Historic Ski Lodge on 112-Acre Vineyard

Top rated by guests
The cottage/ski lodge: Now on the National Register of Historic Places
Recently restored 1950s retro kitchen
Kitchen: farmhouse sink, dishwasher, gas stove/oven, retro refrigerator.
Entrance to Gilbert's Hill
Walking paths
review stars
10.0Outstanding
(40 Ratings)
"We loved our stay at Gilbert hill. It’s a beautiful spot, incredibly convenient, the house is comfortable, and the hosts welcoming. It’s the perfect location to access Woodstock, Silver Lake in Barnar..."
Libby H.
Don't miss out! Price and availability may change
10.0 / 10.0
Outstanding(40 Ratings)

Cottage in Woodstock, VT

4 guests · 2 bedrooms · 1 bath

Reasons to book

Guests love it hereGuests give this property a top rating
High-end valueWell priced for this area
Book with confidenceWe partner with the top travel sites so you know you're getting a great deal on the perfect rental

About this cottage rental

**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. **

Map of Woodstock, VT


Ratings and reviews

10.0 / 10.0
Outstanding(40 Ratings)
10.0 / 10.0Outstanding·Jul 2025
We loved our stay at Gilbert hill. It’s a beautiful spot, incredibly convenient, the house is comfortable, and the hosts welcoming. It’s the perfect location to access Woodstock, Silver Lake in Barnard and we love Abracadabra coffee right up the road. Howard and Mary Margaret take immaculate care of the property.
10.0 / 10.0Outstanding·Jun 2025
Amazing place, hosts, location! We can’t say enough good things about our stay and are already planning on a return trip!
10.0 / 10.0Outstanding·Oct 2024
Our stay in Woodstock was memorable, as we were introduced to the area's historical importance. An example of this would be The Billings Farm and Museum, an absolute must-see. Adding to that was our fortunate stay at Gilberts Farm. This beautifully restored property abounds with its own history, as reflected by the many skiing photos displayed on the walls. The owners tastefully chose furnishings to reflect a time they want you to experience. Everything is sparkling clean, warm, and cozy. We had so much fun cooking in the gorgeous retro kitchen. If ever in the area again, we would absolutely stay here.Thankyou Marianne and Michael
5.0 / 10.0·Oct 2020
Cannot say enough about this property So clean and comfortable. The owners very nice even left a little something (maple syrup and King Arthur pancake mix. I would definitely like to visit again and will be recommend this beautiful cottage to others!

$$$$
vrbo logo

FAQs

Is parking included with this cottage?

Parking is not specified as an available amenity at Historic Ski Lodge on 112-Acre Vineyard. For more information, we encourage you to contact the property about where to park.

Is there a pool at this cottage?

We didn’t find pool listed as an amenity for this cottage. It may be worth double checking if a pool is important for your stay.

Is Historic Ski Lodge on 112-Acre Vineyard pet friendly?

Unfortunately, this cottage is not pet-friendly. Try searching again and filter for "Pets Allowed"


Explore similar stays in Woodstock

Explore all stays