Vacation rentals in Wilmington

A bathroom features natural wood paneling and a brick accent wall. A compact vanity with a sink is complemented by a mirror and overhead lighting. Shelves hold neatly folded towels, while a washer and dryer unit is integrated into the design, presenting a functional space.

4.91 out of 5 average rating, 243 reviews

Wilmington A-Frame- Cozy and Convenient

Entire charming and chic A-frame chalet conveniently located to all the amenities Wilmington has to offer. Walk into town to enjoy dining, shopping and trail hiking or take a short 15 minute drive to Mount Snow for a day of outdoor adventure. Relax on the water at Harriman Reservoir, just a 2 mile drive from the house. House is also conveniently located along the Moover route. Relax back at the house while enjoying time on the front porch or an evening on the couch. Located on Main Street.

4.96 out of 5 average rating, 132 reviews

A gently sloping field is depicted, bordered by trees with autumn foliage. A red barn and a white building are visible in the distance, set against a bright blue sky with scattered clouds. The landscape conveys a peaceful rural setting.

Home in Townshend

Lawrence Cottage

Deep in the West River Valley region of Windham County, Lawrence Cottage is in a gorgeous and uncluttered setting upon Windham Hill. If you long for solitude, serenity and beauty, we have the perfect escape for you. We are convenient to all local amenities and activities and an easy drive from Boston or New York. We are near Townshend, Jamaica and Lowell Lake State Parks, Magic Mountain, Mount Snow and Stratton Mountain Resorts. This is Vermont--of course we welcome people of all backgrounds.

4.92 out of 5 average rating, 120 reviews

Condo in Dover

Base of M.S. All Seasons Fun. Deck/HotT/Pool/Sauna

Sunsil Loft @ MountSnow, your ideal Getaway. Walk to the Base. Unbeatable access to skiing, hiking, biking. Vermont never stops to surprise you with its outdoor adventures, great food and views. The loft offers a cozy gas fireplace, private deck. The kitchen has all you need to prep meals. You also have access to the pool (Summer), sauna, hot tub and GYM. Whether you’re skiing, hiking and biking in summer, or enjoying the fall foliage, our loft is your perfect home base in the Green Mountains.

4.96 out of 5 average rating, 107 reviews

The exterior showcases a blue wooden cabin with large windows reflecting its natural surroundings. A spacious deck is visible in the foreground, providing a welcoming access point. Autumn foliage surrounds the property, indicating a peaceful, rural setting.

Cabin in Wilmington

Peaceful Cabin Perfect for All Seasons

A little blue gem hidden in hills of Southern Vermont. This 4-bedroom, 1.75-bath cabin places you just 7.4 miles from Mount Snow, 2.5 miles from the Haystack Mountain Trail, and 2 miles from the Wilmington Village Historic District. Whether you're discovering an assortment of hiking trails, enjoying a historic walk in Bennington, soaking up the summer sun on the Harriman Reservoir, hitting the winter slopes, or admiring the beauty of a vibrant New England autumn, you will love your stay here!

4.99 out of 5 average rating, 349 reviews

Tiny homes in Wilmington

Beautiful Timber Frame Retreat

This cabin retreat is situated on a natural clearing in the beautiful Green Mt. Forrest. Surrounded by a dense grove of spruce trees gives you complete privacy. It's only a quick 5 minute drive to great restaurants, breweries, and shops in downtown Wilmington. It's also less than 20 minutes to Mt. Snow. There's great hiking at Molly Stark State Park right across the street and amazing lakes all within a 10 minute drive! No WIFI and cell service is not great so it is a great place to unplug!

4.92 out of 5 average rating, 149 reviews

A comfortable living area features a dark leather sofa with two accent pillows and a coffee table atop a patterned rug. A dining table with four chairs is positioned nearby, and natural light enters through a window dressed with light curtains. Wall decor includes vintage skis and decorative deer antlers.

Apartment in Wilmington

Globetrotter Retreat too - Minutes to the Mountain

Newly renovated, fully furnished in heart of quaint mountain village; minutes to Mount Snow, Green Mountains & lakes. Year round outdoor activities: snow sports in winter, watersports/hiking in summer. Quiet 1 bedroom apt on 2nd floor sleeps 4 people in comfort. Private balcony overlooks tranquil woods & rolling river. Steps to restaurants, bars & shopping. Supermarket is a short walk. Free Moover bus stop across the street ride for free to local destinations! 18 years or older guests only.

5 out of 5 average rating, 113 reviews

The image displays a serene winter scene of a dark-green chalet nestled among snow-covered trees. Two sections of the interior show a cozy living space with modern leather furniture and a spacious dining area, both featuring large windows that bring in natural light.

Cabin in Wilmington

Mid-mod VT Dream Chalet near skiing, lake & forest

Surround yourself in nature and cozy modern comfort. The romantic mid-mod-styled chalet backs to 10 acres of peaceful forest yet is just 12 min drive to Mount Snow for great skiing. 3 min. to the boat launch of gorgeous Lake Whitingham where you can rent jetskis & boats or go swimming & fishing. Hike trails to the charming town of Wilmington with its coffee shops & restaurants. Pools & hot tub up the road at clubhouse. Just steps away from iceskating, pickleball, hiking & snowmobile trails.

4.9 out of 5 average rating, 142 reviews

A cozy living space features a sectional sofa and a wooden entertainment unit with a large TV. In the background, a kitchen area is visible, equipped with wooden cabinets and essential appliances. A round dining table with chairs is seen, illuminated by soft overhead lighting.

