Holiday rentals in Rutland

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Top-rated holiday rentals in Rutland

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Guest favourite

Tiny home in Clarendon

4.88 out of 5 average rating, 173 reviews

Secluded tiny house resort - DOG FRIENDLY

New tiny house, never lived in, but made to be comfortable. All amenities included: Air-condition, heat, WiFi, TV with cable, shower, tub, dry toilet, small full loft bed and full size couch futon, fire pit, river for swimming or fishing right out the door, small refrigerator, microwave, hot plate, toaster.ear three ski resorts (Killington, Okemo, Pico), Appalachian Long Trail two miles away, swinging bridge on trail beginning, White Rock hiking, lakes near for paddle boarding. Hot tub shared.

21–28 Jun

$127 SGD per night

Guest favourite

Home in Rutland

4.81 out of 5 average rating, 291 reviews

Home Sweet Home

Single family house within walking distance of downtown Rutland. Many restaurants, bars, movies, bowling, farmer's market, etc to do. 15-20 minute drive to Pico and Killington. 30 minutes to Okemo. Mountain bike parks near by- Pine Hill, Killington and Okemo. Adventure park at Killington. 4 bedrooms, 1.5 baths. House sleeps 8+comfortably. Room for more if needed. Keurig coffee maker in kitchen, microwave, toaster, crock pot. Kitchen is fully furnished. AC units on first floor and second.

28 Sep – 5 Oct

$193 SGD per night

Guest favourite

Apartment in Killington

4.95 out of 5 average rating, 128 reviews

🎿Cozy Fireplace Condo-Mins. to Everything 🚵

Seeking Adventure? This end unit garden level condo is 6 minutes to Killington AND Pico! Quick access to the Appalachian Trail to ATV, mountain bike, hike, and swim. Relaxing? Work remotely with fast Wi-Fi, hang on the porch swing, or unwind in front of the wood fireplace. Hop in the power adjustable king bed, pull the darkening shades, and turn on the sound machine for restful sleep so you can wake up and do it again! A portion of each stay is donated to local VT nonprofits

6–13 Aug

$136 SGD per night

Guest favourite

Tiny home in Pittsford

4.96 out of 5 average rating, 155 reviews

Charming tiny house with great VT location!

Curious about tiny home living!? This newly constructed 180 sq ft. house will let you experience comfort in charming farmhouse/cottage style. (Shiplap walls anyone?) Only 25 min to Killington, and 12 min from Mtn Top Inn, Downtown Rutland, or Brandon VT makes the location very convenient. Situated on over 2 acres of private back yard, overlooking beautiful Sugar Hollow Brook in the heart of Pittsford, Vermont. Walking distance to village general store, library and the Pittsford trail system.

30 Apr – 7 May

$163 SGD per night

Guest favourite

Guest suite in Castleton

4.98 out of 5 average rating, 118 reviews

Mi Casa es su Casa!

Relax in this refurbished quiet Lake view rental. Minutes from Lake Bomoseen/Crystal Beach. Large family room, Cast iron wood-stove. Wall of windows w/lake views. 65" 4K TV, surround sound system. Wi-Fi access. Galley kitchen includes range, microwave, Keurig, fridge & wine cooler. Spacious bedroom, queen size bed w/ heated mattress pad. Lots of storage. Full bathroom. Private deck w/Adirondack chairs. Kayaks & boat launch. 25 min to Rutland, 35 min to Pico & 47 min Killington Ski Resorts.

16–23 Oct

$155 SGD per night

Guest favourite

Flat in Middletown Springs

4.88 out of 5 average rating, 204 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.

10–17 Jun

$96 SGD per night

Guest favourite

Guest house in Wallingford

4.98 out of 5 average rating, 586 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!

22–29 Nov

$190 SGD per night

Guest favourite

Flat in Clarendon

4.92 out of 5 average rating, 131 reviews

Vermont Horse Farm

Enjoy a morning cup of coffee on the patio overlooking the horse pastures or an evening by a fire under the gazebo with a fire pit on this idyllic Vermont horse farm with glorious views. Close to many activities, such as hiking, skiing and swimming. Scenic retreat on a family owned and working farm. Here we have horses, donkey, chickens, goats, and of course our dogs and cats. There is a short hiking trail with beautiful views and a picnic table by the stream.

14–21 Nov

$139 SGD per night

Guest favourite

Cabin in Fair Haven

4.97 out of 5 average rating, 152 reviews

Private and cozy cabin with Lake Bomoseen views!

Secluded yet only a few minutes from all amenities with Wifi! Close to Bomoseen State Park, Glen Lake, boat launches, and stores! Perfect place to stay if you don't want to camp with the rest of your group at the state park, overflow from a place on the lake, visiting the college, or just a beautiful get away. Large deck to enjoy the views, screen porch, fireplace, even a short hiking trail around the property! Two well behaved dogs ok for small cleaning fee.

26 Oct – 2 Nov

$189 SGD per night

Guest favourite

Guest house in Castleton

4.97 out of 5 average rating, 233 reviews

Bomoseen Bungalow

Located near Lake Bomoseen and Castleton University. This is a charming upstairs apartment in a quiet, residential neighborhood. Walking distance to boat rentals and to a local country store. This apartment provides you with a cozy stay - a bedroom with a queen size bed, sofa bed, and air mattress. There is Roku television, a heat pump for air conditioning or heat, Keurig coffee maker, and more. This is a non smoking unit.

10–17 Oct

$119 SGD per night

Guest favourite

Flat in Poultney

4.94 out of 5 average rating, 306 reviews

Cozy Poultney Village Apartment

We enjoy booking our two-story in-law apartment with a private entrance that is attached to our 1850 Poultney Village home. We are located a block away 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.

24 Feb – 3 Mar

$109 SGD per night

Guest favourite

Flat in Rutland

4.96 out of 5 average rating, 522 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.

4–11 Jun

$135 SGD per night