Vacation rentals with a patio in Middlebury

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Top-rated patio rentals in Middlebury

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Top guest favorite

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, 161 reviews

The Looking Glass, a modernistic escape

Welcome to The Looking Glass, a modernistic escape located in Barnard, Vermont! With floor to ceiling, south facing windows, you’ll be relaxing in comfort while taking in breathtaking views of the Green Mountains! You’ll love our commercial grade kitchen, boasting high-end cookware, a Wolf range and Subzero fridge. Take the spiral staircase upstairs to enjoy a long bath before calling it a night in the spacious king bed. Explore Silver Lake & Woodstock! Hike, bike or ski the neighboring trails

Top guest favorite

A bright and spacious loft area is highlighted by tall windows allowing natural light to illuminate the room. A well-equipped kitchenette is visible, along with a cozy seating arrangement featuring a small table and two chairs, next to a large bed dressed in soft linens.

Guest suite in Starksboro

4.94 out of 5 average rating, 103 reviews

Private Suite in the Green Mountains

Relax in a country setting, centrally located to Vermont attractions. This private apartment in the trees boasts three beds and a full kitchen. With views of the Green Mountains, you will be a short drive away from quaint towns, skiing, breweries, hiking, and swimming. On the property, enjoy the fresh mountain air, changing leaves, and local flora and fauna. In summer, cool off after a hike or bike in the shared pool. In winter, you're 15 minutes to Mad River Glen and 30 to Sugarbush Ski Resort.

Top guest favorite

An aerial view showcases a large, red two-story building with a metal roof nestled among lush greenery. The property features multiple decks and a private outdoor space. The surrounding landscape provides a serene backdrop of trees and grass, enhancing the natural setting.

Guest suite in Lake Bomoseen

4.96 out of 5 average rating, 219 reviews

Mi Casa es su Casa!

Relax in this refurbished quiet Lake view rental. Minutes from Lake Bomoseen/Crystal Beach. Large family room, Cast iron wood-stove. Wall of windows w/lake views. 65" 4K w/ surround sound. w/ game hook-up. Wi-Fi. Galley kitchen includes range, microwave, Keurig, fridge & wine cooler. Spacious bedroom, queen size bed w/ heated mattress pad. Lots of storage.Full bathroom. Private deck w/Adirondack chairs. Kayaks & boat launch. 15 miles to Rutland, 35 min to Pico & 47 min Killington Ski Resorts.

Top guest favorite

A serene landscape is captured, showcasing a reflective pond surrounded by lush greenery. A variety of trees are positioned nearby, some displaying vibrant yellow leaves against a backdrop of rolling hills and a dramatic sky filled with clouds.

Barn in Ripton

4.94 out of 5 average rating, 221 reviews

Charming Barn Guesthouse Near Middlebury College

Come stay at our lovely renovated barn guesthouse in the Green Mountains of Vermont near Middlebury College. Perfect spot for a quiet retreat or home base for your outdoor adventure! 3 min. to Rikert Nordic Center, 9 min. to Middlebury SnowBowl. 40 min. to Sugarbush. 1 hr to Killington. Sleeps 1-6 people on 3 floors: entry level living area and laundry; mid-level with kitchen, bedroom, and bathroom ; upstairs loft bedroom suite with seating area (futon, chairs, bookcase, and TV), and desk.

Top guest favorite

A spacious guest suite features a king bed with a light-colored bedspread and decorative pillows. Two bedside tables with lamps are on either side, while large windows allow natural light to fill the room. Light-colored walls and wood flooring enhance the welcoming atmosphere.

Guest suite in South Burlington

5 out of 5 average rating, 257 reviews

Suite Escape - Quiet retreat, close to everything!

Spacious guest suite nestled in a quiet family neighborhood, private entrance, use of shared deck with seating overlooking backyard. King bed and full kitchen with all necessities. Washer/dryer in unit and large walk-in shower. L-shaped sectional with smart 65” TV (no cable). Centrally located within minutes to all Colleges, UVM Med Ctr, Down Town Burlington, Lake Champlain and Golf Courses. This entire property is non-smoking; including tobacco and cannabis products as well as e-cigarettes.

