
Holiday rentals with outdoor seating in Middlesex
Find and book unique rentals with outdoor seating on Airbnb
Top-rated rentals with outdoor seating in Middlesex
Guests agree: these rentals 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.

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.

The Summit House - remodeled unique A-frame
Welcome to The Summit House, a completely renovated A-Frame cabin less than 1 mile to downtown Stowe. Wake up to views of the morning light casting through the forest from your glass wall bedroom. Relax after a day exploring the mountains in the huge spa style rainfall shower. Settle down after dinner around the modern wood burning fireplace while watching your favorite shows on the 50" TV. It's not just a rental, it's an experience. The latest addition to the OM Home Residences collection.

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.

The Rustic Retreat at Twin Ponds
Take it easy and make yourself right at home in our woodsy cabin tucked away in the Cold Hollow Mountains. As you head down the drive, let your worries fade away - you’re now on cabin time. Relax in the clawfoot tub after a day of travel or prepare a home-cooked meal in the well equipped kitchen. When morning comes, enjoy your coffee while cozied up in front of the fireplace or stay in bed and take in the views. And with plenty of woods to explore, it's your perfect escape at your pace.

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

Peaceful setting with Mountain Views
Rent the entire house. Primary bdrm w/ private bath, 2 bdrms that accommodate 4 people w/ shared full bath, one bonus room w/ pull out couch and a 1/2 bath . Updated kitchen, propane stove (looks like a wood stove) covered porch, exercise room, games, fully equipped kitchen, hot tub (from Memorial Day till Thanksgiving), outdoor fire pit, all on 8 acres. Located centrally to three ski resorts, mountain biking, hiking , kayaking, swimming, you name it. An inviting home in any season!

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.

Waldhaus - Modern Forest Cabin
Escape to our beautifully designed Vermont cabin, transformed into a modern, cozy, and sun-filled retreat. From the moment you step inside, you'll feel at home in this inviting space. The entire cabin & yard will be yours during your stay. High-speed fiber WiFi keeps you connected and dogs are welcome. We're just 15-20 min from Mad River Glen, Mt. Ellen & Sugarbush. Many restaurants & stores are within 15 min to Waitsfield, 20 min to Waterbury.
Popular amenities for outdoor seating rentals in Middlesex
House rentals with outdoor seating

The Stowey Deer | King Bed | 15 Min to Skiing

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

The 1919 Mountain Farmhouse, new hot tub and patio

Brand new Beautiful Modern Clean Home On River

The Barnbrook House

Spacious Eco-Friendly Stowe Home for Family Fun

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

Vermont Getaway Home - Perfect Location
Apartment rentals with outdoor seating

Hideaway studio: breweries, skiing, dogs welcome

1880 Purple Village Victorian

Lofty Dreams

Private Getaway on Lake Lamoille

Two-Bedroom apartment in the Green Mountains

Entire 2nd Floor Walk to Montpelier

Mountain Road Apartment, Optimal Location

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

One level condo in the heart of Stowe Village!

Lovely 3-BR Stonybrook Townhouse With Mtn Views

Renovated 4-bedroom House: Hot Tub & Outdoor Space

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

Meadow Lane Farm House

Northeast Kingdom Little Piece of Heaven

NEW: Stylish Ski On/Ski Off Mountainside Retreat

Smugglers' Notch Relaxing Mountainside Retreat
When is the best time to visit Middlesex?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £138 | £136 | £125 | £102 | £111 | £107 | £136 | £116 | £128 | £135 | £110 | £134 |
| 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 70 holiday rentals in Middlesex

Nightly prices starting at
Middlesex holiday rentals start at £44 per night before taxes and fees

Verified guest reviews
Over 7,380 verified reviews to help you choose

Family-friendly holiday rentals
40 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
40 properties have a dedicated workspace

Wifi availability
70 of Middlesex holiday 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
- Jay Peak Resort
- Sugarbush Resort
- Killington Resort
- Pico Mountain Ski Resort
- Bolton Valley Resort
- Fort Ticonderoga
- Cannon Mountain Ski Resort
- Jay Peak
- Stowe Mountain Resort
- Jay Peak Resort Golf Course
- Dartmouth College
- Pump House Indoor Waterpark
- Middlebury College
- Montshire Museum of Science
- University of Vermont
- ECHO, Leahy Center for Lake Champlain
- Shelburne Museum
- Warren Falls
- Shelburne Vineyard
- Snow Farm Vineyard & Winery
- Waterfront Park
- Elmore State Park
- Kingdom Trails
- Quechee Gorge





