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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Top guest favourite
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, 134 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 favourite
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.
Flat in Wilmington
4.88 out of 5 average rating, 329 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 favourite
A comfortable living area showcases a gas fireplace beneath a large television mounted on the wall. A dark sofa sits beside a small coffee table, and light flows in through a glass door, which is accented by sheer curtains. Decorative elements enhance the space.
Apartment in Dover
4.85 out of 5 average rating, 141 reviews

Walk to Mt. Snow-Spa-Summer Pool

*Exterior construction on siding until end of May *Amenity rich studio only a 5 min walk to Mt. Snow's famed Magic Carpet (runs on weekends) *Gas Fireplace *Queen memory foam Murphy bed *Queen pull out with memory foam mattress *Well appointed kitchen *65" curved UHD TV *25Mbps Wifi *USB wall outlets *Blue tooth music streaming to TV *Ample closet space *Patio with rocking chair *Easy 1st floor access *Fitness center access *Hot tub *Outdoor pool seasonal *Loaner amenities such as phone charger

Top 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, 122 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
The inviting living room features a modern wood-burning stove against a backdrop of light wooden walls. A comfortable dark sofa is arranged around a round wooden coffee table, complemented by a decorative plant. Natural light filters through the windows, enhancing the cozy atmosphere.
Cabin in Londonderry
4.95 out of 5 average rating, 239 reviews

Summit View Cottage:Ski | Hot tub|Fireplace3bd 2ba

Summit view cottage boasts 3 acres in the beautiful green mountains, we are 1,700 feet up in elevation . At this brand newly built PET FRIENDLY cabin you will have 3 bedrooms and 2 full bathrooms, which will sleep 7 comfortably. We have a brand new 6 person HOT TUB! You will find yourself within 15 minutes to the world famous Stratton mtn, 15 minutes from Bromley mtn and a close 4 minutes to the local Magic mtn.Very close proximity to the town of Manchester, which has great shops and restaurants

Top guest favourite
Tiny home in Wilmington
4.99 out of 5 average rating, 352 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, 118 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 favourite
The exterior of a charming house features a gabled roof and a welcoming front porch with a wooden rocking chair. Lush green grass surrounds the home, and neatly trimmed shrubs are visible, complemented by tall trees in the background against a partly cloudy sky.
Home in Bennington
4.99 out of 5 average rating, 348 reviews

Southern Vermont Home

Beautiful home that offers privacy on over one acre of land. It is only a short drive to the conveniences of downtown shopping, restaurants, Bennington College, and much more. This house is 35 minutes from Manchester's famous outlets, 20 minutes from Williamstown, MA, and 45 minutes from Albany, NY. Bromley and Mount Snow ski areas are 40 minutes. The home has wonderful finishes and you will feel right at home upon arrival. Please come explore Vermont from our country escape!

Guest favourite
Home in Wilmington
4.9 out of 5 average rating, 166 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.

Top guest favourite
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, 823 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 favourite
A charming red chalet is nestled among snow-covered trees, complemented by a clear winter sky. Icicles hang from the roof, and a wooden deck is partially visible, showcasing the inviting entrance adorned with festive decor.
Chalet in Wilmington
5 out of 5 average rating, 122 reviews

Mt Snow Chalet: Peaceful Escape w/Hot Tub

Escape to the serene beauty of Vermont's Green Mountains at the Mount Snow Chalet, a charming retreat nestled on a private wooded lot in the desirable Chimney Hill community of Wilmington. 🏠🌳 Just minutes from the slopes of Mount Snow, our chalet offers the perfect blend of rustic charm and modern amenities for an unforgettable getaway. Designed with love and care, we invite you to relax and stay awhile! 🥰

Top guest favourite
The exterior of a charming chalet is framed by lush trees, featuring a stone pathway leading to a welcoming entrance with large windows. A deck with an umbrella and outdoor seating is visible to the right, creating an inviting outdoor space.
Cabin in Wilmington
4.92 out of 5 average rating, 165 reviews

Chalet with Hot Tub and Game Room

Escape to The Sugar Maple Chalet, a stylish modern retreat in Wilmington, VT, perfect for families & groups. Just minutes from Mount Snow, this 4-bed, 3-bath home offers a private hot tub, stone fireplace, and a game room. Enjoy fast Wi-Fi for remote work and resort amenities like an indoor pool. Your ideal base for skiing, hiking, and exploring Southern Vermont.

Popular amenities for Wilmington holiday rentals

When is the best time to visit Wilmington?

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Frequently Asked Questions

  • Are there pet-friendly vacation rentals in Wilmington?

    Four-legged friends are welcome in Wilmington. Choose from more than 150 vacation rentals for guests traveling with pets.

  • 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 Wilmington vacation rentals on Airbnb with pools?

    Yes! Dive into the perfect getaway at one of over 90 vacation homes with pools in Wilmington, available on Airbnb. Make a splash and soak up the sun in style!

  • Are there family-friendly chalet rentals in Wilmington?

    Wilmington has more than 30 family-friendly chalet rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

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

    Experience the best of Wilmington with our house 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 air conditioning?

    Absolutely! We offer over 70 house rentals with air conditioning in Wilmington. Enjoy a tailored experience with all the comforts you desire.

  • Do bed and breakfast rentals in Wilmington have wifi?

    Absolutely! We offer over 10 bed and breakfast rentals with wifi in Wilmington. Enjoy a tailored experience with all the comforts you desire.

  • Do apartment rentals in Wilmington have a bbq area?

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

  • 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.

  • What are the most popular amenities for Bed And Breakfast Rentals in Wilmington?

    Enhance your stay in our Bed And Breakfast Rentals with the most popular amenities: over 10 homes with wifi, over 10 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.

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 £60 per night before taxes and fees

  • Verified guest reviews

    Over 15,690 verified reviews to help you choose

  • Family-friendly holiday rentals

    260 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 150 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

    350 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

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