Holiday rentals with outdoor seating in Middlesex

4.96 out of 5 average rating, 289 reviews

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

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.

4.95 out of 5 average rating, 603 reviews

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

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.

4.97 out of 5 average rating, 196 reviews

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

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.

4.96 out of 5 average rating, 259 reviews

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

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

4.99 out of 5 average rating, 151 reviews

Home in Waterbury Center

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.

4.98 out of 5 average rating, 120 reviews

Treehouse in Moretown

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!

Guest suite in Waterbury Center

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.

4.96 out of 5 average rating, 292 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!

4.94 out of 5 average rating, 236 reviews

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

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.

Guest house in Waterbury Center

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.

4.99 out of 5 average rating, 261 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

4.96 out of 5 average rating, 164 reviews

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.

Flat in Montpelier

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.

Guest suite in East Montpelier

A spacious living area is filled with natural light from large windows, showcasing a comfortable sofa and a small dining table with two chairs. Refinished maple floors create a warm ambiance, while vintage wallpaper adds character to the space.

4.92 out of 5 average rating, 329 reviews

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.

4.94 out of 5 average rating, 193 reviews

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

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.

Popular amenities for outdoor seating rentals in Middlesex

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with outdoor seating

4.96 out of 5 average rating, 550 reviews

The uniquely shaped house, adorned with shingles, is surrounded by lush greenery. Large windows reflect the vibrant foliage, allowing natural light to illuminate the structure. The natural stone wall complements the rustic aesthetic, creating a harmonious blend with the wooded landscape.

Home in Fairlee

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

4.99 out of 5 average rating, 106 reviews

The farmhouse is displayed with a classic white exterior and a metal roof. A welcoming front porch is flanked by steps leading up to the entrance. Surrounding fields stretch into the distance beneath a clear blue sky, showcasing the home's peaceful rural setting.

Home in East Montpelier

The 1919 Mountain Farmhouse, new hot tub and patio

4.93 out of 5 average rating, 121 reviews

A spacious living area showcases vaulted ceilings with exposed wooden beams. A dark sectional sofa is positioned near a modern coffee table, facing large glass doors that open to a forested view. A sleek kitchen features stainless steel appliances and a wood-burning stove adds warmth.

Home in Stowe

Brand new Beautiful Modern Clean Home On River

4.97 out of 5 average rating, 212 reviews

A comfortable living area features two dark sofas arranged around a central coffee table on a textured area rug. A lamp stands beside one sofa, and a stone fireplace adds warmth to the space. Large windows allow natural light to illuminate the room.

Home in Waterbury Center

Vermont Getaway Home - Perfect Location

4.97 out of 5 average rating, 220 reviews

A warmly lit cabin emerges from the surrounding trees, framed by a quiet, snow-covered dirt road. Soft light spills from the windows, creating a welcoming glow in the tranquil, darkened landscape.

Home in Rochester

The Guest House at Sky Hollow

4.99 out of 5 average rating, 145 reviews

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

Forest Hideaway

4.96 out of 5 average rating, 141 reviews

Two white Adirondack chairs are positioned on a grassy expanse, surrounded by autumn foliage. Trees with vibrant orange and yellow leaves create a scenic backdrop against a clear blue sky, showcasing the natural beauty of the 8-acre property.

Home in Waterbury Center

Peaceful setting with Mountain Views

Home in Waterbury Vermont

A spacious living area features a large, sectional grey sofa adorned with colorful cushions. A coffee table sits in front, accompanied by a small decorative bowl. Natural light filters through large windows, enhancing the warm wooden flooring and inviting atmosphere.

4.95 out of 5 average rating, 140 reviews

Cozy Hideaway w Hot Tub — Perfect for Ski Weekend!

Apartment rentals with outdoor seating

4.86 out of 5 average rating, 126 reviews

Flat in Northfield

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

4.96 out of 5 average rating, 250 reviews

A cozy living area features a green couch adorned with colorful throw pillows and a warm blanket. A round blue chair offers additional seating, complemented by a simple black coffee table placed on a striped rug. Natural light brightens the space from nearby windows.

Flat in Richmond

Hideaway studio: breweries, skiing, dogs welcome

4.94 out of 5 average rating, 217 reviews

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.

Flat in Waterbury

1880 Purple Village Victorian

4.87 out of 5 average rating, 334 reviews

The entrance door features a clear sign that reads 'Dragonfly Apartment,' mounted above a polished doorknob. The door displays a glass panel that allows natural light to filter through, while a lush green landscape can be seen through the window.

Flat in Bristol

"Dragonfly Apartment" Private Bristol Apartment

4.79 out of 5 average rating, 197 reviews

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.

Flat in Waterbury

Modern & Charming Waterbury Village Apt - 1

5 out of 5 average rating, 116 reviews

The exterior of the property is viewed from the gravel driveway, featuring a red barn-style section and a white house with multiple windows. The green lawn surrounds the house, and the lake is visible in the background, framed by trees.

Flat in Morristown

Private Getaway on Lake Lamoille

4.87 out of 5 average rating, 747 reviews

The exterior of the duplex is showcased, featuring a welcoming porch with two umbrellas over a seating area. Steps lead up to the porch, surrounded by lush greenery and neatly arranged flower beds, and the house is embraced by mature trees.

Flat in Montpelier

Entire 2nd Floor Walk to Montpelier

4.97 out of 5 average rating, 139 reviews

A stone patio is featured with a circular arrangement of wooden chairs surrounding a firepit. Lush greenery is visible nearby, and a covered porch adorned with hanging flowers is accessible from the upper level of the building.

Flat in Stowe

Mountain Road Apartment, Optimal Location

Apartment rentals with outdoor seating

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.

4.94 out of 5 average rating, 274 reviews

One level condo in the heart of Stowe Village!

A spacious studio features large windows with views of the outside landscape. A king-sized bed with a patterned duvet occupies the center, complemented by a queen sleeper sofa. A small table and chairs, along with a stylish armchair, create a comfortable seating area.

4.96 out of 5 average rating, 103 reviews

3rd Floor Studio @ The Lodge at Spruce Peak

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.

4.85 out of 5 average rating, 175 reviews

Cozy 2 bed, 2Bath, fireplace, amazing location!

4.95 out of 5 average rating, 173 reviews

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.

Apartment in Cambridge

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

The living area features a plush area rug with a soft texture, surrounded by comfortable seating. A dark grey sofa and two accent chairs are complemented by round woven ottomans. A colorful abstract artwork hangs on the wall, enhancing the space's decor.

4.95 out of 5 average rating, 135 reviews

Lovely 3-BR Stonybrook Townhouse With Mtn Views

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, 141 reviews

Renovated 4-bedroom House: Hot Tub & Outdoor Space

The kitchen features modern white cabinetry paired with natural wood countertops. Open shelving displays glassware and utensils, while a sleek stainless-steel stove and retro-style refrigerator are incorporated. Ample countertop space is available for meal preparation, enhancing functionality in this well-organized area.

4.86 out of 5 average rating, 168 reviews

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

A spacious living area features a spiral staircase leading to the upper level. A light-colored couch is positioned beside a wooden coffee table, with a rug underneath. The kitchen is visible in the background, showcasing dark cabinetry and modern appliances, with a dining table that seats four.