Holiday rentals in Rutland
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Top-rated holiday rentals in Rutland
Guests agree: these stays are highly rated for location, cleanliness and more.
Cozy - Killington 40 min. Woodstock-Hanover-Piano!
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
Clean, cozy, beautiful studio in the heart of WRJ.
This beautiful studio is in a new building built in 2021. It is a clean, quiet, place to stay in a building of young professionals. Walking distance to restaurants, bars, art galleries, and all this historic town has to offer. Within a 3-min walk: Tuckerbox, Wolf Tree, Big Fatty’s, Northern Stage. 10 min: King Arthur Baking 10 min: Dartmouth College 15 min: Dartmouth Hitchcock Medical Center 25 min: VT Law School Perfect, cozy place for visiting parents, traveling nurses, professionals, etc.
Bog Mt Retreat Downstairs Suite
Welcome to your perfect first floor retreat. Woodland trails on the property, local hikes like BOG MT, a beautiful waterfall and so many more. Bring your kayaks and paddle Grafton Pond or Pleasant Lake and jump off the rock at Blueberry Island. Only 30 minutes from Sunapee Mountain Ski Area & 21 minutes from Ragged MT Ski Resort. Whether you're seeking the thrill of the slopes, the tranquility of nature, or a bit of both, our Airbnb is the gateway to an unforgettable New Hampshire experiences.
Falcon House: VT Chalet w/Sauna, Bike to Village
Welcome to Falcon House! A modern VT chalet w/sauna at the edge of a 60 acre forest ∙ Outdoor Finnish sauna, shower, yoga platform & hiking trails ∙ 5 min to Woodstock village, 20 min to ski Killington ∙ Spotlessly clean, tastefully furnished, well stocked with thoughtful amenities ∙2 bedrooms, 2 full baths. Lofted king master has ensuite +Lower level den w/double futon ∙ Chefs kitchen, fireplace, 2 TVs & WiFi ∙ Brookside deck w/BBQ & dining ∙Follow Falcon House on Social @falcon_house_vt
Weasley's Enchanted Treehouse @ Vermont ReTREEt
Welcome to our enchanting treehouse! We crafted this unique and magic inspired dwelling for any admirer of a beloved wizarding world, or anyone who appreciates isolation in a fun space. As you cross the elevated walkways, you'll feel like you're entering a wizards treehome in the forest. The 1,100 sqft treehouse is nestled in and among trees, providing a magical and secluded escape from life. Have a question or hesitations? reach out check out our other listings for glamping style treehouses
The Oaks - secluded rural estate w/ amazing views
Relax in this private house secluded off a 1,000-ft driveway in the hills of NH overlooking Mt. Ascutney and the Connecticut River valley. This is the 45-acre estate known as "The Oaks" previously owned by painter Maxfield Parrish. Huge oak trees and rocky ledges abound. Great for gatherings with family or friends. Close to Dartmouth College, Woodstock, and ski areas - or just sit on the porch and take in the views. Weddings and reunions can be hosted (tent rentals and catering by others).
Sunset Cabin - your private romantic hideaway
Your private woodlands retreat awaits. Nestled atop a beautiful 10 acre meadow with 25 acres of woods for you to enjoy; this rustic, pet friendly cabin is a perfect romantic hideaway. Two trout ponds are steps from your door for fishing and swimming. Just minutes from Mt. Ascutney's hiking/biking trails and in the middle of fantastic cycling country. Near local race including the VT100, Vt overland, VT50. Sunset Cabin is a marvelous spot for enjoying fall foliage and exploring VT!
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.
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.
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.
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.
Okemo A-Frame - Floor Hammock, Sauna & Hot Tub
Welcome to the Okemo A-Frame! With an oversized deck, featuring outdoor dining, a barrel sauna, and hot tub you'll enjoy the outdoors year round. Enter into an open-concept dining area, kitchen, and living room with stylish mid-century malm fireplace. Take your rest in one of the three bedrooms or cozy up on the indoor floor hammock. Located 10 minutes from Okemo Mountain Resort and the town of Ludlow enjoy skiing, shopping, dining, and all that Vermont has to offer.
Popular amenities for Rutland holiday rentals
Stay near Rutland's top sights
Other great holiday rentals in Rutland
~The ClubHaus~
Private Riverside Studio* Upper Valley*Vermont
Cabin on the Hill
Luxury Cabin#1 Hot Tub Fire Pit Kayak Paddle Board
Beautiful Woodstock Home-Perfect for entertaining
Boulder House - Extraordinary Luxury in the Woods!
Luxury Barn Retreat in Woodstock
Sugar River Treehouse
When is the best time to visit Rutland?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £151 | £169 | £169 | £138 | £154 | £169 | £187 | £187 | £199 | £211 | £159 | £190 |
| Avg. temp | -5°C | -4°C | 1°C | 7°C | 14°C | 19°C | 22°C | 21°C | 16°C | 10°C | 4°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 holiday rentals in Rutland
Total holiday rentals
Explore 110 holiday rentals in Rutland
Nightly prices starting at
Rutland holiday rentals start at £38 per night before taxes and fees
Verified guest reviews
Over 9,330 verified reviews to help you choose
Family-friendly holiday rentals
60 properties offer extra space & child-friendly amenities
Pet-friendly holiday rentals
Find 40 rentals that welcome pets
Rentals with dedicated workspaces
40 properties have a dedicated workspace
Wifi availability
110 of Rutland holiday rentals include wifi 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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- Okemo Mountain Resort
- Stratton Mountain
- Sugarbush Resort
- Squam Lake
- Killington Resort
- Pats Peak Ski Area
- Weirs Beach
- Magic Mountain Ski Resort
- Stratton Mountain Resort
- Monadnock State Park
- Pico Mountain Ski Resort
- Mount Snow Ski Resort
- Tenney Mountain Resort
- Ragged Mountain Resort
- Fox Run Golf Club
- Bromley Mountain Ski Resort
- Hildene, The Lincoln Family Home
- Crotched Mountain Ski and Ride
- Ice Castles
- Montshire Museum of Science
- Dartmouth College
- Emerald Lake State Park
- Mount Sunapee Resort
- Squam Lakes Natural Science Center