
Vacation rentals with outdoor seating in Middlesex
Find and book unique accommodations with outdoor seating on Airbnb
Quick stats about vacation rentals with outdoor seating in Middlesex

Total vacation rentals
Explore 70 vacation rentals in Middlesex

Nightly prices starting at
Middlesex vacation rentals start at $85 CAD per night before taxes and fees

Verified guest reviews
Over 7,390 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
70 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!
Top-rated accommodations with outdoor seating in Middlesex
Guests agree: these accommodations with outdoor seating are highly rated for location, cleanliness, and more.

The Canopy House—Remodeled Vermont A-Frame Near Downtown
Awarded as one of the top Airbnb's in New England by Condé Nast and Boston Globe! Featured on multiple global publications. Watch the snowflakes fall from the comfort of the 6-person outdoor hot tub, with first-class stargazing to be had all year long. Back inside, the vaulted interior features OM Home Furniture, while a 50” TV with soundbar sits above a real fire. Less than a two mile drive to all downtown Stowe has to offer. 3 BD 2 BA modern A-Frame with two living rooms, 6 person hot tub, Fireplace, two new Roku TV's , soundbar, AC unit, WiFi, deck and back patio, rainfall shower, high-end mattresses, Sonos speaker and furnished by OM Home Furniture. Close to Main Street, 5 miles to Von Trapp, 9 miles to Stowe Mountain Resort and .5 miles from rte 100 to get you easily in and out of town. you will have access to entire house accept for one personal closet in back downstairs bedroom. Less than a 2-mile drive to downtown Stowe, this home is on a hill just off Route 100. Nearby Von Trapp is full of restaurants and other amenities. Ski and snowboard from Stowe Mountain Resort 9 miles away, with picturesque hiking in the summer. I would highly recommend a four wheel or all wheel drive vehicle. House is on a hill with a pretty steep road leading to it.

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.

Secluded Luxury Treehouse - Hot Tub + Projector
Our treehouse is a haven of well-being, peace, and elegance. In our stunning modern treehouse we have brought relaxation to a whole new level. Surrounded amongst us is nothing but woods & wildlife. An experience not to be missed. Put your favorite movie on the projector, get Zen in the cozy sun room, jam out to music on the record player, or grab a towel, and head for the custom cedar hot tub. It is time to create core memories that will never be forgotten. Welcome to a little slice of heaven.

4-Season Treehouse @ Bliss Ridge; Best Views in VT
Insulated, 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. Fabulous “Jotul” fireplace, indoor hot shower / plumbing, fresh mtn spring water, stable access ramp. Our original treehouse, "The Bird’s Nest" is open May-Oct. WiFi avail at the barn! Cell svc works! No pets.

Stunning Views near Stowe /Mountain private home
Retreat and relax at this incredibly located & 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 minutes to the attractions of Stowe, Waterbury and Mad River Valley. Enjoy the hiking trails very close to this cozy home or the nearby ski slopes of Stowe. Sweeping views of the mountains throughout the house. Serene and lovely.

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

The Spring Hill House
Escape to a haven of natural beauty and tranquility at The Spring Hill House. Our unique bow roof home offers breathtaking views of Camel’s Hump and the majestic Green Mountains, the perfect setting for a rejuvenating getaway. Despite being removed from the hustle and bustle of city life, The Spring Hill House is still centrally located, providing easy access to some of Vermont's most popular destinations. Please note: We have a firm no kids policy due to the open loft and stairs.

Gorgeous Treehouse High on Mountain-Amazing View!
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!

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.

Stunning timber frame home on Cady Hill
Wrap yourself in the warmth of our recently finished, one-of-a-kind timber frame straw bale home - aka DD's House. Owner-built in honor of our beloved Grandma DD, we welcome you and yours to enjoy some trailside quality time together as you relax after a day of skiing, hiking, mountain biking, or simply enjoying the beauty of Stowe, Vermont. Located right next to Stowe's Cady Hill Forest, this thoughtful design will present you with truly unique construction and finish details.

