Vacation rentals in Rutland County

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Top-rated vacation rentals in Rutland County

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favorite

Condo in Killington

4.95 out of 5 average rating, 124 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

Aug 25 – Sep 1

G$20,858 GYD per night
Guest favorite

Tiny home in Pittsford

4.96 out of 5 average rating, 154 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.

Jun 2 – 9

G$25,026 GYD per night
Guest favorite

Guest suite in Castleton

4.98 out of 5 average rating, 111 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.

Aug 16 – 23

G$24,711 GYD per night

Popular amenities for Rutland County vacation rentals

Other great vacation rentals in Rutland County

Guest favorite

Home in Granville

4.85 out of 5 average rating, 149 reviews

Home by the Mettowee River- Simply the best!

Aug 14 – 21

G$20,451 GYD per night
Superhost

Bungalow in Castleton

4.81 out of 5 average rating, 299 reviews

Lake Bomoseen Bungalow

Oct 8 – 15

G$23,663 GYD per night
Superhost

Apartment in Rutland

4.88 out of 5 average rating, 145 reviews

Zen Studio

Jul 6 – 13

G$25,923 GYD per night
Guest favorite

Apartment in Fair Haven

4.85 out of 5 average rating, 152 reviews

Spacious One Bedroom - Walk To Town, Restaurants

Nov 15 – 22

G$23,889 GYD per night
Guest favorite

Apartment in Pittsford

4.99 out of 5 average rating, 116 reviews

Waterfront cottage walk-out suite.

Jun 24 – Jul 1

G$21,402 GYD per night
Guest favorite

Cottage in Brandon

4.91 out of 5 average rating, 264 reviews

Henrietta’s Hideaway-Walk Downtown!

Jun 25 – Jul 2

G$19,281 GYD per night
Guest favorite

Apartment in Chittenden

5.0 out of 5 average rating, 222 reviews

Vermont Country Suite

Nov 19 – 26

G$30,327 GYD per night
Guest favorite

Condo in Ludlow

4.92 out of 5 average rating, 118 reviews

Okemo Ski-in/Ski-out, Steps to lift Condo

Aug 7 – 14

G$21,095 GYD per night
Guest favorite

Apartment in Clarendon

4.91 out of 5 average rating, 129 reviews

Vermont Horse Farm

Oct 25 – Nov 1

G$21,247 GYD per night
Guest favorite

Cottage in Whitehall

4.99 out of 5 average rating, 160 reviews

Hillside Cottage @ The Mettawee Retreat

Nov 28 – Dec 5

G$32,179 GYD per night
Guest favorite

Castle in Clarendon

4.98 out of 5 average rating, 433 reviews

Kingsley Grist Mill, Covered Bridge and Waterfall.

Nov 18 – 25

G$82,600 GYD per night
Guest favorite

Home in Rutland

4.87 out of 5 average rating, 75 reviews

Lovely 2-Bedroom on 25 acres

May 12 – 19

G$19,554 GYD per night

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