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Check prices for these dates

Next weekend
21 Saf. - 23 Saf.
In two weeks
28 Saf. - 2 Rab. I
In one month
14 Rab. I - 16 Rab. I
In two months
11 Rab. II - 13 Rab. II

Compare 27 Cabin Rentals in Sheffield with updated reviews, rates, and availability.

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, (210)
"The cabin is quiet, tidy, and comfortable. It is within driving distance of several hiking trails and was a great place to spend a long weekend. The host was friendly and communicative, and made sure that we had everything we needed for a nice stay. "
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns
Sandisfield Vacation Rental | 4BR | 3BA | 1,978 Sq Ft | Stairs Required

Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns

9.6 out of 10, Exceptional, (39)
"A nice cabin in the woods. Only issue was rodents at the property. We had four sighting in three days. Would stay again if they resolved the mouse problem."
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns
Romantic Log Cabin on Privately-Owned Lake with Fireplace
Property grounds

Romantic Log Cabin on Privately-Owned Lake with Fireplace

9.8 out of 10, Exceptional, (80)
"Amazing location on a completely private small lake just a few minutes off the Taconic Parkway. Host is very helpful, and very artistic. Sleeping on a pull out couch was initially off-putting, but it is very high quality and fairly comfortable, and works for the space. So many birds to see and hear! Nice hiking trails on the large property, which has adjacent preserved land. "
Romantic Log Cabin on Privately-Owned Lake with Fireplace
Guesthouse Cabin vacation rentals in Berkshire County
Property grounds

Guesthouse Cabin vacation rentals in Berkshire County

10.0 out of 10, Exceptional, (5)
"Two very comfortable nights. Cabin is well appointed. Great kitchen and outdoor space. Tremendous views, amazing star gazing. Very private. "
The price is SAR 1,894
SAR 3,255 total
includes taxes & fees
18 Feb - 19 Feb
Guesthouse Cabin vacation rentals in Berkshire County
Berkshires Cabin 2 Mi to Appalachian Trail!
Otis Vacation Rental | 3BR | 2BA | 1,200 Sq Ft | Stairs to Access

Berkshires Cabin 2 Mi to Appalachian Trail!

9.8 out of 10, Exceptional, (11)
"The hosts were extremely responsive and helpful, providing us with hiking ideas, questions regarding the house and suggesting best shopping spots for incidentals. The living room was cozy, seating five comfortably. The kitchen was well stocked so cooking a Thanksgiving meal was a pleasure. We thoroughly enjoyed ourselves."
Berkshires Cabin 2 Mi to Appalachian Trail!
Romantic and Secluded Berkshire's Gem
Living area

Romantic and Secluded Berkshire's Gem

9.8 out of 10, Exceptional, (13)
"This was a perfect meet up spot for us and our friends from Westchester. It was cozy and clean and warm! A perfect spot to enjoy skiing at Butternut and to stay warm during and play in the snow during a snowstorm!"
Romantic and Secluded Berkshire's Gem
Tolland Cabin w/ Private Hot Tub & Grill!
Tolland Vacation Rental | 2BR | 2BA | 1,200 Sq Ft | Stairs Required

Tolland Cabin w/ Private Hot Tub & Grill!

9.4 out of 10, Exceptional, (12)
"I want to preface my review by stating we had a wonderful time. We needed a getaway to unplug and relax and we were able to do just that. The area was beautiful, nature-plenty, quiet, secluded. There were a few unexpected glitches but nothing that we couldn't improvise around. Having said that, the listing said queen size beds, but they were only full, so my husband and I stayed in separate rooms which was sad . We also felt the people that prepped the home for our stay, must have ran short of...
Tolland Cabin w/ Private Hot Tub & Grill!
Berkshires Log Cabin by Evergreen Home
Cozy log cabin nestled among snow covered trees. The perfect winter wonderland!

Berkshires Log Cabin by Evergreen Home

10.0 out of 10, Exceptional, (7)
"We pulled in to a lighted log cabin that was lit by lights around the porch. You feel as if you are alone in the middle of the woods. It seemed all the restaurants were 20 minutes away. No shortage of good restaurants. We went to Tanglewood twice and what a treat. We saw Kool and the Gang and John Baptiste. Great performers playing in the Berkshires."
Berkshires Log Cabin by Evergreen Home
Half Moon by AvantStay | 4BR Cabin w/ Large Deck & Yard
Spacious interior with tall ceilings and lots of light.

Half Moon by AvantStay | 4BR Cabin w/ Large Deck & Yard

9.6 out of 10, Exceptional, (9)
"Great property. Exactly as advertised. "
Half Moon by AvantStay | 4BR Cabin w/ Large Deck & Yard
'The Mill River Cabin’ w/ Fireplace & River View!
Mill River Vacation Rental | 2BR | 1BA | Stairs Required | 1,100 Sq Ft

'The Mill River Cabin’ w/ Fireplace & River View!

9.8 out of 10, Exceptional, (37)
"The Mill River Cabin is the perfect location for a vacation focused on relaxation and communing with nature! We recently enjoyed a beautiful fall week at this property. Highlights included time spent on the deck overlooking the Konkapot River, evening campfires, hiking the large number/variety of trails very nearby, Hancock Shaker Village and the Norman Rockwell Museum. This rustic cabin has everything you need to make for an enjoyable stay. It's a good idea to bring your food and other...
'The Mill River Cabin’ w/ Fireplace & River View!
West Cornwall Cabin ~ 4 Mi to Covered Bridge!
West Cornwall Vacation Rental | 2BR | 2BA | Stairs Required | 1,521 Sq Ft

West Cornwall Cabin ~ 4 Mi to Covered Bridge!

