House holiday 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, 244 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.

4.94 out of 5 average rating, 113 reviews

A bright living space is surrounded by floor-to-ceiling windows, offering views of vibrant foliage and serene waterways. A small wooden table is positioned on a natural wood floor, highlighting the connection to the outdoor landscape. Warm sunlight filters through the trees, creating a calm ambiance.

Home in Guilford

Vermont Mirror House

Escape to our stunning glass house nestled in the Vermont forest. This modern retreat offers breathtaking 360-degree views of lush wilderness and beautiful waterways. Unwind in the hot tub, warm up by the cozy fireplace, or rejuvenate in the sauna. Floor-to-ceiling windows bring nature indoors! Perfect for romantic getaways, small families or simply work away from work with fiber wifi. Experience tranquility during all seasons in this one-of-a-kind hideaway. Book now for an unforgettable escape!

4.96 out of 5 average rating, 133 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.

A cozy living area features a dark gray sofa with decorative cushions, complemented by two wooden armchairs. A timber-framed window offers a view of the outdoors. A coffee table holds a small centerpiece, and vintage skis are mounted on the wall above the seating.

4.87 out of 5 average rating, 126 reviews

MtSnow* HotTub* Pool * AirHockey* PingPong * Darts

Welcome to our ❄newly listed❄lodge style home! HOT TUB✅ Our home is located on private 2.6 acre lot with beautiful views of Mount Snow in the distance. Our home offers easy access to night life/restaurants and much more. Whether you are skiing, hiking, biking, kayaking or just enjoying the fresh Vermont air, you'll love the comfort of our home. Enjoy a space that is truly convenient, comfortable, child-friendly and fun for you to enjoy during your hard-earned vacation time in southern Vermont!

4.96 out of 5 average rating, 133 reviews

Walk To Town, Hottub, Firepit, Games, Mt Snow

Welcome to our family-friendly home in Wilmington, Vermont! Perfect for group getaways. Our home offers a blend of comfort and convenience. Just a short walk from Wilmington's charming downtown, with easy access to restaurants, shops, and groceries. Mount Snow is only a 12-minutes away, making this an ideal base for both winter skiing adventures and summer hikes. Whether you're here for outdoor fun or cozy nights by the fire pit, our home is ready to make your Vermont getaway unforgettable!

4.94 out of 5 average rating, 319 reviews

A modern interior is showcased with wooden walls and flooring, featuring a cozy bed positioned near large windows. A compact dining area is visible, with a small table and two chairs. An air conditioning unit is installed on the wall, contributing to the space's comfort.

Home in Winhall

Modern Cabin with Hot Tub & EV Charging Station

Welcome to the Tea House - a retreat in the woods of Vermont. Set on nearly 5 acres, the location is private and peaceful without feeling remote. Just minutes to skiing at Stratton Mountain, Bromley and Magic. A short drive to Manchester with shops and restaurants. Relax and unwind in a cozy, modern space that lends itself to mindful living. Vinyl records, good books, stargazing from the hot tub. Your Vermont adventure awaits. - Private Hot Tub Open All Year - EV Charging Station - AC/Heat

4.89 out of 5 average rating, 114 reviews

An open-concept living area features a dining table set for six, with a gas fireplace framed by a white brick mantel. A television is positioned on a stand nearby, with comfortable seating arranged around the room. Natural light filters in through adjacent windows.

Home in Dover

Private Hot Tub, 2 Min to Mt Snow, Cozy Fireplace!

Newly renovated house, available all year, only 2 min from Mt Snow! New beds, mattresses, heat baseboards, dining table and chairs. To top it off a brand new outdoor hot tub in the backyard! Fully equipped kitchen and linens provided. Essentials as a starter kit provided for the first couple days. Families and friends will enjoy an open concept living with bar counter overlooking a dining area with fireplace and TV lounge. One pet allowed but must be disclosed at reservation (fee applies).

5 out of 5 average rating, 104 reviews

A white farmhouse with a spacious front porch features rocking chairs and a welcoming front yard. A friendly dog is seen sitting on the green grass, surrounded by autumn foliage. The structure's windows and a gabled roof enhance its charming exterior.

Home in Bennington

Vermont Farmhouse •Walk to Village & Hiking Trails

Experience the magic of this restored 1860s Vermont farmhouse, where historic charm meets modern luxury. This 1,700 sq ft retreat offers 2 cozy bedrooms, 2.5 baths, and sun-drenched living spaces. Relax in Adirondack rockers on the expansive deck, explore 280 acres of woodland trails right outside your door, or take a short stroll into the village. Later, gather at the fire pit for s’mores under the stars. Welcome to your quintessential New England escape at The Vermont Farmhouse.

