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Ski-in/Ski-out vacation rentals in Addison County

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Top-rated ski-in/ski-out rentals in Addison County

Guests agree: these ski-in/ski-out homes are highly rated for location, cleanliness, and more.

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Home in Warren

4.82 out of 5 average rating, 112 reviews

Charming Sugarbush Standalone Condo

Situated on the mountain with a panoramic view, this stand alone condo - ski-on/ski-off (winter) / spectacular vistas (fall) / Mad River fun (summer) / blissful bloom (spring) - will be your home away from home. This spacious, three-floored home is filled with light and great for couples, families, business travelers, or solo adventurers. Friendly property manager, Constancia is able to greet guests and offer recommendations. Please find our cleaning protocol in "Other things to note" section.

Cottage in Rochester

4.99 out of 5 average rating, 76 reviews

Cozy cottage near Killington & Sugarbush

Escape the real world at this charming and cozy cottage tucked away in a corner of 17 acres of rolling grassy hills. Take in the unmatched views of the hollow from the living room or wrap-around porch. Endless nearby trails for hiking/biking/xc skiing, and Rochester's stores, cafes, and restaurants are less than 10 minutes away. Grocery store, berry picking, lakes, swimming holes, golfing, restaurants, breweries, and wineries all within an easy drive. Killington/Sugarbush both ~35 minutes away.

Home in Warren

4.87 out of 5 average rating, 129 reviews

Oma's House

Large comfortable well-loved family home situated on the mountain at Sugarbush Lincoln Peak.Ski-in/ski-out on the mountain with proper conditions for intermediate to advanced skiers. Gorgeous mountain views overlooking the ski area situated perfectly to enjoy all Vermont has to offer along with a cozy gas fireplace to enjoy after a long day of skiing. The home features a layout perfect for families or wedding guests coupled with a fully equipped kitchen and a plethora of sleeping arrangements.

Hut in Ripton

4.92 out of 5 average rating, 163 reviews

Skylight Hut. Glamping, hiking, biking, foliage

Hiker, gravel/mountain biker's paradise! Our quiet glamping retreat provides easy access to miles of wilderness. The hut has a cozy bed, kitchenette, and camping basics making for an easy and cozy getaway. Follow a trail to the Catamount Trail or drive a few minutes to the Long Trail. Enjoy miles of gravel biking from the door or go to Moosalamoo or Rochester for prime mountain biking trails. In the evening, sit on the deck under a blanket of stars and warm your toes by the fire. Paradise!

Treehouse in Moretown

5 out of 5 average rating, 53 reviews

4-Season Treehouse @ Bliss Ridge; Best Views in VT

WARM & COZY LUXURY! 1-of-a-kind, INSULATED, 5*, Interior luxe bathroom, @Bliss Ridge - 88acre, OG hill farm private estate surrounded by 1000s acre of wilderness. Our 2 architectural wonders = real treehouses, built withIN the living trees, not on stilts, not cabins. Big TH is equipped w a fabulous yotel fireplace, indoor hot shower / plumbing, fresh mtn spring water. Our original Dr. Seuss treehouse, "The Bird’s Nest" is uninsulated, open May-Oct. The Big Treehouse is accessed by stable ramp

Condo in Warren

4.93 out of 5 average rating, 73 reviews

Mountainside condo at Sugarbush!

Sugarbush at your doorstep! Ski, walk, hike, or bike from this cozy 1-br slope-side condominium steps from all resort amenities. Enjoy multiple dining options and mountain activities without getting in your car. Located on the first floor of the Center Village Condominium building, this unit offers ground-level access and designated parking. Enjoy the Mad River Valley with a short drive to Warren Village and Waitsfield for shops, dining, breweries and more. Please read all listing details.

Home in Warren

4.92 out of 5 average rating, 205 reviews

Beautiful guesthouse -perfect for long stays

Come stay, work, and ski all season. Guesthouse above our garage for rent in the heart of East Warren. Ski on/off Blueberry Lake Cross Country Center access. Just 5 miles from Sugarbush Resort and 10 miles from Mad River Glen. guesthouse has private outdoor parking and entry. Gigabit internet service with high speed wifi. This is a net zero rental unit generating all of it power from on property solar. offered operation thanks to Tesla Powerwalls. This is directly adjacent our home.

Condo in Warren

4.92 out of 5 average rating, 137 reviews

Another Day in Paradise at Sugarbush Mountain

Steps to Sugarbush Mountain in Warren, Vermont. This a one bedroom, one bath condo located in Center Village on Sugarbush Mountain. Pull out sofa is also available in the main living room. Perfect for skiing, snow shoeing, mountain biking & hiking. Condo is walking distance to chairlift. Short drive to Warren Falls, Mad River Glen, Mount Ellen and many delicious restaurants. The condo is within walking distance (5 minutes) to Clay Brook Hotel, where many weddings are held.

Home in Addison

4.96 out of 5 average rating, 202 reviews

Brthtkng New Premier Lake Champlain Wfrnt Escape!

