Holiday rentals with breakfast in Montgomery

Sunrise/Sunset Tiny House w/ Mountain Views

We are a tiny house rental run by a 7th generation Vermont family. Set on a hillside overlooking rolling farmland & established sugarbush, with views of the green mountains from Mansfield to Elmore, this bright & modern tiny house offers a getaway in the heart of Vermont. Minutes from Green River Reservoir state park & a short drive to Stowe & Smugglers Notch resorts, come experience the semi off-grid tiny house lifestyle with modern amenities & enjoy some of the best views Vermont has to offer.

Very clean and charming 2 BR, close to everything!

Enjoy this newly updated apartment in Winooski, VT (Vermont's Brooklyn). This charming house is one of the original carriage homes in Winooski. Newly converted to a duplex, enjoy this private apartment within walking distance to downtown Winooski's restaurants and bars. Less than 1 mile from the local colleges in Burlington and Colchester, including University of Vermont, St. Michaels College and Champlain College. You have your own private entrance with free parking for 2 cars in the driveway.

Choiniere’s Cozy Cabin

Relax with the whole family & your friends at this peaceful place. The property is located in a secluded, private setting, approximately half a mile off the main road. You'll be surrounded by nature and enjoy a truly tranquil experience. All weekly rentals include a complimentary Local Foods package. Ground Beef & Eggs, Franklin VT Monument Farm VT Milk Pure VT Maple Syrup, Sheldon VT Sartwell Maple BBQ Sauce & Candies, Franklin VT VT Pancake Mix & Blueberries, Franklin VT (when available)

Peaceful Country Cabin

Relax and unwind at this charming country getaway. Located directly on the VAST trail. A short 20 minute drive to Kingdom Trails mountain biking and wonderful dining options in Burke. Shopping and restaurants right in Island Pond are 5 minutes away. Skiing at Burke Mountain is fantastic and only 18 miles away. Enjoy the goats and chickens on site as you take a break from the fast paced life. Handmade goats milk soaps, lotions and other products available on site as well as farm fresh eggs!

Rustic cabin, cedar hot tub, pond, canoes, WIFI

The Osprey cabin at Walker Pond is a new cabin (2021) with a custom cedar hot tub! It is a rustic retreat with plenty of modern convenience and is just 120 feet from Walker Pond. Walker Pond is approximately 20 acres and is home to plenty of wildlife, small fish and birds. You are welcome to enjoy our 40 acres of forest/wetland, go canoeing in one of our canoes, or enjoy the common campfire-flower garden area. The cabin is located just 5 minutes from downtown Newport, very convenient.

Tiny House by Winooski Falls, Vermont River House

River House is across from the Winooski Falls and is part of Burlington's historic mill neighborhood. It's a 10 minute walk to the Winooski Circle which is full of restaurants and activity. Downtown Burlington and Lake Champlain are a 10 min (2 mile) drive away. This unique, arty tiny house features hardwood floors, a small kitchen and bathroom, and a shared outdoor space. There is a queen bed upstairs in the loft and a full sized couch downstairs which can be made up for sleeping.

Stunning Pleasant Valley Home

Stunning Pleasant Valley Home! This modern mountain home is situated on over 12 acres of gorgeous Vermont land and is perfect for your next vacation. The traditional post and beam construction mixed with modern flare is sure to make you feel like you are someplace special. This picturesque property is private with lush landscaping and multiple areas to relax and unwind. Enjoy views from the front porch rockers or of the mountain ranges while sitting on the back veranda.

Tiny House at Camp Comyns

NO check in. Total privacy. Tiny House with a big heart! This magical place is located 3 miles from Waterbury (I-89 exit 10), walking distance to Camel's Hump hiking trails and the Long Trail. Cross Vermont biking, VAST snow mobile trails, kayaking, swimming, fishing, skiing and more. Breathtaking views of mountains, gorgeous foliage. Great restaurants, breweries and live music all within five miles. Plenty of parking. Close to Stowe, Montpelier, and Burlington.

Sherburne Suite

Relax in comfort in Vermont's beautiful North East Kingdom with our indoor suite, a private patio area and a fire pit. You will have close access to outdoor activities at Burke Mountain and Kingdom Trails. We are right across the street from the VAST trail system, boasting more than 100 miles of snow machine trails in Lyndonville alone! For your first day/night, we will provide snacks and farm fresh eggs. Mountain / Gravel Bike instruction/guiding Is available!

Waldhaus - Modern Forest Cabin

Escape to our beautifully designed Vermont cabin, transformed into a modern, cozy, and sun-filled retreat. From the moment you step inside, you'll feel at home in this inviting space. The entire cabin & yard will be yours during your stay. High-speed fiber WiFi keeps you connected and dogs are welcome. We're just 15-20 min from Mad River Glen, Mt. Ellen & Sugarbush. Many restaurants & stores are within 15 min to Waitsfield, 20 min to Waterbury.

1797 Vt Farm House See the Stars!

1797 Vt Farm House sits quiet and serene at the end of a peaceful country road. With no street lights or sounds to mar the night, experience a rare gift of silence. See the Milky Way like never before. Ample room allows your group of up to 10. ( each guest over 4 is $32 per night) You will have the whole place to yourself as a private, peaceful retreat. Yet Burlington, Lake Champlain, and Smuggler's Notch are only 25-30 minutes away!

The North Country Cabin

Nestled between the White Mountains and Vermont’s Northeast Kingdom, North Country Cabin is your perfect basecamp—or quiet escape. Step outside to world-class hiking, biking, and skiing, then unwind back home with a wrap-around porch, vaulted ceilings, and cozy pellet stove. Take in mountain views from the deck, gather around the fire pit, read in the loft, or relax with a movie in the finished basement. You won’t want to leave.