Vacation rentals in Wilmington

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Top-rated vacation rentals in Wilmington

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite
The entryway features a welcoming entrance with a wooden door, adorned with a green wreath. A glimpse into the bright interior reveals modern seating and natural light streaming through large windows, enhancing the inviting space that awaits inside.
Chalet in Wilmington
4.97 out of 5 average rating, 140 reviews

Snug Chalet - Wi-Fi + Close to Mount Snow

This stylish 1971 chalet is a country retreat with modern comforts for you and your family... complete with strong WiFi and a fenced-in dog yard! The minimal cabin is tucked in the trees and set up for families and friends, pet & kid-friendly. 10-15 Minutes to Mount Snow 10-15 Minutes to Downtown Wilmington This is a country house, not a boutique hotel :) If booking during winter or spring months, we HIGHLY recommend a 4wd vehicle as the weather can cause some tough road conditions (snow/mud).

Top guest favorite
A cozy living area features a dark sofa adorned with colorful throw pillows. Natural light enters through a window, illuminating the space. A coffee table rests in front, complemented by a comfortable side chair and ottoman. Wall décor includes vintage items, enhancing the inviting atmosphere.
Apartment in Wilmington
4.89 out of 5 average rating, 332 reviews

Globetrotter Retreat - Minutes to the Mountain

Newly renovated, fully furnished apt 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 sleeps 4 people in comfort. Private balcony overlooks rolling river. Steps from many restaurants, bars & shopping. Supermarket is a short walk. FreeMoover bus stop across the street - leave your car parked & ride for free to local destinations! No guest under 18 years old.

Guest favorite
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.
Home in Wilmington
4.91 out of 5 average rating, 253 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.

Guest favorite
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
4.94 out of 5 average rating, 137 reviews

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!

Guest favorite
A large outdoor pool is surrounded by a wooden deck with lounge chairs and umbrellas. The background features a multi-story building with expansive windows. Vibrant autumn trees with colorful foliage frame the scene, providing a serene and inviting atmosphere.
Home in Wilmington
4.9 out of 5 average rating, 168 reviews

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

Unwind in this cozy 4BR, 2BA retreat featuring an outdoor fire pit, 2 fireplaces and access to indoor/outdoor pools, hot tub, gym, and clubhouse amenities. Comfortably sleeps 8 (King, Queen, Full + trundle, bunk room) and includes a Pack ’n Play for little ones, perfect for families and groups. Whether you’re here for skiing, hiking, lake days, or fall foliage, enjoy the perfect blend of mountain charm, modern comfort, and great location near Wilmington’s shops, dining, and outdoor adventures.

Superhost
A uniquely designed raised container home features multiple levels and large windows that offer expansive views of the surrounding landscape. The structure includes a covered outdoor area below, and the combination of dark wood and metal creates a striking exterior appearance.
Shipping container in Whitingham
4.92 out of 5 average rating, 106 reviews

The House of Pi

Hot Breakfast and Lunch INCLUDED every day in your stay. Our general store will make you fresh egg sandwiches and coffee. Subs or pizza lunch. Welcome to Pi π aka Lakefront Loft. One of a kind custom built 34 foot high raised container home overlooking a beautiful southern VT lake with direct lakefront property with your own private dock. Our spacious home custom designed and built with 8 shipping containers boasts every amenity you want. 3 master bedrooms designed with amazing panoramic views.

Guest favorite
The outdoor pool is surrounded by a chain-link fence and features a concrete deck. Sun lounges and chairs are positioned nearby, with a colorful beach towel draped over a lounge chair. Lush greenery frames the area, providing a serene setting.
Home in Wilmington
4.88 out of 5 average rating, 186 reviews

Adams Farm-"The Little Farmhouse"

A Clean Ranch style home with hardwood floors located on a 100-acre Historic Vermont Farm. Retired farmers live in separate farmhouse & are available throughout your stay. Conveniently located just minutes away from MT Snow Ski Resort, Hermitage Resort, Stratton Mt. for Skiing, Snowboarding, Tubing, Hiking & Mountain Biking. 3 miles from downtown Wilmington. Minutes to public beaches and lakes. Use our trails for snowshoeing, X-Country Skiing or hiking. Our Pool is avail July -Labor day

Top guest favorite
Tiny home in Wilmington
4.99 out of 5 average rating, 377 reviews

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!

Top guest favorite
Cabin in Wilmington
5 out of 5 average rating, 125 reviews

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.

Top guest favorite
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 home in Dover
5 out of 5 average rating, 215 reviews

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.

Top guest favorite
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.
Guest suite in Wilmington
4.93 out of 5 average rating, 831 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!

Top guest favorite
An inviting outdoor space features colorful chairs surrounding a fire pit, set against a winter backdrop. A cozy seating area on a deck showcases modern decor, including a patterned throw and a view of rolling hills framed by an oversized circular window.
Cottage in Shaftsbury
4.98 out of 5 average rating, 766 reviews

Schoolhouse Spa Retreat on a Vermont Farm

Escape to our historic and lovingly-renovated schoolhouse on a 250-acre verified-regenerative farm, where Green Mountain views meet modern comfort. Unwind in your private hot tub and barrel sauna after exploring farm trails, then fall asleep to the gentle sounds of sheep grazing in the pastures below. This is Vermont at its most authentic—working farm life with all the luxury. Level 2 EV charger, in-unit washer/dryer, and ductless AC for summer comfort.