7/19/20 : UPDATE - We are fully compliant with all local, state and federal safety protocols. Call /text Us fir any questions, at 978-502-6282 . Be Well, Be Safe & We Look Forward to Having You as Our Guests! We are the #1 Premier Lake Champlain Breathtaking New Property with 250'+ Prime Lake Champlain West/Sunset/Adirondack Mtn. facing w/Amazing Sunsets & Jacuzzi Tub in Master Bath Overlooking Lake,Mountains & Amazing Sunsets and 250+ 5 Star Reviews!

Condo in Warren

4.98 out of 5 average rating, 56 reviews

Newly renovated condo at base of Sugarbush!

Walk to the chairlift from this sleek little condo in the historic Sugarbush village, just 500 yards from the base of Lincoln Peak. This newly renovated and thoughtfully decorated condo is the perfect place to relax after a day of skiing, hiking, canoeing, or rock jumping. This location is amazing! There is one restaurant IN THE BUILDING, the chair lifts and the Recreation Center with pools, tennis, & fitness gym are a short 500 yard walk away.

Chalet in Stockbridge

4.94 out of 5 average rating, 34 reviews

360 View Mountaintop Sanctuary

Ultimate remote mountain experience in Vermont's Green Mountains, 15 min to Killington Wow!: - Designer modern eco-chalet, off grid and on solar power - True privacy on 150+ acres, while 15 minutes to Killington Ski, 5 minutes to world class mountain bike trails. - 360° panoramic view on mountaintop, fire pit - Connected to VAST trail, walking trails on property - Hike, Bike, Ski, Snowshoe, Stargaze, Views!

Rental unit in Waitsfield

4.91 out of 5 average rating, 337 reviews

Renovated 2024! Spacious Apartment Living

Exceptional value! Renovated for 2024! Mid-century meets farmhouse. Relaxing and comfortable first floor apartment full of natural light and clean lines. Once a barn carefully reconstructed into two apartments. A true rustic Vermont experience as you relax after a day of skiing, hiking, mountain biking, or simply enjoying the beauty of the Mad River Valley. The perfect Vermont getaway.

Vacation rentals for every style

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Chalets

Adventure-ready homes with après-ski style

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Convenient locations with everyday essentials

Popular amenities for Addison County ski-in/ski-out rentals

Free parking on premises

Air conditioning

Ski-in/ski-out house rentals

Home in Warren

5 out of 5 average rating, 55 reviews

Mountain Escape-Beautiful Views, New Home

Home in Warren

5 out of 5 average rating, 16 reviews

Quintessential Vermont Country and Ski Home

Home in Warren

4.74 out of 5 average rating, 31 reviews

Walk to lifts 3BR Ski In/Out Mountainview Ski In/O

Home in Middlebury

4.62 out of 5 average rating, 45 reviews

Ralphaels Roost

Home in Warren

4.8 out of 5 average rating, 65 reviews

Sugarbush Resort Mountain Condo

Home in Waitsfield

4.81 out of 5 average rating, 16 reviews

Historic 3BR | Mountainview | Snowmobile Trails

Home in Huntington

5 out of 5 average rating, 3 reviews

Huge 10 Acre Mountain Retreat - LONG TRAIL!

Family-friendly, ski-in/ski-out home rentals

Private room in Roxbury

5 out of 5 average rating, 34 reviews

Johnnycake Flats Inn, fully licensed, Garden Room

Condo in Warren

4.86 out of 5 average rating, 178 reviews

Ski In/Ski Out with upgrades!

Condo in Warren

4.87 out of 5 average rating, 52 reviews

Sugarbush Slopeside 2BR/2BA Condo

Condo in Warren

4.83 out of 5 average rating, 47 reviews

Sunny One Bedroom Condo-Warren, V T- Pet Friendly

Home in Warren

4.89 out of 5 average rating, 91 reviews

4br, 3ba with 2 master bedrooms, Sauna, Hot Tub

Private room in Roxbury

5 out of 5 average rating, 11 reviews

Johnnycake Flats Inn, fully licensed, Train Room

Condo in Waitsfield

4.8 out of 5 average rating, 60 reviews

Cute & Cozy 1BR w/ Hot Tub @ Sugarbush Mt. Ellen

Townhouse in Warren

4.63 out of 5 average rating, 119 reviews

Townhouse on Sugarbush Access Road

Ski-in/ski-out condo rentals

Condo in Warren

4.96 out of 5 average rating, 93 reviews

Ski-in, Ski-Out / 4 beds / seasonal pool

Condo in Warren

4.81 out of 5 average rating, 16 reviews

Sugarbush/Mad River Valley Gem - 4Br/2Ba and VIEWS

Condo in Warren

4.78 out of 5 average rating, 37 reviews

Family condo by the slopes of Sugarbush

Condo in Warren

4.8 out of 5 average rating, 154 reviews

Mountainside Condo at Sugarbush, Vt

Condo in Warren

4.84 out of 5 average rating, 89 reviews

Sugarbush Mountainside Retreat - Ski in Ski out

Condo in Warren

4.84 out of 5 average rating, 19 reviews

Ski-in, Ski-out 4 BR Sugarbush Condo

Condo in Warren

4.78 out of 5 average rating, 50 reviews

Sugarbush Two-Bedroom Condo with Fireplace

Condo in Warren

4.97 out of 5 average rating, 37 reviews

Ski On Ski Off from our Welcoming Slope Side Condo

Destinations to explore