
Vacation rentals in Rutland
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Top-rated vacation rentals in Rutland
Guests agree: these stays are highly rated for location, cleanliness, and more.

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.

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.

Cozy Contemporary Downtown Texaco
Stay with us if you’d like to be in the center of downtown Castleton. Stores, restaurants, the college and hike/bike rail trail are an easy walk. This is a very convenient location. We are also a short 30-40 minute drive to Pico and Killington ski areas. Five minutes to Lake Bomoseen. Recently updated, heat and AC, full bath, Wi-Fi, Qled tv, a comfortable king sized memory foam bed, a complete kitchenette. Reserved parking adjacent to entry. Everything you need for an overnight or longer stay

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.

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.

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

Killington Retreat | Deck-Fire Pit-Mountain Views!
Welcome to your new Vermont escape! This custom-built 2BR/1BA pet and smoke free home is nestled in the foothills of the green mountains. Our home sits on a 14 acre lot and is close to hiking, skiing, a horse farm, lakes and Rutland (10 mins). You will love the woodwork, luxury white bedding, floor-to-ceiling windows, massive sunny deck, and peace and quiet. There is plenty of space for family memory making, your peaceful mountain retreat awaits!

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.

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.

Cozy Poultney Village Apartment
I enjoy booking my two-story in-law apartment with a private entrance, which is attached to my 1850 Poultney Village home. I am located a block from Main Street with shops, books, and eateries. I am in the lakes region of Vermont, close to both Lake St. Catherine and Lake Bomoseen. Killington is 35 miles away. We am also located a mile from the NY border and the entrance to Lake George and the Adirondacks.

Castleton Cottage
This is a newly renovated first floor one bedroom apartment. It has all the amenities of home including a walk-in shower, full kitchen, and a pull-out sofa. It is within walking distance of Lake Bomoseen and its many amenities, including boat rentals and creemees. This is a non-smoking unit. Please let us know if you have any questions.

Log Cabin Getaway near Middlebury and Green Mtns
Located at the junction of the Green Mountains and the Champlain Valley, this quiet space sits on 70 forested acres. Enjoy nature in this free-standing secluded space and discover what Addison County has to offer from an easy to access location.
Popular amenities for Rutland vacation rentals
Other great vacation rentals in Rutland

Nice, Large Modern Apartment

Cozy Slopeside Studio at Pico

Scenic Vermont Green Mountain Retreat

Cook's Nook

Dream Catcher Farm

Spacious Ski Chalet Near Killington w/ Pool Table

Kingsley Homestead

*Pet Friendly* The Madden Mountain Home
When is the best time to visit Rutland?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | R3,234 ZAR | R3,217 ZAR | R2,999 ZAR | R2,547 ZAR | R2,647 ZAR | R2,496 ZAR | R2,513 ZAR | R2,513 ZAR | R2,597 ZAR | R2,748 ZAR | R2,681 ZAR | R3,066 ZAR |
| Avg. temp | -7°C | -6°C | 0°C | 7°C | 14°C | 18°C | 21°C | 20°C | 15°C | 9°C | 3°C | -3°C |
Frequently Asked Questions
Are there pet-friendly vacation rentals in Rutland?
Four-legged friends are welcome in Rutland. Choose from more than 40 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 $60 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there family-friendly apartment rentals in Rutland?
Rutland has more than 20 family-friendly apartment rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
Do house rentals in Rutland have wifi?
Absolutely! We offer over 50 house rentals with wifi in Rutland. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Rutland have air conditioning?
Absolutely! We offer over 40 house rentals with air conditioning in Rutland. Enjoy a tailored experience with all the comforts you desire.
Quick stats about vacation rentals in Rutland

Total vacation rentals
Explore 120 vacation rentals in Rutland

Nightly prices starting at
Rutland vacation rentals start at R838 ZAR per night before taxes and fees

Verified guest reviews
Over 6,230 verified reviews to help you choose

Family-friendly vacation rentals
80 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 40 rentals that welcome pets

Rentals with dedicated workspaces
60 properties have a dedicated workspace

Wi-Fi availability
120 of Rutland vacation rentals include wi-fi access

Popular amenities for guests
Guests love Gym, BBQ grill, and Laptop-friendly workspace across Rutland rentals

4.9 Average rating
Rutland stays are highly rated by guests—averaging 4.9 out of 5!
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