Vacation rentals in Rutland County

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Top-rated vacation rentals in Rutland County

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Guest favorite

An aerial view showcases a large, red two-story building with a metal roof nestled among lush greenery. The property features multiple decks and a private outdoor space. The surrounding landscape provides a serene backdrop of trees and grass, enhancing the natural setting.

Guest suite in Lake Bomoseen

4.96 out of 5 average rating, 205 reviews

My house is your house!

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 w/ surround sound. w/ game hook-up. Wi-Fi. 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. 15 miles to Rutland, 35 min to Pico & 47 min Killington Ski Resorts.

Top guest favorite

The exterior of the suite features a two-story house with blue siding and large windows. A red door provides a focal point. The lawn is adorned with colorful flamingo decorations alongside a landscaped garden, and a gravel path leads to the entrance.

Apartment in Pittsford

4.99 out of 5 average rating, 143 reviews

Waterfront cottage walk-out suite.

Private entrance suite overlooking Burr Pond. Conveniently close to Mountain Top Inn & Resort (3.7 miles), Killington/Pico ski resorts and Rutland. Swim, kayak, bike and hike. Take advantage of more than 12 miles of the Pittsford Trail Network. The serenity of country living coupled with the amenities of Rutland! We’re on a short dirt road off of a steep hill. Front or 4 wheel drive vehicles with good all season or snow tires required in the winter. Not suitable for toddlers or young children.

Guest favorite

A charming tiny house is set against a backdrop of trees, featuring a light exterior with shiplap and a metal skirt. Warm lighting emanates from the front porch lantern, while the entrance is framed by a decorative wreath. A small porch leads to the welcoming entry door.

Tiny home in Pittsford

4.96 out of 5 average rating, 180 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.

Top guest favorite

The image captures a serene lakeside property surrounded by trees. Two private decks are visible alongside the water, with steps leading to the docks. Canoes and kayaks are neatly arranged, enhancing the outdoor experience. The warm glow from the home suggests a welcoming environment.

Home in Poultney

4.93 out of 5 average rating, 337 reviews

Waterfront Vermont Lake House w/ Canoe/Kayak/SUPs

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

Top guest favorite

A cozy living area features a deep leather sofa positioned near a stone fireplace. A large window opens to the balcony, inviting natural light. A TV is mounted above a wooden mantle, and a small table and chair provide a space for work or dining.

Condo in Killington

4.99 out of 5 average rating, 102 reviews

Elegant Alpine Condo *Pool*

Newly renovated 1-bedroom Whiffletree condo with upscale alpine style, minutes from l bike park, adventure center, and golf course. Please note there is no air conditioning, but the cool mountain air and provided fans typically keep the space comfortable. Fully stocked with essentials and includes a locker for your gear. Relax and enjoy the onsite outdoor pool. Easy access to summer fun and scenic Vermont trails. Sleeps up to 4 with a king bed and queen pullout sofa. Killington Reg #007718

Guest favorite

The historic Italianate home features a white exterior, with classic green shutters adorning tall windows. A spacious porch is supported by graceful columns, providing numerous seating options. The surrounding yard displays mature trees, enhancing the charm of the property set against a serene backdrop.

Apartment in Middletown Springs

4.89 out of 5 average rating, 259 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.

Top guest favorite

A charming guesthouse with a red exterior is set against a backdrop of vibrant greenery and colorful flower beds. Various flowers in shades of orange, pink, and purple border the property, while tall trees provide natural shade. The tranquil setting invites relaxation in nature.

Guesthouse in Wallingford

4.98 out of 5 average rating, 704 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!

Top guest favorite

The tiny log cabin is nestled among lush green trees, showcasing a wooden exterior with a sloped roof. A spacious front porch features a swing and seating area, providing a serene view of the surrounding nature.

Cabin in Granville

4.98 out of 5 average rating, 187 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.

Guest favorite

A spacious living room features a comfortable sofa and armchair, enhancing relaxation. A large television is positioned in front, with decorative elements and artwork on the walls. Soft lighting from lamps and windows creates a welcoming ambiance in the well-designed space.

Guest suite in Clarendon

4.95 out of 5 average rating, 172 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

Top guest favorite

The exterior of a renovated one-room schoolhouse is presented, set amidst lush green foliage. A vibrant red door stands out against the white walls, while a well-maintained hedge borders the property. Surrounding trees provide a serene backdrop, creating a peaceful atmosphere.

Home in Rutland

5 out of 5 average rating, 138 reviews

One Room School House. No Cleaning Fees!

Renovated one room school house. Spacious, open space. Music room has been converted into a bedroom. European style kitchen area. High ceilings with fans and air-conditioner. Propane fireplace. Off-street parking. High speed internet and 65 inch Roku TV with surround sound. Three season screened porch. Also, we have recently introduced a NO CLEANING FEE policy as our way of saying "Thank You" for respecting our property and guidelines.

Guest favorite

A vibrant bedroom features floral wallpaper and peach curtains. A spacious bed adorned with colorful pillows is positioned against one wall. Two windows allow natural light to fill the room. The pink door adds a cheerful touch, while a cozy chair is placed nearby.

Apartment in Rutland

4.87 out of 5 average rating, 193 reviews

Baby Queens Barbie-core Studio Apt (dog friendly)

Enjoy a stylish experience at this centrally-located place. This studio apartment is perfect for the solo traveller or couple. The queen bed is super comfy. Brand new and renovated throughout. The kitchen is stocked for basic cooking. I'll make sure there is always coffee and cream for you. Pets are welcome if they do not get up on the furniture. It's easy access to downtown Rutland to enjoy yoga studios, restaurants, and coffee shops.

Top guest favorite

The exterior of a traditional white house features a spacious covered porch lined with wooden railings and supported by columns. Potted plants and hanging baskets add greenery, while the entrance is framed by multiple windows. A gravel driveway leads up to the porch.

Apartment in Rutland

4.96 out of 5 average rating, 618 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, skiing, golf, 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.