Title: Guesthouse Cabin vacation rentals in Berkshire County - Latest Reviews, Deals & Photos 2026 - Expedia.ca [See all properties](http://www.expedia.ca/Hotel-Search?regionId=&selected=99962392&adults=2&children=&sort=RECOMMENDED&useRewards=false&semdtl=&userIntent=&vip=false) Entire cabin # Guesthouse Cabin vacation rentals in Berkshire County ## Photo gallery for Guesthouse Cabin vacation rentals in Berkshire County ![Interior - Guesthouse Cabin vacation rentals in Berkshire County (Sheffield)](https://images.trvl-media.com/lodging/100000000/99970000/99962400/99962392/eca50f2a.jpg?impolicy=resizecrop&rw=598&ra=fit) ![Interior - Guesthouse Cabin vacation rentals in Berkshire County (Sheffield)](https://images.trvl-media.com/lodging/100000000/99970000/99962400/99962392/51b9c734.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Smart TV, fireplace, books - Guesthouse Cabin vacation rentals in Berkshire County (Sheffield)](https://images.trvl-media.com/lodging/100000000/99970000/99962400/99962392/565807cf.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Exterior - Guesthouse Cabin vacation rentals in Berkshire County (Sheffield)](https://images.trvl-media.com/lodging/100000000/99970000/99962400/99962392/a764aae5.jpg?impolicy=resizecrop&rw=297&ra=fit) ![Property grounds - Guesthouse Cabin vacation rentals in Berkshire County (Sheffield)](https://images.trvl-media.com/lodging/100000000/99970000/99962400/99962392/d00ad195.jpg?impolicy=resizecrop&rw=297&ra=fit) - Overview - Location - Amenities - Policies Escape to Undermountain Lodge, nestled between natural spring lakes with panoramic mountain views. Spread across three levels, this serene cabin offers four inviting bedrooms and an expansive deck for up to 12 guests. Enjoy the charming dining room, well-appointed kitchen, and cozy living room or step outside to unwind by the firepit at the roundabout. ## Reviews 10 Exceptional ### Entire cabin 4 bedrooms2 bathroomsSleeps 12 ## Popular amenities - Kitchen - Pet friendly - Air conditioning - Outdoor Space - Parking available - Barbecue grill ## Add dates for prices Check-in Check-out Travellers ## About this property ### Entire place You'll have the entire cabin to yourself and will only share it with other guests in your party. ### Guesthouse Cabin vacation rentals in Berkshire County Undermountain Lodge offers an escape to a serene cabin, nestled between pristine natural spring lakes with panoramic mountain views, it comfortably accommodates up to 12 guests. Beyond the 6th guest, there's a $135 per person fee. Couples enjoy special discounts, inquire for details. Whether with family or friends, find solace in this tranquil retreat from everyday life. Book now for an unforgettable escape. Undermountain Lodge boasts four inviting bedrooms, comfortably accommodating up to 12 guests. Spread across three levels, it offers two bathrooms, a spacious living room, a charming dining room, and a well-appointed kitchen. The property also features an expansive deck and a covered porch, surrounded by abundant outdoor space. Here's a detailed breakdown of the bedrooms: Bedroom #1 (Upstairs): This room features two queen beds and showcases rustic log and shiplap walls, providing a cozy and rustic atmosphere. Bedroom #2 (Main Floor): Offering a queen bed and adorned with rustic log walls, this bedroom exudes warmth and comfort. Bedroom #3 (Finished Lower Floor): With a queen bed and rustic cedar walls, this bedroom offers a unique and natural aesthetic. Bedroom #4 (Finished Lower Floor): Perfect for a group, this room boasts two queen beds and natural shiplap walls, providing a comfortable and welcoming environment. The main floor includes a bathroom with a shower, a spacious living room, a dining room, and a well-equipped kitchen. For added relaxation, there's an upstairs bathroom with a tub. Step outside to discover a covered porch furnished with comfortable seating, complete with love seats and chairs. Two picnic tables offer a scenic spot to enjoy meals while taking in views of the picturesque valley. Additionally, there's a firepit located in a charming roundabout area, nestled between two ponds, perfect for cozy evenings under the stars. Your stay at Undermountain Lodge promises