Vacation rentals with a patio in Castleton

A new hot tub with jets is positioned under a wooden structure, surrounded by grass and landscaped areas. A tranquil view of distant mountains and trees is visible in the background, creating a peaceful outdoor setting.

4.88 out of 5 average rating, 217 reviews

Killington/Okemo, 7p Hot tub, Spacious, Mtn.views!

Mid week deals! Killington Mnt-20min drive, Lake Bomoseen-20min, Pico Mnt-15min Okemo-30min, Downtown Rutland-5min (bars/dining/shopping) Mnt Top Inn-18min, Hiking-10 min. , Neighborhood pool with tennis courts, basketball courts, playground. Beautiful mnt views, peaceful brook on 1+ acre. Spacious home with hot tub, AC, firepit, fooseball table, grill, deck, patio, screenroom, 2 kitchens, 2 living rooms, washer/drier, fully stocked kitchens. Very fast wifi/netflix/youtubeTV/nintendo switch.

4.92 out of 5 average rating, 187 reviews

An organized kitchen features white cabinetry with glass accents and decorative hardware. Stainless steel appliances, including double ovens and a gas stove, are highlighted. A countertop is prepared with utensils and a cutting board, while a textured backsplash adds subtle detail.

Home in Fair Haven

Historic 4 Bed 2 Bath Victorian Estate Fast Wifi

Ski season has begun! Take it easy at this unique and historic property. Picturesque Victorian Estate next to the Castleton River perfect for weddings and events. You can wake up with birds chirping and fall asleep to the frogs croaking. Church bells ring throughout the day while relaxing on the covered porch. Walk the historic slate sidewalk to the park and downtown for shopping and dining. Minutes to many lakes and trails. Day trips to Killington, Woodstock, Lake George, Vergennes, & Rutland.

Guest suite in Lake Bomoseen

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.

4.97 out of 5 average rating, 243 reviews

My house is your house!

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.

4.97 out of 5 average rating, 141 reviews

The cabin exterior features a two-story wooden structure surrounded by lush greenery. A stone patio with multiple seating options provides access to the lawn. Large windows enhance the views, while a balcony adds dimension to the facade.

Cabin in Comstock

East Cabin

The East Cabin is quietly tucked between the beautiful Green Mountains of VT and the gorgeous Adirondacks of NY. Soak up the morning sun on your private stone patio while mother nature comes to life on the pond and fields. Take a day trip to beautiful Lake George or Historic Saratoga Springs. Grill steaks on BBQ and eat S’mores by the campfire at night. For the winter season, there are many major ski resorts close by. We also have the West Cabin available for your extended family and friends.

4.93 out of 5 average rating, 147 reviews

Home in Killington

Gorgeous Dog Friendly 2BR 2.5 Bath w/ Pool Sauna

Our 2-bedroom, 2.5-bath Airbnb, nestled in Vermont’s Green Mountains, invites you to escape into a haven of year-round adventure. Enjoy breathtaking views of a scenic pond, skiing through pristine slopes, bike along winding trails, or hike amidst the number 1 ranked foliage in the USA. Rejuvenate in the indoor pool and spa, with hot tubs, steam rooms, sauna and gym. Unwind by the cozy fireplace, creating unforgettable memories. Experience the charm and beauty of Killington like never before.

4.95 out of 5 average rating, 37 reviews

Apartment in Clarendon

Trestle Farm

Trestle Farm, formerly a 50-year horse rescue ranch, which we are transforming into a floriculture farm. 12 acres of open meadows to enjoy. If you’re looking for a bit of old, rustic Vermont, Trestle Farm offers all you need for a peaceful getaway, and yet it is just minutes to Rutland. With over 30 years of estate caretaking experience, we're now opening Trestle Farm to share the experience. Access is NOT suitable for a 2-wheel-drive vehicle in winter. Our cars are 4-wheel with snow tires!

4.81 out of 5 average rating, 159 reviews

An old barn features weathered wooden siding and large windows, set against a backdrop of vibrant autumn foliage. A maple tree with bright orange leaves provides a natural canopy, while a carpet of fallen leaves covers the grassy ground, creating a serene outdoor scene.

