
Holiday rentals with outdoor seating in Rutland
Find and book unique Holiday Houses with Outdoor Seating on Airbnb
Top-rated Holiday Houses with Outdoor Seating in Rutland
Guests agree: These Holiday Houses with Outdoor Seating 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!

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.

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.

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.

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
Popular amenities for Rutland outdoor seating rentals
Holiday House Rentals with Outdoor Seating

Romantic Mountain Getaway

Private Oasis Under 10 Mins from Woodstock

Cozy Bow House Perched in Trees w/ Hot Tub & View

The Barnbrook House

Killington Retreat | Deck-Fire Pit-Mountain Views!

Stylish Ascutney Cabin with Mountain Views

The Quechee Haus: VT Retreat with Outdoor Hot Tub

The Guest House at Sky Hollow
Apartment rentals with outdoor seating

Private Apt. on Farm, Hot Tub with views!

Dog heavenly! Private, beautiful and relaxing.

Peaceful Ludlow Base 5 minutes to Okemo

Quiet Vermont Farmhouse

Vermont Country Suite

Charming & Peaceful Upper Valley 1BR Retreat

Mountain View Apartment

Style and Comfort- Perfect Year Round Location
Condo rentals with outdoor seating

Main St Escape | Explore Downtown Ludlow

Bright Ski on/off Condo Full Kitchen-Free Shuttle!

Dog-Friendly Mtn Escape/Pool/Gym/Hiking Trails

⭐️Cozy Ski On/Ski Off 2-Bed/Bath w/Fireplace

CozyCub- Location, Fireplace, Ski Off/Shuttle On!

Serene Top Floor Condo (resort style amenities)

Modern Killington Farmhouse Condo: Close to Resort

Okemo Ski-in/Ski-out, Steps to lift Condo
When is the best time to visit Rutland?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $317 NZD | $380 NZD | $362 NZD | $266 NZD | $291 NZD | $319 NZD | $374 NZD | $303 NZD | $314 NZD | $360 NZD | $287 NZD | $390 NZD |
| 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 |
Quick stats about holiday rentals with outdoor seating in Rutland

Total holiday rentals
Explore 50 holiday rentals in Rutland

Nightly prices starting at
Rutland holiday rentals start at $89 NZD per night before taxes and fees

Verified guest reviews
Over 6,220 verified reviews to help you choose

Family-friendly holiday rentals
30 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wi-Fi availability
50 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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- Rentals with outdoor seating Windsor County
- Rentals with outdoor seating Vermont
- Rentals with outdoor seating United States
- Squam Lake
- Stratton Mountain
- Okemo Mountain Resort
- Sugarbush Resort
- Weirs Beach
- Monadnock State Park
- Stratton Mountain Resort
- Pats Peak Ski Area
- Magic Mountain Ski Resort
- Tenney Mountain Resort
- Mount Snow Ski Resort
- Ragged Mountain Resort
- Dartmouth Skiway
- Pico Mountain Ski Resort
- Crotched Mountain Ski and Ride
- Hildene, The Lincoln Family Home
- Dorset Field Club
- Hooper Golf Course
- Lucky Bugger Vineyard & Winery
- Bromley Mountain Ski Resort
- Autumn Mountain Winery
- Whaleback Mountain
- Fox Run Golf Club
- Northeast Slopes Ski Tow




