Holiday houses in Rutland

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Top-rated holiday rentals in Rutland

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Top Guest favourite
A charming cottage is set against a backdrop of lush trees, with a deck extending from the front. The warm, orange sky creates a serene atmosphere, casting soft light on the exterior of the house and surrounding landscape.
Guesthouse in Hartland
4.96 out of 5 average rating, 197 reviews

Cottage for Two/Solo Getaway/Musician's Retreat

Luxurious, well appointed cottage with beautiful sunrise view located between Woodstock VT and Hanover NH. An inspiring treat for musician’s getaway is a fully restored 1929 Steinway L. Full kitchen, custom cabinets, gas fireplace, energy efficient heat pump, washer, dryer and very comfortable queen bed. A romantic getaway in the woods, a place to relax, work in peace, or explore the beauty and history of the area. Hiking, biking, fly fishing, hot air balloon rides and shopping are all close by.

Guest favourite
A bright kitchen area is complemented by a vibrant yellow wall. Wooden cabinetry holds kitchen essentials above a small countertop. Two bar stools are positioned at a wooden table. Natural light enters through large windows, illuminating the cozy studio space with an inviting atmosphere.
Apartment in North Hartland
4.84 out of 5 average rating, 116 reviews

Private Riverside Studio* Upper Valley*Vermont

This unique place has a style all its own. Perfect for a traveling nurse or anyone who needs a relaxing getaway or a remote place to work. This studio apartment has river and garden views and is conveniently located in the New England Village of North Hartland. A 15-20 minute drive to Dartmouth College or DHMC. Take country walks across the twin covered bridges right from your doorstep. Relax on the front porch and watch the bald eagles and peregrine falcons search for prey along the river.

Top Guest favourite
Cottage in Hartland
4.94 out of 5 average rating, 141 reviews

Adorable Dog Friendly Cottage w/FIOS

Bright and clean 2-story cottage on a 20-acre oasis. 10% off for guests using only one bedroom (cannot be combined with other discounts). Details in property description. With a view of the hills, flanked by woods and open pastures, the cottage includes 2 bedrooms (1 up w/Queen, 1 down w/full bed, 1 bath (2nd floor - shower only), kitchen/living/dining area (2nd floor), and laundry. For groups or more space, view my other listing located on the same acreage: airbnb.com/h/hartlandvacationhome

Guest favourite
A modern cabin is situated among trees, surrounded by greenery. Two Adirondack chairs are positioned near a fire pit, which has gentle smoke rising. A picnic table rests nearby, providing a comfortable outdoor gathering space with views of the natural landscape.
Tiny home in Hartland
4.94 out of 5 average rating, 312 reviews

Private Modern Cabin w/View of Fields, Hills

Enjoy a modern private cabin in the heart of Vermont's pastoral Upper Valley Region. Combining "Glamping" with the comforts of a permanent structure, the "HakuBox" (Haku means "to exhale") was designed to sit lightly on the land and offer a simple, restorative experience. Note: no shower, but swimming holes nearby! Queen bed, fire pit w/grill, free firewood, Adirondack chairs, picnic table, free coffee & tea, dog-friendly with cable trolley, food & water bowls. $39 pet fee applies.

Top Guest favourite
A cozy living area features a mixture of seating options, including a tufted sofa and a vintage-style sofa adorned with decorative cushions. Natural wood floors enhance the warmth of the space, while artwork on the walls and a circular coffee table complete the inviting atmosphere.
Barn in Chester
4.99 out of 5 average rating, 695 reviews

Inviting studio apartment above barn in Vermont

This custom build apartment is located just 10 minutes from I91. In the winter you are 30 minutes away from some of the best skiing around. Located on 85 private acres with great views this is the perfect winter get away. In the summer you can relax by the firepit, hike in the woods, work in the gardens (just kidding), collect breakfast from the chickens or visit some of the local breweries. We are as close or as far away as you would like us to be with our house right next door.

Top Guest favourite
The private guest house is surrounded by lush greenery, featuring a covered porch with a chimney and hanging planters. A well-maintained lawn leads to the house, while a backdrop of rolling hills enhances the tranquil setting.
Cottage in Windsor
4.97 out of 5 average rating, 416 reviews

Ogden's Mill Farm

Private guest house situated on over 250 acres, with fully equipped gourmet kitchen and great views of quiet fields and valley. Pond with diving board for swimming in the summer. Giant sledding hill is a favorite of children and adults alike. Trails on property for hiking, xc- skiing, and snowshoeing. 15 mins to Woodstock VT. 45 mins to Killington,Pico and Okemo. Great restaurants and shopping nearby. Hanover and Norwich VT 20 mins. Please note not handicapped accesible.

Top Guest favourite
The kitchen area features a large island with seating and modern appliances. Natural wood paneling complements the high cathedral ceiling. Glass doors open to a scenic view of the surrounding hills, providing ample natural light and a connection to the outdoors.
Barn in Woodstock
5 out of 5 average rating, 280 reviews

THE LOFT, stunning views from a timber framed barn

Welcome to "The Loft". The loft is a newly built apartment on the top floor of a timber framed barn. The owners are designer/builders who have combined the elements of old world craftsmanship with high tech efficiency to create a living space that is bright, airy and yet cozy. Powered by solar, this attached carriage barn is located on a quiet back road 3.5 miles from Woodstock Village and 3 miles from GMHA. The Loft has its own private entrance, parking and a sunset balcony.