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 Twin Bunks) 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.

A well-maintained home features a spacious porch with green chairs and is surrounded by a lush lawn and trees. The gravel driveway offers ample parking space, while the bright blue sky enhances the serene outdoor setting.

4.95 out of 5 average rating, 301 reviews

Wilmington. In Town Village Home

Beautifully renovated bright, 125 year old home in town. House thoroughly cleaned and sanitized after each stay. Touchless flushing toilets. Mini-Split air conditioning in each bedroom and on the main level. Minutes to MT Snow. Easy walk to town for food and shopping. Deerfield river directly across the street. 2 min from the lake. Valley hiking trails within sight. There is a 2 car limit. A request for additional vehicles needs to be made prior to check-in.

4.86 out of 5 average rating, 131 reviews

A sprawling grassy yard is surrounded by trees, providing natural shade. A wooden deck and seating area are positioned in the background, inviting outdoor relaxation. The white house is visible beyond the tree line, contributing to the serene countryside setting.

Home in Readsboro

Snowy Cozy Vermont Winter Escape

Our home is nestled in the Green mtns, with quick access to the road. A babbling brook lulls you from the master bedroom, a clawfoot soaking tub, stocked home. Hiking, antiques, shops, lakes, ski, snowboard, covered bridges, local inns, mountain views! Scenic roads, ski nearby Mt. Snow, VAST snowmobile trails, Mt.Greylock, Mass MOCA museum, N.Adams, MA, Berkshires, Bennington, Wilmington. Great location! PEACEFUL PERFECT ROMANTIC Vermont getaway! ☺

4.99 out of 5 average rating, 167 reviews

The kitchen features modern appliances, including a stainless steel refrigerator and a sleek oven range. An orange barn-style door adds a pop of color, contrasting with the navy cabinetry. Cooking utensils are organized in a vibrant holder, and a soft area rug is placed on the floor.

Home in North Adams

North Adams Getaway-walk to MASS MoCA

BRAND NEW! Ready for guests to enjoy all the Berkshires has to offer! Whether you are visiting for work or pleasure, with family or friends this is a perfect place for you. Located in downtown North Adams you are surrounded by breath taking mountains and foliage, nestled between award winning museums, access to great food, and a short drive to ski resorts, breweries, Tanglewood, the highest peak in MA, and more. A true outdoorsman paradise. BOOK NOW!

Popular amenities for house rentals in Wilmington

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.98 out of 5 average rating, 205 reviews

The classic two-story farmhouse features white siding with black shutters. A green door welcomes visitors, while lush greenery and blooming lilac bushes create a natural frame. The surrounding lawn is expansive, emphasizing the peaceful rural setting.

Home in Salem

Magical Farm Getaway - a must visit!

4.89 out of 5 average rating, 137 reviews

Home in Colrain

The 1770 House

4.97 out of 5 average rating, 100 reviews

Home in Winhall

Secluded Luxury Lodge On Stratton w/ Heated Pool

A spacious dining area features a long, rustic table set with a black and white checkered runner. Large windows offer views of the surrounding woods. A comfortable sofa sits in the corner, alongside an armchair, creating a cozy space for relaxation. A modern light fixture hangs from the high ceiling.

5 out of 5 average rating, 14 reviews

Silver Moose Lodge (Mt Snow)

A comfortable living area features a sectional gray sofa adorned with decorative pillows, a coffee table at the center, and two armchairs. Natural light filters in through large windows dressed in light curtains, illuminating the hardwood floor and creating a cozy atmosphere.

4.88 out of 5 average rating, 182 reviews

Adams Farm-"The Little Farmhouse"

4.93 out of 5 average rating, 231 reviews

A Colonial home is positioned on a green lawn, showcasing a charming brick façade and a classic porch. Large trees provide shade, while an American flag is displayed proudly by the door. Nearby, a design studio is visible, highlighting the spacious front yard.

Home in Keene

The Brick House on Washington Street

The kitchen features a central island with seating for eight, surrounded by wood cabinetry and modern appliances. Natural light filters through the large windows, highlighting the sleek black countertop and hardwood floors, creating a functional and inviting space for meal preparation.

