West Chop Rentals By Owner

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 Vacation Rentals in West Chop:

• In-Town Certified National Historic Oak Bluffs Property -
• Multiple Ensuites, Central Air, Perfect Location
• Charming, Clean And Well Maintained Home Walking Distance To Town And Beach
• Contemporary Pet-Friendly Year-round Retreat. In the Woods, Walk to Town.
• Close to town, beautifully updated
• Sea Captain's Victorian studio bedroom apartment. Pets OK
• Modern 4 bed/3.5 bath Farmhouse, private HEATED POOL and AC on bike path
• Classic Downtown Property
• Well-Appointed 3 bedrm 4 bathrm with AC and 50+ 5-star reviews!
• Historic Home in East Chop

There are many large, family-friendly vacation homes available in West Chop; however, here are the most popular family rentals listed on our site:

• Modern, luxury 5-bed, 4.5-bath w/full basement! Now booking for 2026!
• Islander's Retreat
• Quaint, ranch style home in Oak Bluffs with central air
• Your Summer Home - Close to Beach, Shops, Cafes, & Ferry! 50+ ⭐️⭐️⭐️⭐️⭐️ Reviews

Yes, there are 539 self-catering vacation homes in West Chop that have hot tubs, swimming pools, & other amenities.

There are more than 539 luxury villas and vacation homes in or near West Chop. Filter by price to compare find the most expensive places to stay on Hawaiibeachcomber.

Yes, there are 539 pet friendly vacation homes and places to stays that are available in or near West Chop that you may consider.