Entire home
Historic Ski Lodge on 112-Acre Vineyard
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Reviews
10 out of 10, Loved by Guests
Top 10% based on
2 bedrooms1 bathroomSleeps 483.6 sq m
Popular amenities
Rooms & beds
2 bedrooms (sleeps 4)
Bedroom 2
1 Queen Bed
Master Bedroom
1 Queen Bed
1 bathroom
Bathroom
Bathtub · Toilet · Shower only
Spaces
Deck or patio
Kitchen
Outdoor play area
Garden
Dining area
About this property
Historic Ski Lodge on 112-Acre Vineyard
**10% discount on 7 nights or more; 25% discount on 28 nights or more.
Rental Amenities:
Over 900 square feet of living space including a parlor (living room) with visual flame heater, Smart TV and ski memorabilia; a full kitchen with gas stove, retro refrigerator, dishwasher, microwave, cookware and dinnerware; a full bath with separate tub and shower; two separate bedrooms, each with a queen-sized bed; a mudroom with washer/dryer, utility sink and gear storage; and, direct access to all that Gilbert’s Hill has to offer including peaceful hiking trails for picnics among the wildflowers.
- Includes linens and towels
- Free WiFi
- A private deck with gas grill and fire pit overlooking vineyard
- Access to acres of hillside pastures, woods, etc.
- Ample, free, off-street parking.
- storage for recreational gear (bikes, boots, etc.)
- Smart TV with free access to Netflix (no cable)
- Keurig coffee maker and French press
- Fresh-cut flowers from our farm (when in season)
History:
Gilbert’s Hill farm is the birthplace of downhill skiing in America — it is the site of the country’s first ski rope tow. This special place is both a State Historic Site and on the National Register of Historic Places.
Recently renovated, the Gilbert’s Hill cottage (ski lodge) was built in 1936 as a place for skiers to warm by the fire, eat, drink and socialize between runs on the most popular ski hill in the country. It housed a sandwich bar, ski school and ski rental shop. Dozens of Olympic skiers got their start training at Gilbert’s Hill and the famed Austrian skier and instructor, Sig Buchmayr, directed the ski school. After the ski tow closed in the early 1950s the structure was converted into a home for Clinton Gilbert’s son and his war bride from France. Our recent renovation retained the cottage’s historic layout and as much of the original materials possible (pine paneling, flooring, bathroom tub, kitchen cabinets, etc).
The Gilbert’s Hill cottage is a one-of-kind vacation rental — 100% of the proceeds from your stay support the restoration and maintenance of this National landmark.
Location:
Gilbert’s Hill is centrally located with easy access to the best Vermont has to offer — Woodstock Village is repeatedly voted one of the most beautiful towns in America.
- We neighbor Marsh-Billings-Rockefeller National Historical Park with its miles of carriage paths and hiking trails, acres of woods and ponds.
- 2 miles to Appalachian Trail National Park access (gorgeous views)
- Minutes drive to three local ski areas including Killington (with summer activities like mountain biking)
- Two miles to Woodstock town center with quaint shops, restaurants, bars, the town hall theater, town green, historic architecture
- Minutes to Long Trail Brewery, Harpoon Brewery (and other award-winning craft brewers nearby)
- 1 mile to Billings Farm & Museum and minutes to the Vermont Institute of Natural Science (outstanding activities for families/kids)
- Nationally-recognized dairy operations nearby (Ben & Jerry’s, Vermont Farmstead Cheese Co., Plymouth Artisan Cheese, etc)
- Dozens of covered bridges, authentic villages, historic general stores, small town libraries, museums and country fairs less than an hour’s drive.
** Please contact the owners: we’re happy to share our private, guest website with a comprehensive visitors’ guide to the best local activities (amazing farm-to-table restaurants, iconic general stores, wineries, craft breweries, nostalgic farmer’s markets, etc.) plus expanded information on the property and local history. **
Rental Amenities:
Over 900 square feet of living space including a parlor (living room) with visual flame heater, Smart TV and ski memorabilia; a full kitchen with gas stove, retro refrigerator, dishwasher, microwave, cookware and dinnerware; a full bath with separate tub and shower; two separate bedrooms, each with a queen-sized bed; a mudroom with washer/dryer, utility sink and gear storage; and, direct access to all that Gilbert’s Hill has to offer including peaceful hiking trails for picnics among the wildflowers.
