Holiday rentals with outdoor seating in Rutland

4.97 out of 5 average rating, 203 reviews

A charming cottage is set against a backdrop of lush trees, with a deck extending from the front. The warm, orange sky creates a serene atmosphere, casting soft light on the exterior of the house and surrounding landscape.

Guest house in Hartland

Cozy - Killington 40 min. Woodstock-Hanover-Piano!

Luxurious, well appointed cottage - Beautiful sunrise view located between Woodstock VT and Hanover NH. Inspiring treat for musician’s getaway is a fully restored 1929 Steinway Full kitchen, custom cabinets, gas fireplace, energy efficient heat pump, washer, dryer. VERY comfortable queen bed. Romantic getaway in the woods, relax, work in peace, explore the beauty and history of the area. Hiking, biking, fishing, hot air balloon rides and shopping are all close by. Long (90 day) or weekend rental

4.85 out of 5 average rating, 124 reviews

A bright kitchen area is complemented by a vibrant yellow wall. Wooden cabinetry holds kitchen essentials above a small countertop. Two bar stools are positioned at a wooden table. Natural light enters through large windows, illuminating the cozy studio space with an inviting atmosphere.

Flat in North Hartland

Private Riverside Studio* Upper Valley*Vermont

This unique place has a style all its own. Perfect for a traveling nurse or anyone who needs a relaxing getaway or a remote place to work. This studio apartment has river and garden views and is conveniently located in the New England Village of North Hartland. A 15-20 minute drive to Dartmouth College or DHMC. Take country walks across the twin covered bridges right from your doorstep. Relax on the front porch and watch the bald eagles and peregrine falcons search for prey along the river.

Superhost

A rustic cabin surrounded by tall trees is showcased. A light-colored entrance door and two windows are displayed at the front. Adjoining the cabin, a grassy area features a stone pathway leading to a pair of white adirondack chairs, inviting relaxation.

Guest suite in Hartford

4.88 out of 5 average rating, 154 reviews

Adorable one bedroom studio in 1844 farmhouse.

Keep it simple at this peaceful and centrally-located place. We have a beautiful 1844 farm house located in Quechee, that has been in our family for over a hundred years. It is located less than a 1/4 mile from the Quechee Gorge and Antique Mall. The farm includes fifty acres of land and trails with wonderful views of Mt. Ascutney, Killington and more. We also abut the state park which has twelve hundred acres of land. All perfect for hiking, snowshoeing, snowshoeing, biking or just relaxing.

4.99 out of 5 average rating, 160 reviews

A newly renovated house is nestled among tall trees, surrounded by lush greenery. The structure features multiple windows reflecting sunlight, with a wooden deck visible in the foreground, leading to a serene setting that invites outdoor relaxation.

Home in Woodstock

Beautiful Woodstock Home-Perfect for entertaining

Newly renovated - 4 bedroom, 3 bath house, perfect for relaxing or entertaining. Close to all that the Woodstock Village and the Upper Valley has to offer. Amazing location! Only 1.5 mi to the Woodstock Green. Explore the property and feast on the blackberries in summer, raid the tomato garden in the late summer/early fall, and pick the wild fall apples for munching or baking. Bring your snowshoes or cross country skis (in winter) or hiking shoes in summer and explore the property and beyond!

4.99 out of 5 average rating, 121 reviews

A modern kitchen is showcased with sleek cabinetry and a vibrant red stove. Natural light flows through large sliding glass doors, illuminating a dining area with a contemporary light fixture and a glass-top table surrounded by four chairs, enhancing the open layout.

Home in Sharon

The Willow House: a Modern Vermont Retreat

Just 7 miles (12 minutes ) to the Dartmouth Campus, this newly re-built little house sits beside its own pond on the edge of a sheep pasture. All the comforts of a modern home in 600sqft. Enjoy access to hiking trails and State Forest lands as well as an easy drive to world-class skiing an hour away and all that the Dartmouth College community offers just minutes away. This is the best of pastoral Vermont, with outside living-dining space ( south facing deck and north facing screen porch).

4.99 out of 5 average rating, 301 reviews

The kitchen area features a large island with seating and modern appliances. Natural wood paneling complements the high cathedral ceiling. Glass doors open to a scenic view of the surrounding hills, providing ample natural light and a connection to the outdoors.