Farmhouse with Sunset Mountain Views
Unbeatable Vermont setting, panoramic mountain views and gorgeous sunsets. Located one mile off Rt 100, 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 Village, 18 to lifts, 30 to Sugarbush, 35 min Burlington. The pictures and our 5 star reviews say it all!

Morningstar Meadow - your home in Vermont
You have a home in Vermont! 5-star one-bedroom apartment has country charm and contemporary panache. A perfect retreat to enjoy rural serenity, stunning views, woods and fields. Everything you need: well-appointed with attractive, high quality furnishings, separate entrance, full kitchen, open living/dining area, cozy bedroom with queen bed. Cable TV, WiFi, and cell service. Plentiful free parking. Recent guests claimed heat an issue. It is not. No complaints before or since.
Popular amenities for Middlesex outdoor seating rentals
House rentals with outdoor seating

Stowey Deer Retreat

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

The 1919 Mountain Farmhouse, new hot tub and patio

Modern Farmhouse on 25 Acres - Superb Views

Spacious Eco-Friendly Stowe Home for Family Fun

Vermont Getaway Home - Perfect Location

Forest Hideaway

Peaceful setting with Mountain Views
Apartment rentals with outdoor seating

Modern & Central Treehouse Apartment

Contemporary Studio in Montpelier

Mountain View Retreat | Private Deck + Fast WiFi

Private Getaway on Lake Lamoille

Entire 2nd Floor Walk to Montpelier

Gurdy's Getaway-Downtown 1 BDRM

Mary's House in Moretown Village

Hiking, Biking, Craft beer & Award Winning Dining
Condo rentals with outdoor seating

One level condo in the heart of Stowe Village!

Renovated 4BD House: Hot Tub, Sauna & Backyard

CozyCub- Pool, AC, Hiking, Mountain Biking, Tennis

Meadow Lane Farm House

Northeast Kingdom Little Piece of Heaven

Cozy Condo - AC & Pool. Close to Golf & Bike

The Cozy Condo at Smuggs Resort!

NEW: Stylish Ski On/Ski Off Mountainside Retreat
When is the best time to visit Middlesex?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $264 CAD | $261 CAD | $240 CAD | $196 CAD | $213 CAD | $205 CAD | $261 CAD | $223 CAD | $245 CAD | $258 CAD | $212 CAD | $257 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 |
Destinations to explore
- New York City Vacation rentals
- Montreal Vacation rentals
- Boston Vacation rentals
- Quebec City Vacation rentals
- Jersey City Vacation rentals
- Newark Vacation rentals
- Portland Vacation rentals
- Mont-Tremblant Vacation rentals
- Providence Vacation rentals
- Newport Vacation rentals
- York County Vacation rentals
- Cambridge Vacation rentals
- Apartment rentals Middlesex
- Rentals with a fireplace Middlesex
- Family-friendly rentals Middlesex
- Rentals with a firepit Middlesex
- Pet-friendly rentals Middlesex
- Rentals with a patio Middlesex
- House rentals Middlesex
- Rentals with a washer and dryer Middlesex
- Rentals with outdoor seating Washington County
- Rentals with outdoor seating Vermont
- Rentals with outdoor seating United States
- Jay Peak Resort
- Sugarbush Resort
- Pico Mountain Ski Resort
- Dartmouth College
- Bolton Valley Resort
- Jay Peak
- Stowe Mountain Resort
- Fort Ticonderoga
- Killington Resort
- University of Vermont
- Cannon Mountain Ski Resort
- Middlebury College
- Jay Peak Resort Golf Course
- Montshire Museum of Science
- ECHO, Leahy Center for Lake Champlain
- Kingdom Trails
- Snow Farm Vineyard & Winery
- Pump House Indoor Waterpark
- Shelburne Museum
- Warren Falls
- Shelburne Vineyard
- Cold Hollow Cider Mill
- Fairbanks Museum & Planetarium
- Elmore State Park