Popular amenities for Wilmington vacation rentals

When is the best time to visit Wilmington?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$72,802 GYDG$73,430 GYDG$58,995 GYDG$44,560 GYDG$48,116 GYDG$49,790 GYDG$52,091 GYDG$51,673 GYDG$51,254 GYDG$54,392 GYDG$55,229 GYDG$70,292 GYD
Avg. temp-5°C-4°C1°C8°C14°C18°C21°C20°C16°C9°C4°C-2°C

Frequently Asked Questions

  • What are the best places to stay in Wilmington?

    Staying near the center of Wilmington has convenient access to shops, dining, and seasonal events, while rentals near lakes or wooded areas are enjoyed for a quieter atmosphere and nature views.

  • What are the best things to do in Wilmington with kids?

    Families often visit the local ice cream shop, play at parks, or explore nature trails with gentle terrain. In the colder months, tubing hills and sledding spots are popular with children.

  • What are some of the best things to do in Wilmington?

    Explore Wilmington’s historic main street, browse local art galleries, and walk along nearby lake or forest trails. In winter, snowshoeing and beginner-friendly slopes are popular, while summer brings farmers markets and outdoor concerts.

  • How is the weather in Wilmington?

    Wilmington experiences cold, snowy winters around 13–32°F (-11–0°C), and warm, humid summers near 57–81°F (14–27°C) with frequent rainfall. Spring brings mild weather, while autumn is known for cool temperatures and vibrant leaf color.

  • When is the best time to visit Wilmington?

    Late spring and early autumn are frequently suggested for milder weather, wildflowers, and colorful foliage. Winter draws visitors who enjoy snow sports, while summer is known for festivals and outdoor recreation.

  • What are the best places to visit in Wilmington?

    Wilmington has a historic village center with locally owned shops, nearby trails for outdoor activities, and scenic lakes. Art galleries and small museums highlight regional history and creative traditions.

  • What are some hiking trails in Wilmington?

    Explore gentle paths around Lake Whitingham or venture onto wooded trails in the Green Mountain National Forest. Wilmington also has walking routes that pass through forested hills and open meadows.

  • What are some family activities we can do in Wilmington?

    Families often explore local farms, enjoy nearby lakes, or experience outdoor activities like hiking and sledding. In winter, Wilmington has snow play areas and is known for slopes suited for beginners.

  • What are some of the best day trip ideas from Wilmington?

    Consider exploring nearby covered bridges, visiting small art towns, or hiking in forested parks around southern Vermont. Local breweries and cheese makers often welcome visitors for tastings.

  • Are there any pet friendly accommodations available in Wilmington?

    Wilmington has a variety of pet-friendly vacation rentals, such as cottages and cabins with outdoor access. Parks and walking paths around town make it easier to enjoy the area with dogs.

  • What are some local tips for visiting Wilmington?

    Dress in layers, as temperatures can change quickly in the mountains, and bring waterproof shoes for rainy days. Many enjoy visiting during the week for a quieter experience, and shopping for local maple products is often recommended.

  • What is Wilmington known for?

    Wilmington is known for its historic main street, mountain views, and access to year-round outdoor activities. The area has a tradition of maple sugaring and showcases vibrant fall colors every autumn.

  • What are the best hidden gems to explore in Wilmington?

    Many enjoy seeking out covered bridges around Wilmington, local artisan workshops, and quiet forest trails less traveled by visitors. Smaller farm stands and independent book shops also add charm.

  • What are the best foods to try in Wilmington?

    Local foods often suggested in Wilmington include Vermont cheddar cheese, maple syrup treats, and fresh apple cider doughnuts. Farm-to-table dining and locally roasted coffee are also popular.

  • What should I bring for a trip to Wilmington?

    Pack layers, a rain jacket, and sturdy shoes for changing weather conditions and outdoor activities. Bringing a reusable water bottle and a daypack is often helpful for hiking or exploring local markets.

  • What is the nightlife in Wilmington like?

    Nightlife in Wilmington has relaxed taverns, small music venues, and spots with local craft drinks. Live performances, open mic nights, and community gatherings are common in smaller venues.

  • What are the most popular events or festivals in Wilmington?

    Wilmington is known for recurring events like fall foliage festivals in autumn and winter celebrations tied with snow sports. Local farmers markets and craft fairs often highlight regional food and art throughout the warmer months.

  • Are there family friendly vacation rentals in Wilmington?

    Vacation rentals in Wilmington include many family-friendly options, such as cozy cabins, homes with outdoor space, and accommodations near recreation areas. Larger places for groups are also commonly found.

Quick stats about vacation rentals in Wilmington

  • Total vacation rentals

    Explore 350 vacation rentals in Wilmington

  • Nightly prices starting at

    Wilmington vacation rentals start at G$14,644 GYD per night before taxes and fees

  • Verified guest reviews

    Over 16,610 verified reviews to help you choose

  • Family-friendly vacation rentals

    250 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 130 rentals that welcome pets

  • Vacation rentals with a pool

    90 properties feature pools

  • Rentals with dedicated workspaces

    170 properties have a dedicated workspace

  • Wi-Fi availability

    340 of Wilmington vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Gym, BBQ grill, and Laptop-friendly workspace across Wilmington rentals

  • 4.9 Average rating

    Wilmington stays are highly rated by guests—averaging 4.9 out of 5!

Destinations to explore

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  3. Vermont
  4. Windham County
  5. Wilmington