
Condo holiday rentals in Windham County
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Top-rated condo rentals in Windham County
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3 Story Condo - 5 Minutes to Mount Snow!
Charming Dover Green condo just minutes from Mount Snow Ski Resort & Lake Whitingham. This well kept 2 bedroom, 2 bathroom, plus loft bedroom features open concept living, dining, vaulted ceilings, natural woodwork, 65" TV, and a wood burning fireplace. With easy access to Mount Snow, the village of Wilmington, nearby lakes, hiking, and biking, there is so much to do for tremendous year round enjoyment. There is nearby access walkable from the unit to the public MOOver shuttle to get around town
4.94 out of 5 average rating, 165 reviews
Base of M.S. All Seasons Fun. Deck/HotT/Sauna
Sunsil Loft @ MountSnow, your ideal Getaway. Walk to the Base. Unbeatable access to skiing, hiking, biking. Vermont never stops to surprise you with its outdoor adventures, great food and views. The loft offers a cozy gas fireplace, private deck. The kitchen has all you need to prep meals. You also have access to the pool (Summer), sauna, hot tub and GYM. Whether you’re skiing, hiking and biking in summer, or enjoying the fall foliage, our loft is your perfect home base in the Green Mountains.
4.92 out of 5 average rating, 128 reviews
Slopeside @ Seasons on Mount Snow (Ski-In/Out)
⌲ Escape to Seasons on Mount Snow & stay in our fully equipped 3 bedroom condo where you can you can ski-in & out directly from the condo building! ⌲ Enjoy the log burning fire (wood provided), smart TV & boardgames plus the fabulous Seasons on Mount Snow facilities which include a gym, pool, hot tub, sauna & fire pit. ⌲ Spring thru fall activities in the area include hiking, biking, tennis & pickleball (at Seasons), scenic rides, lakes, golf, camp, spa & enjoying the stunning fall colors.
4.92 out of 5 average rating, 105 reviews
~10% OFF~Walk To Mountain~Amenities
⭐️"Beautiful place in a great location - recently renovated, super clean and across the street from town." ⇒ Center of Stratton Village, walking distance to restaurants, shops, and the lifts🚶♂️🏔 ⇒ Private balcony with amazing views 🌅 ⇒ Dedicated workspace 📝 ⇒ Gas fireplace 🔥 ⇒ Fully equipped Chef's kitchen👩🍳 ⇒ Central AC/Heat ⇒ Onsite garage parking for 1 vehicle 🅿️ ⇒ Community amenities: pools, hot tubs, sauna, fitness center, tennis court, hiking trail, washer/dryer ⇒ 67 mbps Wifi
4.88 out of 5 average rating, 111 reviews
Great Amenities-Season Condo gym-sport center-pool
True ski in ski out ground floor condo w/ private entrance. Wood burning fireplace, wood included! King size bed in master, true Queen murphy bed, 1-memory foam cot, plus air mattress. Fully stocked & functional kitchen, including Keurig & Mr. coffee. Full bath w/blow dryer. Seating; kitchen counter, expandable table, wine barrel bar top. Walk out the door & down the steps to the NEW Sundance high speed lift. Take the Seasons trail home. Brand new state of the art Sports Center included.
4.94 out of 5 average rating, 107 reviews
Premier Stratton Village Location - Pool & Hot Tub
-- Walk across the street to Stratton Ski Lifts -- Conveniently located near the Stratton Village, this condo places you at the center of all the mountain activities - skiing, mountain biking, events, weddings, shopping & dining. This updated studio includes gas fireplace, AC, stainless appliances, and nice décor. Long Trail House condos boasts underground heated parking, year-round outdoor pool with patio and multiple hot tubs, and sauna. Come visit and relax in the Vermont mountains.
4.97 out of 5 average rating, 214 reviews
Luxury Stratton condo just steps to the lift!
Enjoy this beautifully renovated 1 bed/1 bath condo with a live fireplace conveniently located steps from the mountain and Stratton Village! The Tamarack chair lift is only a few hundred yards away! Washer and dryer in unit to warm up your wet clothes after a long day of skiing or mountain biking. Fully stocked kitchen, 50’ TV w/ AppleTV, cable, Amazon Alexa, 5G WiFi, Firewood and more! This is one of the nicest Ober Tal condos available for rent!
4.97 out of 5 average rating, 120 reviews
MountSnow ski on/off condo in Vermont
Pool and Sports Center is open. Hours vary by day BBQ available for use by the outdoor pool pavilion On Mount Snow, Across from the Tin Lizzy trail leading to the Sundance Base Lodge and access to the Seasons Pass trail leading back to the condo. Very unique Condo in seasons as it has high vaulted ceilings. Condo is a 2 bedroom, 2 bathroom with 2nd bedroom on 2nd floor. Plenty of tennis and pickleball courts Best parking on the mountain
4.93 out of 5 average rating, 113 reviews
Mt Snow Ski In/Out at Seasons
Directly on the mountain. Minutes walk to 2 trails. Full kitchen, dishwater, washer/dryer, microwave. Fireplace with free wood. Large screen TV in living room and tv in each bedroom. Plenty of board games. King size bed in Master. Free parking for 2 cars. Ground floor with deck with tables and chairs for relaxing. The pool (indoor & outdoor) and hot tubs are free to renters as is fully equipped gym (all year) and tennis courts in summer.
4.88 out of 5 average rating, 262 reviews
Walk to Mt. Snow-Spa-Summer Pool
*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 chairs *Easy 1st floor access *Fitness center access *Hot tub *Outdoor pool seasonal *Loaner amenities such as phone charger
4.86 out of 5 average rating, 147 reviews
Mtn. view, easy access to village
WINTER 2026-2027 DATES NOW OPEN! Rennovations recently completed! After a decade of visiting the mountain as guests, we finally have a place to call our own. We are so excited to host you in our home soon! Stratton Mountain boasts fun all year round, and our condo places you just steps from it all! When it's time to recharge, take in the views and fresh mountain air from the balcony, cozy up next to the fire, or spread out.
4.92 out of 5 average rating, 26 reviews
Mount Snow Ski Chalet
Beautiful 2Bd/2Ba condo with a gorgeous view of the mountain. It takes 10 min to walk to the ski area or even faster with the free Moover bus. Every room features different art design while living room's fireplace creates warm and cozy vibe. Apartment is equipped with smart lock for your convenience. Possible to use as Work from Home space. Condo is located within quick drive to coffeeshop, restaurants and seven eleven.
4.85 out of 5 average rating, 117 reviewsPopular amenities for Windham County condo rentals
Weekly condo rentals

