Holiday houses in Rutland

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Top-rated holiday rentals in Rutland

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Guest favourite

Home in Rutland

4.81 out of 5 average rating, 289 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.

14 – 21 Dec

$1,850 AUD total

Guest favourite

Condo 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

25 July – 1 Aug

$1,579 AUD total

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.

11 – 18 June

$1,483 AUD total

Guest favourite

Guest suite in Castleton

4.98 out of 5 average rating, 117 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.

22 – 29 Dec

$1,433 AUD total

Guest favourite

Apartment 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.

27 June – 4 July

$926 AUD total

Guest favourite

Guesthouse in Wallingford

4.98 out of 5 average rating, 585 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!

18 – 25 Nov

$1,649 AUD total

Guest favourite

Cabin in Granville

4.98 out of 5 average rating, 132 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.

2 – 9 Jan

$1,412 AUD total

Guest favourite

Apartment 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.

4 – 11 July

$1,262 AUD total

Guest favourite

Apartment in Clarendon

4.95 out of 5 average rating, 263 reviews

Dog heavenly! Private, beautiful and relaxing.

Bright, secluded, second floor one room suite with private bathroom overlooking Mill River and across a covered bridge. No neighbors visible, but near town. Fly fish in the back yard, sit around the firepit, enjoy fall foliage, and hike and ski. Swinging bridge and Appalachia long trail very nearby. Close to three ski resorts: Killington, Okemo, and Pico. Dogs are welcome and loved, with plenty of room to run. Comfortable queen-sized bed and couch.

$129 AUD per night

Guest favourite

Guesthouse in Castleton

4.97 out of 5 average rating, 231 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.

17 – 24 Oct

$1,073 AUD total

Guest favourite

Apartment 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.

12 – 19 Mar

$952 AUD total

Guest favourite

Apartment 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.

12 – 19 June

$1,175 AUD total

Holiday rentals for every style

Get the amount of space that is right for you

Popular amenities for Rutland holiday rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Stay near Rutland's top sights

Walmart3 locals recommend

Vermont Tap House11 locals recommend

Hannaford Supermarket24 locals recommend

Gill's Delicatessen6 locals recommend

Johnny Boys Pancake House20 locals recommend

ALDI4 locals recommend

Other great holiday rentals in Rutland

Guest favourite

Cabin in Fair Haven

4.97 out of 5 average rating, 151 reviews

Private and cozy cabin with Lake Bomoseen views!

25 Dec – 1 Jan

$1,771 AUD total

Guest favourite

Apartment in Pittsford

4.99 out of 5 average rating, 116 reviews

Waterfront cottage walk-out suite.

4 – 11 June

$1,320 AUD total

Guest favourite

Condo in Killington

4.88 out of 5 average rating, 199 reviews

Killington-Pico ski in/out Studio at base of Pico

26 June – 3 July

$1,433 AUD total

Guest favourite

Apartment in Chittenden

5.0 out of 5 average rating, 222 reviews

Vermont Country Suite

20 – 27 Mar

$1,618 AUD total

Guest favourite

Cabin in West Rutland

4.88 out of 5 average rating, 153 reviews

VT MOUNTAIN LOG CABIN, CLOSE TO KILLINGTON/PICO

29 Oct – 5 Nov

$2,385 AUD total

Guest favourite

Castle in Clarendon

4.98 out of 5 average rating, 433 reviews

Kingsley Grist Mill, Covered Bridge and Waterfall.

12 – 19 Sept

$4,621 AUD total

Guest favourite

Guesthouse in Pawlet

4.91 out of 5 average rating, 282 reviews

Picturesque Cabin on the Mettowee

29 Apr – 6 May

$1,420 AUD total

Guest favourite

Cabin in Rochester

4.95 out of 5 average rating, 389 reviews

Black haus: a hip, cool house hidden in a forest.

11 – 18 Jan

$1,720 AUD total

Show all

Quick stats about holiday rentals in Rutland

Total rentals	120 properties
Wi-Fi availability	120 properties include access to Wi-Fi
Rentals with dedicated workspaces	60 properties have a dedicated workspace
Pet-friendly rentals	30 properties allow pets
Family-friendly rentals	80 properties are a good fit for families
Total number of reviews	4.9K reviews

Holiday houses in Rutland

Top-rated holiday rentals in Rutland

Home in Rutland

Condo in Killington

Tiny home in Pittsford

Guest suite in Castleton

Apartment in Middletown Springs

Guesthouse in Wallingford

Cabin in Granville

Apartment in Clarendon

Apartment in Clarendon

Guesthouse in Castleton

Apartment in Poultney

Apartment in Rutland

Holiday rentals for every style

Houses

Apartments

Hotels

Popular amenities for Rutland holiday rentals

Stay near Rutland's top sights

Other great holiday rentals in Rutland

Cabin in Fair Haven

Apartment in Pittsford

Condo in Killington

Apartment in Chittenden

Cabin in West Rutland

Castle in Clarendon

Guesthouse in Pawlet

Cabin in Rochester

Quick stats about holiday rentals in Rutland

Total rentals

Wi-Fi availability

Rentals with dedicated workspaces

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Destinations to explore