Barn in Woodstock

THE LOFT, stunning views from a timber framed barn

Welcome to "The Loft". A lofted space on the top floor of a timber framed barn. The owners are designer/builders who have combined the elements of old world craftsmanship with high tech efficiency to create a living space that is bright, airy and yet cozy. Powered by solar, this attached carriage barn is located on a quiet back road 3.5 miles from Woodstock Village and 3 miles from GMHA. The Loft has its own private entrance, parking and a sunset balcony. For more go to @theloft.vt

4.96 out of 5 average rating, 274 reviews

The rustic cabin, surrounded by lush trees, features a porch with a picnic table. The wooden structure is designed with a gabled roof and large windows, providing a welcoming entrance. Flower boxes adorn the front, enhancing the natural setting.

Cabin in West Windsor

Sunset Cabin - your private romantic hideaway

Your private woodlands retreat awaits. Nestled atop a beautiful 10 acre meadow with 25 acres of woods for you to enjoy; this rustic, pet friendly cabin is a perfect romantic hideaway. Two trout ponds are steps from your door for fishing and swimming. Just minutes from Mt. Ascutney's hiking/biking trails and in the middle of fantastic cycling country. Near local race including the VT100, Vt overland, VT50. Sunset Cabin is a marvelous spot for enjoying fall foliage and exploring VT!

4.94 out of 5 average rating, 318 reviews

A modern cabin is situated among trees, surrounded by greenery. Two Adirondack chairs are positioned near a fire pit, which has gentle smoke rising. A picnic table rests nearby, providing a comfortable outdoor gathering space with views of the natural landscape.

Tiny home in Hartland

Private Modern Cabin w/View of Fields, Hills

Enjoy a modern private cabin in the heart of Vermont's pastoral Upper Valley Region. Combining "Glamping" with the comforts of a permanent structure, the "HakuBox" (Haku means "to exhale") was designed to sit lightly on the land and offer a simple, restorative experience. Note: no shower, but swimming holes nearby! Queen bed, fire pit w/grill, free firewood, Adirondack chairs, picnic table, free coffee & tea, dog-friendly with cable trolley, food & water bowls. $39 pet fee applies.

4.97 out of 5 average rating, 223 reviews

A charming cabin constructed from natural materials is nestled among lush trees in a forested area. Sunlight filters through the leaves, casting dappled shadows on the ground. The cabin features large windows that invite the surrounding greenery inside.

Tiny home in Hartland

Cabin on the Hill

Enjoy a stay in the hills of Vermont - glamping at its finest! A 5-10 minute hike UPhill to a secluded getaway in the heart of Vermont. Amenities include a quaint outhouse, a unique outdoor shower, a 2 burner outdoor gas stovetop and a fire pit to roast marshmallows. The 12x14 screened in cabin with ladder accessed loft sleeps 2 comfortably. Don't worry about bringing pots and pans - cabin is equipped with dishes and a water supply. Adjustable LED lights to light up the night.

4.98 out of 5 average rating, 174 reviews

A well-appointed bedroom showcases a spacious bed dressed in white linens, complemented by decorative pillows. A wooden bench is situated at the foot of the bed. A large mirror and artful wall decor enhance the serene atmosphere, while natural light enters through a large window.

Home in West Windsor

Birdie's Nest Guesthouse

Welcome to our newly renovated studio apartment, nestled among the trees in the serene hills of West Windsor, Vermont. Elevated on the second floor, this separate structure offers a tranquil escape with breathtaking views of Mount Ascutney and our own private pond. Immerse yourself in the comforts of this thoughtfully designed studio apartment, surrounded by the natural beauty of the Vermont landscape. Every detail has been curated to ensure your utmost comfort and enjoyment.

4.98 out of 5 average rating, 292 reviews

A cozy cabin is nestled among the trees, showcasing a rustic wooden exterior with large windows. It overlooks a gentle slope covered in green grass and wild plants, with sunlight filtering through the canopy above, creating a serene and inviting atmosphere.

