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Vacation rentals with outdoor seating in Middlesex

Find and book unique outdoor seating rentals on Airbnb

Top-rated outdoor seating rentals in Middlesex

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

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Top guest favorite

A modern cabin is nestled among tall trees, elevated on stilts. Large windows offer a glimpse of the interior space, featuring a minimalist design. The surrounding greenery creates a natural setting, while the pathway leading to the cabin is lined with earth tones.

Cabin in Morristown

5 out of 5 average rating, 187 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.

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

4.97 out of 5 average rating, 235 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

An open living area features a wooden dining table surrounded by black chairs. A cozy lounge area includes a navy blue sofa and a wooden coffee table, complemented by a patterned area rug. Exposed beam ceilings add a rustic touch to the bright space.

Home in Waterbury Center

4.99 out of 5 average rating, 138 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 favorite

The spacious studio features a large king bed adorned with a floral duvet and decorative pillows. A cozy seating area with two armchairs is positioned near a window, allowing natural light to fill the room. Rich wood flooring complements the inviting layout.

Guest suite in Waterbury Center

4.98 out of 5 average rating, 167 reviews

Brand New Cozy Mountain Guest Suite in Waterbury

Cozy, private, spacious mountain studio above our garage in historic Waterbury Center. Full kitchen and full bathroom, quiet private deck with mountain views to watch the sunrise each morning. The unit is tucked away under the Worcester Mountains so you can enjoy a comfortable, quiet Vermont experience. Hiking and mountain biking trails are 5-10 minutes away. Stowe is 15 minutes and Waitsfield is 20 minutes away, easy access to I-89 and a 35 minute drive to Burlington to visit Lake Champlain

Top guest favorite

Guest suite in Waterbury Center

4.95 out of 5 average rating, 266 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!

A charming treehouse is nestled among lush green trees, featuring large windows that glow warmly at dusk. A connecting bridge is illuminated with string lights, creating a welcoming pathway. Ferns and forest foliage add to the natural surroundings, enhancing the serene woodland atmosphere.

Treehouse in Moretown

4.97 out of 5 average rating, 154 reviews

Treehouse at Bliss Ridge Farm - Best Views in VT!

This treehouse, the Birds Nest, is open May-Oct. Our “4-Season Treehouse @ Bliss Ridge,” is open year-round: https://www.airbnb.com/h/bigtreehouseatblissridgefarm — NEW SAUNA on property! Dr. Seuss-inspired tree home perched @top of 88-acre, organic hill farm, surrounded by 1000s acres of wilderness. Designed by B'fer Roth, DIY network host of The Treehouse Guys - an authentic treehouse built WITHIN living trees, not stilts! Private hiking & panoramic views of Worcester range, MR valley!

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

4.95 out of 5 average rating, 214 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 favorite

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.

Guesthouse in Waterbury Center

4.99 out of 5 average rating, 234 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

A charming single-story house sits on a well-manicured lawn, surrounded by lush greenery and flowering shrubs. The exterior features large windows that invite natural light indoors, and a gentle sloping landscape leads towards a serene backdrop of trees.

Home in Moretown

4.96 out of 5 average rating, 192 reviews

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.

Top guest favorite

A cozy studio space is shown, highlighting a gray dresser and a red chair with a patterned cushion. The open kitchen area is visible in the background, featuring shelving with kitchen items, a small dining table, and modern appliances, all under soft lighting.

Apartment in Montpelier

4.95 out of 5 average rating, 144 reviews

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 an 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.

A spacious living area features large windows framing mountain views and a cozy fireplace. Natural wood accents complement the soft furnishings, including a circular glass coffee table atop a patterned area rug. A dining table for two is positioned near the sliding doors leading to the outdoor deck.

Home in Moretown

4.98 out of 5 average rating, 290 reviews

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! COMPLETE COVID-19 CLEANING

A private mountain home is nestled among lush greenery, featuring a wooden exterior and a metal roof. The structure is complemented by a welcoming porch and surrounded by a neatly maintained lawn, creating a serene atmosphere against the forest backdrop.

