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Vacation rentals in Rutland County

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Top-rated vacation rentals in Rutland County

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Bungalow in Castleton

4.79 out of 5 average rating, 320 reviews

Lake Bomoseen Bungalow

My place is nestled on a private road on Lake Bomoseen in beautiful VT. 50 minutes from Killington, Pico, and Okemo Mtns and close to Castleton University. You’ll love the cozy, one room guest cottage that awaits you. Although my house sits between the cottage and the lake front, the bungalow still offers beautiful lake views with a lake front patio area 50 ft down the driveway. Use my kayaks or bring your own, dock space available for small boats. Boat rental available at a local marina.

Cabin in Wells

4.95 out of 5 average rating, 176 reviews

Gatsby's Getaway

Ready to disconnect and recharge? Welcome to Gatsby's Getaway! Watch the sun rise over the Green Mountains and Little Lake from the comfort of your deck. If the weather doesn't agree, enjoy your morning coffee in front of the cozy fireplace in your charming bungalow, complete with cathedral ceilings and sliding glass doors. Close to hiking & biking trails, and many outdoor activities. 10 minutes to nearby Granville, NY or Poultney, VT. While not a 'tiny' house, it is a cozy cabin of 600sqft.

Rental unit in Chittenden

5 out of 5 average rating, 239 reviews

Vermont Country Suite

Located in Chittenden, VT, we are in the heart of the Green Mountains. We are just down the road from the Mountain Top Inn wedding venue and Cross Country Skiing Center. The apartment is an easy 15-20 minute drive to Pico and Killington ski areas. The suite is perfect for winter and summer adventuring or just a quiet get away in Vermont. * We are following the guidelines set up by the W.H. O. and we are leaving a window between reservations to disinfect our suite due to Covid-19.

Rental unit in Middletown Springs

4.89 out of 5 average rating, 235 reviews

Apartment in Vermont Historic Home

This lovely renovated 3-room apartment is attached to our 1885 Vermont italianate home, located is historic Middletown Springs, Vermont. We have been working on restoring this house, listed on Vermont's registry of historic homes, for a dozen years now. The apartment has its own entrance, full kitchen, and one spacious bedroom. The third room is a large sitting room with a shower and closet bath. Enjoy your morning coffee on the front porch, meet our chickens, and explore our garden.

Guesthouse in Wallingford

4.98 out of 5 average rating, 638 reviews

Vermont Home Central to Ski Areas-No Cleaning Fees

Comfortable guesthouse located conveniently on US Route 7 near ski areas. Half hour from Manchester Outlet Stores. Near Long Trail/Appalachian Trail, Weston and Dorset Playhouses and miles of scenic country roads. Close to Elfin Lake and White Rocks National Recreation Area.Great for couples, small families, solo adventurers, and business travelers. Queen size bed and full kitchen. Great for overnight stay or week-long vacation to enjoy the beauty of Vermont. No cleaning fees!

Cabin in West Rutland

4.87 out of 5 average rating, 166 reviews

VT MOUNTAIN LOG CABIN, CLOSE TO KILLINGTON/PICO

REAL VERMONT LOG CABIN ON MOUNTAIN, W/ PINE WOOD WALLS & FURNISHINGS. 16 MILES TO PICO SKI RESORT, JUST A LITTLE FARTHER TO KILLINGTON. PRIVATE SETTING W/ 2 BEDROOMS, 2 FULL BATHS. 1 QUEEN BED, 1 DOUBLE & SINGLE BUNK BED, COUCH AND AIR BED THAT LOOKS/FEELS LIKE A REGULAR BED. HOUSE SLEEPS 6. FIRE PIT & GRILL. GREAT IN FALL FOR LEAF PEEPING. CLOSE TO DINING, MOVIES, SKATING & STORES IN RUTLAND. SEE CHECK IN INSTRUCTIONS FOR CABIN INFO. PLS COMPLETE 1 PAGE CONTRACT PRIOR TO ARRIVAL.

Cabin in Granville

4.98 out of 5 average rating, 158 reviews

Quaint log cabin nestled in the woods

Enjoy a break from the daily grind at this lovely tiny log cabin nestled among beech and ash trees. This tiny cabin provides peace and quiet on nearly 4 wooded acres just minutes from the town of Granville, NY. A full kitchen, living room, one bathroom and a loft bedroom complete with stackable washer/dryer provide a place to relax and soak in nature. The spacious front porch grants a protected outdoor space to watch the wildlife and enjoy the fresh air with your family and pup.

Home in Poultney

4.93 out of 5 average rating, 101 reviews

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.

Guest suite in Clarendon

4.95 out of 5 average rating, 132 reviews

River House Apartment - Dog friendly

Entire downstairs of a house with one double bed. There is nice bathroom with shower. There is a microwave, coffee, massage chair, outdoor grill and picnic table. Internet and cable provided with fire stick for the TV. Fire pit and hot tub are shared by other guests. Up to three and all size dogs or pets are allowed and welcome. The three acres has a lovely place for them to run and has been sprayed for ticks and mosquitos. Please note: key replacement $30 if lost or taken

Home in Clarendon

4.96 out of 5 average rating, 269 reviews

Custom 2BR Vacation Retreat in Killington Valley!

Welcome to your new Vermont escape! This custom-built 2BR/1BA pet and smoke free home is nestled in the foothills of the green mountains. Our home sits on a 14 acre lot and is close to hiking, skiing, a horse farm, lakes and Rutland (10 mins). You will love the woodwork, luxury white bedding, floor-to-ceiling windows, massive sunny deck, and peace and quiet. There is plenty of space for family memory making, your peaceful mountain retreat awaits!

Rental unit in Poultney

4.95 out of 5 average rating, 331 reviews

Cozy Poultney Village Apartment

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

Rental unit in Rutland

4.96 out of 5 average rating, 568 reviews

Your home away from home

Another glorious time of year in Vermont! Our house is close to the mountains (Killington, Pico, Okemo). You'll love our space for its central location to lakes, hiking, restaurants and dining, downtown, art and culture, shopping and medical facilities.This first floor apartment with its home-like atmosphere has a separate entrance. It is good for couples, small families, solo adventurers, and business travelers.

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Adventure-ready homes with après-ski style

Popular amenities for Rutland County vacation rentals

Free parking on premises

Air conditioning

Other great vacation rentals in Rutland County

Home in Rutland

4.8 out of 5 average rating, 323 reviews

Home Sweet Home

Home in Rutland

4.88 out of 5 average rating, 86 reviews

Lovely 2-Bedroom on 25 acres

Rental unit in Wallingford

5 out of 5 average rating, 39 reviews

49 River Street

Cottage in Wells

4.96 out of 5 average rating, 26 reviews

Private cottage - lake and mountain views

Farm stay in Clarendon

5 out of 5 average rating, 51 reviews

Dream Catcher Farm

Tiny home in Rutland

4.97 out of 5 average rating, 39 reviews

Curious Little Cottage

Home in Fair Haven

5 out of 5 average rating, 30 reviews

Snow country guest house

Rental unit in West Rutland

4.87 out of 5 average rating, 60 reviews

Mountain View Apartment

Destinations to explore