both comfort and the opportunity to immerse yourself in the beauty of the outdoors. Modern Rustic Comfort: The house is fully furnished in a modern rustic log style, offering a cozy and inviting atmosphere. Spacious Dining: The kitchen and dining areas are generously sized, accommodating up to 12 people comfortably. Well-Equipped Kitchen: The kitchen is equipped with a sink, copper counter space, refrigerator, electric oven and cooktop, dishwasher, a Keurig coffee maker, and a large classic stovetop espresso machine. We provide all necessary dishware, cookware, cooking utensils, eating utensils, and select pantry items for your convenience. Comfort and Convenience: Linens, towels, soaps, shampoo, and conditioner are provided. However, feel free to bring your own personal bathroom items. Entertainment: Enjoy TVs in the main living space and bedrooms 2, 3, & 4\. Stay connected with free Spectrum Wifi Internet. Outdoor Delight: Unwind by the firepit at the roundabout, furnished with 6 Adirondack chairs, offering a panoramic view. Safety and Information: Detailed instructions on water and fire safety are provided in the house, along with information about local activities, shopping, and dining options. ## Property amenities ### Internet - Available in the cabin: WiFi ### Parking and transportation - Parking on site ### Kitchen - Blender - Coffee grinder - Coffee/tea maker - Cookware, dishware, and utensils - Dishwasher - Kitchenette - Microwave - Oven - Paper towels - Refrigerator - Spices - Stovetop - Toaster ### Dining - Dining table ### Bedrooms - 4 bedrooms - Bedsheets provided ### Bathroom - 2 bathrooms - Shampoo - Soap - Toilet paper - Towels provided ### Living spaces - Dining table - Fireplace - Living room - Separate dining area ### Entertainment - Books - Games - Smart TV with cable/satellite channels ### Outdoor areas - Barbecue grill - Firepit - Garden - Outdoor furniture - Patio ### Comfort - Air conditioning - Heating ### Pets - Pet friendly - One pet total (up to 50 lbs per pet) ### Suitability/Accessibility - Smoking not allowed ### Services and conveniences - Iron/ironing board ### Safety features - Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property) - Smoke detector (host has indicated there is a smoke detector on the property) ### General - At least 80% lighting from LEDs - Energy-saving switches in guestrooms - Garden - Water-efficient showers - Water-efficient toilets ## Similar properties ![Lobby](https://images.trvl-media.com/lodging/1000000/130000/128300/128208/ed6ed4e8.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Quality Inn Great Barrington Great Barrington - Breakfast included - Parking included - Free WiFi - Air conditioning 8.4 Very good 1,002 reviews CA $91 CA $101 total includes taxes & fees Mar 23 - Mar 24 [](https://www.expedia.ca/Hotel-Search?startDate=2026-03-23&endDate=2026-03-24&selected=128208&PinnedHotelID=128208&HadPinnedHotel=true®ionId=-1&adults=2) ![Exterior](https://images.trvl-media.com/lodging/1000000/900000/892300/892229/eb9d0598.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Holiday Inn Express Hotel & Suites Great Barrington by IHG Great Barrington - 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Air conditioning 8.8 Excellent 2,279 reviews CA $132 CA $162 total includes taxes & fees Mar 8 - Mar 9 [](https://www.expedia.ca/Hotel-Search?startDate=2026-03-08&endDate=2026-03-09&selected=1066423&PinnedHotelID=1066423&HadPinnedHotel=true®ionId=-1&adults=2) ![Lobby lounge](https://images.trvl-media.com/lodging/77000000/76300000/76297700/76297618/3d64e1fb.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Berkshires Untold Lenox - Pet friendly - Parking included - Free WiFi - Restaurant 9.0 Wonderful 867 reviews CA $112 CA $125 total includes taxes & fees Mar 23 - Mar 24 [](https://www.expedia.ca/Hotel-Search?startDate=2026-03-23&endDate=2026-03-24&selected=76297618&PinnedHotelID=76297618&HadPinnedHotel=true®ionId=-1&adults=2) ![Exterior](https://images.trvl-media.com/lodging/1000000/920000/913200/913175/9d0420c7.