10.0 out of 10, Exceptional, (5)
"My wife and I stayed here for a few days, and I must say that our experience was wonderful!! We were looking to unwind without distractions, and this home was perfect! A truly rural location in a beautiful part of our state. Quiet, comfortable, with privacy and peace. The host was the best to put it mildly. Very responsive and clearly wishes every guest to have the best time possible! This is one of VRBO's finest!! We would not even think twice about returning for another visit!! Thank you...
West Cornwall Cabin ~ 4 Mi to Covered Bridge!
Ideal location for summer and winter activities with plenty of outdoor space.
Living-room

Ideal location for summer and winter activities with plenty of outdoor space.

9.6 out of 10, Exceptional, (70)
"As is our custom we picked a place to celebrate Thanksgiving with our family. The location is usually in an area that is quiet, out in the country. This property did not disappoint us. Vivianna is a great host, always answering any questions or concerns. Great location, tucked away off the road, but close to all things one may need. Great fireplace, cozy living room dining area and bedrooms. We would recommend this property to anyone who is looking for a place to just relax and enjoy the...
Ideal location for summer and winter activities with plenty of outdoor space.
Private Hot Tub: Spacious Austerlitz Ski Cabin!
Austerlitz Vacation Rental | 3BR | 3BA | 2,500 Sq Ft | 2 Steps to Enter

Private Hot Tub: Spacious Austerlitz Ski Cabin!

2.0 star property
10.0 out of 10, Exceptional, (2)
"A group of 10 friends (we are in out 40's) and I stayed here for a yearly gathering that we do. Every person was amazed at the rental. It was warm, clean, inviting and the kitchen jad everything that i needed to feed 10 people over the weekend.The game room was amazing and kept the group active indoors. It had a beautiful fireplace and wood stove. The adjacent room had a dining table, another wood stove and some very thoughtful items in a welcome basket. Next to that was the kitchen/living...
Private Hot Tub: Spacious Austerlitz Ski Cabin!
A-Frame Cabin w/ Furnished Deck in Becket!
Becket Vacation Rental | 2BR | 1BA | 1,100 Sq Ft | Stairs Required to Enter

A-Frame Cabin w/ Furnished Deck in Becket!

8.4 out of 10, Very Good, (6)
"This A-frame cabin was the perfect location for some Berkshire R&R. Close to so many of western MA's greatest attractions, we had a great time visiting Tanglewood and museums, and touring local towns and restaurants. The property was clean, as described, and very comfortable. Communicating with our hosts was very simple. We will be happy to return!"
A-Frame Cabin w/ Furnished Deck in Becket!
East Otis Reservoir Cabin w/ Porch - Walk to Lake!
East Otis Vacation Rental | 2BR | 1BA | 720 Sq Ft | 2 Steps for Entry

East Otis Reservoir Cabin w/ Porch - Walk to Lake!

8.4 out of 10, Very Good, (8)
"Lovely cottage. Very clean. Everything we needed. We had a great time!"
East Otis Reservoir Cabin w/ Porch - Walk to Lake!
Chester by AvantStay | Amazing Views, Secluded Home, A True City Escape!
Amazing views from your private city escape.

Chester by AvantStay | Amazing Views, Secluded Home, A True City Escape!

9.2 out of 10, Wonderful, (7)
"It was a beautiful property!"
Chester by AvantStay | Amazing Views, Secluded Home, A True City Escape!
Modern Cabin Near Tanglewood
Living area

Modern Cabin Near Tanglewood

10.0 out of 10, Exceptional, (8)
"A wonderful cabin with all the amenities you will need. Clean, beautifully decorated, and so much room. Highly recommend! Will be back for sure. "
Modern Cabin Near Tanglewood
Lakeshore cabin with private beach and dock
Property grounds

Lakeshore cabin with private beach and dock

10.0 out of 10, Exceptional, (3)
"We love this place! It is conveniently located for Tanglewood and the Rockwell museum, quiet and secluded. The cabin and grounds show much care and attention by thoughtful owners. "
Lakeshore cabin with private beach and dock
Newly Renovated Cabin in the Country
Exterior

Newly Renovated Cabin in the Country

10.0 out of 10, Exceptional, (29)
"We booked this escape as a 1/2 way point between family in NJ and MA and what a hidden gem it is! Dog friendly was a priority, but the magic of this place was a welcomed surprise. All weekend we commented on wishing we stayed longer and that we must come back to really enjoy the property and cozy feel that warms the soul! The cabin is meticulously maintained and it is very clear that the family loves their home away from home! Can’t wait to return!!"
Newly Renovated Cabin in the Country
Artist's Camp on Lake Mahkeenac
Interior

Artist's Camp on Lake Mahkeenac

9.6 out of 10, Exceptional, (18)
"Great location, comfortable, beautiful setting and nice porch! "
Artist's Camp on Lake Mahkeenac
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 Sheffield

Guesthouse Cabin vacation rentals in Berkshire County
Property grounds

Guesthouse Cabin vacation rentals in Berkshire County

10.0 out of 10, Exceptional, (5)
"Two very comfortable nights. Cabin is well appointed. Great kitchen and outdoor space. Tremendous views, amazing star gazing. Very private. "
The price is SAR 1,894
SAR 3,255 total
includes taxes & fees
18 Feb - 19 Feb
Guesthouse Cabin vacation rentals in Berkshire County
Antique Farmhouse Totally Restored
Sunrise lights up the front of the house. Moon sets over the mountain.

Antique Farmhouse Totally Restored

9.8 out of 10, Exceptional, (85)
"Place is great. Has a old farmhouse feel with an update. Lots of spots within the house for people to hang out. We did a family birthday get together and had a great time. "
Antique Farmhouse Totally Restored
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 Ponds at Foxhollow
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.