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Holiday houses in Rutland

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Top-rated holiday rentals in Rutland

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

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Top Guest favourite
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
4.97 out of 5 average rating, 236 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 favourite
The exterior of the chalet is shown in twilight, with soft light emanating from a window. The rustic wooden structure features a sloped roof and is surrounded by snow-covered ground and trees in the background.
Guesthouse in Granville
4.91 out of 5 average rating, 952 reviews

Moon Valley Country Retreat no clean fee pets yes

Unique centrally located, peaceful country chalet between the Adirondack and Green Mountains on 60 acres. Starlink available if your phone doesn't work here. Near Lk George, Lk Champlain, & VT. Hike, fish, swim nearby. Air conditioners on the main floor for the summer months. Our 9120 watt solar array powers our property. During the cold months enjoy the wood stove. All wheel drive a must in winter. We have a spacious deck by the shared pool, pergola, and a shady deck by the stream.

Guest favourite
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, 271 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 favourite
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, 192 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 favourite
Home in Clarendon
4.95 out of 5 average rating, 313 reviews

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!

Top Guest favourite
The exterior of the converted schoolhouse is visible, surrounded by a blanket of fresh snow. Snow-covered bushes line the property, and a flag is displayed by the entrance. Leafless trees provide a serene contrast against the winter landscape.
Home in Rutland
5 out of 5 average rating, 145 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.

Top Guest favourite
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, 653 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.

Top Guest favourite
Apartment in Poultney
4.94 out of 5 average rating, 373 reviews

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.

Top Guest favourite
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, 131 reviews

Elegant Alpine Condo

Newly renovated 1-bedroom Whiffletree condo with an upscale alpine feel—just minutes from the slopes, access road, and snow tubing. Fully stocked with essentials and includes a ski locker for your gear. Shuttle in/out service available weekends (Dec–April), or ski home when conditions allow (check Killington trail status). Sleeps up to 4 with a king bed and queen pullout sofa. Killington Reg #007718

Top Guest favourite
Apartment in Castleton
4.97 out of 5 average rating, 111 reviews

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.

Guest favourite
An exterior view of a two-story building is presented, showcasing a white facade with architectural detailing. A gentle ramp leads to a central entrance, flanked by manicured shrubs. Ample green yard space surrounds the structure, complemented by a clear blue sky overhead.
Apartment in Rutland
4.86 out of 5 average rating, 102 reviews

Cozy Corner Nook

Comfortable and quiet 1 bedroom first floor apartment. Easy access in the heart of Rutland City. Walk to restaurants. Plenty of parking. Plenty of amenities close by and within walking distance. 20 minute drive to Killington, Okemo or Pico ski areas. Centrally located .Pine Hill Park is just down the street from the house.

Top Guest favourite
A rustic cabin is surrounded by snow-covered evergreen trees, with smoke gently rising from the chimney. The wooden structure features a sloped roof and a front porch, warmly inviting guests into a serene winter landscape.
Cabin in Leicester
4.98 out of 5 average rating, 842 reviews

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 holiday rentals

When is the best time to visit Rutland?

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Avg. price$290 AUD$288 AUD$269 AUD$228 AUD$237 AUD$224 AUD$225 AUD$225 AUD$233 AUD$246 AUD$240 AUD$275 AUD
Avg. temp-7°C-6°C0°C7°C14°C18°C21°C20°C15°C9°C3°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 house rentals in Rutland?

    Rutland has more than 50 family-friendly house 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 holiday rentals in Rutland

  • Total holiday rentals

    Explore 120 holiday rentals in Rutland

  • Nightly prices starting at

    Rutland holiday rentals start at $75 AUD per night before taxes and fees

  • Verified guest reviews

    Over 6,230 verified reviews to help you choose

  • Family-friendly holiday rentals

    80 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 40 rentals that welcome pets

  • Rentals with dedicated workspaces

    60 properties have a dedicated workspace

  • Wi-Fi availability

    120 of Rutland holiday 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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