The Sunset Inn: Ski Okemo, Walk to Town, 4 Beds/4 Baths | House in Cavendish, VT

Enjoy a stylish, vintage experience at this centrally-located post and beam home, built in 1787 and now owned by lifelong best friends, Ashleigh and Sophia. Walk to park, brewery, bakery, restaurants and Singleton's: the best Vermont market ever. Just 5 minutes to bustling Ludlow Village, 10 Minutes to Okemo Mountain, 30 minutes to Killington and Woodstock, 1 hour to Mt. Snow, 3 hours off the Bridgeport Ferry.
The space
This incredible home was built by Captain Leonard Proctor, 2nd Lieutenant in the Revolutionary War circa 1787, and named the “Sunset Tavern." Current owners and lifelong best friends, Ashleigh and Sophia renamed this gem, "The Sunset Inn."
Captain Proctor, originally from Massachusetts, moved to Cavendish, Vermont after the Revolution. In the unbroken forest near Cavendish, he founded Proctorsville. He and his wife, Mary Keep Proctor, lived in this home for over 30 years. Their youngest son, John Proctor, also lived here with his family. In the later years, the Jenny family lived here for many years: which is why this home's adjoined one-bedroom vacation rental is named, “The Jenny House.”
Interestingly enough, at one time the home had a glove factory attached to the back. This very special post and beam home is standing stronger than ever. It is famous for its fancy hand-carved decorations around the roofline, on the corner posts and around the center doorway. Additionally, the original fan window is still in operation on the third floor. It’s a special feeling to glance over at that window, wondering about those in history who have done the same.
Although our home has lived quite a long life, it has been thoughtfully and cosmetically updated with glowing pride of ownership over the years; most recently renovated by a local builder and Ludlow-based interior designer. The Sunset Inn features custom walnut cabinetry, Vermont Danby marble kitchen island and master bath, six decorative fireplaces, 100% high thread count cotton bedding, and so much more.
We are thrilled to be the rightful owners of such a gorgeous piece of history. The coziness and good energy is palpable and our children, family and friends are so excited to be able to create memories here; and we are just as excited to be able to share this home’s vintage beauty with our guests too! You won’t know where to look first, as there’s so much genuine, historic beauty to be absorbed. Come experience a true, awe-inspiring visit that will leaving you wanting more exposed beams and wide planks wood floors in your life — you’ll just have to come back again and again!
Guest access
You will have full access to the house except for half of the first floor which is closed off as our one-bedroom “Jenny House” is apartment. This apartment has a separate entrance on the back deck. There are absolutely no shared spaces between the guests inside the house. The back deck is separated into two sections: one side for The Jenny House guests and one side for The Sunset Inn guests. Technically it’s shared, but there’s a divider to delegate private spaces: * think hotel room balcony * … even though it’s a deck :) The backyard area and fire pit are reserved solely for our Sunset Inn guests.
Other things to note
A few important things to note:
1. This is a multi-family home comprised of The Sunset Inn and The Jenny House. The Jenny House is a one bedroom apartment with a private entrance from the back deck. This apartment is half of the first floor of the home. There is a separate Airbnb listing for The Jenny House -- you are welcome to book if you want even more space - The Jenny House + The Sunset Inn would be a total of approx. 4,000 sq. ft. and an interior door can be arranged to be accessed to connect the two, for your stay.
The Sunset Inn has a private entrance on the back deck, as well as the front door. There are absolutely NO shared spaces between the Jenny House and Sunset Inn guests except for splitting deck space (as described in the Guest Access section above) and sharing a driveway. The Sunset Inn guests have access to enjoy the backyard and fire pit, while the Jenny House guests do not. Given the fact that you may be enjoying our home at the same time as another small group (Jenny House has a max. occupancy of 4) we ask everyone to remain respectful of neighboring guests, at all times. We ask that you do not block in any other guest cars in the driveway; we have quiet hours between 10pm and 8am; absolutely no parties; pets or smoking of any kind. We have stayed in our main home, The Sunset Inn, at the same time as hosting guests in The Jenny House and it’s been absolutely perfect. There should not be any issues and there should be amazing memories made for all!
2. The Sunset Inn's first floor King Bedroom is a mirror image of The Jenny House. This can be utilized as a suite for a group of guests within your party. The first floor suite in addition to the King Bed, has a full bathroom, kitchenette, and twin pull out sofa in a open living area. If guests are using this bedroom as a private suite, we recommend your fellow guests come and go through our front door as the back door would require passing through this bedroom. However, when we use the house -- we use both doors and don't mind the pass through -- we are all friends at The Sunset Inn!
3. We provide 100% cotton linens and towels, Pantene shampoo and conditioner, Dove body wash, ground coffee, pods and green tea bags. We have Tide laundry detergent for our washing machine if you choose to do any loads during your stay, ample toilet paper and paper towels. Spices, basic cooking oils and a fully stocked kitchen including all-clad pots and pans.
4. We have three smart TVs with complimentary Sunset Inn account access to Netflix, Hulu Live, ESPN+ and Disney+. We have many family-friendly board games, PS5 console with a Madden 23, NHL and Sonic games (bring your own favorites too, if you'd like!), and a Bluetooth Sonos speaker.
5. For the little ones, we have toddler toys, booster seat, pack and play with sheets, stand up baby bouncer seat, toddler bed rail, baby monitor and sound machines.
6. Each bedroom has a portable fan, velvet hangers and a hamper. We also offer a full-size air mattress and twin sofa pull out couch with extra blankets in the first floor master bedroom.
We want you to feel right at home!

The Sunset Inn: Ski Okemo, Walk to Town, 4 Beds/4 Baths is located in Proctorsville. The Sunset Inn: Ski Okemo, Walk to Town, 4 Beds/4 Baths provides accommodation, featuring Child Friendly, among other amenities. This House features Child Friendly, to make your stay a comfortable one.

The Sunset Inn: Ski Okemo, Walk to Town, 4 Beds/4 Baths has 4 Bedrooms , 4 Bathrooms, and max occupancy of 12 people. The minimum rental for this property is 1 nights, but this can change depending on the season you plan on staying. Previous guests have given good rated it, and VRBO labeled it a top-rated House because of the excellent services rendered by the owner or manager of this House, and has consistently provided great experiences for their guests. Most families or guests that use it recommend it to their friends and some of them are repeat guests. House has a friendly neighborhood, and the Proctorsville has interesting places to visit. If you want to learn more about the House in Proctorsville, such as places to visit and things to do nearby, you can check below to learn more.