Top Guest favourite
A charming cabin constructed from natural materials is nestled among lush trees in a forested area. Sunlight filters through the leaves, casting dappled shadows on the ground. The cabin features large windows that invite the surrounding greenery inside.
Tiny home in Hartland
4.97 out of 5 average rating, 220 reviews

Cabin on the Hill

Enjoy a stay in the hills of Vermont - glamping at its finest! A 5-10 minute hike UPhill to a secluded getaway in the heart of Vermont. Amenities include a quaint outhouse, a unique outdoor shower, a 2 burner outdoor gas stovetop and a fire pit to roast marshmallows. The 12x14 screened in cabin with ladder accessed loft sleeps 2 comfortably. Don't worry about bringing pots and pans - cabin is equipped with dishes and a water supply. Adjustable LED lights to light up the night.

Top Guest favourite
A cozy cabin is nestled among the trees, showcasing a rustic wooden exterior with large windows. It overlooks a gentle slope covered in green grass and wild plants, with sunlight filtering through the canopy above, creating a serene and inviting atmosphere.
Guesthouse in Woodstock
4.98 out of 5 average rating, 271 reviews

Cozy Little Spot (Self Check-in)

Contactless check-in. Cozy guest house, cabin-studio-getaway; enjoy the sounds of a stream outside the window (next to the bed). Views of a larger brook below. The"Cabin"is nestled in the trees giving a feeling of floating above the brook below. The interior is decorated w/family heirlooms gathered from around the country. Nothing fancy, just a cozy simple getaway. 3.25 mi from town. Choose from a variety of activities in town or hop on nearby trails. NO PETS ALLOWED.

Top Guest favourite
The spacious interior of the yurt features a circular design with natural wood and fabric elements. Comfortable seating areas include a queen-sized futon and a wooden sofa. Large windows allow natural light to fill the space, while a wood stove provides warmth.
Guesthouse in Hartland
4.95 out of 5 average rating, 1,023 reviews

Yurt In The Woods - Private Refuge

The Yurt In The Woods is 30 ft in diameter - 700 spacious sq. ft. It's surrounded by trees and has a yard. 2 night stays required for Weekends. October 6th and 12th are currently vacant if you want a fall foliage trip. There is a "one" night stay fee of $50 Allowed 2 dogs with the agreement to my animal policy & $50 fee WiFi 1,000 megabits per second a fiber network Outdoor Gas Grill , Outdoor Fire Circle, and Outdoor Shower available May - October

Guest favourite
A spacious bedroom features a large bed with a decorative canopy and plush pillows. Soft lighting from a chandelier enhances the room's ambiance. A patterned carpet covers the floor, while elegant curtains frame the windows, and a cozy seating area includes a small side table.
Apartment in Claremont
4.89 out of 5 average rating, 172 reviews

Beautiful 1 bedroom apartment with balcony

Bienvenue chez nous! Experience comfort and modern beauty in this completely renovated apartment attached to a historic Victorian home. The one bedroom apartment has a private bathroom and your own balcony to enjoy. Close to popular skiing areas of Mt Sunapee (20 minutes) and Okemo (35 minutes), in addition to enjoying local hiking and cycling at Mt Ascutney, Moody Park, and Arrowhead.

Top Guest favourite
A spacious guest room features a king bed and a twin trundle bed. A chandelier hangs from the beamed ceiling, and natural light is provided by large windows with sheer curtains. Decorative elements include a mirror and a wall display of photos, enhancing the cheerful atmosphere.
Farm stay in Plainfield
4.97 out of 5 average rating, 255 reviews

Renovated 1817 Hobby Farm Close to Dartmouth

Come stay at PRIVATE GUEST QUARTERS on our hobby farm in Plainfield Village! Experience country living with a 20-minute proximity to Dartmouth University. You can see gorgeous views of Mount Ascutney from your window, hike to the French Ledges, visit St. Gaudens Park, or J.D. Sallingers farm. Every season is beautiful here! Or learn how to make macarons :) if you are brave enough.

Popular amenities for Rutland holiday rentals

When is the best time to visit Rutland?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price$350 NZD$392 NZD$392 NZD$320 NZD$357 NZD$392 NZD$402 NZD$444 NZD$435 NZD$435 NZD$362 NZD$402 NZD
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Quick stats about holiday rentals in Rutland

  • Total holiday rentals

    Explore 110 holiday rentals in Rutland

  • Nightly prices starting at

    Rutland holiday rentals start at $87 NZD per night before taxes and fees

  • Verified guest reviews

    Over 9,030 verified reviews to help you choose

  • Family-friendly holiday rentals

    50 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 40 rentals that welcome pets

  • Rentals with dedicated workspaces

    40 properties have a dedicated workspace

  • Wi-Fi availability

    110 of Rutland holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi and Pool across Rutland rentals

  • 4.9 Average rating

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

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