
Holiday rentals with outdoor seating in Middlesex
Find and book unique Holiday Houses with Outdoor Seating on Airbnb
Top-rated Holiday Houses with Outdoor Seating in Middlesex
Guests agree: These Holiday Houses with Outdoor Seating are highly rated for location, cleanliness and more.

Cady’s Falls Cabin
Welcome to our treehouse inspired, modern cabin overlooking The Kenfield Brook on Terrill Gorge. We are located 5 miles from Stowe and its attractions, and just a few minutes from downtown Morrrisville with all its amenities. Just upstream from the picturesque Cady’s Fall swimming hole and across the brook from the amazing Cady’s Falls bike trails, our cabin is perched atop the hillside. With its simple, minimalist design it’s easy to immerse yourselves in nature and feel at home in the trees.

Cozy Country Retreat Close to Town
Wake up to the sounds of nature, a cup of coffee on the porch, or cozied up by the fire with a book. Prepare simple meals in the kitchenette, or head out to local restaurants within a ten minute drive. Enjoy being comfortable while close to nature. Guests love the comfortable bed, and the pullout futon makes it an affordable option for families. Nearby walking trails, swimming holes, mountain biking, gravel biking out the door, and cross-country ski areas nearby. Fire pit with wood provided.

200 acre Stowe area Bunkhouse.
Hello and welcome to our Red Road Farm 'Bunkhouse' -- We're so happy to host you! Sitting on our 200 acre estate this authentic barn offers our guests a chance to relax in the beautiful rolling hills of Vermont. Access the vast majority of our historic Stowe area land -- from our apple orchards to our extensive walking paths in fields and woodland. We hope that you can experience such fun and quiet time in our cozy, western-style bunk room. Located only a 10 minute drive from downtown Stowe.

the little house
Come rejuvenate in our sweet little cabin tucked into the Vermont mountains. It has such wonderful healing energy! ✨ Cozy up to read a book next to the fireplace or book a private healing session at my studio in Montpelier, VT. I have a passion for creating welcoming, safe spaces that support your nervous system & empower your soul. ❤️ -On site Minister Brook access--5 min. walk -Lots of skiing, hiking, water to explore -18 min to Montpelier- funky downtown, eccentric shops & restaurants

4-Season Treehouse @ Bliss Ridge; Best Views in VT
thermostat control! LUXURY! 1-of-a-kind, 5⭐️Interior bathroom, @Bliss Ridge - 88acre, OG farm, private estate surrounded by 1000s acre of wilderness. NEW SAUNA& cold plunge!!! Our 2 architectural wonders = real treehouses, built withIN the living trees, not stilted cabins. Equipped w. a fabulous yotel fireplace, indoor hot shower / plumbing, fresh mtn spring water, stable access ramp. Our original Dr. Seuss treehouse, "The Bird’s Nest" is open May-Oct. WiFi avail at the barn! Cell svc works!

Farmhouse with Sunset Mountain Views
Unbeatable Vermont setting, panoramic mountain views and gorgeous sunsets. Located one mile off Rt 100, 18 minutes to Stowe, minutes from the best skiing, bike trails, kayaking, and hiking in the east. The apartment is a sunny, bright and private space, cheerfully decorated, with the comfiest beds and coziest linens. And great outdoor spaces to relax in at the end of the day! 10 min to Stowe, 18 to lifts, 30 to Sugarbush, 35 min Burlington. The pictures and our 5 star reviews say it all!

Off Grid Secluded Cabin on 37 Acre Farm
In a secluded, hand-crafted off the grid cabin, come and enjoy the elements with us at Drift Farmstead. A 3-minute walk leads you through gardens and pasture, to Ravenwood, a small, intimate cabin with everything you need. Be it an extended weekend tucked in seclusion, amongst the birds, river and trees, or find the comforts of a 37 acre small farm nestled in the mountains and settle in, working from afar. Top shelf skiing at Sugarbush is near, along with Vermont's finest grub and beer.

A true Vermont get-away cabin in the woods
Badger Cottage offers a true rustic Vermont experience nestled in the woods with spectacular views and a quiet and peaceful ambiance. Once a barn, carefully reconstructed on the owners’ property, and modernized to today’s standards, this post and beam cabin is warm and cosy in winter and cool in summer. Well behaved dogs are very welcome and will enjoy the walks in the woods. Covid vaccinations are required. The owners live in an adjacent house with their very friendly Border Terrier

Gorgeous Treehouse! Big views, Cozy warm fireplace
Lilla Rustica is an elevated cabin among the trees. Private, with Stunning views this was built by "The Tree House Guys" a local Vermont company whom can be found having a season on the DIY network. Tons of detail, while keeping the design natural and simple. Unbelievable views of Camels hump State park. A loft with one queen bed and downstairs has a queen bed with three sides of the bed having windows facing the views. Hiking offered right from the cabin. An awesome getaway!