Barn in Mount Holly

Mapleside Escape: Sugar/Ski house

Your Mapleside Rustic Retreat awaits! This gem is nestled amidst the picturesque landscapes of southern Vermont and only a 12 minute drive to Okemo/Jackson Gore, 35 minutes to Killington/Pico. If the season is right it offers the unique opportunity to see some pure VT maple syrup being made! Skiing, snowboarding, hiking and mountain biking trails await, making this spot an ideal base for year-round fun. Come explore nearby towns which offer charming shops, dining, and cultural experiences.

4.98 out of 5 average rating, 48 reviews

An expansive lakeside deck features a large round table and multiple lounge chairs for outdoor relaxation. The deck overlooks the calm surface of the lake, framed by trees and offering unobstructed views of the surrounding landscape.

Home in Castleton

New Listing! Luxury waterfront Lake Bomoseen home!

This gorgeous direct lakefront private residence is a completely remodeled multi-level home featuring a gourmet kitchen with Subzero/Viking appliances, all new cabinetry and granite countertops. The half bar kitchen stool seating opens into the large dining area with seating for 10+ as well as the expansive 2X HEIGHT GREAT ROOM with exposed wood beams, stone gas fireplace and lounging area all framed by the WALL OF WINDOWS displaying UNOBSTRUCTED 'DOWN THE LAKE' VIEWS OF LAKE BOMOSEEN!

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.

4.93 out of 5 average rating, 203 reviews

CozyCub- Location, Fireplace, Ski Off/Shuttle On!

Delight in this friendly, fully renovated (2022) modern ski condo next to Killington's popular Snowshed base area, learn-to-ski trails, and golf course. Shuttle-On / Ski-Off to the condo during peak season. The location is prime for accessing everything the area has to offer. Relax for some streaming after a day on the mountain on the 65" TV. Enjoy the Whiffletree condo association's outdoor pool and tennis courts in the summer, settle in by the gas fireplace, or head out to explore.

4.97 out of 5 average rating, 169 reviews

The exterior of Bearfoot Cottage is highlighted, featuring a combination of wood and metal finishes. A spacious deck with steps leads to the entrance, framed by large windows. A fire pit sits nearby, complemented by comfortable seating arrangements on the gravel surface.

Tiny homes in Chester

Bearfoot Cottage: Tiny House w/ Hot Tub near Okemo

Tiny living at its best! Welcome to Bearfoot Cottage, a custom-designed Tiny House escape nestled on 15 acres in Southern Vermont. Enjoy the entire property to yourself with hot tub, Char-Griller BBQ, & Solostove firepit. Hike or snowshoe Ladybug Trail to our babbling brook. Then explore the best of Okemo Valley all at your fingertips! Ski/Snowboarding (+more Winter sports), biking, hiking, fishing, dining, breweries, and live music/nightlife. Your vacation is what you make it!

5 out of 5 average rating, 49 reviews

A welcoming entrance sunroom is highlighted by large windows allowing natural light to fill the space. Two comfortable swivel chairs are positioned by the window, accompanied by a small side table and a lamp. A decorative plant adds a touch of greenery.

Home in Castleton

Main Street Retreat

VT Adventures Await This newly renovated 3 bedrooms, 2 full bathrooms, washer & dryer, dishwasher home offers a perfect base for exploring South Central Vermont’s outdoors. Conveniently located minutes from NY, VTSU Castleton, Lake Bomoseen and numerous other lakes, ski areas, hiking and biking trails and golf courses. Whether you’re seeking adventure or relaxation, this home is designed to complement your stay in every season. Sleeps 6. NO PETS, SMOKING/VAPING, or PARTIES

Superhost

An A-frame cabin is nestled among trees with autumn leaves in vibrant shades. A large deck extends from the cabin, featuring a hot tub and outdoor dining area. A barrel sauna is positioned nearby, completing the inviting outdoor space.