- Includes linens and towels
- Free WiFi
- A private deck with gas grill and fire pit overlooking vineyard
- Access to acres of hillside pastures, woods, etc.
- Ample, free, off-street parking.
- storage for recreational gear (bikes, boots, etc.)
- Smart TV with free access to Netflix (no cable)
- Keurig coffee maker and French press
- Fresh-cut flowers from our farm (when in season)
History:
Gilbert’s Hill farm is the birthplace of downhill skiing in America — it is the site of the country’s first ski rope tow. This special place is both a State Historic Site and on the National Register of Historic Places.
Recently renovated, the Gilbert’s Hill cottage (ski lodge) was built in 1936 as a place for skiers to warm by the fire, eat, drink and socialize between runs on the most popular ski hill in the country. It housed a sandwich bar, ski school and ski rental shop. Dozens of Olympic skiers got their start training at Gilbert’s Hill and the famed Austrian skier and instructor, Sig Buchmayr, directed the ski school. After the ski tow closed in the early 1950s the structure was converted into a home for Clinton Gilbert’s son and his war bride from France. Our recent renovation retained the cottage’s historic layout and as much of the original materials possible (pine paneling, flooring, bathroom tub, kitchen cabinets, etc).
The Gilbert’s Hill cottage is a one-of-kind vacation rental — 100% of the proceeds from your stay support the restoration and maintenance of this National landmark.
Location:
Gilbert’s Hill is centrally located with easy access to the best Vermont has to offer — Woodstock Village is repeatedly voted one of the most beautiful towns in America.
- We neighbor Marsh-Billings-Rockefeller National Historical Park with its miles of carriage paths and hiking trails, acres of woods and ponds.
- 2 miles to Appalachian Trail National Park access (gorgeous views)
- Minutes drive to three local ski areas including Killington (with summer activities like mountain biking)
- Two miles to Woodstock town center with quaint shops, restaurants, bars, the town hall theater, town green, historic architecture
- Minutes to Long Trail Brewery, Harpoon Brewery (and other award-winning craft brewers nearby)
- 1 mile to Billings Farm & Museum and minutes to the Vermont Institute of Natural Science (outstanding activities for families/kids)
- Nationally-recognized dairy operations nearby (Ben & Jerry’s, Vermont Farmstead Cheese Co., Plymouth Artisan Cheese, etc)
- Dozens of covered bridges, authentic villages, historic general stores, small town libraries, museums and country fairs less than an hour’s drive.
** Please contact the owners: we’re happy to share our private, guest website with a comprehensive visitors’ guide to the best local activities (amazing farm-to-table restaurants, iconic general stores, wineries, craft breweries, nostalgic farmer’s markets, etc.) plus expanded information on the property and local history. **
Add dates for prices
Amenities
Kitchen
Washing machine
Dryer
Free WiFi
Air conditioning
Outdoor space
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House Rules
Check in after 3:00 PM
Check out before 10:00 AM
Children
Children allowed: ages 0–17
Suitable for children but not toddler proofed
Events
Events allowed: family gatherings, birthday parties, weddings
Up to 150 persons in barns, greenhouse and tent
Pets
No pets allowed
Smoking
Smoking is not permitted
Smoking outdoors is allowed
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
Parties and events (including family gatherings, birthday parties and weddings) are allowed on site. Maximum attendees: 99
Note from host: Up to 150 persons in barns, greenhouse and tent
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit and a deadlock
We should mention
A car is recommended for transport to and from this property
About the area
Woodstock
Located in Woodstock, this cottage is in a rural area and on a river. Billings Farm and Museum and Red Wagon Toy Company are local attractions and those in the mood for shopping can visit Quechee Gorge Village and King Arthur Baking Company. Union Arena Community Center and Sugarbush Farm are also worth visiting. Make sure you get close to the area's animals with activities such as game walks and birdwatching.

Woodstock, VT
What's nearby
- Marsh-Billings-Rockefeller National Historical Park - 20 min walk - 1.7 km
- Saskadena Six Ski Area - 5 min drive - 5.4 km
- Dartmouth College - 25 min drive - 32.0 km
- Killington Resort - 27 min drive - 32.7 km
- Okemo Mountain Resort - 43 min drive - 52.0 km
Getting around
Restaurants
- Dunkin' - 15 min drive
- Richardson's Tavern - 5 min drive
- Cumberland Farms - 5 min drive
- Simon Pearce Restaurant, Retail & Glassblowing - 16 min drive
- Mon Vert Cafe - 4 min drive
Frequently asked questions
Reviews
10
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window10/10
Cleanliness
10/10
Check-in
10/10
Communication
10/10
Location
10/10
Listing accuracy
Reviews
4 June 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 4 nights in May 2025
10/10 Excellent
Christopher M.
