Condo vacation rentals in Winhall

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Popular amenities for Winhall condo rentals

Weekly condo rentals

Guest favorite

Condo in Dover

4.87 out of 5 average rating, 235 reviews

Mt Snow Ski In/Out at Seasons

AnthonyRating, 5 stars2 weeks ago
Andrew’s description and check in instructions were extremely detailed. Host was very easy to contact/communicate with and very accommodating. Clear instructions for check in/out, how to get to unit and how to ski in ski out. Unit description and photos are accurate. I would consider staying here in the future again.
Guest favorite
A welcoming living area is highlighted by a large sectional sofa adorned with various cushions. A coffee table holds eclectic items, while a television is mounted above a fireplace. Natural light enters through sliding doors, framed by patterned curtains, leading to a view of outdoor scenery.

Condo in Ludlow

4.97 out of 5 average rating, 32 reviews

The Okemo Love Lounge (Ski In Ski Out)

MikeRating, 5 stars1 month ago
Very kind and welcoming hosts. Perfect ski on ski off condo right near Lyft and Main Lodge. Very responsive and helpful checking in for that. We came from a few hours away, very pleased and would recommend Basquli‘s place to anybody. Great time!
Guest favorite
A welcoming entrance to Crown Point is depicted, featuring a large sign with bold lettering. The sign is framed by a wooden structure and surrounded by vibrant flowers in various colors, adding a touch of natural beauty to the landscape.

Condo in Stratton

4.92 out of 5 average rating, 13 reviews

Stratton two bedroom condo on a shuttle

Molly And EvanRating, 5 stars1 week ago
We enjoyed staying with our kids for a ski weekend! The condo was well stocked with sheets and towels and it was easy to access. The mudroom makes it especially easy for a place to put ski clothing and we appreciated that! I'm always curious about the coffee set up in the places we stay: this place has a Keurig and a standard Mr. Coffee, make sure you bring your own coffee and (round basket) filters. The kitchen had everything we needed to heat up food. It is well set up with pots, pans and dishes. Easy internet access. Comfortable furnishings. The shuttle picks up right outside the building in the morning and drops off in the same place in the afternoon. (As a note, we've stayed at other ski mountains where the shuttles run as a loop all day: this one does not. It goes only to the base in until 12 and only from the base starting at 1, so you'll want to plan accordingly.) We lucked out with 8" of powder one of the mornings we were there and had a fantastic stay overall!
Superhost
A living room features a wood-burning fireplace with an exposed brick surround, accompanied by neatly stacked firewood. A large flat-screen television is mounted above the mantle. Natural light enters through sliding glass doors, which lead to an outdoor seating area.

Condo in Dover

4.8 out of 5 average rating, 104 reviews

Cozy Mount Snow 1 Bed : Hot tub, Sauna, Deck

JoeRating, 5 stars5 days ago
my wife and absolutely loved our stay at Paul's place. It was perfect for a mid week ski trip!
Guest favorite
The living room features a high wooden ceiling and a large, central fireplace. Sofas and a loveseat provide ample seating, while artwork depicting skiing is mounted above the fireplace. Windows allow natural light to enter, offering a view of the outside.

Condo in Ludlow

4.95 out of 5 average rating, 97 reviews

Okemo Ski Condo, Steps from Trails. Modern & Cozy

StacyRating, 5 stars2 weeks ago
Beautiful ski condo! Fit our needs perfectly. Large downstairs bedroom for us and a fun loft area for our kids. Location was great and 5 min walk to the slopes. Maria was a great communicator and there is a late check out time which is great for a weekend trip. Would definitely stay again!
Guest favorite
The condo building is surrounded by a thick blanket of snow, with multiple units visible. The exterior features a green color and large windows. Snow collects on rooftops and the ground, creating a serene winter scene with trees in the background.

Condo in Dover

4.92 out of 5 average rating, 110 reviews

3 Story Condo - 5 Minutes to Mount Snow!

NicholasRating, 5 stars2 days ago
Ken was very responsive and helpful both before and during the stay. The condo was clean and exactly as described, with helpful and thorough instructions to check in.
Guest favorite
A cozy living area is highlighted by a stone fireplace, topped with a wooden mantle. A large television is mounted on one wall, while plush seating surrounds a wooden coffee table. Stacked firewood is neatly arranged beside the fireplace, adding to the warm ambiance.

Condo in Dover

5 out of 5 average rating, 23 reviews

Lyon Family Lodge - Ski-in/ski-out

BethRating, 5 stars1 month ago
Great location, ski on ski off and very nice community not far from restaurants. Jared was very responsive and flexible with check in time. Overall a great condo on the mountain and would stay here again.
Guest favorite

Condo in Stratton

4.91 out of 5 average rating, 55 reviews

Ski On/Off Condo in the Heart of Stratton Village!

