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.

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Top guest favorite
Guesthouse in Hartland
4.96 out of 5 average rating, 197 reviews

Cozy Getaway- Ski, Woodstock, Hanover

Luxurious, well appointed cottage - Beautiful sunrise view located between Woodstock VT and Hanover NH. Inspiring treat for musician’s getaway is a fully restored 1929 Steinway Full kitchen, custom cabinets, gas fireplace, energy efficient heat pump, washer, dryer. VERY comfortable queen bed. Romantic getaway in the woods, relax, work in peace, explore the beauty and history of the area. Hiking, biking, fishing, hot air balloon rides and shopping are all close by. Long (90 day) or weekend rental

Guest favorite
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
4.85 out of 5 average rating, 118 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 favorite
Cottage in Hartland
4.94 out of 5 average rating, 144 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 favorite
The exterior of a charming yellow house is surrounded by lush greenery and colorful landscaping. A stone pathway leads to the entrance, framed by well-maintained shrubs and ornamental features. Tall trees provide privacy and a natural backdrop, enhancing the serene outdoor atmosphere.
Home in Plainfield
4.9 out of 5 average rating, 148 reviews

Historic Home on 17 acres of land. Go escape!

This place is a dream. Please enjoy the outdoors and everything this amazing place has to offer. The pool will be reopened around May 2025 (weather dependent. It is a heated pool and salt water. Pool rules: absolutely no diving. No children under the age of 18 should be near or in the pool area without supervision under any circumstances. NO glassware by the pool. If there is an incident with glass near the pool area please tell our property manager immediately. If you need anything ask!

Guest favorite
The outdoor view showcases a house illuminated with colorful holiday lights against a backdrop of dark, snowy terrain. A covered porch is visible, adding charm to the property. Snow blankets the ground, and evergreen trees frame the scene, enhancing the winter ambiance.
Guest suite in Hartford
4.91 out of 5 average rating, 413 reviews

Sunny Side Airbnb (dog friendly)

Sunny Side Airbnb is located on a secluded 10+ acre property with plenty of outdoor space for dogs to run around and a short hiking trail with views. The Airbnb is located on the farther end of the house with a deck overlooking garden views, a fire pit, and an open field. Convenient location near shops and restaurants. Just over a mile from I-89 off Rt 4 in Quechee, Vt. A short drive to WRJ and W Lebanon, NH, 9.1 miles to Woodstock, VT, 11 miles to Hanover, NH, and 13.4 miles to DHMC.

Top guest favorite
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, 283 reviews

THE LOFT, stunning views from a timber framed barn

Welcome to "The Loft". A lofted space 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. For more go to @theloft.vt

Superhost
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 favorite
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, 428 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 favorite
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, 223 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 favorite
A well-appointed bedroom showcases a spacious bed dressed in white linens, complemented by decorative pillows. A wooden bench is situated at the foot of the bed. A large mirror and artful wall decor enhance the serene atmosphere, while natural light enters through a large window.
Home in West Windsor
4.98 out of 5 average rating, 162 reviews

Birdie's Nest Guesthouse

Welcome to our newly renovated studio apartment, nestled among the trees in the serene hills of West Windsor, Vermont. Elevated on the second floor, this separate structure offers a tranquil escape with breathtaking views of Mount Ascutney and our own private pond. Immerse yourself in the comforts of this thoughtfully designed studio apartment, surrounded by the natural beauty of the Vermont landscape. Every detail has been curated to ensure your utmost comfort and enjoyment.

Guest favorite
The historic farmhouse features a white exterior with a gabled roof, surrounded by lush greenery. A large tree provides shade in the front yard, and flower gardens can be seen along the stone pathway leading to the porch, which has seating for relaxation.
Apartment in Taftsville
4.79 out of 5 average rating, 179 reviews

Quiet Vermont Farmhouse

Rent a quiet two-bedroom apartment in our 1850's farmhouse in historic Taftsville, Vermont. We are close to the fascinating history, arts, and shopping of Woodstock VT, and near several downhill and cross country ski and snowshoe centers, Marsh-Billings-Rockefeller National Historical Park, and lots of hiking trails, as well as within a short drive of Hanover NH and White River Junction VT. Come enjoy our warm hospitality, wander our gardens, and enjoy our shared patio.

Top guest favorite
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, 278 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.

Popular amenities for Rutland vacation rentals

When is the best time to visit Rutland?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$41,774 GYDG$46,787 GYDG$46,787 GYDG$38,223 GYDG$42,609 GYDG$46,787 GYDG$51,800 GYDG$51,800 GYDG$55,142 GYDG$48,875 GYDG$43,236 GYDG$48,040 GYD
Avg. temp-5°C-4°C1°C7°C14°C19°C22°C21°C16°C10°C4°C-2°C

Frequently Asked Questions

  • What are the best places to stay in Hartland?

