
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.

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.

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.

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

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!

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.

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.

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.

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.

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

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 vacation rentals
Other great vacation rentals in Rutland

Charming apartment on the Windsor Green

Luxury & Privacy in Woodstock - Barn at Rose Hill

Peaceful Vermont Cottage

Walk to Trails & Village +Pets - Highland Cabin

Private Farmhouse with in ground pool!

Chic Cabin for Co-working & Relaxing by Killington

Cozy Mountain Cabin w/ Hot Tub & Incredible View

Hilltop Hideaway in Woodstock
Frequently Asked Questions
Where should I stay in Hartland?
Make yourself at home in Hartland by choosing from our most frequently booked neighborhoods. We have over 70 vacation rentals in Hartland 4 Corners, and over 320 vacation rentals in Village of Woodstock.
Do apartment rentals in Hartland have a kitchen?
Absolutely! We offer over 10 apartment rentals with a kitchen in Hartland. Enjoy a tailored experience with all the comforts you desire.
Do apartment rentals in Hartland have wifi?
Absolutely! We offer over 10 apartment rentals with wifi in Hartland. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly vacation rentals in Hartland?
Hartland has more than 50 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
What are the most popular amenities for Apartment Rentals in Hartland?
Enhance your stay in our Apartment Rentals with the most popular amenities: over 10 homes with wifi, over 10 homes with a kitchen, over 10 homes with free parking, and more. Indulge in the ultimate retreat, tailored to your preferences.
Are there vacation rentals with a dedicated workspace in Hartland?
Yes! Work meets play with ease at over 40 vacation rentals in Hartland featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly vacation rentals in Hartland?
Four-legged friends are welcome in Hartland. Choose from more than 40 vacation rentals for guests traveling with pets.
Do apartment rentals in Hartland have free parking?
Absolutely! We offer over 10 apartment rentals with free parking in Hartland. Enjoy a tailored experience with all the comforts you desire.
How much does it cost to stay in boutique hotel rentals in Hartland?
Experience the best of Hartland with our boutique hotel rentals, starting at about $110 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do farmstay rentals in Hartland have air conditioning?
Absolutely! We offer over 10 farmstay rentals with air conditioning in Hartland. Enjoy a tailored experience with all the comforts you desire.
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 $50 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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