Top guest favorite

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

4.96 out of 5 average rating, 117 reviews

Lake Dunmore Getaway — Foliage Views & Ski Retreat

About this space Perched directly on the shores of Lake Dunmore, our lakefront getaway transforms into a four-season escape when the temperatures drop. In autumn, enjoy foliage views over the water, crisp mornings on the deck, and easy drives to Vermont’s most scenic byways. When winter arrives, we’re your basecamp for adventure — just 30 minutes to Middlebury Snow Bowl, 45 minutes to Killington or Sugarbush, and minutes to local snowmobile trails, ice fishing spots, and Middlebury College.

Top guest favorite

A circular fire pit is surrounded by three rustic wooden benches, positioned on a grassy area among lush trees. Two adults and a child sit comfortably, enjoying the warm glow of the fire. Behind them, the unique treehouse structure, with large windows, blends into the natural setting.

Treehouse in Moretown

5 out of 5 average rating, 102 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!

Guest favorite

A wooden cabin is set against a backdrop of colorful autumn foliage. The exterior features multiple large windows and a spacious deck with seating arrangements, including two lounge chairs. A grill and stacked firewood are visible on the deck, inviting outdoor gatherings.

Cabin in Roxbury

4.97 out of 5 average rating, 257 reviews

Off Grid Secluded Cabin on 37 Acre Farm

In a secluded, hand-crafted off the grid cabin, come and enjoy the elements with us at Drift Farmstead. A 3-minute walk leads you through gardens and pasture, to Ravenwood, a small, intimate cabin with everything you need. Be it an extended weekend tucked in seclusion, amongst the birds, river and trees, or find the comforts of a 37 acre small farm nestled in the mountains and settle in, working from afar. Top shelf skiing at Sugarbush is near, along with Vermont's finest grub and beer.

Top guest favorite

The exterior of the cottage displays a modern design with light gray siding and a vibrant purple door. A small porch offers space to relax, while surrounding trees enhance the peaceful environment. A pathway is visible, leading to the entrance of the home.

Home in Middlebury

4.97 out of 5 average rating, 177 reviews

Purple Door Cottage in the heart of Middlebury!

Purple Door Cottage is located in the heart of Middlebury on a peaceful side street. Completely renovated, AC & heat everywhere, lots of comfy beds, great deck with grill and fire ring, fast WiFi, king bedroom for the parents, fun guest room with 1 queen, 1 full & 1 twin, full bath & 1/2 bath. Walk to restaurants, shops, grocery stores, and even the College! Incredibly well designed home can comfortably accommodate a couple or a crowd! Brand new 55" Smart TV, new beds, linens, sofas, etc.

Guest favorite

A spacious living room is depicted featuring comfortable sofas and a stylish coffee table. Natural light enters through a window with dark curtains, while a decorative rug adds warmth to the wood floor. A welcoming entryway is visible in the background.

Apartment in Middlebury

4.97 out of 5 average rating, 109 reviews

Spacious Home Near Heart of Middlebury Fiber Wifi

Enjoy a cozy, stylish and private experience at this centrally located large 3 bedroom home. Free ultra fast Fiber Wifi. (4) 4k smart tv's including one large 65 inch curved for your enjoyment. Close to Middlebury College. Visit nearby hiking trails, Lake Dunmore, Branberry beach and much more. Near Middlebury College Snow Bowl and Robert Frost Trails for Beautiful nature views. Restaurants and shops within walking distance and a short drive or bike ride to downtown Middlebury.

Top guest favorite

A bright bedroom features a spacious bed adorned with white linens and subtle blue detailing. Natural light enters through two windows, accompanied by blinds. A potted plant adds a touch of greenery, while built-in shelving provides storage options.

Apartment in Middlebury

4.98 out of 5 average rating, 144 reviews

Mountain View Retreat

This clean, quiet, ground-level apartment enjoys an out-of-town feel and expansive mountain views while being conveniently located to the town of Middlebury, Middlebury College, the Green Mountain National Forest, the Middlebury College Snow Bowl and the Rikert Nordic Center, and more. This 1 bedroom/1 bath apartment features an open living concept and a fully equipped kitchen and is just 1.5 miles from restaurants and grocery stores and 2 miles from the college.

Guest favorite

A modern house with wooden exterior is shown from an elevated perspective, surrounded by autumn foliage. A hot tub is positioned on a spacious deck, which includes a seating area with four chairs and a small table. Scenic mountain views and vibrant trees enhance the natural setting.

Tiny home in Warren

4.99 out of 5 average rating, 261 reviews

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*