Holiday rentals in Rupert

Elegant & Rustic VT Cabin - A Peaceful Getaway.

Nestled on 10 hillside acres just outside the small town of West Rupert, our cabin offers a relaxing "get-away-from-it-all," yet is convenient to all that southern VT and eastern NY has to offer. Perfect for a romantic weekend with a special someone, a relaxing country vacation with family, or a fun retreat with good friends. 3 BRs (plus sleeping loft) and full bath. Hike, bike, ski, golf, fish, shop, swim, dine, antique, explore, etc...or just relax and do nothing. Make yourself at home!

Waterfront Vermont Lake House w/ Panoramic Sauna

We invite you to come stay and experience all of the beauty that Vermont has to offer at Lake St. Catherine. Located on the west side of the lake off a quiet private drive with almost 100ft of lake frontage, there are few spots with a better view. Watch the sun rise each morning from either our private decks. Explore the lake by canoe or kayak; both available for our guests. If the dates you're looking for are booked, message us for availability at our second location! Follow us @vtlakehouse

Vermont barn apartment

The Barn Apartment at Sykes Hollow Farm is in the gorgeous Mettowee Valley with 4 friendly horses, entertaining chickens, mountain views and a host who cares about you. The farm is a quiet, private, peaceful place with 30 acres to roam, but still close to Dorset and Manchester. Fields, mountains and a pond are all here. Good for couples and solo travelers who want an amazingly beautiful setting. This listing is more than a rental... it's an entire farm. Powered by solar to help the planet!

Moon Valley Country Retreat no clean fee pets yes

Unique centrally located, peaceful country chalet between the Adirondack and Green Mountains on 60 acres. Starlink available if your phone doesn't work here. Near Lk George, Lk Champlain, & VT. Hike, fish, swim nearby. Air conditioners on the main floor for the summer months. Our 9120 watt solar array powers our property. During the cold months enjoy the wood stove. All wheel drive a must in winter. We have a spacious deck by the shared pool, pergola, and a shady deck by the stream.

The Hygge Loft- mid-mod cabin on 70 forested acres

The Hygge Loft: a midcentury modern-designed cabin nestled among 70 acres of privately-owned forest with rivers & hiking trails. Enjoy sipping an espresso or wine while listening to vinyl records, cozied up by the wood-burning fireplace. Take a walk in the forest to the river or stargaze by the firepit on the private deck. Indulge in a luxurious bath or snuggle up in the ultra comfy king-size bed with views of treetops and sky all around. It’s the kind of place you’ll never want to leave!

Big Green Barn - Manchester Village Vermont

Unique Vermont Barn Experience! 1880s restored barn on 2 acres in Manchester Village across from Southern Vermont Arts Center. Converted to a photo studio in 2004 when we moved from NY; spacious, comfortable, solar-powered, approx. 1 mile to Main St. (town roads, no sidewalk), close to shopping, restaurants, golf, hiking, skiing, etc. Beautiful views, Mount Equinox front, the Green Mountains back. No pets. Not suitable for children under 12. (License number MRT-10126712)

The Smithy Cottage at Consider Bardwell Farm

The historic “Smithy" at Consider Bardwell Farm is the original building used for blacksmithing by Consider Bardwell, himself, in the 1800s. Complete with brand-new, architect-designed kitchen and bathroom, wood-burning fireplace, and stone patio for outdoor grilling and dining, the Smithy is beautiful inside and out. Enjoy meeting our goats and all the local goodies and products that we can stock in your cottage.

Cozy Poultney Village Apartment

I enjoy booking my two-story in-law apartment with a private entrance, which is attached to my 1850 Poultney Village home. I am located a block from Main Street with shops, books, and eateries. I am in the lakes region of Vermont, close to both Lake St. Catherine and Lake Bomoseen. Killington is 35 miles away. We am also located a mile from the NY border and the entrance to Lake George and the Adirondacks.

Suite on Salem

Keep it simple at this peaceful and centrally-located place. Walking distance to Salem Central, Fort Salem Theater, the Historic Salem Courthouse, Jacko's, Salem Art Work, On a Limb Bakery, and more. Come stay in our secure 2-room suite plus bathroom with a separate entrance uniquely filled with local art and antiques. Includes cube-sized refrigerator, coffee maker, and microwave for use.

White Doe Farm•Lovingly restored Antique Farm Home

Built circa 1860, our Rupert, VT farmhouse has been fully renovated for modern comfort while still retaining original rustic touches like original hardwood floors, a Rumford fireplace, and an antique wood-burning stove. We'd love to host your next family gathering, romantic getaway, or solo retreat! Minutes to Dorset, and Manchester. Micro-Wedding inquiries welcome!

Vermont Farm Schoolhouse w/ Hot Tub, Sauna & Views

Escape to our historic schoolhouse on a 250-acre regenerative farm, where Green Mountain views meet modern comfort. Unwind in your private hot tub and barrel sauna after exploring farm trails, then fall asleep to the gentle sounds of sheep grazing in the pastures below. This is Vermont at its most authentic—working farm life with all the luxury.

Hilltop Country Views Studio Apartment

Enjoy a relaxing stay in the country. Easy access to Vermont & Saratoga. Eat local produce. Fresh eggs, bread and butter or oatmeal for your first breakfast, coffee and tea provided. Go shop, ski, hike or stay put & enjoy a good book! (After you're confirmed, please let us know if you're vegan, and or glucose or lactose intolerant.)