Condo vacation rentals in Windham County

Find and book unique condos on Airbnb

Top-rated condo rentals in Windham County

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Guest favorite

Condo in Dover

5.0 out of 5 average rating, 36 reviews

Four Seasons Slope-side Getaway at Mount Snow

Come stay at our lovely slopeside condominium at seasons of Mount Snow where you’ll be staying in spacious one bedroom unit with a comfortable king size bed and a wonderful pull out couch that comfortably sleeps 4. In winter we are right on the mountain giving you a true ski in ski out. In summer the rivers the mountain and hiking is right out our back door as we enjoy mountain biking hiking golfing and relaxing around the mountain environment. Our unit is well equipped for a wonderful vacation

May 29 – Jun 5

G$23,296 GYD per night

Guest favorite

Condo in Dover

4.87 out of 5 average rating, 31 reviews

Ski Condo 5 Min from Mt Snow

Your family will be close to everything when you stay at this centrally-located condo. Cozy and clean, only 5 minutes from Mount Snow Ski Resort for skiing and snowboarding in the winter or golf and mountain biking in the spring, summer, and fall. A two minute walk to the Snow Republic Brewery. Close to the towns of Dover and Wilmington for shops, restaurants, and country charm. Just minutes from hiking for the outdoor enthusiasts and only ten minutes from the tranquil Lake Raponda. *New couches

May 28 – Jun 4

G$26,516 GYD per night

Guest favorite

Condo in Wilmington

5.0 out of 5 average rating, 6 reviews

Ski2Tee

Visiting during the winter? Hit the slopes for some downhill skiing then stop by the Waffle House for a treat. Take a hike on the Mt Haystack Trail. Head to the White House Inn with the kids for sledding! Go on a snowmobiling tour with your besties. Visiting during the Summer? Play 18 holes of golf. View the first hole off our deck. Feel the breeze as you flip burgers on the BBQ. Visit the Harriman Reservoir for boating, swimming, fishing, and more! Enjoy our home with your family and friends.

Oct 18 – 25

G$24,799 GYD per night

Guest favorite

Condo in Dover

4.99 out of 5 average rating, 100 reviews

Winter Dream! The Handle Lodge at Snowtree Condos

The Handle Lodge at Snowtree Condos is a charming and modern 1BR condo at the base area of Mount Snow. Comfortably sleeps 6 adults and is fully equipped with everything you'll need for a fun getaway with family and friends. Make a meal in the new and beautiful kitchen or step out on the balcony for stunning mountain views. Our modern and cozy decor, the lovely views, and proximity to the mountain make it a great place to relax and recharge. Check us out on IG for more content: @TheHandleLodge

Sep 16 – 23

G$35,287 GYD per night

Guest favorite

Condo in Stratton

4.94 out of 5 average rating, 138 reviews

Updated Ski in/Ski out Stratton Condo!

Enjoy our cozy ski-in ski -out condo in the Ober Tal complex at Stratton. This newly renovated condo offers a warm, welcoming stay with modern farm house charm! Located just above the base of the mountain, our condo is a stones throw from the nearest lift ( 200 ft) and a ski lovers dream. Unwind after a long day of skiing/snowboarding or take convenient 5 minute stroll to the Village for a bite to eat or some shopping. *Mountain biking & concerts offered in the summer season.*

Jun 7 – 14

G$27,219 GYD per night

Superhost

Condo in Dover

4.84 out of 5 average rating, 157 reviews

Mount Snow Close, Great Price, Lots of Room

This is a chalet duplex. You’re renting entire top 2 floors - no shared spaces. However, there’s an Airbnb rental in the lower unit of this house. Separate entrances & no indoor shared space. 2 bedrooms on the main level with a full bathroom and 2 bedrooms on the second level with a full bathroom. On site washer and dryer The kitchen comes equipped for cooking needs. ****The house has a lower level that has a 2 bedroom 1 bath Airbnb rental unit. No shared space but FYI.****

Dec 6 – 13

G$43,214 GYD per night

Guest favorite

Condo in Londonderry

4.95 out of 5 average rating, 43 reviews

Magical Ski-In/Ski-Out Condo at Magic w/ game room

Relax trailside at Magic Mountain at our ski in/ski out condo. Our 1 bedroom, 1 bath condo sleeps four with a queen size bed and a bunk bed. We have a couch if you add a few more and have a blow-up queen mattress for added sleeping space. The condo has a game room area just down the hall. On the lower level you have access to a locker room to store your skis etc. and a very small fitness area. Outside find picnic tables and fire pits all overlooking the mountain.

Apr 15 – 22

G$21,483 GYD per night

Guest favorite

Condo in Brattleboro

4.92 out of 5 average rating, 284 reviews

Private & Quiet Studio Apt. in Vermont

Clean, comfortable , quiet and snug, this studio apartment is a great place to come and relax in. It has a comfy QUEEN size bed with a 40” LCD at its foot, a kitchen set up for cooking and a desk with a view of a green field. This apartment is situated on the ground floor of our detached garage. Our garage sits behind our home, well away from the street. We live in a residential neighborhood that is conveniently located near I91, Route 30, Route 9 and Downtown .

Oct 5 – 12

G$18,979 GYD per night

Superhost

Condo in Dover

4.94 out of 5 average rating, 53 reviews

Mt. Snow Dream Mtn View+Fireplace!

180-degree views of Mt. Snow in this spacious 2 bedroom, 2 bath open floor plan condo featuring central fireplace. Spread out under high ceilings in the quiet master suite and wake up to mountain sunrise on the private deck. Tuck your guests, friends, or kids away in the twin bedroom at the other end of the unit. Ski/Board at Mt. Snow accessed by foot, Moover Shuttle (winter), or car. An all-in-one getaway! New for 2023- second bathroom has been renovated!

Sep 1 – 8

G$22,956 GYD per night

Superhost

Condo in Stratton

4.88 out of 5 average rating, 107 reviews

Perfect Location! Steps to Village and Mountain

One-bedroom condo with beautiful rear-facing view of Mill Pond! Sleeps 4 with a Queen bed and a Full-size pull-out couch. Living room features a gas fireplace and smart TV (cable TV included; personal account required for Netflix and other streaming features). Access to pool, hot tubs, and sauna on-premises. Just steps away from the restaurants and shops in Stratton Mountain Village and the Base Lodge - no need to drive or wait for a shuttle!

Aug 27 – Sep 3

G$33,156 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 7 – 14

G$19,863 GYD per night

Guest favorite

Condo in Stratton

4.96 out of 5 average rating, 118 reviews

Cozy condo within walking distance to the slopes.

Cozy condo within walking distance of the slopes and restaurants and shops at Stratton Mountain Village. After a day on the slopes relax in the hot tub or take a dip in the heated pool or maybe enjoy some time in the sauna. Then enjoy sitting in front of the gas fireplace and maybe watch a movie. TV is a smart TV, basic cable is included - personal password needed for Netflix, Hulu, etc.

Jun 10 – 17

G$28,802 GYD per night