Apartment in Wilmington

Walk To Wilmington Village

This charming apartment is on a quiet side road overlooking historic downtown Wilmington, Vermont. Hear the church bells nearby while enjoying a relaxing evening on the deck. Take a stroll downtown and visit restaurants, shops, bars, and giftshops. Easy access to Moover, free bus to Mount Snow. Washer/dryer Smart TV with premium streaming services The front porch, side porch, and the yard on that side is all private and for you to enjoy. Please note, I live next door, and I have a dog.

Tiny homes in Brattleboro

The compact kitchen features modern appliances, including a microwave and refrigerator, paired with wooden cabinetry and a dining area. Light-colored wood flooring extends throughout, and a staircase leads to the sleeping loft above. Decor elements include framed artwork and a vase of flowers positioned on the counter.

4.86 out of 5 average rating, 225 reviews

Sweet Vermont Tiny Home Get Away

Your unique Vermont retreat is just a click away! Come stay in this custom built tiny house in southern Vermont. We are an easy walk to the train station, art museum, restaurants, shops, and many beautiful nature spots in and around Brattleboro VT, plus a 40 minute drive to the Mount Snow ski area, and local hiking, swimming, boating, skiing, and skating opportunities. A nature lover's paradise! Enjoy the great outdoors and small town living, or cozy up in the tiny house and just relax.

5 out of 5 average rating, 207 reviews

The cabin features a wooden exterior surrounded by lush greenery, with large windows allowing natural light to enter. A wooden deck extends from the side, leading to a cozy outdoor area and an adjacent structure, contributing to the rustic charm of the setting.

Tiny homes in Dover

Rustic Cabin in foothills of Green Mountains

Rennsli Cabin is off grid + nestled on a forested plateau in the foothills of the Green Mountains. You will feel like you are in the middle of nowhere, unplugged and able to regenerate. Kitchen is equipped with cooking essentials, water, coffee, tea, milk, fresh eggs + homemade soap. It has an indoor compost toilet, outhouse + outdoor shower (May-Oct) Most seasons, the cabin is 100ft from parking, but weather conditions may require an 800 ft walk from parking at main house.

4.9 out of 5 average rating, 164 reviews

4BR Cabin w/ Hot Tub & Pools –15 mins to Mt Snow

Family-friendly cabin in Chimney Hill, just 15 min to Mount Snow & 35 to Stratton! Relax in our 4BR, 2BA home with a hot tub, indoor and outdoor pools, fire pit, clubhouse gym, fully equipped kitchen & cozy living spaces. Sleeps 8 comfortably (King, Queen, Full + trundle, 2 Twins) with a Pack ’n Play for little ones. Perfect for skiing, hiking, or unwinding year-round. Enjoy mountain charm, modern comfort, and easy access to trails, lakes, and Wilmington’s shops & dining.

Guest suite in Wilmington

A spacious great room features a comfortable seating area with a white couch, eclectic armchair, and colorful floor design. Artistic decorations are placed on the walls and shelves, with a kitchenette visible in the background. A piano and drums are positioned nearby for guest use.

4.93 out of 5 average rating, 813 reviews

Architectural GuestSuite

The Guest Suite is located on the first floor of an architectural studio in historic Wilmington, Vermont. Please enjoy the piano, drums, and art supplies! The Guest Suite is both UNIVERSALLY ACCESSIBLE, TOBACCO FREE, and ANIMAL FREE due to allergies in our family. LineSync Architecture staff will be working from 8:30am - 5ish upstairs, and once in a while on the weekends. When guests are in we try to be super sensitive and quiet, but footsteps will be heard!

Popular amenities for Wilmington vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Wilmington

4.95 out of 5 average rating, 22 reviews

Chalet in Wilmington

Lake View Ski Chalet - Mount Snow and Downtown

The exterior of a newly constructed wooden home is framed by greenery, with natural stone accents enhancing its rustic appeal. A spacious porch is adorned with potted plants, and large windows invite light into the inviting interior. Access to the upper level is provided by exterior stairs.

4.88 out of 5 average rating, 17 reviews

New Construction Ski/Lake home

4.94 out of 5 average rating, 34 reviews

A charming log cabin is nestled among snow-covered trees, showcasing its wooden exterior and peaked roof. Icicles hang from the eaves, and a small shed is visible nearby. Fresh snow blankets the surrounding landscape, creating a serene winter scene.

Cabin in Stamford

La Cabañita - The Little Cabin

5 out of 5 average rating, 11 reviews

Condo in Dover

Walk to Dining, Arcade & Bar- 5 Min to Mt. Snow

A warm-colored wooden house stands in a snowy landscape, surrounded by tall evergreen trees. Snow blankets the ground and clings to the branches of a nearby flowering shrub. Soft snowfall creates a serene winter scene against a clear blue sky.

4.95 out of 5 average rating, 62 reviews

5BR Mtn Escape with Salt Hot Tub

4.81 out of 5 average rating, 59 reviews

A comfortable sleeping area features a spacious bed with soft, neutral-colored bedding. Two small nightstands are mounted on either side of the bed, each with wall-mounted lamps. A framed photograph hangs above the headboard, adding a serene touch to the room.

Apartment in Dover

Betimor North apt 2 updated 06/2023 Mt. Snow

4.94 out of 5 average rating, 63 reviews

The living area features a comfortable sofa adjacent to decorative chairs, arranged around a central coffee table. A vintage-style rug lies beneath, and natural light enters through a window adorned with light curtains. Wall art adds character to the cozy space.

Apartment in Wilmington

Bookstore BNB