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West Chop Winter Rentals & Holiday Homes
Discover winter rentals West Chop - We found 303 exact matches
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About West Chop Winter Rental on Rent By Owner
Planning on a winter vacation in West Chop? Discover 303 places to stay in West Chop, for those traveling with their family, friends, in groups, or for a wedding retreat.
At Rent By Owner, we have a wide range of listings for accommodations in West Chop, MA that are perfect for your winter trip or seasonal escape. Our listings have private vacation homes, cabins, condos, villas, resorts, or pet-friendly apartments that you would love. RBO winter vacation homes have top amenities, including Wi-Fi, heated indoor/outdoor swimming pools, spas, hot tubs, outdoor grills, and cozy fireplaces.
West Chop winter accommodation starts at GB £623, and the most popular properties in West Chop are cabins, bungalows, and rental homes by owner. Planning snowboarding on your next winter vacation? We have many snowboard-friendly ski resorts, chalets, and cabins that are available for you to rent. These rentals are available for both short-term stays and long-term stays, whether you are traveling for a weekend, monthly, or a longer stay, RBO will make your winter trip memorable.
Rent By Owner offers a great deal for travelers planning on renting a place in West Chop, to enjoy these benefits and to book your winter vacation homes, go to RBO filter option, enter your travel date, check the filters to narrow down your property type and amenities, then choose from a long list of our winter vacation rentals without hassle. Our interactive map is also available, to view all places to stay in or around West Chop and unlock even more amazing deals.
Frequently Asked Questions About West Chop Winter Rentals
There are a lot of options in West Chop. If you plan on staying in the West Chop area, consider making a reservation for a few nights at one of these properties as these have been rated the top Winter Rentals in West Chop:
- In-Town Certified National Historic Oak Bluffs Property -
- Close to town, beautifully updated
- Sparkling Waterfront Gem, Spectacular Views, Private Beach, Great for Kayaks
- Modern, luxury 5-bed, 4.5-bath w/full basement! Now booking for 2026!
- Downtown Captain's Mansion- The Dexter- Family, pet, and event friendly
- Well-Appointed 3 bedrm 4 bathrm with AC and 50+ 5-star reviews!
- Classic Downtown Property
- Historic Home in East Chop
- FABULOUS Makonikey OCEANFRONT With Private Beach !Wrap Around Deck, Pets Ok, A/C
- LOCATION & QUALITY! Right in town, freshly renovated, near everything u need!
- In-Town Certified National Historic Oak Bluffs Property -
- Less Than 1 Mi to Beaches Home with Deck in Oak Bluffs
- Mansion House Inn And Spa
- LOCATION & QUALITY! Right in town, freshly renovated, near everything u need!
See all pet-friendly vacation rentals in West Chop on Rent By Owner