Guest house in Woodstock

Cozy Little Spot (Self Check-in)

Contactless check-in. Cozy guest house, cabin-studio-getaway; enjoy the sounds of a stream outside the window (next to the bed). Views of a larger brook below. The"Cabin"is nestled in the trees giving a feeling of floating above the brook below. The interior is decorated w/family heirlooms gathered from around the country. Nothing fancy, just a cozy simple getaway. 3.25 mi from town. Choose from a variety of activities in town or hop on nearby trails. NO PETS ALLOWED.

4.95 out of 5 average rating, 1,040 reviews

Guest house in Hartland

Yurt In The Woods - Come to the Yurt.

The Yurt In The Woods is 30 ft in diameter - 700 spacious sq. ft. It's surrounded by trees and has a yard. 2 night stays required for Weekends. October 6th and 12th are currently vacant if you want a fall foliage trip. There is a "one" night stay fee of $50 Allowed 2 dogs with the agreement to my animal policy & $50 fee WiFi 1,000 megabits per second a fiber network Outdoor Gas Grill , Outdoor Fire Circle, and Outdoor Shower available May - October

Popular amenities for outdoor seating rentals in Rutland

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with outdoor seating

4.98 out of 5 average rating, 149 reviews

A bright living area is illuminated by large picture windows showcasing panoramic views of rolling green hills. Comfortable seating arrangements include a sofa and armchair, positioned around a wooden coffee table. A cozy fireplace and a projector screen are visible, enhancing the inviting space.

Home in Pomfret

Private Oasis Under 10 Mins from Woodstock

4.87 out of 5 average rating, 123 reviews

A sign reading 'The Oaks' is prominently displayed in front of the property. Colorful metal flowers are set in the lush green grass, framed by a backdrop of blooming trees and a partially visible building. Soft clouds pass overhead, creating a serene outdoor atmosphere.

Home in Plainfield

The Oaks - secluded rural estate w/ amazing views

4.98 out of 5 average rating, 228 reviews

A comfortable sofa adorned with decorative pillows and a cozy throw stands before a wall of glass doors. The view of Lake Sunapee stretches beyond, framed by trees and vibrant outdoor furniture on the deck.

Home in Sunapee

@SunapeeSeasons—Across from Dewey Beach, Lake View

4.99 out of 5 average rating, 114 reviews

A red cabin is nestled within a lush green forest, surrounded by trees. A gravel driveway leads up to the entrance, while a vibrant lawn extends in the foreground. The bright blue sky and soft clouds create a serene backdrop.

Home in Norwich

Relaxing Countryside Oasis!

4.9 out of 5 average rating, 144 reviews

A cozy living area features two comfortable sofas facing a stone fireplace, where a gentle flame is visible. Light filters through a window adorned with lace curtains, enhancing the rustic wood paneling. A small coffee table sits centrally, and framed artwork is displayed on the walls.

Home in New London

Hideaway Cottages, Cottage A

4.95 out of 5 average rating, 175 reviews

A spacious living area features a modern wood-burning fireplace framed by light brick, with a mounted flat-screen TV above. Comfortable grey sofas and a wooden coffee table are arranged to encourage relaxation, while a wooden staircase leads to the upper level.

Home in Hartford

The Quechee Haus: VT Retreat with Outdoor Hot Tub

4.98 out of 5 average rating, 149 reviews

A dining area is seen through an open doorway, featuring a wooden table surrounded by six chairs. Warm lighting is provided by a chandelier above, while a bowl of flowers centers the table. A patterned rug lies beneath, and cabinetry is visible in the background.

Home in Hartford

Charming, Cozy Cape

4.97 out of 5 average rating, 229 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

Apartment rentals with outdoor seating

4.93 out of 5 average rating, 266 reviews

An outdoor deck features a round table surrounded by four black metal chairs, offering a panoramic view of rolling hills and trees. The clear blue sky complements the lush greenery of the landscape.

Flat in Townshend

Private Apt. on Farm, Hot Tub with views!

5 out of 5 average rating, 115 reviews

A cozy seating area is presented, featuring a patterned rug beneath a wooden coffee table. A sofa with light-colored cushions and decorative pillows is accompanied by a lamp providing warm light. A chest of drawers and a framed artwork add character to the inviting space.

