
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.

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!

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.

Sunny 2BR w/ Pond + Fireplace | Walk to Stowe
At this quiet 2BR on five green acres, you’ll start your mornings with coffee by the pond and end your days by the fire. Bring your bikes to ride over to Cady Hill, snow shoe or hike in Smuggler’s Notch, or stroll the flat mile into town for dinner. Inside, you’ll find toxin-free cookware, natural fiber bedding, and crisp spring-fed water straight from the tap. With a bunk room for the kids and a king suite for you, it’s a calm, well-kept base for year-round adventure in Stowe.

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.

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*

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!
Popular amenities for outdoor seating rentals in Middlesex
House rentals with outdoor seating

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

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

Peaceful setting with Mountain Views
Apartment rentals with outdoor seating

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

Overlook at the Office

1880 Purple Village Victorian

Private Getaway on Lake Lamoille

Entire 2nd Floor Walk to Montpelier

Mary's House in Moretown Village

Village Suite

Private Apartment w/Mountain views & Hot Tub
Apartment rentals with outdoor seating

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

2 bed, 2Bath, New AC, fireplace, amazing location!

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

Renovated 4-bedroom House: Hot Tub & Outdoor Space

Newly Renovated 2 Bedroom Condo centrally located

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

Northeast Kingdom Little Piece of Heaven

Updated large condo across from AT and skiing
When is the best time to visit Middlesex?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $306 SGD | $299 SGD | $211 SGD | $181 SGD | $196 SGD | $189 SGD | $224 SGD | $207 SGD | $205 SGD | $213 SGD | $220 SGD | $263 SGD |
| 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 $78 SGD 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 & 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
60 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 a fireplace Middlesex
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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
- Cochran's Ski Area
- Pico Mountain Ski Resort
- Jay Peak Resort Golf Course
- Autumn Mountain Winery
- Lucky Bugger Vineyard & Winery
- Pump House Indoor Waterpark
- Northeast Slopes Ski Tow
- Montshire Museum of Science
- Mt. Eustis Ski Hill
- Cozy Cottages & Otter Valley Winery
- Ethan Allen Homestead Museum
- Leahy Center for Lake Champlain
- Burlington Country Club
- Country Club of Vermont
- Killington Adventure Center
- Vermont National Country Club
- Lincoln Peak Vineyard
- Shelburne Vineyard