Holiday rentals in Middletown Springs

East Cabin

The East Cabin is quietly tucked between the Green Mountains of VT and the Adirondacks of NY. Soak up the morning sun on your private stone patio while mother nature comes to life on the pond and fields. Take a day trip to beautiful Lake George or Historic Saratoga Springs. Grill steaks on the BBQ and eat S’mores by the campfire at night. Farm fresh products for purchase at our farm store, including our own pasture raised beef. We also have the West Cabin available for your family and friends.

Bright & Cheery 3 bedroom home w/ WiFi & laundry.

Bright, cheery, clean, and nicely updated house located just outside of a classic VT town in the middle of farm country. The entire house is yours w/ 3 bedrooms that comfortably sleep up to 7, full kitchen, washer-dryer, high speed WiFi, 55” TV, and plenty of parking. Located w/in 45minutes of 3 major Ski Slopes and just a few minutes from multiple large lakes with tons of fishing, swimming, and hiking. The area has restaurants, diners, bars, and unique Vermont stores for you to explore.

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.

Vermont Lake House

Create memories with the entire family at this lake house. It is situated on Lilly Pond which connects to Lake St. Catherine. This house has 4 bedrooms, a game room, an extra tv room, 2 full bathrooms and an outdoor shower. This is a nature enthusiasts dream with hiking, boating, kayaking, skiing, fishing and hunting all at your fingertips! After a day of adventures, kick back and relax while enjoying the picturesque views of the water. There is something for everyone here in all 4 seasons

Chalet on a Hill w/ Mountain & Lake View, Hot Tub

A beautiful chalet situated between mountains and Lake St Catherine. Whether on the deck or inside the house, you can enjoy the tranquil and serene view of the mountains and the lakes. At over 3000 sq ft, the house offers multiple gathering areas, including separate living room(s), a sociable kitchen, a pool table, and a bar. A perfect home for a retreat. Located less than 10 mins from Lake St Catherine Park and country club and many hiking and mt-biking options for the active guests.

Waterfront Vermont Lake House w/ Panoramic Sauna

Waterfront on Lake St. Catherine, with almost 100ft of private lake frontage and a view that's hard to beat. Watch the sunrise from the deck or from inside our new panoramic barrel sauna. Explore the lake by kayak or canoe — both included for guests. Keep an eye out for both bald eagles and loons. There's also a fire pit for evening s'mores — firewood included as well. Great for families — we've got a crib, a bunk room for the kids, and a bookshelf of board games for those rainy days.

Off-Grid Meadow Cabin Glamping Retreat

Escape the hustle and bustle and immerse yourself in the tranquility of nature with a unique glamping experience. All the comforts of home but with no WiFi or electricity! Enjoy a short hike up to the cabin where you will find a cozy queen-sized bed inside a well-equipped, converted 1800’s corn barn, complete with an outdoor kitchen and breathtaking views. Step back in time as you experience our clean and well maintained outhouse/privy. We are minutes from hiking and biking trails!

Tiny Cabin on the Slate Valley Trails

Escape to a peaceful woodland getaway on the Slate Valley Trails. This cozy cabin is the perfect basecamp for outdoor adventure or a quiet VT retreat. Surrounded by forest & nature, the cabin offers rustic charm. Step outside & be instantly connected to biking, hiking, and nature trails. Spend your days exploring & evenings relaxing by the fire or watching the stars through the trees. Perfect for couples, solo adventurers, or small groups looking to explore Vermont’s natural beauty.

Cozy Home in Poultney, Vermont.

If you are looking for a cozy spot to relax in a small town, with fast internet and easy access to lots of fun activities, this house is it! On the main floor of the house, there is an open layout that includes a library, a small bar, a dining room, a kitchen, a bathroom, and two bedrooms. Downstairs, there is a finished basement that includes a large family area with a huge couch (perfect for movies), a workspace, and a laundry space. Private parking and lots of outdoor space.

Relaxing Lakeside Cottage w/ Dock + EV charger

Retreat to our tranquil lake cottage on the south end of Lake St Catherine. This cozy, peaceful home is right on the water with a small dock and a smokeless fire pit in the backyard. It has an EV charger, Wi-Fi, well-equipped kitchen (sharp knives, high end coffee setup), natural fiber linens and towels, and is walking distance to the charming Wells Country Store. Also close to Slate Valley Trails, Vermont State University Castleton, and Saratoga Performing Arts Center (SPAC).

Charming Vermont Schoolhouse

Kick back and relax in this calm, stylish space. A beautifully restored schoolhouse circa 1860 welcomes you. Situated on a quiet country road this adorable home on one wooded acre has lovely mountain views and a peaceful setting. Nearby you will find skiing, hiking trails and quaint Vermont towns with shops and restaurants. Manchester and Rutland are 30 min. drives, Dorset is just 20 min. Granville NY has a large grocery store and other shops and is only a 15 min. drive.

Kingsley Grist Mill Waterfall & Private Beach OMG

One of the "World's Most Amazing Vacation Rentals " as seen on the exciting NetFlix series, s.2, ep.7 and on HGTV's "You Live in What?, s.2, ep.1. Join us this season for the romance, the history, the breakfast, the natural mineral spring tap water, the concert, the rafting, the architecture and the legacy of the KGM, Vermont's Wright-esque falling water masterpiece. No cleaning fees added. Come make history with us ! Near Killington & Okemo Mtns.