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires Great Barrington - Pool - Breakfast included - Parking included - Free WiFi 9.4 Exceptional 768 reviews CA $207 CA $232 total includes taxes & fees Apr 5 - Apr 6 [](https://www.expedia.ca/Hotel-Search?startDate=2026-04-05&endDate=2026-04-06&selected=913175&PinnedHotelID=913175&HadPinnedHotel=true®ionId=-1&adults=2) ![Property amenity](https://images.trvl-media.com/lodging/21000000/20880000/20875100/20875006/98528d27.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG South Lee - Pool - Hot tub - Air conditioning - Tennis court 9.0 Wonderful 848 reviews CA $160 CA $205 total includes taxes & fees Mar 8 - Mar 9 [](https://www.expedia.ca/Hotel-Search?startDate=2026-03-08&endDate=2026-03-09&selected=20875006&PinnedHotelID=20875006&HadPinnedHotel=true®ionId=-1&adults=2) ![Room, 2 Queen Beds, Non Smoking](https://images.trvl-media.com/lodging/2000000/1080000/1076200/1076188/220f6cfe.jpg?impolicy=fcrop&w=469&h=201&p=1&q=medium) ### Monument Mountain Motel Great Barrington - Parking included - 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Apr 2 [](https://www.expedia.ca/Hotel-Search?startDate=2026-04-01&endDate=2026-04-02&selected=11449113&PinnedHotelID=11449113&HadPinnedHotel=true®ionId=-1&adults=2) [Compare similar properties](/Hotel-Search?startDate=2026-03-19&endDate=2026-03-20&selected=99962392&PinnedHotelID=99962392&HadPinnedHotel=true®ionId=-1&adults=2&comparePropertyIds=99962392,128208,892229,54944,1066423) ## Policies ### Check-in Check-in time starts at 3:00 PM Minimum check-in age: 21 ### Check-out Check-out before 11:00 AM ### Special check-in instructions You will receive an email from the host with check-in and check-out instructions Information provided by the property may be translated using automated translation tools ### Pets Pets allowed Service animals are welcome, and are exempt from fees 1 total (up to 50 lbs per pet) Note from host: There is a fee of $300 for pets. ### Children and extra beds Children are welcome ### Events No events allowed ### Smoking Smoking is not permitted ## Important information ### You need to know Extra-person charges may apply and vary depending on property policy Government-issued photo identification and a credit card, debit card, or cash deposit may be required at check-in for incidental charges Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed Onsite parties or group events are strictly prohibited Host has indicated there is a carbon monoxide detector on the property Host has indicated there is a smoke detector on the property This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation Property Registration Number C0453882670 ## About the area Sheffield is home to this cabin. Ashley House and Great Barrington Historical Society & Museum are cultural highlights, and some of the area's attractions include Harney and Sons Tea Tasting Room and Mahaiwe Performing Arts Center. [Visit our Sheffield travel guide](https://www.expedia.ca/Sheffield.dx157238) [View more Cabin rentals in Sheffield](https://www.expedia.ca/Sheffield-Cabins.d157238-aaCabins.Travel-Guide-Accommodation) ![Map](https://maps.googleapis.com/maps/api/staticmap?&size=660x330&map_id=3b266eb50d2997c6¢er=42.070213,-73.426346&zoom=13&channel=expedia-HotelInformation&maptype=roadmap&scale=1&path=color:0xFFFFF|weight:2|fillcolor:0x005AEB7F|enc:%7Dux_Gtad_M%3FU%3FU%40U%3FQ%40U%40U%3FSBS%40U%40U%40SBSBUBSBSBUBQBSDSBSDSDSDSDSDQFSDQFSDQFQFSHQFOFQHQFQHOFQHOHOJOHOHMHOJMHOJOJMJKJMJMJKJMJKLKJKLMLIJILKLILILIJGNILILGLGNGLGLENELGNELENCNCLENCNCNCLANCN%3FLCNAN%3FN%3FNAN%3FN%3FL%40N%3FN%3FN%40NBN%3FLBN%40NBNBLBNDLBNBNDLDNFLDLDNFLFLFLFNHLHLFLHLHJHLJLHLHJLLJJJJJLLJJHLLLJJHNJLHNJLJNHLHNHNHPHLHPFNHPFPHPFNFPFRFPDPFRFPDRFPDRDRBRDRDRBRDRBPBTBRBRBT%40R%40RBT%40T%40R%40R%40T%3FT%40P%3FT%3FT%3FT%3FR%3FT%3FTAP%3FTATATAPATCTARARCTCRCRCTCREPCRERERCRERERGPERGPGREPGPGRGPGNIPGPIPGNIPILIPININILKNKNILKLINKLMJILKJMLKJKJMLKJMHMHMJKHMHMHMHMFOHMFMFMFOFMDMFODMDODOBMBODMBOBOBO%40MBO%3FOBO%40O%40O%3FM%3FO%3FO%3FO%3FO%3FOAOAMCO%3FOCMAOCOCOCMEOCOCMEOEMEOGMEMGOGMGMGMIOGKIMIMIMIMKKIMIMKKMMKKKKMKKKMKKKMKMKOIMKOIOIMIOKOIOIOGQIOGQIQGQGOIQGSGQEQGSEQGSEQESESESESCSESCQCSCUCSCSCUCSASAUAUCQ%3FUAUAU%3FQAU%3FU%3FS&key=AIzaSyCYjQus5kCufOpSj932jFoR_AJiL9yiwOw&signature=f5RE-HagUT2eMHeLAvfhX1639s8=) Sheffield, MA ### What's nearby - ![Lots of great views on CT/MA Appalachian Trail