
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.

Farm Stay - Working livestock farm
Come stay in our apartment connected to the barn on our active working farm. We are located 3 miles from the state capitol building in Montpelier, but you would never know it up here. You can cross country ski, snowshoe, hike, or bike out your front door, and we are located within 45 min. from Sugarbush, Stowe, Mad River Glen, & Bolton Valley. You can also check out the local beer & spirits scene, or just relax at the farm. Guests are always welcome to tour the grounds and see the animals.

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.

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 in the comfort of little house. 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

Stowe, Vermont - Private Second floor apartment.
Private One bedroom apartment, on the second floor. Two adults only, one adult must be minimum age 25 Our reservation availability opens three months out. Air conditioning. Fireplace. no pets. no smoking, vapping, or e- cigarettes. Trout pond, poles available. Downtown village 3.2 miles. Burlington International Airport - 37 miles Stowe Mountain Resort - 11 miles - 18 minutes Von Trapps lodge & Brewery - 7.2 mikes - 17 minutes Ben & Jerry’s Factory - 18 miles - 18 minutes.

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

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.

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!

Cottage Farmhouse Apartment in Heart of Vermont!
Welcome to our charming second-floor cottage-apartment in our historic 1830s brick farmhouse! This cozy space is completely redecorated for guests and features a comfortable queen bed in the sleeping area, a vintage farmhouse kitchen, and a lovely living/dining room with maple floors and travertine in the bathroom. Enjoy the peaceful country setting with eastern mountain views and active farm fields. Wake up to glorious morning sun and blackout shades for a good night’s sleep.

Meadow Woods Cabin, private, cozy and unconnected
Enjoy beautiful sunsets from your rocking chair on the cabin's wonderful porch. There is a large, well equipped kitchen, open space floor plan, new shower unit and plenty of closet space in the bedroom. Easy access to VAST snowmobile trails, within an hour's drive to 3 ski areas (Stowe, Smuggler's Notch and Jay Peak), X-Country skiing right outside the door or in Craftsbury or Stowe. Elmore State Park is 3 miles away. Hiking trails and kayaking abound!

Dramatic Views at the Above the Clouds Guesthouse
As featured in Conde Nast Traveler (1/21/22) Peaceful & impeccable retreat with a 180 degree view of Vermont's tallest mountains. Near Vermont's premier skiing, hiking, & outdoor adventures, you’ll love the sunset views and cozy atmosphere (huge sheepskin in front of the fireplace) and the attention to detail (live-edge wood details, spa-like bathroom). This is an incredible retreat for couples and families, adventurers and business travelers alike!

Worcester Mountain Cabin · Wildlife & Cozy Nooks
**Weekend promotion Book 2 nights (Fri & Sat, Sun 50% off)** A modern cabin retreat in Vermont’s wild, undeveloped Worcester Mountain Range. Surrounded by wildlife, forest views, this cozy hideaway features a curated library, record player, art supplies, and space to create or simply rest. Explore local culture, skiing, swimming holes, and soulful retreats — or settle in, light a candle, and do nothing at all. Well-behaved pets welcome.

Ray's Getaway
Kick back and relax in this spacious one-bedroom apartment with a private entryway and patio overlooking the majestic Green Mountains. Located just one-half mile from the beautiful Waterbury reservoir, it is perfect for swimming, boating and fishing. (And ice fishing in the winter!) A superb location within a half hour drive to three hospitals, four major ski areas, and less than three miles from all downtown Waterbury has to offer!
Popular amenities for Middlesex outdoor seating rentals
House rentals with outdoor seating

The Stowey Deer | King Bed | 15 Min to Skiing

Full House 3 Bedrooms/3.5 Baths

The 1919 Mountain Farmhouse, new hot tub and patio

Spacious Eco-Friendly Stowe Home for Family Fun

Sunny 2BR w/ Pond + Fireplace | Walk to Stowe

Modern design in the woods, private, beautiful

Forest Hideaway

Cozy Hideaway w Hot Tub — Perfect for Ski Weekend!
Apartment rentals with outdoor seating

Slopeside Bolton Valley Studio

Stowe Charm in South Village

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

Spacious, Private Apartment w/ Mountain Views!

Entire 2nd Floor Walk to Montpelier

Mountain Road Apartment, Optimal Location

Mary's House in Moretown Village

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!

Smooth 2-minute Ski to the Lift •Smuggs Condo

Renovated 4-bedroom House: Hot Tub & Outdoor Space

Newly Renovated 2 Bedroom Condo centrally located

Northeast Kingdom Little Piece of Heaven

The Hygge House - Downtown Stowe

Smugglers' Notch Relaxing 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 | $319 CAD | $312 CAD | $220 CAD | $188 CAD | $205 CAD | $197 CAD | $251 CAD | $214 CAD | $236 CAD | $248 CAD | $203 CAD | $247 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 $68 CAD per night before taxes and fees

Verified guest reviews
Over 6,930 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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- House rentals Middlesex
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- Rentals with outdoor seating Washington County
- Rentals with outdoor seating Vermont
- Rentals with outdoor seating United States
- Jay Peak Resort
- Sugarbush Resort
- Killington Resort
- Pico Mountain Ski Resort
- Jay Peak
- Bolton Valley Resort
- Cannon Mountain Ski Resort
- Fort Ticonderoga
- Jay Peak Resort Golf Course
- Pump House Indoor Waterpark
- ECHO, Leahy Center for Lake Champlain
- Montshire Museum of Science
- Dartmouth College
- Stowe Mountain Resort
- University of Vermont
- Shelburne Museum
- Middlebury College
- Waterfront Park
- Shelburne Vineyard
- Kingdom Trails
- Lake Champlain Chocolates
- Boyden Valley Winery & Spirits
- Snow Farm Vineyard & Winery
- Warren Falls