Stratton Resort 4 bedroom 3 bath Condo 0.5mile Ski
4.98 out of 5 average rating, 66 reviews
Cozy Mount Snow 1 Bed : Hot tub, Sauna, Deck
4.79 out of 5 average rating, 163 reviews
Great Ski In / Ski Out Location!
5.0 out of 5 average rating, 31 reviews
Fully Renovated 3 BR Condo - 0.8 mi to Mt. Snow
5.0 out of 5 average rating, 12 reviews
Ski In/Out, Cozy 3Bed condo steps to Village
4.98 out of 5 average rating, 58 reviews
Village Watch Lux Loft
5.0 out of 5 average rating, 7 reviews
Walk to Food/Entertainment, 5 Min Drive to Mt Snow
5.0 out of 5 average rating, 17 reviews
Cozy Condo-4 Minute Walk to Skiing at Mount Snow!
4.96 out of 5 average rating, 78 reviewsPet-friendly condo rentals

Magical Ski-In/Ski-Out Condo at Magic w/ game room
4.97 out of 5 average rating, 92 reviews
Ski Condo 5 Min from Mt Snow
4.91 out of 5 average rating, 69 reviews
10th Hole Haystack Golf Course in Wilmington VT
4.96 out of 5 average rating, 28 reviews
Walk-to-Lifts Mt Snow Ski Condo
4.97 out of 5 average rating, 36 reviews
Alpine escape w/ hot tub & fireplace
5.0 out of 5 average rating, 23 reviews
Stratton Mt. Condo with a Hot Tub! Sleeps 12!
4.92 out of 5 average rating, 12 reviews
Stratton Mtn Resort! NEW Reno cozy condo! SEASONAL
4.57 out of 5 average rating, 14 reviews
Gorgeous, new apartment laundry
4.7 out of 5 average rating, 10 reviewsCondo rentals with a pool

Luxury Condo*Walk to Village*Hot Tub*Pool*Golf*MTB
5.0 out of 5 average rating, 106 reviews
Slopeside condo - walk to the lift
4.87 out of 5 average rating, 15 reviews
Stratton Studio by Sunapee Stays - Walk to Lifts
4.94 out of 5 average rating, 88 reviews
Ski On/Off 2BR w/Pool, Fireplace & Arcade
4.95 out of 5 average rating, 61 reviews
Your Vermondo awaits: Steps to Lifts & Village.
5.0 out of 5 average rating, 61 reviews
Summer in the mountains!
4.98 out of 5 average rating, 98 reviews
Slopes N Seasons | Trailside Condo at Mount Snow
4.97 out of 5 average rating, 35 reviews
Walk to lifts & Village,Year round pool&hot tubs
4.99 out of 5 average rating, 92 reviewsDestinations to explore
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- Okemo Mountain Resort
- Stratton Mountain
- Saratoga Race Course
- Jiminy Peak Mountain Resort
- Berkshire East Mountain Resort
- June Farms
- Monadnock State Park
- Pico Mountain Ski Resort
- Magic Mountain Ski Resort
- Stratton Mountain Resort
- Bousquet Mountain Ski Area
- Hildene, The Lincoln Family Home
- Killington Resort
- Rensselaer Polytechnic Institute
- Mount Monadnock
- Emerald Lake State Park
- Bromley Mountain Ski Resort
- University of Massachusetts Amherst
- Massachusetts Museum of Contemporary Art
- Mount Sunapee Resort
- Mount Greylock
- National Museum of Racing and Hall of Fame
- Hancock Shaker Village
- Camp Plymouth State Park
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