Home in Middlesex

4.94 out of 5 average rating, 183 reviews

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.

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Popular amenities for Middlesex outdoor seating rentals

Free parking on premises

Air conditioning

House rentals with outdoor seating

Top guest favorite

A spacious deck features several black reclining chairs arranged around a white table. Vivid autumn foliage is visible in the background, along with distant mountains and a clear blue sky. The scene invites relaxation in a serene outdoor setting.

4.98 out of 5 average rating, 129 reviews

Romantic Mountain Getaway

A large multi-story home is depicted, featuring a spacious covered porch that wraps around the front. The well-maintained lawn is visible, bordered by trees and greenery, creating an inviting outdoor atmosphere. The sky is clear, with a few clouds scattered throughout.

Home in Waterbury Center

4.92 out of 5 average rating, 111 reviews

Full House 3 Bedrooms/3.5 Baths

A hanging chair is positioned in front of large floor-to-ceiling windows, offering expansive views of the surrounding hills and trees. A small table and chairs are visible nearby, with a rug placed on the polished concrete floor. Natural light creates a relaxed atmosphere.

Home in Barnard

4.99 out of 5 average rating, 153 reviews

The Looking Glass, a modernistic escape

A covered outdoor patio features a comfortable seating area with a gray sofa and colorful pillows, alongside a dining table with yellow chairs. A serene view of the lake is visible through the railing, with nearby trees and a cloudy sky completing the scene.

Home in Salisbury

4.95 out of 5 average rating, 111 reviews

Picture Perfect Lake Dumore Home

Top guest favorite

Home in Tunbridge

4.98 out of 5 average rating, 404 reviews

The Barnbrook House

4.98 out of 5 average rating, 159 reviews

Spacious Eco-Friendly Stowe Home for Family Fun

An open living space features wooden beams overhead and large windows that allow natural light. A cozy seating area with leather chairs and a coffee table is situated beside a modern kitchen, equipped with stainless steel appliances and a dining table with stools.

4.95 out of 5 average rating, 102 reviews

Mountain Meadow Modern Home

Top guest favorite

The single-story home features a modern wooden exterior with large windows that allow natural light to enter. A spacious deck is equipped with outdoor seating and leads to a grassy area surrounded by trees. The inviting structure presents a blend of warmth and contemporary design.

Home in Starksboro

4.98 out of 5 average rating, 127 reviews

Forest Hideaway

Apartment rentals with outdoor seating

A cozy sitting area features a gray couch and a comfortable armchair positioned around a small, round table. A television is situated on a wooden cabinet, with light filtering in through a window draped with patterned curtains. An air conditioning unit is visible near the window.

Apartment in Stowe

4.87 out of 5 average rating, 158 reviews

The Nest in Stowe

Top guest favorite

The Victorian home features a turret and vibrant blue exterior, framed by lush gardens filled with colorful flowers. A welcoming porch with white railings and hanging flower baskets invites relaxation, while large windows reflect the sunlight. A driveway and neighboring buildings are visible.

Apartment in Waterbury

4.94 out of 5 average rating, 208 reviews

1880 Purple Village Victorian

A welcoming living space is highlighted by a rich area rug, contrasting against the wooden floor. Comfortable seating includes an armchair and a coffee table, and a wall-mounted TV is visible. Natural light is provided through large windows with curtains, adding to the airy atmosphere.

Apartment in Waitsfield

4.92 out of 5 average rating, 353 reviews

Spacious, Private Apartment w/ Mountain Views!

A welcoming patio area is displayed, featuring a wooden deck with bistro-style seating. Two bright yellow chairs surround a small table, while a full-sized grill is positioned nearby. The entrance features a glass door with a welcoming sign above it, surrounded by green lawn.

Apartment in Waterbury

4.78 out of 5 average rating, 190 reviews

Modern & Charming Waterbury Village Apt - 1

Top guest favorite

A cozy corner features a comfortable chair adorned with decorative pillows. A small wooden bookshelf displays books, while a potted plant adds a touch of greenery. A slim lamp provides soft lighting, and a faux tree stands nearby beside large windows allowing natural light.

