
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.

Refined, serene and like no other, Marlboro, VT.
Our elegant, supremely comfortable, and private guesthouse is surrounded by a wonderful garden and 350 acres of woodland in the quiet of rural Vermont. We are 30 minutes from Brattleboro to the east, with its many shops and restaurants, and 12 minutes from the small town of Wilmington to our west, with some restaurants, shops, and a supermarket However, we always recommend bringing groceries, etc., for your first night and next morning. We are pleased to offer a 20% discount for 7 days or more!

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).

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.

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.

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!

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.

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!

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.

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.

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!

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.

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 holiday rentals
Other great holiday rentals in Wilmington

Cozy Brookside Getaway

Vermont Village Retreat Near Mount Snow

Modern Chalet-private deck/firepit/ clubhouse pool

“Down Under” A peaceful mountain escape in Vermont

Game Room, near skiing and lake, walk to downtown

Secluded cabin on brook near skiing and lakes

Vermont Log Cabin- New Construction w/ EV charger!

The Greylock Cabin
When is the best time to visit Wilmington?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | € 268 | € 292 | € 219 | € 182 | € 196 | € 203 | € 212 | € 211 | € 209 | € 222 | € 225 | € 287 |
| Avg. temp | -5°C | -4°C | 1°C | 8°C | 14°C | 18°C | 21°C | 20°C | 16°C | 9°C | 4°C | -2°C |
Frequently Asked Questions
Are there pet-friendly vacation rentals in Wilmington?
Four-legged friends are welcome in Wilmington. Choose from more than 130 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 vacation rentals in Wilmington?
Wilmington has more than 250 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
How much does it cost to stay in hotel rentals in Wilmington?
Experience the best of Wilmington with our hotel rentals, starting at about $80 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do bed and breakfast rentals in Wilmington have air conditioning?
Absolutely! We offer over 10 bed and breakfast 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 cabin rentals in Wilmington have a gym?
Absolutely! We offer over 10 cabin rentals with a gym in Wilmington. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for House Rentals in Wilmington?
Enhance your stay in our House Rentals with the most popular amenities: over 160 homes with wifi, over 70 homes with air conditioning, over 40 homes with a gym, over 80 homes with a bbq area, 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 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!
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- Okemo Mountain Resort
- Stratton Mountain
- Saratoga Race Course
- Berkshire East Mountain Resort
- Jiminy Peak Mountain Resort
- Monadnock State Park
- Magic Mountain Ski Resort
- Stratton Mountain Resort
- Mount Snow Ski Resort
- Bousquet Mountain Ski Area
- Saratoga Spa State Park
- Fox Run Golf Club
- June Farms
- Norman Rockwell Museum
- Bromley Mountain Ski Resort
- Hildene, The Lincoln Family Home
- Naumkeag
- National Museum of Racing and Hall of Fame
- Berkshire Botanical Garden
- Hancock Shaker Village
- New York State Museum
- Emerald Lake State Park
- Rensselaer Polytechnic Institute
- Mount Holyoke College