Contemporary Studio in Montpelier
Keep it simple at this peaceful and centrally-located place just minutes from downtown Montpelier. A contemporary studio set within the charm of a historical building. Relax under the apple tree with your morning coffee or take a five minute walk into town for freshly-baked pastries. Discover what our vibrant little city has to offer without ever getting into your car. No matter the season, there are great places nearby to explore for swimming, hiking, biking, and skiing.

Luxury Glass Tiny House - Mountain View + Hot Tub
Immerse yourself in nature at Vermont's most unique Airbnb, located in the heart of the Green Mountains. This upscale mirrored glass house was built in Estonia and combines Scandinavian design with jaw-dropping Vermont views for an unforgettable experience. You'll return home feeling rejuvenated after relaxing in a hot tub overlooking Sugarbush Mountain or waking up with a panorama of Blueberry Lake at your feet. *One of Airbnb’s Most Wish-listed Stays of 2023*

The Caterpillar House: Tiny w/ Hot Tub & Fire Pit
Escape to our charming tiny house—The Caterpillar House—where comfort meets minimalist living in scenic Elmore, Vermont. Ideal for solo travelers, couples, or small families seeking a peaceful retreat. Enjoy a private hot tub, fire pit under the stars, and direct snowmobile trail access—perfect for summer and winter getaways. Located on our shared property, this cozy haven is surrounded by nature for a truly relaxing stay.
Popular amenities for Middlesex outdoor seating rentals
Holiday House Rentals with Outdoor Seating

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

Mountain View Farmhouse w/ Orchard White Christmas

The 1919 Mountain Farmhouse, new hot tub and patio

Brand new Beautiful Modern Clean Home On River

18 Lake Stunning View of Champlain in Adirondacks

Vermont Getaway Home - Perfect Location

Forest Hideaway

The Barn - Modern Living in Small Town Vermont
Apartment rentals with outdoor seating

Slopeside Bolton Valley Studio

River's Bend NEW 1-bd Apt - 8 Mins to Montpelier

VT Hideaway studio: breweries,hiking, dogs welcome

1880 Purple Village Victorian

Private Getaway on Lake Lamoille

Entire 2nd Floor Walk to Montpelier

The Perfect Cozy Weekend Escape

Mountain Road Apartment, Optimal Location
Condo rentals with outdoor seating

3rd Floor Studio @ The Lodge at Spruce Peak

One level condo in the heart of Stowe Village!

Ski in/out – Smugglers’ Notch Condo

Cozy 2 bed, 2Bath, fireplace, amazing location!

Lovely Ski-in / Ski-out Studio at “Smuggs”⭐️

Renovated 4-bedroom House: Hot Tub & Outdoor Space

SnowCub Pets Indoor Pool Hot Tub Sauna, FirePlace

Modern Farmhouse Condo: fast WiFi+close to it ALL!
When is the best time to visit Middlesex?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $353 AUD | $346 AUD | $244 AUD | $209 AUD | $227 AUD | $218 AUD | $278 AUD | $238 AUD | $262 AUD | $244 AUD | $254 AUD | $304 AUD |
| Avg. temp | -6°C | -5°C | 0°C | 8°C | 15°C | 20°C | 22°C | 21°C | 17°C | 10°C | 4°C | -2°C |
Quick stats about holiday rentals with outdoor seating in Middlesex

Total holiday rentals
Explore 60 holiday rentals in Middlesex

Nightly prices starting at
Middlesex holiday rentals start at $90 AUD per night before taxes and fees

Verified guest reviews
Over 6,590 verified reviews to help you choose

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

Pet-friendly accommodation
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
40 properties have a dedicated workspace

Wi-Fi availability
60 of Middlesex holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi and Pool across Middlesex rentals

4.9 Average rating
Middlesex stays are highly rated by guests—averaging 4.9 out of 5!
Destinations to explore
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- Rentals with a fireplace Middlesex
- Apartment rentals Middlesex
- Rentals with a patio Middlesex
- Rentals with a fire pit Middlesex
- Family-friendly rentals Middlesex
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- Pet-friendly rentals Middlesex
- House rentals Middlesex
- Rentals with outdoor seating Washington County
- Rentals with outdoor seating Vermont
- Rentals with outdoor seating United States
- Sugarbush Resort
- Jay Peak Resort
- Bolton Valley Resort
- Pico Mountain Ski Resort
- Cannon Mountain Ski Resort
- Fort Ticonderoga
- Cochran's Ski Area
- Dartmouth Skiway
- Lucky Bugger Vineyard & Winery
- Pump House Indoor Waterpark
- Jay Peak Resort Golf Course
- Country Club of Vermont
- Northeast Slopes Ski Tow
- Autumn Mountain Winery
- Montshire Museum of Science
- Ethan Allen Homestead Museum
- Mt. Eustis Ski Hill
- Leahy Center for Lake Champlain
- Cozy Cottages & Otter Valley Winery
- Burlington Country Club
- Vermont National Country Club
- Killington Adventure Center
- Lincoln Peak Vineyard
- Shelburne Vineyard