    Hartland has vacation rentals in rural settings, some with mountain or forest views, and historic farmhouses often attract visitors seeking a tranquil getaway. Staying near the village center can provide easier access to local shops and cultural sites.

  • What are the best things to do in Hartland with kids?

    Families can explore local parks, visit nearby farms for seasonal activities, or enjoy nature trails suited for children. Community centers may host public events, and picking fruit or participating in outdoor games is often suggested by visitors.

  • What are some of the best things to do in Hartland?

    Explore woodland hiking trails, attend community arts events, or visit farms where you can learn about local agriculture. Many travelers enjoy walking along the riverbanks or browsing the offerings at year-round markets.

  • How is the weather in Hartland?

    Hartland has cold, snowy winters, generally between 13–37°F (-11–3°C), and warm, pleasant summers near 59–83°F (15–28°C). Spring and fall feature colorful foliage and mild temperatures, with rainfall sprinkled throughout the year.

  • What are the best places to visit in Hartland?

    Hartland has historic buildings including the Hartland Public Library, traditional covered bridges, and locally run galleries. Outdoor spaces and trails around the village are frequently suggested for visitors who enjoy nature.

  • What are some hiking trails in Hartland?

    Hartland has gentle woodland paths and more moderate hikes through scenic forests or along rivers. The surrounding area features trail networks that are frequently suggested for both relaxed walks and more adventurous treks.

  • What are some family activities we can do in Hartland?

    Families can visit u-pick farms, enjoy picnics in public parks, or join guided wildlife walks. Attending craft fairs or local workshops is often recommended for interactive experiences with kids.

  • What are some of the best day trip ideas from Hartland?

    Popular nearby destinations include historic villages known for artisan shops, outdoor recreation areas, and museums focused on the region’s arts or agricultural history. Exploring nature preserves or seasonal farmers markets can also create memorable day trips.

  • Are there any pet friendly accommodations available in Hartland?

    Many vacation rentals in Hartland welcome pets, especially those located on larger properties or near trails. Check individual listing descriptions to ensure amenities meet your needs when traveling with animals.

  • What are some local tips for visiting Hartland?

    Layer your clothing for changing weather, especially in spring and fall. Chat with local artisans at weekend markets for regional insights, and consider bringing cash for smaller vendors in town.

  • What is Hartland known for?

    Hartland is known for its rural landscapes, historic covered bridges, and a tradition of small-scale farming. Seasonal community events and outdoor recreation are frequently associated with the area.

  • What are the best hidden gems to explore in Hartland?

    Visitors often discover quiet footpaths, tucked-away art studios, or small family-run farms open to guests. Some enjoy historic cemeteries or little-known picnic spots along forested routes.

  • What are the best foods to try in Hartland?

    Hartland has dishes featuring Vermont cheddar, locally raised meats, and fresh produce from surrounding farms. Maple syrup is frequently suggested, especially enjoyed on pancakes or baked goods.

  • What should I bring for a trip to Hartland?

    Pack layers to prepare for changing temperatures and rain gear for occasional showers, especially if exploring outdoors. Sturdy footwear is helpful for hiking, and reusable water bottles are encouraged for environmental reasons.

  • What is the nightlife in Hartland like?

    Nightlife in Hartland is relaxed, with local taverns and occasional live music events in community spaces. Evenings are often spent enjoying conversation, regional beverages, or small gatherings at local venues.

  • What are the most popular events or festivals in Hartland?

    Hartland hosts frequently suggested summertime fairs, seasonal farmers markets, and winter holiday gatherings. Community concerts and craft shows often take place during holiday weekends and peak foliage season.

  • Are there family friendly vacation rentals in Hartland?

    Hartland has a range of family friendly vacation rentals, including homes with spacious yards and amenities like full kitchens. Many listings highlight board games, outdoor play equipment, or proximity to parks suitable for children.

  • When is the best time to visit Hartland?

    Late spring through early fall is often recommended for mild temperatures and outdoor activities, while autumn draws visitors for vibrant foliage. Winter months are popular with those seeking snow and a quieter atmosphere.

Quick stats about vacation rentals in Rutland

  • Total vacation rentals

    Explore 110 vacation rentals in Rutland

  • Nightly prices starting at

    Rutland vacation rentals start at G$10,443 GYD per night before taxes and fees

  • Verified guest reviews

    Over 9,030 verified reviews to help you choose

  • Family-friendly vacation rentals

    50 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 40 rentals that welcome pets

  • Rentals with dedicated workspaces

    40 properties have a dedicated workspace

  • Wi-Fi availability

    110 of Rutland vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, 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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