4.92 out of 5 average rating, 24 reviews

Stylish Chimney Hill Home - Close to Mt. Snow!

A spacious great room is showcased with high ceilings and natural wood walls. A large sectional sofa is positioned alongside a coffee table, with bright light filtering through large windows. A dining area with bar stools is visible in the background, enhancing the open layout.

4.83 out of 5 average rating, 76 reviews

Hot Tub + Clubhouse Pool | 10 min Mt Snow

Weekly house rentals

A snow-covered retreat is nestled among tall evergreen trees, featuring a light wooden exterior and large glass windows. A private hot tub is visible on the deck, surrounded by a winter landscape, inviting guests to unwind in nature.

4.87 out of 5 average rating, 23 reviews

The Birdhouse Retreat w/Hot Tub

5 out of 5 average rating, 67 reviews

An open living area features vaulted ceilings and large windows, allowing natural light to fill the space. A comfortable leather sofa sits adjacent to a dining table, with views of the surrounding greenery visible outside. A spacious kitchen island adds functionality to the layout.

Home in East Dover

Pristine Magical Retreat Cottage 15 min to Mt Snow

5 out of 5 average rating, 46 reviews

Large Game Room, near skiing, walk to downtown

The exterior of a two-story blue house is shown, surrounded by lush greenery. A spacious wooden deck is visible, equipped with outdoor seating. The yard features a well-maintained lawn, bordered by trees that display autumn colors under a vibrant sky.

5 out of 5 average rating, 30 reviews

Downtown Wilmington Home

The cabin is set back from the winding gravel driveway, surrounded by lush green grass and trees. Brightly colored autumn foliage adds a touch of warmth against the rustic brick exterior and red roof. The peaceful atmosphere is enhanced by natural surroundings.

4.85 out of 5 average rating, 95 reviews

Secluded cabin on brook near skiing and lakes

5 out of 5 average rating, 10 reviews

Central & Stylish 3 Bedroom Retreat |Winter Chalet

5 out of 5 average rating, 30 reviews

A communal space features a large wooden dining table surrounded by black chairs, complemented by a cozy beige sofa. Ski equipment is displayed on the wall, and light tones of wood flooring enhance the inviting atmosphere. A doorway leads to additional areas of the home.

Home in Dover

Cozy Condo near Mt Snow

The exterior of the chalet features a two-story structure surrounded by greenery, with a spacious balcony on the upper level. Soft lighting outlines the balcony, creating a welcoming ambiance. A kayak is situated near the base of the chalet, indicating opportunities for outdoor activities.

4.92 out of 5 average rating, 37 reviews

Newly renovated chalet, 9 min to Mt. Snow

Private house rentals

5 out of 5 average rating, 36 reviews

Home in Jamaica

Stratton Ski House

A spacious living room features a large sectional sofa with decorative pillows, paired with a wooden coffee table. Natural light floods in through large windows, highlighting the hardwood floor. The adjoining dining area, visible in the background, includes a wooden table surrounded by several chairs.

4.97 out of 5 average rating, 61 reviews

Vermont Village Retreat Near Mount Snow

5 out of 5 average rating, 47 reviews

A welcoming entryway features a soft, light-colored bench with yellow accent pillows. Wide plank wooden floors run throughout, and a potted plant adds a touch of greenery. The space is illuminated by a pendant light hanging from the ceiling, with stairs visible in the background.

Home in Bennington

The Old Pine House

4.88 out of 5 average rating, 8 reviews

Home in Dover

Sports Lodge at Mount 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, 63 reviews

5BR Mtn Escape with Salt Hot Tub

A spacious mountain house is presented, surrounded by vibrant fall foliage. The exterior features a light-colored facade with multiple balconies, a large driveway, and a garage. Leaves cover the ground, creating a natural, seasonal carpet leading up to the inviting entrance.

4.93 out of 5 average rating, 41 reviews

Family/Dog Friendly Mountain Home w/ Amenities

The spacious living room features a large sectional sofa in a soft blue hue and a wooden coffee table. Natural light pours in through a large window, illuminating the wooden walls and offering views of the outdoor greenery. Two armchairs and a lamp create a cozy seating area.

5 out of 5 average rating, 15 reviews

10 min to Mt. Snow | Firepit, Games, Shuttle

A spacious living area is illuminated by natural light from large windows. A sleek, modern couch with curved lines sits on warm hardwood flooring. A minimalist rug adds texture to the setting, while a flat-screen television and a simple fireplace are featured on the wall.