LeighRating, 5 stars1 week ago
Great place right in the village. Everything is walking distance. Spacious and well accommodated. Would highly recommend and stay again.

Pet-friendly condo rentals

Guest favorite
The living area features high wooden beam ceilings and exposed brick walls, creating a rustic ambiance. A cozy wood burning fireplace is situated beneath the wall-mounted television. Comfortable seating includes a checkered sofa and a leather chair, all complemented by a central area rug.

Condo in Ludlow

4.95 out of 5 average rating, 133 reviews

Rustic Cozy Ski Condo In Historic Mill

SharleenRating, 5 stars1 day ago
Erin’s place was convenient to town and skiing. The place was exactly as described and beds were comfortable.
Guest favorite
A cozy living room is highlighted by a comfortable sectional sofa facing a modern fireplace, adorned with seasonal greenery. A large mirror reflects natural light from the windows, and a television hangs above a wooden media console, completing the inviting ambiance.

Condo in Dover

4.96 out of 5 average rating, 25 reviews

Mt Snow Condo, 4-min Walk to Sundance Dog Friendly

KatieRating, 5 stars1 month ago
Great stay! Very close to the mountain so you can ski in and out. Had a few hiccups during the stay but Hussein was very responsive and quick to give solutions. Would stay here again
Guest favorite
The exterior of the condominium building is showcased, featuring three levels with large windows that allow natural light in. A central staircase leads to the entrance, flanked by green grass and small shrubs, creating a welcoming appearance.

Condo in Stratton

4.94 out of 5 average rating, 97 reviews

Great 2 bedroom condo at Stratton Mountain

OliviaRating, 5 stars2 weeks ago
This was our second time staying at Dana’s place and we really enjoyed our stay. The place has everything we needed and was very easy to get to the slopes. We took the shuttle and it was very convenient. Will definitely be back!
Guest favorite
A serene view of a calm lake framed by lush greenery and a blue sky dotted with clouds. A wooden dock extends into the water, which showcases a clear, shallow shoreline leading to deeper areas, creating an inviting atmosphere for swimming or relaxation.

Condo in Dover

4.88 out of 5 average rating, 43 reviews

Ski Condo 5 Min from Mt Snow

James McMahonRating, 5 stars1 week ago
Place was great...short drive to Snow...you could actually come home for lunch,...we showed up at night and was hard to tell which condo it was...it was snowing which added to the search...of course...I could have missed an instruction or two.
Guest favorite
A two-story condo is shown with a snow-covered roof and a well-maintained exterior. A vehicle is parked in front, and snow blankets the surrounding area. The backdrop features a snow-covered mountain, displaying ski trails that contour the slopes.

Condo in Stratton

4.92 out of 5 average rating, 64 reviews

Stratton Mountain vacation spot

StephaniaRating, 5 stars2 months ago
Really great stay!! Would recommend to everyone. Comfortable beds, renovated bathrooms, really squeaky clean, easy walk to the ski resort, super convenient free shuttle to the ski resort. Patrick was super responsive and helpful throughout the whole weekend.
Guest favorite
The chalet duplex features a two-toned exterior with a dark wooden upper level and a white lower level. A spacious outdoor deck is visible, complemented by greenery and well-maintained shrubs, creating a serene setting within a natural landscape.

Condo in Dover

4.85 out of 5 average rating, 163 reviews

Mount Snow Close, Great Price, Lots of Room

AllisonRating, 5 stars4 weeks ago
Awesome home. Classic chalet style ski house. Loved, loved, loved it and will definitely come back. Hosts were super accommodating. Highly recommend.
Guest favorite

Condo in Londonderry

4.95 out of 5 average rating, 58 reviews

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

StephanieRating, 5 stars5 days ago
Place was perfect! Right on the mountain for easy access to Magic Mountain. The kids loved the game room! Patrick and Erin were easy to communicate with and very responsive. We can’t wait to come back next year!
Guest favorite

Condo in Wilmington

4.96 out of 5 average rating, 26 reviews

10th Hole Haystack Golf Course in Wilmington VT

JenRating, 5 stars4 months ago
This condo was perfect for a fall family get-away. We loved the view from the deck and the warmth of the fireplace. It is close to the charming main street in Wilmington. The grounds are lovely and make for a nice place to walk. The condo was very clean and so well stocked with plenty of towels, extra pillows, blankets etc... The kitchen was full of much appreciated extras...coffee, hot chocolate, "smore" ingredients as well as plenty of things like foil, trash bags, soaps etc. It really was a home away from home. Sean's list of things to do and places to go is complete and very helpful. We thoroughly enjoyed our stay!

