Holiday rentals in Wilmington

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Top-rated holiday rentals in Wilmington

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

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Guest favourite
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 favourite
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, 140 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 favourite
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, 171 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.

Top guest favourite
A spacious deck is showcased with several outdoor chairs arranged to overlook a lush landscape. The surrounding trees and rolling hills create a serene backdrop, with partially cloudy skies above, inviting relaxation and enjoyment of the natural setting.
Chalet in Wilmington
4.96 out of 5 average rating, 179 reviews

Mountain View Retreat: 5 Mi to MT Snow, Hot Tub

Come escape to Wilmington, Vermont. Stunning views of Mt. Snow, a small stream, and a large hot tub on 12 secluded acres. Only 10 minutes to Mount Snow and 30 minutes to Stratton our home is the perfect getaway for your VT adventure with all of your family and friends. Come ski, snowboard, snowmobile, hike, kayak, mountain bike, swim, or fish just minutes away! After your long day exploring come relax in the hot tub, by the fire, in the game room, or just out on our deck taking in the sunset!

Guest favourite
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 favourite
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 favourite
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.

Guest favourite
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.
Flat in Wilmington
4.9 out of 5 average rating, 147 reviews

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.

Guest favourite
The A-Frame chalet is set amidst vibrant autumn foliage, showcasing a wrap-around deck with wooden railings. A balcony extends above, offering a view of the surrounding trees and an inviting outdoor space with seating.
Chalet in Dover
4.85 out of 5 average rating, 308 reviews

The Mountain A-Frame at Mount Snow

Entire chalet-style A-Frame in Mount Snow with mountain views. Less than 1 mile from the base of Mount Snow and close to all the fun in the Green Mountains: AT access, swimming holes, covered bridges and more! Across the street you can hop on the Moover shuttle that takes you right to the mountain! 2 minute walk to market, coffee shop and local bar. 2 bedrooms + 1 loft, 1 bath, wrap around deck, cooking necessities, Smart TV and WiFi. You can find us on social (tag us!) @themountainaframe

Top guest favourite
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, 216 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.

Guest favourite
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.
Home in Wilmington
4.95 out of 5 average rating, 313 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.

Superhost
A modern cabin features a contrasting black exterior and wooden accents, nestled among lush trees. A wide deck with railing leads to the entrance, offering a welcoming space to enjoy the surrounding nature. Large windows provide ample natural light and views of the forest.
Tiny home in Athens
4.86 out of 5 average rating, 179 reviews

LUXE Forest Retreat

Here you will experience a full sensory immersion in nature while simultaneously enjoying all the comforts of a custom built luxury home. The SY House derives its name from the Japanese expression Shinrin-yoku, which directly translates to "forest bathing... A practice of therapeutic relaxation where one spends time in a forest or natural atmosphere, focusing on sensory engagement to connect with nature." The essence of this house is nature.

Popular amenities for Wilmington holiday rentals

When is the best time to visit Wilmington?

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Avg. price$448 SGD$452 SGD$363 SGD$274 SGD$296 SGD$307 SGD$321 SGD$318 SGD$316 SGD$335 SGD$340 SGD$433 SGD
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 holiday rentals in Wilmington

  • Total holiday rentals

    Explore 350 holiday rentals in Wilmington

  • Nightly prices starting at

    Wilmington holiday rentals start at $90 SGD per night before taxes and fees

  • Verified guest reviews

    Over 16,610 verified reviews to help you choose

  • Family-friendly holiday rentals

    250 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 130 rentals that welcome pets

  • Holiday rentals with a pool

    90 properties feature pools

  • Rentals with dedicated workspaces

    170 properties have a dedicated workspace

  • Wifi availability

    340 of Wilmington holiday rentals include wifi 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