7 Oct 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Great place and stay.
Christopher M.
Stayed 4 nights in Oct 2024
10/10 Excellent
Libby H.
29 July 2025
Liked: Cleanliness, check-in, communication, location, listing accuracy
Magical place!
Libby H.
Stayed 12 nights in Jul 2025
10/10 Excellent
Christine A.
14 Oct 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
A Great Stay!
Christine A.
Stayed 3 nights in Sep 2023
10/10 Excellent
Carl R.
16 Oct 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Nostalgic Ski Hut
Carl R.
Stayed 4 nights in Oct 2023
10/10 Excellent
Bonnie B.
21 Oct 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Idyllic
Bonnie B.
Stayed 6 nights in Oct 2024
10/10 Excellent
Scott W.
16 Aug 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Excellent.
Scott W.
Stayed 3 nights in Aug 2023
10/10 Excellent
Elizabeth G.
1 Sept 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Always wonderful
Elizabeth G.
Stayed 3 nights in Aug 2023
10/10 Excellent
Carol B.
1 July 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Historic Gem!
Carol B.
Stayed 3 nights in Jun 2023
10/10 Excellent
mandy a.
20 July 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Fantastic!
mandy a.
Stayed 3 nights in Jul 2024
10/10 Excellent
Christina S.
24 June 2020
Liked: Cleanliness, check-in, communication, location, listing accuracy
Wonderful cottage and hosts!
Christina S.
10/10 Excellent
Mary M D.
16 Aug 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
A++
Mary M D.
Stayed 5 nights in Aug 2023
10/10 Excellent
Barbara F.
9 Oct 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Unbelievable!
Barbara F.
Stayed 5 nights in Oct 2023
10/10 Excellent
Timothy H.
6 June 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Touch of heaven
Timothy H.
Stayed 7 nights in May 2023
10/10 Excellent
Annemieke v.
4 June 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
Lovely home! Stay here if you can.
Annemieke v.
Stayed 4 nights in May 2024
10/10 Excellent
Derek and Danielle H.
21 June 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Don’t let the secret out.
Derek and Danielle H.
Stayed 5 nights in Jun 2023
10/10 Excellent
Marianne M.
23 Oct 2024
Liked: Cleanliness, check-in, communication, location, listing accuracy
A Lovely and Comfortable Step Into The Past
Marianne M.
Stayed 3 nights in Oct 2024
10/10 Excellent
Lisa M.
23 Oct 2023
Liked: Cleanliness, check-in, communication, location, listing accuracy
Cozy, Cute and Comfy!
Lisa M.
Stayed 3 nights in Oct 2023
10/10 Excellent
Jo S.
22 Oct 2022
Liked: Cleanliness, check-in, communication, location, listing accuracy
Beautiful private cottage
Jo S.
Stayed 6 nights in Oct 2022
10/10 Excellent
Mark D.
15 Aug 2022
Liked: Cleanliness, check-in, communication, location, listing accuracy
Fantastic Experience in a Beautiful Location
Mark D.
Stayed 8 nights in Aug 2022
10/10 Excellent
Verified traveller
11 Aug 2022
Liked: Cleanliness, check-in, communication, location, listing accuracy
A wonderful stay!
Verified traveller
Stayed 5 nights in Jul 2022
10/10 Excellent
mary b., Boca Raton
18 July 2022
Liked: Cleanliness, check-in, communication, location, listing accuracy
Charming and nostalgic
mary b.
Stayed 7 nights in Jul 2022
10/10 Excellent
lori c., Lewisburg, PA USA
16 July 2022
Liked: Cleanliness, check-in, communication, location, listing accuracy
A historic and cozy stay close to Woodstock!
lori c.
Stayed 7 nights in Jul 2022
10/10 Excellent
Karen H.
24 June 2022
Liked: Cleanliness, check-in, communication, location, listing accuracy
Charming Cottage with Interesting History
Karen H.
Stayed 7 nights in Jun 2022
10/10 Excellent
John R.
27 Apr 2022
Liked: Cleanliness, check-in, communication, location, listing accuracy
Amazing Accomodations
John R.
Stayed 3 nights in Apr 2022
About the host
Hosted by Howard Krum
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