Flat in Wallingford

49 River Street

4.95 out of 5 average rating, 358 reviews

An open living space is captured, featuring a comfortable couch, a colorful chair, and a round coffee table. Natural light brightens the room, highlighting a kitchenette area and coordinating furnishings across the suite. High ceilings contribute to an airy atmosphere, creating a welcoming environment.

Flat in Clarendon

Dog heavenly! Private, beautiful and relaxing.

4.81 out of 5 average rating, 201 reviews

The historic farmhouse features a white exterior with a gabled roof, surrounded by lush greenery. A large tree provides shade in the front yard, and flower gardens can be seen along the stone pathway leading to the porch, which has seating for relaxation.

Flat in Taftsville

Quiet Vermont Farmhouse

4.99 out of 5 average rating, 128 reviews

The exterior of the white house is framed by green landscaping, featuring black shutters on the windows. A covered porch with hanging flower baskets invites visitors, while solar panels sit atop the roof. A well-maintained garden complements the welcoming atmosphere.

Flat in Hancock

Two-Bedroom apartment in the Green Mountains

4.9 out of 5 average rating, 125 reviews

The rustic farmhouse is set on a spacious green lawn, showcasing a classic red exterior with a metal roof. Large windows provide ample natural light, and the surrounding trees create a serene country atmosphere.

Flat in West Rutland

Mountain View Apartment

4.96 out of 5 average rating, 607 reviews

The exterior showcases a rustic wooden building surrounded by lush greenery and vibrant shrubs. A winding stone path leads to the entrance, while large glass doors provide a welcoming view into the interior. The setting is serene and integrated with nature.

Flat in Londonderry

Vermont Getaway Apartment

4.99 out of 5 average rating, 108 reviews

A cozy living area features a comfortable blue couch paired with a matching armchair. A wooden dining table with black chairs is set near a well-equipped kitchen. A fireplace is visible, with a modern TV mounted above. Light filters through large windows dressed with sheer curtains.

Flat in Killington

Jack S'Bearo- AC, Pool, Mountain Views, Hiking Gym

Apartment rentals with outdoor seating

4.99 out of 5 average rating, 142 reviews

The dining area features a large wooden table surrounded by six stools. A metal-framed desk and chair are present nearby, along with a coffee maker and additional kitchen appliances. Light wood flooring complements the neutral walls, creating a spacious and functional environment.

Apartment in Ludlow

Main St Escape | Explore Downtown Ludlow

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.

4.95 out of 5 average rating, 207 reviews

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

4.96 out of 5 average rating, 142 reviews

A living area is presented with a spacious purple sectional sofa and an accent chair, creating a comfortable seating arrangement. A wooden coffee table occupies the central space, and large windows allow natural light to fill the room, revealing a snow-covered landscape outside.

Apartment in Grantham

Cozy Light-filled Condo in Charming Eastman

The living area features a spacious navy sofa adorned with colorful pillows and a light wooden coffee table. A round dining table with black chairs is present, alongside a large mirror and soft lighting that enhance the inviting space. Natural light filters through the sliding doors.

4.89 out of 5 average rating, 152 reviews

Cozy Mountain Retreat w Views | Pool, Hot Tub, Ski

4.95 out of 5 average rating, 119 reviews

The exterior of the condominium building is showcased, featuring three levels with large windows that allow natural light in. A central staircase leads to the entrance, flanked by green grass and small shrubs, creating a welcoming appearance.

Apartment in Stratton

Great 2 bedroom condo at Stratton Mountain

A warm living area is highlighted by a wood-burning fireplace, providing a cozy focal point. A comfortable sofa and coffee table fill the space, while a large flat-screen TV is mounted above the fireplace. A friendly dog sits on the floor, enhancing the welcoming vibe.

4.94 out of 5 average rating, 293 reviews

Ski Basecamp with Pup • Sleeps 6 • Pool/Hot Tub

A modern studio space is presented with wood paneling and a vaulted ceiling. Stainless steel kitchen appliances are featured alongside a dining table and a comfortable seating area. Two vintage ski boards are mounted on the wall, and a sliding glass door provides access to a private balcony.

4.79 out of 5 average rating, 331 reviews

Serene Top Floor Condo (resort style amenities)