Holiday rentals with outdoor seating in Middlesex

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Top-rated rentals with outdoor seating in Middlesex

Guests agree: these rentals with outdoor seating are highly rated for location, cleanliness and more.

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Top guest favourite
A charming barn-style structure is shown with a spacious driveway leading up to its entrance. The architecture features a peaked roof and wood paneling, complemented by the neatly arranged firewood at the side. Lush green grass surrounds the entryway, inviting exploration.
Farm stay in Berlin
4.96 out of 5 average rating, 287 reviews

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.

Top guest favourite
Cabin in Morristown
5 out of 5 average rating, 227 reviews

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.

Top guest favourite
The interior of the yurt features a cozy living area with a seating arrangement that includes a loveseat and a futon. A queen-sized bed is positioned in the corner, with high-quality linens. A pellet stove provides warmth, complemented by colorful lanterns hanging from the ceiling.
Yurt in Montpelier
4.94 out of 5 average rating, 598 reviews

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.

Top guest favourite
Aerial view of the vibrant Vermont landscape, showcasing rolling hills adorned with a diverse palette of fall foliage. The rustic barn sits among expansive fields, framed by trees displaying bright autumn colors, with distant mountains in the background under a partly cloudy sky.
Barn in Morristown
4.97 out of 5 average rating, 195 reviews

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.

Guest favourite
The exterior of a charming cabin is surrounded by snow-covered trees and a blanketed yard. A bold red door contrasts with the dark wooden facade and multiple windows, inviting entry. The peaceful winter setting emphasizes the cabin's rustic charm.
Cabin in Worcester
4.96 out of 5 average rating, 257 reviews

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

Guest favourite
A modern cottage is depicted, with a wooden exterior and large windows glowing softly in the evening light. In the foreground, a fire pit made of stone is seen, featuring glowing embers, surrounded by grassy areas and some trees providing a natural backdrop.
Cottage in Worcester
4.95 out of 5 average rating, 223 reviews

Worcester Mountain Cabin · Wildlife & Cozy Nooks

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 (the backyard is a dog’s dream). After booking, enjoy our insider welcome guide with local trial maps and hidden gems.

Top guest favourite
Home in Waterbury Center
4.99 out of 5 average rating, 150 reviews

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.

Top guest favourite
Treehouse in Moretown
4.98 out of 5 average rating, 118 reviews

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!

Top guest favourite
A winter landscape displays snow-covered mountains under a blue sky, with soft white clouds. A forest of bare trees, dusted with snow, lines the foreground, leading to a snowy field. The serene atmosphere invites a sense of tranquility and natural beauty.
Guest suite in Waterbury Center
4.96 out of 5 average rating, 290 reviews

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!

Guest favourite
The exterior of Alder Brook Cottage is shown, featuring rustic wooden siding and a metal roof. A wooden footbridge leads to the front door, surrounded by trees and patches of snow. Bright windows are visible, enhancing the cabin's inviting appearance.
Tiny home in Hardwick
4.94 out of 5 average rating, 231 reviews

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.

Top guest favourite
The cottage, featuring a wooden exterior and large windows, is surrounded by greenery and natural rock formations. A stone pathway leads to the entrance, which is sheltered by an overhanging roof. Sunlight illuminates the peaceful setting, highlighting the rustic charm of the structure.
Guest house in Waterbury Center
4.99 out of 5 average rating, 258 reviews

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

Guest favourite
An elevated cabin nestled among trees features a wooden exterior with large windows. A spacious deck is furnished with seating, providing a serene outdoor space surrounded by lush greenery.
Treehouse in Moretown
4.94 out of 5 average rating, 512 reviews

Gorgeous Treehouse! Big views, Cozy warm fireplace

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!

Popular amenities for outdoor seating rentals in Middlesex

When is the best time to visit Middlesex?

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Avg. price$303 SGD$297 SGD$209 SGD$179 SGD$195 SGD$187 SGD$239 SGD$204 SGD$225 SGD$209 SGD$218 SGD$261 SGD
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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 $77 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!