Wilmington vacation rentals

Book unique vacation rentals, houses, and more on Airbnb

Top-rated vacation rentals in Wilmington

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

0 of 0 items showing

1 of 3 pages

Guest favorite

Apartment in Wilmington

4.91 out of 5 average rating, 109 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.

Mar 18 – 25

G$21,166 GYD per night

Guest favorite

Tiny home in Wilmington

4.99 out of 5 average rating, 140 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!

Sep 30 – Oct 7

G$45,748 GYD per night

Guest favorite

Apartment in Wilmington

4.97 out of 5 average rating, 126 reviews

The Loft @ Adams Farm-a great stay near Mt. Snow

Spacious & clean in Historic Duplex Farmhouse located minutes from MT Snow Ski Area & Stratton for Skiing, Snowboarding & Tubing. VAST trails just across the road. Shop & eat in the quaint villages of Wilmington & Dover. Private entrance and 3-stories of space with farmstyle decor & lovely views. 0ver 100-acres for you to Snowshoe , X-Country ski or just hike & explore. Plenty of parking for snowmobile trailers. Walking distance to Local Farm Store. Our pool is available July 1-Labor Day

Sep 23 – 30

G$27,336 GYD per night

Guest favorite

Cabin in Jamaica

4.99 out of 5 average rating, 185 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.

Jul 11 – 18

G$30,567 GYD per night

Guest favorite

Chalet in Dover

4.93 out of 5 average rating, 265 reviews

A charming VT chalet

Charming chalet nestled in the Mt Snow valley. Relax to the sound of a babbling brook in the back yard while you hang around a stone fire pit! Unwind in the quiet serenity of this country home complete with fully equipped kitchen with a newly installed gas fireplace , a comfy open living room with flat screen cable tv & DVD player Roko & High speed Internet . We have a lock box located on the post near the front entrance. combo provided upon arrival . Washer & dryer located on first level.

Dec 7 – 14

G$32,115 GYD per night

Guest favorite

Barn in Marlboro

4.95 out of 5 average rating, 263 reviews

The Studio With a View. Bring your dog, too!

Our stylish Studio, a not so tiny Tiny House, is nestled into the Southern Vermont hillside and surrounded by nature. Enjoy the view from the deck, and cozy up in the newly renovated flower barn with a cup of coffee or tea and a great book. Well-mannered dogs are welcome, they will enjoy the fenced-in area right off the deck. Features: efficiency kitchen and dining area, cozy living space, queen-size bed, and a full bathroom. The large covered porch overlooks fields and trees.

Aug 26 – Sep 2

G$29,244 GYD per night

Guest favorite

Apartment in Marlboro

4.94 out of 5 average rating, 223 reviews

Shakespeare’s Folly Side Farm and AirBnB.

Located on a gorgeous south-facing hillside in Marlboro, VT, Shakespeare's Folly Side Farm is a light, airy, quiet apartment with stunning views, beautiful gardens, and walking paths. We have friendly goats and dogs, vegetable and flower gardens and a small orchard, with raspberries and blueberries. Free picking in the summer. A magical and inspiring place of rolling lawns and 40 mile views yet so close to the many rich cultural and recreational options in southeast Vermont.

Mar 18 – 25

G$30,113 GYD per night

Guest favorite

Apartment in Wilmington

4.92 out of 5 average rating, 107 reviews

Walk To Wilmington Village (Reduced Spring Rate)

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. Brand new washer/dryer Smart TV with a variety of premium streaming services The entire covered porch, side porch, and the yard on that side is all private and for you to enjoy.

May 18 – 25

G$18,912 GYD per night

Guest favorite

Apartment in Bennington

4.96 out of 5 average rating, 139 reviews

Cooper's Place

Small bright and cozy apartment nestled in the Shires of Vermont. A mid-modern space with VT flare and all of the amenities you need to enjoy your getaway. Housed behind a unique building that was once a manufacturer of concrete blocks and is still a hardscape retail store located in downtown Bennington called Morse Brick & Block. Enjoy the porch or have a fire in the fire pit. Take a trip to the Bennington Monument and Museum. Close to hiking trails and ski areas.

Sep 14 – 21

G$24,954 GYD per night

Guest favorite

Guest suite in Wilmington

4.92 out of 5 average rating, 713 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!

Jul 15 – 22

G$24,513 GYD per night

Guest favorite

Condo in West Dover

4.94 out of 5 average rating, 181 reviews

Comfy Condo - 2 Min Walk to Carinthia Grommet Lift

One BR condo. Corner unit, 1st floor. 2 min walk to Carinthia Magic Carpet. Minutes drive to golf and mountain biking. 1 BR with Queen bed and full bath with jetted tub. Sofa bed and wood burning fireplace in LR. TV with DVD and Roku in LR. WiFi. Kitchen is small but has everything. Washer/dryer. Storage closet for skis & clubs. Plenty of dining nearby. Perfect for couples, solo adventurers, and small families. Plenty of parking on site.

Nov 18 – 25

G$20,119 GYD per night

Guest favorite

Apartment in Bennington

4.93 out of 5 average rating, 527 reviews

The Octopus's Garden

Welcome to the Octopus' Garden, a warm and cozy oasis located in the heart of Bennington, VT. This relaxing one bedroom suite, infused with amenities and much love, comfortably accommodates 2 people. This peaceful space is only a 10 minute walk to art, shops and dining and is the perfect hub for a variety of activities in Southern Vermont and Western Massachusetts.

