
Vacation rentals with outdoor seating in Middlesex
Find and book unique accommodations with outdoor seating on Airbnb
Top-rated accommodations with outdoor seating in Middlesex
Guests agree: these accommodations with outdoor seating are highly rated for location, cleanliness, and more.

Camel's Hump Remote Mountain Cottage
Escape to this peaceful getaway with beautiful mountain views. Our cottage is ideal for the adventure seeker, nature lover or remote worker. Located less than two miles from Camel’s Hump trail head and less than 30 miles from ski resorts, including Stowe, Sugarbush, Bolton, Cochran and Mad River. The area offers plenty of outdoor activities from hiking, cross country skiing, snow shoeing, mountain biking, fishing, swimming, kayaking and only 15 min from local restaurants, breweries and shops.

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

Stunning Views near Stowe / Private mountain home
Retreat and relax at this incredibly located and uniquely designed home nestled in the heart of ski country. This three bedroom, two bathroom vacation home is perfect for families or couples looking to enjoy Vermont's beauty and recreation. Very private location yet close to the amenities of Waterbury, Stowe and Mad River Valley. Enjoy the hiking trails, minutes away from this cozy home or the nearby ski slopes of Stowe. Sweeping views of the mountains throughout the house. Serene and lovely.

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.

Alder Brook Cottage: A Tiny House in the Woods
From the moment you cross the cedar footbridge over Alder Brook, you'll know you're somewhere special. Featured in Boston Magazine and CabinPorn, Alder Brook Cottage is an inspired, rustic dream cabin located in the woods of Vermont's Northeast Kingdom. Surrounded by a crystal clear stream and 1400 acres of rugged forest, it is the perfect getaway for glampers looking to experience the tiny house life. Minutes away from Caspian Lake, Hill Farmstead Brewery & Craftsbury Outdoor Center.

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

Home on Flower Farm near VT’s best skiing & brews!
Country setting adjacent to a flower farm only 3 minutes off 89 perfectly nestled between mountains that boast hiking, skiing and mountain biking and the best of Vermont's brewery and restaurant scene. 20 minutes to Sugarbush and Mad River Glen, 30 minutes to Stowe and 25 minutes to Bolton Valley (night skiing!). With Waitsfield and Waterbury being less than 10 minutes away, it's an easy drive to two of the finest breweries, Lawsons and Prohibition Pig, that Vermont has to offer.

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.

True Mountain House
This is a very private mountain home surrounded by green and peace. Your private forest. Amazing Views. Very romantic. Open layout. Lots of light. Wood floors and electric heating. Very quiet, relaxing and cozy. It has a decompressing effect on it's guests. Perfect to rest your head. Not suitable for children under 12 years old. Amazing gourmet kitchen. WE HAVE HIGH SPEED INTERNET. Fly into Burlington and rent a car, it will be approximately a 40min. Drive to Middlesex.
Popular amenities for Middlesex outdoor seating rentals
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

Spacious Eco-Friendly Stowe Home for Family Fun

18 Lake Stunning View of Champlain in Adirondacks

Vermont Getaway Home - Perfect Location

The Guest House at Sky Hollow

Forest Hideaway
Apartment rentals with outdoor seating

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

Overlook at the Office

"Hot Tub Hideaway: Private Hot Tub, 9 min to Stowe

Modern & Charming Waterbury Village Apt - 1

Private Getaway on Lake Lamoille

Entire 2nd Floor Walk to Montpelier

Mountain Road Apartment, Optimal Location

Village Suite
Condo rentals with outdoor seating

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

One level condo in the heart of Stowe Village!

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

Renovated 4-bedroom House: Hot Tub & Outdoor Space

The Château -Luxe condo in heart of downtown Stowe

Newly Renovated 2 Bedroom Condo centrally located

Modern Farmhouse Condo: fast WiFi+close to it ALL!

Northeast Kingdom Little Piece of Heaven
When is the best time to visit Middlesex?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $330 CAD | $323 CAD | $228 CAD | $195 CAD | $212 CAD | $204 CAD | $260 CAD | $222 CAD | $244 CAD | $228 CAD | $237 CAD | $284 CAD |
| 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 vacation rentals with outdoor seating in Middlesex

Total vacation rentals
Explore 60 vacation rentals in Middlesex

Nightly prices starting at
Middlesex vacation rentals start at $84 CAD per night before taxes and fees

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

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

Pet-friendly vacation rentals
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
40 properties have a dedicated workspace

Wifi availability
60 of Middlesex vacation rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Middlesex rentals

4.9 Average rating
Middlesex stays are highly rated by guests—averaging 4.9 out of 5!
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- 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
- Cannon Mountain Ski Resort
- Fort Ticonderoga
- Dartmouth Skiway
- Pico Mountain Ski Resort
- Cochran's Ski Area
- Lucky Bugger Vineyard & Winery
- Jay Peak Resort Golf Course
- Autumn Mountain Winery
- Pump House Indoor Waterpark
- Northeast Slopes Ski Tow
- Montshire Museum of Science
- Ethan Allen Homestead Museum
- Mt. Eustis Ski Hill
- Burlington Country Club
- Cozy Cottages & Otter Valley Winery
- Country Club of Vermont
- Leahy Center for Lake Champlain
- Killington Adventure Center
- Vermont National Country Club
- Lincoln Peak Vineyard
- Shelburne Vineyard




