Vacation rentals in Wilmington

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Top-rated vacation rentals in Wilmington

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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, 236 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.

Top guest favorite
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
4.96 out of 5 average rating, 105 reviews

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!

Top guest favorite
Tiny home in Wilmington
4.99 out of 5 average rating, 319 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
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
4.92 out of 5 average rating, 143 reviews

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.

Top guest favorite
A cozy outdoor living area features wooden seating, including a swing and chairs surrounding a fire pit. The camper is positioned on a deck nestled among trees, providing a sense of seclusion. A small table is visible, completing the inviting gathering space.
Camper/RV in Guilford
4.94 out of 5 average rating, 176 reviews

Monadnock Sunrise Forest Hideaway

Enjoy a converted camper as your private getaway in Southern VT. Less than 10 min to downtown Brattleboro, yet nestled in the woods for a quiet retreat. Full galley kitchen and living/lounge area. Wood stove for primary heating (electric backup for not so cold days). Outdoor spaces include a fire pit, deck, pool table, hot outdoor shower, outhouse (composting toilet), and forest for galavanting. The place is a perfect fit for two adults (queen bed) and one kid (63" long fold down couch).

Top guest favorite
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
5 out of 5 average rating, 100 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
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
4.89 out of 5 average rating, 133 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.

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
4.99 out of 5 average rating, 199 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+ hosts provide water, coffee, tea, milk, fresh eggs + homemade soap. There is an indoor compostable toilet + outhouse + outdoor shower. 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
The garden features raised vegetable beds surrounded by a wooden fence. In the background, the charming former church building with a pointed steeple is visible, framed by vibrant autumn foliage in shades of red and orange.
Guest suite in Brattleboro
4.95 out of 5 average rating, 602 reviews

Charming studio in renovated 19th century church.

This spacious studio apartment is located in the former Swedish Congregational Church in historic Swedeville, a secluded hilly neighborhood built by Swedish immigrants in the 1800's. For years it housed Rick and Liza’s stained glass studio, which they have now lovingly and creatively transformed into a residence. The rental is minutes from the interstate and one mile from downtown Brattleboro, but the neighborhood has a rural and somewhat European flavor to it.

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, 802 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!

Guest favorite
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, 294 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.

Top guest favorite
The exterior of a renovated log cabin is presented, featuring a red metal roof and a charming porch with steps leading up. The cabin is surrounded by lush greenery, with rolling hills visible in the background under a clear blue sky.
Cabin in Newfane
4.99 out of 5 average rating, 290 reviews

Log Cabin: Amazing Views, River Frontage, Hot Tub

A sparkling clean, recently renovated log cabin in the woods with beautiful views of river and mountains. Located by the charming villages of Williamsville and Newfane, 12 miles from Mount Snow, and right on the crystal clear Rock River. It's the perfect place for a romantic getaway, a family vacation and quality times with good friends. Now also with outdoor hot tub with views of mountains, river and the wide, open sky above.

Popular amenities for Wilmington vacation rentals

When is the best time to visit Wilmington?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceR5,438 ZARR5,923 ZARR4,451 ZARR3,689 ZARR3,983 ZARR4,122 ZARR4,312 ZARR4,278 ZARR4,243 ZARR4,260 ZARR3,879 ZARR5,196 ZAR
Avg. temp-5°C-4°C1°C8°C14°C18°C21°C20°C16°C9°C4°C-2°C

Frequently Asked Questions

  • Are there vacation rentals with a dedicated workspace in Wilmington?

    Yes! Work meets play with ease at over 170 vacation rentals in Wilmington featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there pet-friendly vacation rentals in Wilmington?

    Four-legged friends are welcome in Wilmington. Choose from more than 140 vacation rentals for guests traveling with pets.

  • Are there Wilmington vacation rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 80 vacation homes with pools in Wilmington, available on Airbnb. Make a splash and soak up the sun in style!

  • How much does it cost to stay in townhouse rentals in Wilmington?

    Experience the best of Wilmington with our townhouse rentals, starting at about $90 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do house rentals in Wilmington have a gym?

    Absolutely! We offer over 50 house rentals with a gym in Wilmington. Enjoy a tailored experience with all the comforts you desire.

  • Do aparthotel rentals in Wilmington have air conditioning?

    Absolutely! We offer over 20 aparthotel rentals with air conditioning in Wilmington. Enjoy a tailored experience with all the comforts you desire.

  • Are there family-friendly townhouse rentals in Wilmington?

    Wilmington has more than 10 family-friendly townhouse rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Do chalet rentals in Wilmington have wifi?

    Absolutely! We offer over 30 chalet rentals with wifi in Wilmington. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Wilmington have a bbq area?

    Absolutely! We offer over 90 house rentals with a bbq area in Wilmington. Enjoy a tailored experience with all the comforts you desire.

  • What are the most popular amenities for Chalet Rentals in Wilmington?

    Enhance your stay in our Chalet Rentals with the most popular amenities: over 10 homes with a bbq area, over 30 homes with wifi, over 10 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.

Quick stats about vacation rentals in Wilmington

  • Total vacation rentals

    Explore 330 vacation rentals in Wilmington

  • Nightly prices starting at

    Wilmington vacation rentals start at R1,212 ZAR per night before taxes and fees

  • Verified guest reviews

    Over 15,740 verified reviews to help you choose

  • Family-friendly vacation rentals

    250 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 140 rentals that welcome pets

  • Vacation rentals with a pool

    80 properties feature pools

  • Rentals with dedicated workspaces

    160 properties have a dedicated workspace

  • Wi-Fi availability

    320 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

  1. Airbnb
  2. United States
  3. Vermont
  4. Windham County
  5. Wilmington