Jul 30 – Aug 6

G$20,315 GYD per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Wilmington vacation rentals

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Air conditioning

Stay near Wilmington's top sights

Dot's106 locals recommend

Anchor Seafood Restaurant68 locals recommend

Wahoo's31 locals recommend

Shaw's73 locals recommend

Maple Leaf Tavern66 locals recommend

La Casita50 locals recommend

Other great vacation rentals in Wilmington

Guest favorite

Guest suite in Brattleboro

4.94 out of 5 average rating, 518 reviews

Charming studio in renovated 19th century church.

Dec 24 – 31

G$19,439 GYD per night

Guest favorite

Guesthouse in Putney

4.97 out of 5 average rating, 196 reviews

Cozy cottage loft and retreat

Jul 22 – 29

G$18,764 GYD per night

Guest favorite

Cabin in Guilford

4.96 out of 5 average rating, 479 reviews

Serenity Now - Couples Retreat or Writer's Dream

Mar 16 – 23

G$37,939 GYD per night

Superhost

Cabin in Wardsboro

4.8 out of 5 average rating, 202 reviews

Log Cabin Near Stratton/Mt Snow

May 14 – 21

G$20,409 GYD per night

Guest favorite

Home in Wilmington

4.94 out of 5 average rating, 241 reviews

Wilmington. Easy walk to center of town.

Jul 22 – 29

G$50,338 GYD per night

Guest favorite

Home in Wilmington

4.99 out of 5 average rating, 171 reviews

Vermont Sugar House Retreat

May 23 – 30

G$44,747 GYD per night

Guest favorite

Barn in Chester

4.99 out of 5 average rating, 493 reviews

Inviting studio apartment above barn in Vermont

Sep 4 – 11

G$21,418 GYD per night

Guest favorite

Cottage in Dover

4.95 out of 5 average rating, 216 reviews

Cozy summer cottage in the woods of southern VT

Jan 4 – 11

G$24,682 GYD per night

Show all

Other great vacation rentals in Wilmington

Guest favorite

Home in Putney

4.95 out of 5 average rating, 307 reviews

Cozy Train Depot in Putney Vermont

May 13 – 20

G$21,031 GYD per night

Guest favorite

Guesthouse in North Bennington

4.98 out of 5 average rating, 150 reviews

Birch House - lake, green trees + modern comforts

Oct 23 – 30

G$32,669 GYD per night

Guest favorite

Apartment in Dummerston

4.96 out of 5 average rating, 160 reviews

HeART Barn Retreat

Sep 7 – 14

G$18,390 GYD per night

Guest favorite

Cabin in Londonderry

4.93 out of 5 average rating, 308 reviews

Stone Fence Cabin

Nov 5 – 12

G$21,367 GYD per night

Guest favorite

Cabin in Newfane

5.0 out of 5 average rating, 150 reviews

Custom cabin by the river in Newfane, VT

Mar 25 – Apr 1

G$29,887 GYD per night

Guest favorite

Condo in Dover

5.0 out of 5 average rating, 36 reviews

Four Seasons Slope-side Getaway at Mount Snow

Jul 17 – 24

G$24,194 GYD per night

Guest favorite

Condo in Wilmington

5.0 out of 5 average rating, 6 reviews

Ski2Tee

Oct 1 – 8

G$24,778 GYD per night

Guest favorite

Chalet in Wilmington

5.0 out of 5 average rating, 59 reviews

Mt Snow Chalet: Peaceful Escape w/Hot Tub

Dec 8 – 15

G$84,784 GYD per night

Show all

Quick stats about vacation rentals in Wilmington

Total rentals
350 properties
Rentals with a pool
90 properties have a pool
Pet-friendly rentals
130 properties allow pets
Family-friendly rentals
260 properties are a good fit for families
Total number of reviews
14K reviews
Nightly prices starting at
G$14,594 GYD before taxes and fees

Frequently Asked Questions

Are there vacation rentals with a dedicated workspace in Wilmington?
Yes! Work meets play with ease at over 180 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 130 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 90 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 hotel rentals in Wilmington?
Experience the best of Wilmington with our hotel rentals, starting at about $70 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 40 house rentals with a gym in Wilmington. Enjoy a tailored experience with all the comforts you desire.
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.
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.
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 house rentals in Wilmington have a bbq area?
Absolutely! We offer over 120 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 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.

Wilmington vacation rentals

Top-rated vacation rentals in Wilmington

Vacation rentals for every style

Chalets

Cabins

Apartments

Popular amenities for Wilmington vacation rentals

Stay near Wilmington's top sights

Other great vacation rentals in Wilmington

Guest suite in Brattleboro

Guesthouse in Putney

Cabin in Guilford

Cabin in Wardsboro

Home in Wilmington

Home in Wilmington

Barn in Chester

Cottage in Dover

Other great vacation rentals in Wilmington

Home in Putney

Guesthouse in North Bennington

Apartment in Dummerston

Cabin in Londonderry

Cabin in Newfane

Condo in Dover

Condo in Wilmington

Chalet in Wilmington

Quick stats about vacation rentals in Wilmington

Total rentals

Rentals with a pool

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Frequently Asked Questions

Are there vacation rentals with a dedicated workspace in Wilmington?

Are there pet-friendly vacation rentals in Wilmington?

Are there Wilmington vacation rentals on Airbnb with pools?

How much does it cost to stay in hotel rentals in Wilmington?

Do house rentals in Wilmington have a gym?

Do bed and breakfast rentals in Wilmington have air conditioning?

Are there family-friendly chalet rentals in Wilmington?

Do apartment rentals in Wilmington have wifi?

Do house rentals in Wilmington have a bbq area?

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

Destinations to explore