Rutland vacation rentals

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Top-rated vacation rentals in Rutland

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

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Guest favorite

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.

Aug 2 – 9

G$20,603 GYD per night

Guest favorite

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.

Jun 14 – 21

G$26,975 GYD per night

Guest favorite

Condo in Killington

4.95 out of 5 average rating, 129 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

Jul 22 – 29

G$26,553 GYD per night

Guest favorite

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.

Jul 2 – 9

G$25,845 GYD per night

Guest favorite

Guest suite in Castleton

4.98 out of 5 average rating, 119 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.

Apr 4 – 11

G$23,280 GYD per night

Guest favorite

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.

Jun 17 – 24

G$14,979 GYD per night

Guest favorite

Guesthouse in Wallingford

4.98 out of 5 average rating, 588 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!

Dec 19 – 26

G$30,184 GYD per night

Guest favorite

Apartment in Pittsford

4.99 out of 5 average rating, 117 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 in the warmer weather. 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 wheel or 4 wheel drive vehicles with good all season or snow tires required in the winter.

May 28 – Jun 4

G$22,489 GYD per night

Guest favorite

Apartment in Clarendon

4.92 out of 5 average rating, 132 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.

Jul 5 – 12

G$20,808 GYD per night

Guest favorite

Cabin in Rochester

4.95 out of 5 average rating, 392 reviews

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

You’ll love our place because of the high ceilings, the rural location, the coziness and its sense of place in nature. Our place is great for couples and solo adventurers who enjoy their privacy, who want to get away from it all but be close enough to a more 'country-urban' vibe. There is a deck for sunning, quite a large front and back yard. A great kitchen for meals at home, a forest to explore and miles of trails to mountain bike or hike.

Nov 23 – 30

G$29,085 GYD per night

Guest favorite

Guesthouse in Castleton

4.97 out of 5 average rating, 235 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.

Apr 10 – 17

G$18,291 GYD per night

Guest favorite

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.

Sep 9 – 16

G$16,755 GYD per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Rutland vacation rentals

Gym

BBQ grill

Laptop-friendly workspace

Wifi

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 vacation rentals in Rutland

Guest favorite

Cabin in Fair Haven

4.97 out of 5 average rating, 152 reviews

Private and cozy cabin with Lake Bomoseen views!

May 8 – 15

G$28,935 GYD per night

Guest favorite

Condo in Killington

4.94 out of 5 average rating, 152 reviews

Bright Ski on/off Condo Full Kitchen-Free Shuttle!

Jun 1 – 8

G$20,668 GYD per night

Guest favorite

Guest suite in Shrewsbury

4.91 out of 5 average rating, 264 reviews

Valley View

Feb 19 – 26

G$19,178 GYD per night

Guest favorite

Apartment in Rutland

4.86 out of 5 average rating, 103 reviews

Charlie's Place

Jul 1 – 8

G$21,841 GYD per night

Guest favorite

Apartment in Chittenden

5.0 out of 5 average rating, 223 reviews

Vermont Country Suite

Feb 9 – 16

G$30,199 GYD per night

Guest favorite

Condo in Killington

4.89 out of 5 average rating, 203 reviews

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

Jul 9 – 16

G$20,758 GYD per night

Guest favorite

Cabin in Granville

4.98 out of 5 average rating, 133 reviews

Quaint log cabin nestled in the woods

Jan 18 – 25

G$24,304 GYD per night

Guest favorite

Castle in Clarendon

4.98 out of 5 average rating, 433 reviews

Kingsley Grist Mill, Covered Bridge and Waterfall.

Sep 12 – 19

G$81,354 GYD per night

Show all

Other great vacation rentals in Rutland

Guest favorite

Cottage in Windsor

4.97 out of 5 average rating, 318 reviews

Ogden's Mill Farm

Apr 22 – 29

G$28,783 GYD per night

Guest favorite

Cottage in Brandon

4.91 out of 5 average rating, 266 reviews

Henrietta’s Hideaway-Walk Downtown!

Dec 6 – 13

G$21,709 GYD per night

Guest favorite

Guest suite in Weybridge

4.99 out of 5 average rating, 233 reviews

Beautiful 1 Bedroom Suite with private entrance

Dec 10 – 17

G$22,224 GYD per night

Guest favorite

Apartment in Hancock

4.95 out of 5 average rating, 146 reviews

Suite in the Green Mountains

May 24 – 31

G$19,527 GYD per night

Guest favorite

Home in Rutland

5.0 out of 5 average rating, 121 reviews

ONE ROOM SCHOOL HOUSE

Dec 6 – 13

G$48,850 GYD per night

Guest favorite

Apartment in Rutland

4.9 out of 5 average rating, 52 reviews

Cozy apt mins to the mountain

Aug 9 – 16

G$19,693 GYD per night

Superhost

Apartment in Rutland

4.86 out of 5 average rating, 83 reviews

Elm Street House

Aug 4 – 11

G$17,968 GYD per night

Guest favorite

Apartment in Rutland

5.0 out of 5 average rating, 12 reviews

Relaxing in Rutland!

Jun 30 – Jul 7

G$21,051 GYD per night

Show all

Quick stats about vacation rentals in Rutland

Total rentals
120 properties
Wifi availability
120 properties include access to wifi
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

Frequently Asked Questions

Are there pet-friendly vacation rentals in Rutland?
Four-legged friends are welcome in Rutland. Choose from more than 30 vacation rentals for guests traveling with pets.
Are there vacation rentals with a dedicated workspace in Rutland?
Yes! Work meets play with ease at over 60 vacation rentals in Rutland featuring dedicated workspaces. Stay connected and productive in your home away from home.
How much does it cost to stay in apartment rentals in Rutland?
Experience the best of Rutland with our apartment rentals, starting at about $50 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do house rentals in Rutland have a bbq area?
Absolutely! We offer over 10 house rentals with a bbq area in Rutland. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Rutland have wireless internet?
Absolutely! We offer over 50 house rentals with wireless internet in Rutland. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly apartment rentals in Rutland?
Rutland has more than 30 family-friendly apartment rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
Do apartment rentals in Rutland have air conditioning?
Absolutely! We offer over 30 apartment rentals with air conditioning in Rutland. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for Apartment Rentals in Rutland?
Enhance your stay in our Apartment Rentals with the most popular amenities: over 50 homes with wireless internet, over 30 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.

Rutland vacation rentals

Top-rated vacation rentals in Rutland

Vacation rentals for every style

Apartments

Houses

Hotels

Popular amenities for Rutland vacation rentals

Stay near Rutland's top sights

Other great vacation rentals in Rutland

Cabin in Fair Haven

Condo in Killington

Guest suite in Shrewsbury

Apartment in Rutland

Apartment in Chittenden

Condo in Killington

Cabin in Granville

Castle in Clarendon

Other great vacation rentals in Rutland

Cottage in Windsor

Cottage in Brandon

Guest suite in Weybridge

Apartment in Hancock

Home in Rutland

Apartment in Rutland

Apartment in Rutland

Apartment in Rutland

Quick stats about vacation rentals in Rutland

Total rentals

Wifi availability

Rentals with dedicated workspaces

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Frequently Asked Questions

Are there pet-friendly vacation rentals in Rutland?

Are there vacation rentals with a dedicated workspace in Rutland?

How much does it cost to stay in apartment rentals in Rutland?

Do house rentals in Rutland have a bbq area?

Do house rentals in Rutland have wireless internet?

Are there family-friendly apartment rentals in Rutland?

Do apartment rentals in Rutland have air conditioning?

What are the most popular amenities for Apartment Rentals in Rutland?

Destinations to explore