Cabin in Mount Holly

4.86 out of 5 average rating, 150 reviews

Okemo A-Frame - Floor Hammock, Sauna & Hot Tub

Welcome to the Okemo A-Frame! With an oversized deck, featuring outdoor dining, a barrel sauna, and hot tub you'll enjoy the outdoors year round. Enter into an open-concept dining area, kitchen, and living room with stylish mid-century malm fireplace. Take your rest in one of the three bedrooms or cozy up on the indoor floor hammock. Located 10 minutes from Okemo Mountain Resort and the town of Ludlow enjoy skiing, shopping, dining, and all that Vermont has to offer.

Popular amenities for Castleton accommodations with an outdoor patio

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Apartment rentals with a patio

4.96 out of 5 average rating, 53 reviews

A historic brick building with large arched windows dominates the street view. The facade features intricate detailing and a welcoming entrance to Big G's Pub, showcasing decorative elements and a charming awning. The upper levels display a classic architectural style.

Apartment in Whitehall

Apartment B, Historic building

5 out of 5 average rating, 9 reviews

A spacious living room is presented with a dark leather couch facing a large wall-mounted television. A wooden coffee table sits in front of the couch. Multiple entryways are visible, leading to an immaculately styled kitchen. A dining area with modern chairs is also included.

Apartment in Glens Falls

High end luxury modern Downtown

4.88 out of 5 average rating, 112 reviews

A charming two-story house is set on a green lawn, surrounded by trees. The home features a light exterior with red accents and a porch. A gravel path curves around the property, leading toward a freshly paved driveway. Sunlight brightens the environment, enhancing the serene atmosphere.

Apartment in Dorset

Cozy two bedroom near Manchester

4.93 out of 5 average rating, 122 reviews

The exterior of a red wooden house is showcased, surrounded by lush green grass and trees. A neatly trimmed garden features colorful flowers, while a small shed is visible in the background. Pebbled pathways provide access to the home's entrance.

Apartment in Mount Tabor

Vermont Ski / Okemo / Killington / Pico / Stratton / Bromley

4.94 out of 5 average rating, 67 reviews

A bright living area features large windows that allow natural light to fill the space. A light-colored sofa and armchair are accompanied by a round coffee table and a woven rug. A bookshelf displays decorative items, and a TV is positioned for viewing.

Apartment in Rochester

Green Mountain Collection: Cozy Vermont Haven

4.94 out of 5 average rating, 84 reviews

A spacious living room features a comfortable leather sofa and a soft armchair positioned around a wooden coffee table. A decorative area rug adds warmth to the hardwood floor. Natural light enters through two windows, with curtains gently framing the views.

Apartment in Glens Falls

1-BR Gem Near Downtown & Nature Escapes

4.94 out of 5 average rating, 17 reviews

A cozy living area is depicted with wood flooring and green walls. A patterned rug anchors the space, complemented by a comfortable couch. A small table holds a plant and lamp, while a chair and side table add functional seating. Natural light filters through the window, adorned with light curtains.

Apartment in Pawlet

Cozy apartment in Pawlet

4.94 out of 5 average rating, 32 reviews

The open kitchen area features modern appliances, including a stove and refrigerator, complemented by light green cabinetry. A cozy sitting area with a sofa is visible, while natural light streams in through the slanted ceiling windows, enhancing the sense of space.

Apartment in Randolph

Hebard Hill Hideaway

House rentals with an outdoor patio

A spacious bedroom features a wood-paneled ceiling and cozy carpeting. A comfortable bed is positioned alongside a textured bedspread. An electric fireplace and a mounted flat screen TV add convenience. Natural light filters through the window, enhanced by a view of the outdoors and tasteful wall decor.

4.97 out of 5 average rating, 76 reviews

Spacious Mountain Retreat 14 mi to Killington

4.95 out of 5 average rating, 132 reviews

A spacious living area features large windows allowing natural light to fill the room. A gray sofa with decorative pillows is centered on a decorative area rug. The open layout connects to the kitchen and dining area, enhancing the inviting atmosphere.

