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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Guest favorite
The custom home features warm wood siding and a welcoming porch with flower boxes. A spacious deck with rustic railings extends from the second floor, while a covered area includes seating. Surrounding greenery enhances the natural setting, creating a serene outdoor ambiance.
Cabin in Wardsboro
4.85 out of 5 average rating, 159 reviews

Mountain side acres

10 years of love and affection went into building our 2 bedroom custom home. Sticking with natural products to blend together the beauty of the surrounding area. Lay in bed at night and listen to river that runs the entire length of the property. The house has a full kitchen with seating for 6. Spacious living room for relaxing or admiring one of the many birds that visit all year round. Two upstairs bedrooms and office space. Walkout basement with full entertainment area, hot tub,exercise room.

Top guest favorite
A cozy tiny cabin, constructed with wooden beams and a sloped roof, is situated among tall trees. The porch features a railing, inviting seating, and a lantern. Sunlight filters through the foliage, casting a soft glow on the forest floor covered in pine needles.
Treehouse in Brookline
4.98 out of 5 average rating, 257 reviews

Glamping Cabin with Hot Tub on Flower Farm

<b>Vermont's Most Wish Listed</b> ﹏﹏﹏ Nestled in a wooded grove on Tanglebloom Flower Farm, this unforgettable glamping-inspired farm stay invites you to escape the everyday & immerse yourself in nature - comfortably. Designed with a clear roof looking up to the trees and screened sides to let in the breeze, the handmade tiny cabin invites you to slow down. Explore southern Vermont's hikes, farmer's markets & swimming holes or stay put. Perfect for a romantic couples retreat or solo getaway.

Guest favorite
A rustic building with wooden siding is partially surrounded by a foggy landscape. An elevated deck with rocking chairs invites relaxation. The entrance features glass doors flanked by large windows, allowing natural light to illuminate the interior. Surrounding greenery creates a serene atmosphere.
Home in Putney
4.93 out of 5 average rating, 421 reviews

Vermont Botanical Studio Apartment

This room is one half of a floor in our studio building (35 sq m). It is the only occupied space in the building, which is separated from the main house by a yard. There is a queen-sized bed, full bath (no-curb shower), and an outdoor shower (not available in the winter) Small kitchen with a sink, fridge, 2-burner induction hob, microwave/convection oven, toaster, coffee pot, and cookware. Arched ceiling, with ceiling fan, large windows, deck, and Maggie's botanical art lining the walls.

Top guest favorite
Tiny home in Wilmington
4.99 out of 5 average rating, 334 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, 144 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
The cabin's exterior showcases a warm wooden facade with large, strategically placed windows. A spacious screened porch extends from the building, inviting natural light and outdoor enjoyment. A stone pathway leads to the entrance, surrounded by landscaped gravel and native vegetation.
Cabin in Jamaica
4.99 out of 5 average rating, 272 reviews

New Cabin in Jamaica

Recently constructed 500sq ft passive solar cabin, 10 minutes to Stratton Mtn., 20 minutes to Mt. Snow and Dover for skiing, shopping, food, or a beer at Snow Republic. Quiet road but very accessible. Perfect area for hiking, biking, relaxing walks along the Ball Mountain Brook or kayaking on Grout Pond or Gale Meadows. Enjoy a campfire in the side yard/former pony corral or relax on the spacious screened in porch. 30 minutes from seasonal farmers market and from Manchester for outlets.

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, 102 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, 203 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
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, 806 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
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, 726 reviews

Vermont Schoolhouse Farm Cottage - Sauna + Hot Tub

This historic schoolhouse overlooks our family's regenerative organic farm. The Schoolhouse is bright & open, with a modern design & peaceful, rustic feel. It is the perfect place to relax & enjoy a country setting with views of the Green Mountains in every direction. We have added a new private deck at the Schoolhouse property, with a hot tub & panoramic barrel sauna. Come to unwind, cook, & enjoy a quintessential Vermont experience on our 250 acre property.

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.

Guest favorite
An open living area features rustic wooden beams and warm lighting. A cozy sofa is positioned near a wood stove, with a small dining table adjacent. The kitchen is visible in the background, showcasing appliances against a backdrop of exposed brick and wood floors.
Cottage in Dover
4.84 out of 5 average rating, 321 reviews

Cozy Camp in Vermont

This cozy camp located in beautiful East Dover, is on a secluded road off the beaten path where the babbling brook can be heard. Close to Mount Snow, Lake Whitingham, Lake Raponda, and only 25 minutes to Brattleboro the adventures are endless! Visit the serenity and beauty of Southern Vermont- especially in Fall during “leaf peeping”. This is a camp-style cottage with rustic charm. Snow tires are a MUST- Nov. - Apr.

Popular amenities for Wilmington vacation rentals

When is the best time to visit Wilmington?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$65,695 GYDG$71,553 GYDG$53,769 GYDG$44,564 GYDG$48,120 GYDG$49,794 GYDG$52,095 GYDG$51,677 GYDG$51,259 GYDG$51,468 GYDG$46,865 GYDG$62,766 GYD
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Frequently Asked Questions

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

    Yes! Work meets play with ease at over 160 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 bed and breakfast rentals in Wilmington?

    Experience the best of Wilmington with our bed and breakfast rentals, starting at about $160 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do private suite rentals in Wilmington have a gym?

    Absolutely! We offer over 10 private suite rentals with a gym in Wilmington. Enjoy a tailored experience with all the comforts you desire.

  • Do apartment rentals in Wilmington have air conditioning?

    Absolutely! We offer over 10 apartment rentals with air conditioning in Wilmington. Enjoy a tailored experience with all the comforts you desire.

  • Are there family-friendly house rentals in Wilmington?

    Wilmington has more than 150 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Do apartment rentals in Wilmington have wifi?

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

  • Do chalet rentals in Wilmington have a bbq area?

    Absolutely! We offer over 10 chalet rentals with a bbq area in Wilmington. Enjoy a tailored experience with all the comforts you desire.

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

    Enhance your stay in our Private Suite Rentals with the most popular amenities: over 10 homes with wifi, over 10 homes with a gym, 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 G$14,645 GYD 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

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  3. Vermont
  4. Windham County
  5. Wilmington