Vacation rentals in Wilmington

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Top-rated vacation rentals in Wilmington

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Guest favourite

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.

Apr. 23 – 30

$171 CAD per night

Guest favourite

Home in Wilmington

4.99 out of 5 average rating, 171 reviews

Vermont Sugar House Retreat

Stay at this unique rustic Vermont getaway. Nestled on a quiet hill in Wilmington, this private retreat will serve as the perfect home base for your Vermont adventures. You'll have the house to yourself without a neighbor in sight. While very private and surrounded by beautiful forest, this house is still only a short 5 minute drive from downtown Wilmington. The house is built around an enormous one-of-a-kind natural stone fireplace that was formed atop the old foundations of a sugar house.

May 6 – 13

$346 CAD per night

Guest favourite

Tiny homes in Wilmington

4.99 out of 5 average rating, 135 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!

Jul. 6 – 13

$400 CAD per night

Guest favourite

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

Apr. 21 – 28

$214 CAD per night

Guest favourite

Cabin in Jamaica

4.99 out of 5 average rating, 184 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.

Aug. 18 – 25

$231 CAD per night

Guest favourite

Chalet in Dover

4.93 out of 5 average rating, 263 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.

Mar. 10 – 17

$260 CAD per night

Guest favourite

Barn in Marlboro

4.95 out of 5 average rating, 262 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.

Mar. 13 – 20

$230 CAD per night

Guest favourite

Home in Wilmington

4.94 out of 5 average rating, 240 reviews

Wilmington. Easy walk to center of town.

Beautifully renovated bright, 120year 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. Fire pit out back. There is a 2 car limit. A request for additional vehicles needs to be made prior to check-in.

Jun. 14 – 21

$399 CAD per night

Guest favourite

Apartment in Wilmington

4.92 out of 5 average rating, 106 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.

Jun. 20 – 27

$195 CAD per night

Guest favourite

Guest suite in Wilmington

4.92 out of 5 average rating, 712 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!

Mar. 9 – 16

$185 CAD per night

Guest favourite

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.

Sep. 29 – Oct. 6

$171 CAD per night

Guest favourite

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.

Aug. 8 – 15

$153 CAD per night

Vacation rentals for every style

Get the amount of space that is right for you.

Popular amenities for Wilmington vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

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 favourite

Guesthouse in Putney

4.97 out of 5 average rating, 195 reviews

Cozy cottage loft and retreat

Mar. 13 – 20

$146 CAD per night

Guest favourite

Apartment in Marlboro

4.94 out of 5 average rating, 221 reviews

Shakespeare’s Folly Side Farm and AirBnB.

Mar. 19 – 26

$217 CAD per night

Superhost

Cabin in Bennington

4.8 out of 5 average rating, 101 reviews

Vermont Cabin - Secluded Woods on South Stream

Oct. 5 – 12

$184 CAD per night

Superhost

Cottage in Dover

4.84 out of 5 average rating, 262 reviews

Cozy Camp in Vermont

May 6 – 13

$169 CAD per night

Guest favourite

Condo in Wilmington

5.0 out of 5 average rating, 6 reviews

Ski2Tee

Sep. 22 – 29

$217 CAD per night

Guest favourite

Home in Wilmington

4.92 out of 5 average rating, 63 reviews

Private home, near Mt. Snow, lake, and downtown

Jul. 15 – 22

$307 CAD per night

Guest favourite

Apartment in Dover

4.97 out of 5 average rating, 31 reviews

Brookside Hideaway Retreat

Jul. 16 – 23

$196 CAD per night

Guest favourite

Cabin in Wilmington

4.96 out of 5 average rating, 77 reviews

Peaceful Cabin Perfect for All Seasons

Apr. 20 – 27

$296 CAD per night

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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	$97 CAD before taxes and fees

Vacation rentals in Wilmington

Top-rated vacation rentals in Wilmington

Apartment in Wilmington

Home in Wilmington

Tiny homes in Wilmington

Apartment in Wilmington

Cabin in Jamaica

Chalet in Dover

Barn in Marlboro

Home in Wilmington

Apartment in Wilmington

Guest suite in Wilmington

Condo in West Dover

Apartment in Bennington

Vacation rentals for every style

Cabins

Apartments

Chalets

Popular amenities for Wilmington vacation rentals

Stay near Wilmington's top sights

Other great vacation rentals in Wilmington

Guesthouse in Putney

Apartment in Marlboro

Cabin in Bennington

Cottage in Dover

Condo in Wilmington

Home in Wilmington

Apartment in Dover

Cabin 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

Destinations to explore