax. A bit toasty on warm days but otherwise enjoyed our stay."
Cottage in the Clouds With Mountain Views
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!
9.4 out of 10, Exceptional, (20)
"Beautiful lake house and ideal for our group of 4 women celebrating our 45th high school reunion. Beautiful lake view and Love that Ozzie’s is just a few miles away. "
Picturesque Cottage with Sunroom on Ashmere Lake!
Stockbridge Home: Walk to Town Beach!
Exterior
Stockbridge Home: Walk to Town Beach!
3.0 star property
Stockbridge Home: Walk to Town Beach!
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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 Richmond

Vacation Village in the Berkshires
Lobby
Vacation Village in the Berkshires
3.0 star property
8.6 out of 10, Excellent, (1715)
" We enjoyed our stay at Vacation Villa and the condo was extremely spacious and comfortable. The only complaint is the very soft bed. Upon check- in we were told we were 15 minutes early and had to stand in another line to wait to get a different room that would be ready at 3:45. Since we are gold members of hotel.com we always ask for a room upgrade and the manager seemed annoyed that we even asked for a room upgrade as well as arriving 15 minutes early and the greeting from all of the...
The price is AED 620
AED 717 total
includes taxes & fees
29 Sep - 30 Sep
Vacation Village in the Berkshires
Jiminy Peak Mountain Resort
Property entrance
Jiminy Peak Mountain Resort
3.0 star property
8.2 out of 10, Very Good, (898)
"Was good everything "
The price is AED 547
AED 600 total
includes taxes & fees
14 Oct - 15 Oct
Jiminy Peak Mountain Resort
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
Welcome to The Freeman Berkshires
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
10.0 out of 10, Exceptional, (30)
"We had a great time at The Freeman! The little touches like fresh fruit and a welcome basket made it even more special for our family getaway."
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
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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