Dukes County Ski Chalets Rentals & Holiday Homes

There are a lot of options in Dukes County. If you plan on staying in the Dukes County area, consider making a reservation for a few nights at one of these properties as these have been rated the top Ski Chalet Rentals in Dukes County:

• In-Town Certified National Historic Oak Bluffs Property -
• Newer construction Edgartown home with AC, and transferable car ferry tkt avail
• On HGTV! New w/Hot Tub, Bocce Court, AC, WALK to Town & Beach!
• Marthas Vineyard Edgartown Cottage - Easy walk to village, outdoor shower, linen
• Quaint Martha's Vineyard Guest Cottage -Edgartown-walk to restaurants and shops
• Idyllic Vineyard House in Desirable Katama/Edgartown – Walk/Bike to Town/Beaches
• Arrowsmith Cottage - Oak Bluffs - 1 mi to Eastville Point Beach via bike path.
• Private Meadow View Family Retreat - 4 BR, AC, Large Yard, Tennis, on Bike Path
• Multiple Ensuites, Central Air, Perfect Location
• Charming, Clean And Well Maintained Home Walking Distance To Town And Beach

There are many ski chalets available in Dukes County; however, here are the most popular ski chalets listed in Dukes County:

• Beautifully handcrafted arts and craft style carriage house chalet
• Modern, luxury 5-bed, 4.5-bath w/full basement! Now booking for 2026!
• Islander's Retreat
• The Christopher, The Edgartown Collection
• Light-Filled Romantic Cottage Close to Village, Beach, Bike Path, Nature Trails

Weekendgetaways offers availability throughout the year, but you can book pre-Christmas, mid-January, or before and after the school break at Easter are the best times for renting in Dukes County.

At Weekendgetaways most of our ski chalets are perfect for families. Check out the complete list of ski chalets in Dukes County to find what works for you.

Yes, there are plenty self-catering family ski chalet in Dukes County that have hot tubs & other amenities.