Home in Salisbury

Lake Dunmore Getaway — Foliage Views & Ski Retreat

4.91 out of 5 average rating, 47 reviews

A charming farmhouse is showcased, featuring a sloped metal roof and a welcoming porch adorned with hanging planters. Green grass surrounds the property, framed by large trees, while open fields can be seen in the background under a clear blue sky.

Home in Bethel

Fred Eddy Farmhouse

4.79 out of 5 average rating, 94 reviews

A cozy house is set against a snowy landscape, featuring a covered front porch with white railings. The exterior showcases neutral tones and is surrounded by trees, providing a secluded atmosphere. Snow covers the ground, enhancing the peaceful winter scene.

Home in Stockbridge

Ski, snow mobile, hiking, fun on slopes & trails!

Superhost

A comfortable living area features a light grey sofa adorned with decorative cushions, positioned near large windows with sheer curtains. A wooden coffee table sits in front, accompanied by a decorative lamp and a small potted plant, creating a calm and inviting environment.

4.86 out of 5 average rating, 35 reviews

Bright and spacious 3+ bedroom near Killington!

An aerial view of the chalet displays its rustic wooden exterior and distinctive metal roofing. Surrounding trees exhibit autumn colors, enhancing the natural setting. The spacious driveway leads to a connected garage structure, while a stone pathway invites guests to the home's entrance.

4.89 out of 5 average rating, 75 reviews

Private Chalet with Golf Simulator and Hot Tub

4.91 out of 5 average rating, 106 reviews

A comfortable living area features a sectional sofa adorned with soft pillows and a wooden coffee table. Natural light floods in through a large window, highlighting the wooden wall paneling. A decorative rug rests under the table, adding warmth to the space.

Home in Dorset

Mountain View Getaway

5 out of 5 average rating, 5 reviews

Home in West Rutland

Marble Hills Vineyard

Condo rentals with a patio

4.99 out of 5 average rating, 137 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.

Condo in Ludlow

Main St Escape | Explore Downtown Ludlow

A cozy living room features a dark leather sofa adorned with decorative pillows. Above the couch, three framed nature-themed art pieces display serene mountain landscapes. A dog rests comfortably on the carpet, with soft lighting from two side lamps enhancing the peaceful ambiance.

4.95 out of 5 average rating, 161 reviews

Dog-Friendly Mtn Escape/Pool/Gym/Hiking Trails

4.93 out of 5 average rating, 76 reviews

A cozy living area features a spacious sectional sofa and a wooden coffee table, with candles placed on top. Artwork depicting mountain scenes decorates the wall, while a glass door leads to the private balcony, allowing natural light to brighten the space.

Condo in Mendon

¤5-15 Mins to Ski Slopes | Fast WiFi | Fireplace¤

A tranquil sleeping area features a cozy bed with soft bedding and accent pillows. Nightstands with lamps are placed on either side, providing gentle light. A large horse portrait adorns the wall above the bed, contributing to the serene ambiance.

4.91 out of 5 average rating, 98 reviews

POW value in this Cozy 2 Bedroom .2 mi to lift

A living room is furnished with a comfortable brown sofa and an armchair beside a wooden coffee table. A rustic wooden fireplace is adorned with festive garland and a flat-screen TV is mounted above it. Natural light enters through a large window, providing a cozy ambiance.

4.85 out of 5 average rating, 222 reviews

⛷☃️Close to lifts. Rustic. Mountain Green Resort🏂❄️…

The exterior of the Mountain Green building is visible, surrounded by snow-covered ground and trees. A clear blue sky complements the scene. A prominent sign marks the property, showcasing various services and property listings. Vehicles are parked nearby, indicating accessibility.

4.84 out of 5 average rating, 19 reviews

Killington Getaway 2bed/1.5 bath

4.94 out of 5 average rating, 98 reviews

A living area features a gray sofa adorned with decorative pillows in various patterns. A wooden coffee table sits in front, and a side table with a lamp complements the space. Light filters through a sliding glass door, which opens to a patio.

Condo in Ludlow

Ground Floor, Okemo True Ski-in/Ski-Out