Apartment in Waterbury

4.98 out of 5 average rating, 355 reviews

Village Suite

Top guest favorite

The kitchen is equipped with wooden cabinetry and essential appliances, including a refrigerator and microwave. A round table with wooden chairs occupies the center, creating a functional dining space. Natural light enters through a window adorned with a lace curtain.

Apartment in Williamstown

4.96 out of 5 average rating, 172 reviews

Garden Getaway

Top guest favorite

A grey tufted sofa is positioned in the living area, featuring decorative pillows with mountain designs. In front of the sofa, a sleek coffee table holds a travel magazine about Stowe, accompanied by a decorative item. Light streams in through nearby windows.

Apartment in Stowe

4.99 out of 5 average rating, 349 reviews

Private Apartment w/Mountain views & Hot Tub

Top guest favorite

A charming two-story white building features a black metal roof and multiple windows with shutters. A covered porch extends across the front, decorated with vibrant flower baskets. Surrounding greenery contributes to the rural setting, with the presence of a neighboring structure visible in the background.

Apartment in Hancock

4.96 out of 5 average rating, 161 reviews

Suite in the Green Mountains

Condo rentals with outdoor seating

Top guest favorite

A view from the balcony showcases the surrounding landscape, highlighting green hills and clear blue skies. Two adjoining buildings are visible, featuring sloped roofs and a variety of architectural styles. The area appears tranquil, with open spaces and scattered trees enhancing the natural scenery.

Condo in Killington

4.94 out of 5 average rating, 174 reviews

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

The kitchen features modern white cabinetry and stainless steel appliances. A spacious island with seating for four enhances the area. Pendant lights provide ambient lighting, while a window offers a view of the outdoors, complemented by warm wood flooring.

4.93 out of 5 average rating, 260 reviews

One level condo in the heart of Stowe Village!

Top guest favorite

A cozy living area featuring a grey sofa adorned with orange cushions. A natural wood coffee table occupies the center, while a mountain-themed wall art piece is prominently displayed in the background. Light enters through sliding glass doors leading to a private deck.

Condo in Cambridge

4.94 out of 5 average rating, 161 reviews

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

A bright living area features a cozy white sectional sofa, a wooden coffee table, and a softly textured rug on a carpeted floor. A fireplace is positioned against a wall with built-in shelving, displaying books and decor. Natural light streams through sliding glass doors.

4.86 out of 5 average rating, 156 reviews

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

Top guest favorite

An aerial view captures a modern farmhouse-style condo surrounded by trees with vibrant autumn foliage. The property features a wide deck, outdoor space, and a gazebo to the side, complemented by a manicured lawn and gravel pathway leading to the entrance.

4.97 out of 5 average rating, 122 reviews

Renovated 4-bedroom House: Hot Tub & Outdoor Space

The modern kitchen features stainless steel appliances, including a refrigerator and microwave. A sleek countertop with a unique wooden base is complemented by open shelving showcasing decorative items. The space is well-lit with natural light and offers a dining area with black chairs.

4.85 out of 5 average rating, 117 reviews

Newly Renovated 2 Bedroom Condo centrally located

A cozy living area is visible, featuring a dining table surrounded by bright yellow chairs. A fireplace is seen, enhancing the space, while a large bear-themed wall mural adds a touch of nature. Natural light floods in from the nearby window.

Condo in Killington

4.93 out of 5 average rating, 167 reviews

CozyCub - Pool, Hiking, Mountain Biking

The living area features a soft gray couch and a black lounge chair, complemented by a textured area rug. Natural light enters through a large window dressed with light curtains. A wooden cabinet and an art piece with an animal illustration are also present.

Condo in Warren

4.83 out of 5 average rating, 115 reviews

Modest Mountain Dacha

Quick stats about vacation rentals with outdoor seating in Middlesex

Total rentals
70 properties
Nightly prices starting at
ﺩ.ﺇ220 before taxes and fees
Total number of reviews
5.9K reviews
Family-friendly rentals
40 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with dedicated workspaces
40 properties have a dedicated workspace

Destinations to explore