Condo rentals with a pool

Guest favorite
A circular outdoor pool is surrounded by a landscaped area, featuring several trees and bushes. The building's large glass entrances reflect natural light. Sun loungers are positioned nearby, and a set of steps leads from the pool to the patio area.

Condo in Stratton

4.98 out of 5 average rating, 62 reviews

Stratton Long Trail House: Quick Walk to Lifts!

TheresaRating, 5 stars1 week ago
We had a fantastic stay at Stratton! The apartment was exactly as described and we really enjoyed the fireplace, hot tubs, and sauna after a long day on the slopes. The host was very responsive and helpful, and the location cannot be beat! We’ll definitely be staying again. Thank you!
Guest favorite
A spacious outdoor heated pool is surrounded by a secure fence, with sun loungers positioned around the deck. Lush greenery and trees are visible in the background, providing a natural setting under a clear blue sky.

Condo in Peru

4.97 out of 5 average rating, 86 reviews

Cozy Mountain Condo - True Ski in Ski out

BarbaraRating, 5 stars1 month ago
We had such a blast for our very short stay. My kids loved the bunk beds and found them to be so cozy. We felt right at home in the condo and it had everything we needed. Laura was a dream to correspond with as well and there were great detailed information for everything to do with the condo, as well as recommendations for what to do. We’d definitely rent again in the future!
Guest favorite

Condo in Ludlow

4.93 out of 5 average rating, 15 reviews

Cozy Slopeside Escape - Ski-In/Out Condo at Okemo

MatthewRating, 5 stars1 week ago
This unit was perfect for ski in/out. It had everything you needed for a ski vacation…..The view was amazing! Our son had a blast watching the snowcats at night! We’ve stayed at multiple locations at Okemo and this one was by far the easiest. The hot tub and pool access made for a great recovery post-ski! We will be back at Ahmad’s place for sure!!!
Guest favorite

Condo in Ludlow

4.92 out of 5 average rating, 101 reviews

One Bedroom Suite Near Okemo

ScottRating, 5 stars1 day ago
Wonderful ski weekend at Okemo. Everything was perfect. We would definitely stay here again. Highly recommend!
Guest favorite

Condo in Dover

5 out of 5 average rating, 57 reviews

Four Seasons Slope-side Getaway at Mount Snow

KatelynRating, 5 stars1 month ago
Condo is perfectly placed between corinthia and the Sundance base. With ski up access which was awesome! The place we clean and spacious and fully stocked with everything we could have needed. The hot tubs and pool were great after long day of skiing. Including an impressive gym and game room with ping pong and video games. We will definelty be returning soon. The host were great to deal with and put a lot of thought into their place and it shows. Thanks again
Guest favorite

Condo in Dover

4.96 out of 5 average rating, 71 reviews

Free Shuttle Mt SNOW / Hot Tub / 2 King Beds

JenniferRating, 5 stars2 weeks ago
Lovely condo, very clean, with incredibly convenient shuttle access to Mt Snow. No food storage containers or stemmed wineglasses, so bring your own. Highly recommend.
Guest favorite
A large outdoor pool is surrounded by lounge chairs and umbrellas, providing a relaxing space. The pool is clear and inviting, with a gentle slope leading to steps for easy access. A building with large windows is visible in the background, framed by lush greenery.

Condo in Dover

4.93 out of 5 average rating, 41 reviews

Cozy Mt Snow 1-bed w fireplace & view

MatthewRating, 5 stars2 weeks ago
Jonathan's place is a quick 2 min drive to the parking lots around Mt Snow or a ~15 min walk. It was spotless upon our arrival and bigger than the pictures make it seem. The king bed was really comfortable and the pull out couch was comfortable enough. Jonathan was very accommodating and responsive throughout our stay and we were able to do a later checkout on Sunday so we could get a half-day of skiing in and have time to freshen up before our long drive home.
Guest favorite
The exterior of a two-story building is shown, featuring a snowy landscape and a festive wreath on the front entrance. Large windows are visible, allowing natural light to illuminate the interior. Snow-covered steps lead up to the welcoming entrance, creating a serene winter atmosphere.

Condo in Dover

5 out of 5 average rating, 18 reviews

Mt. Snow Condo with Pool-Hot Tubs-Sauna MTN Views

MattRating, 5 stars3 weeks ago
Leah was very communicative and the place was exactly as described. We would definitely come back for another trip!

Quick stats about condo rentals in Winhall

  • Total rentals

    30 properties

  • Nightly prices starting at

    $160 before taxes and fees

  • Total number of reviews

    500 reviews

  • Family-friendly rentals

    20 properties are a good fit for families

  • Rentals with a pool

    20 properties have a pool

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

Destinations to explore

  1. Airbnb
  2. United States
  3. Vermont
  4. Bennington County
  5. Winhall
  6. Condo rentals