section. ](https://images.trvl-media.com/place/154559/66794743-4cd4-467c-acbb-2173991d4fad.jpg?impolicy=resizecrop&rw=115.61&rh=65.03&ra=fit&q=high) Mount Riga State Park 5 min drive \- 3.9 km - Mount Everett State Reservation 7 min drive \- 4.3 km - Washinee Lake 9 min drive \- 7.4 km - Taconic Chapel Park 10 min drive \- 7.1 km - Mount Frissell 12 min drive \- 13.0 km ### Getting around - Hudson, NY (HCC-Columbia County) 51 min drive ### Restaurants - Dunkin' 22 min drive - McDonald's 23 min drive - ILSE Coffee 21 min drive - Caddie Shack 20 min drive - State Line Pizza 20 min drive ## Frequently asked questions ### Is Guesthouse Cabin vacation rentals in Berkshire County pet-friendly? ### How much does it cost to stay at Guesthouse Cabin vacation rentals in Berkshire County? ### How much is parking? ### What time is check-in at Guesthouse Cabin vacation rentals in Berkshire County? ### What time is check-out at Guesthouse Cabin vacation rentals in Berkshire County? ### Where is Guesthouse Cabin vacation rentals in Berkshire County located? ## Have a question? Beta Get instant answers with AI powered search of property information and reviews. Ask a question ## Guesthouse Cabin vacation rentals in Berkshire County Reviews ## Reviews ### Exceptional All reviews shown are from real guest experiences. Only travellers who have booked a stay with us can submit a review. We verify reviews according to our guidelines and publish all reviews, positive or negative. [More information](https://www.expedia.ca/lp/b/content-guidelines) 10 - Excellent 10 8 - Good 0 6 - Okay 0 4 - Poor 0 2 - Terrible 0 ### 10 Cleanliness ### 10 Location ### 10 Property conditions & facilities ## Reviews ### 10/10 Excellent #### Tom S. Aug 25, 2024 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Great stay Really enjoyed the cabin. The pictures don’t do the view justice as it’s an amazing vista overlooking the Berkshires. ##### Tom S. Stayed 1 night in Aug 2024 ### 10/10 Excellent #### Robert B. Sep 2, 2024 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Comfort and Views Two very comfortable nights. Cabin is well appointed. Great kitchen and outdoor space. Tremendous views, amazing star gazing. Very private. ##### Robert B. Stayed 2 nights in Aug 2024 ### 10/10 Excellent #### deborah d. Aug 12, 2025 Liked: Cleanliness, check-in, communication, location, listing accuracy Great place. I highly recommend for a group or family. Amazing views! Beautiful property very private and quiet. Cabin was also very well stocked and had great outdoor space. ##### deborah d. Stayed 2 nights in Aug 2025 ### 10/10 Excellent #### Christina Aug 27, 2025 Liked: Cleanliness, property conditions & facilities, communication This was exactly what we were looking for. The property was magnificent the cabin cozy, fully stocked. We plan on coming back soon. ##### Christina Stayed 4 nights in Aug 2025 ### 10/10 Excellent #### Patricia B. Apr 30, 2025 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Beautiful cabin Cute and cozy property with a beautiful view. Unique interior that everyone loved. Not far from attractions. ##### Patricia B. Stayed 1 night in Apr 2025 ### 10/10 Excellent #### ryan r. Aug 6, 2024 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Great spot Stayed here for a bachelor’s weekend and we had a blast! Beautiful property, awesome house with everything 10 of us needed. Would book again! ##### ryan r. Stayed 2 nights in Aug 2024 ### 10/10 Excellent #### Richard C. Dec 29, 2023 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Awsome view from the top of the mountain Undermountain cabin is a very unique property. Worth the stay! ##### Richard C. Stayed 3 nights in Dec 2023 ### 10/10 Excellent #### Bethany C. Jul 1, 2024 Liked: Cleanliness, check-in, communication, location, listing accuracy #### Tanglewood Stay We had a wonderful stay and really enjoyed the log cabin feel and views from the property. We were only there one night and it was our visit to Tanglewood. ##### Bethany C. Stayed 1 night in Jun 2024 ### 10/10 Excellent #### Jim H. Jun 4, 2025 Liked: Cleanliness, check-in, communication, location, listing accuracy Very nice property. A bit light on household products, bedding. ##### Jim H. 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