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Vacation Homes in Chappaquiddick Island

LUXURIOUS New Cottage! 5-min. walk to Main St. And Harbor Beaches

10.0 out of 10, Exceptional, (164)
"Beautiful cottage , great location. Would love to stay again "
LUXURIOUS New Cottage! 5-min. walk to Main St. And Harbor Beaches

Hyannis Hideaway in Cape Cod

10.0 out of 10, Exceptional, (2)
"Awesome private property, close to Main Street and Craigsville beach. My friends and I stay in Hyannis every 4th of July and this home was super accommodating for groups and close to everything. Great stay would recommend. "
The price is SAR 1,334
SAR 2,334 total
includes taxes & fees
14 Sep - 15 Sep
Hyannis Hideaway in Cape Cod

Brand New 5BR - Pool, Hot Tub, A/C – Walk to Beach, Main St. & Ferry - Sleeps 12

10.0 out of 10, Exceptional, (3)
"We had such an amazing stay! The house was absolutely beautiful and had so much space for our family to relax and enjoy. The pool was incredible — the kids practically lived in it the whole trip! The hot tub was also a wonderful bonus! Everything was clean, comfortable, and even better than expected. The hosts were fantastic — quick to answer any questions and made sure we had everything we needed. We would definitely stay here again and highly recommend it to anyone looking for a perfect...
Brand New 5BR - Pool, Hot Tub, A/C – Walk to Beach, Main St. & Ferry - Sleeps 12

Love Sand, Madaket on the Beach , Lovely Seaside Home

10.0 out of 10, Exceptional, (52)
"We thoroughly enjoyed our two nights and are sad to leave. The property is iconically Nantucket. Its location - and the views- is spectacular. It is well equipped for a relaxing family or couples vacation. Hope we can make it back. "
Love Sand, Madaket on the Beach , Lovely Seaside Home

Maushop - 6 Hammock Pond Rd

9.0 out of 10, Wonderful, (34)
"The beach access very nice nice for early morning or evening walks - quiet and private neighborhood. The 2 bedroom unit was comfortable and met our needs."
Maushop - 6 Hammock Pond Rd

Classic Cape home with full kitchen, W/D, firepit & gas grill - walk to beach

5.2 out of 10, (5)
"The living room was moldy, the door doesn’t lock, the insects were in every room; including the bed, the kitchen tools were rusty, the floors were dirty, the place is a mess. The post states a gas grill; there’s only a charcoal grill without any charcoal, the post states resident beach parking pass; there was none, the post states a queen size bed; there wasn’t one. The kitchen floor was completely stripped of tile. Overall the house was dirty and a complete waste of money. The only nice thing...
Classic Cape home with full kitchen, W/D, firepit & gas grill - walk to beach

Located Steps Away To Main Street And .7 Miles From Surf Drive Beach

10.0 out of 10, Exceptional, (198)
"Loved this spot. So easy to get to downtown and Surf Beach. It was fabulous and clean!"
The price is SAR 777
SAR 2,091 total
includes taxes & fees
11 Sep - 12 Sep
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach

Popponesset-Exclusive Waterfront Home, Firepit, Hot Tub, & central A/C

10.0 out of 10, Exceptional, (179)
"The best and the most relaxing stay in Cape Cod. Close to ocean, breathtaking views , beautiful and very comfortable house. "
The price is SAR 934
SAR 2,839 total
includes taxes & fees
15 Sep - 16 Sep
Popponesset-Exclusive Waterfront Home, Firepit, Hot Tub, & central A/C

Totally Renovated Central AC Dog Friendly Near Golf

9.6 out of 10, Exceptional, (7)
"Was a great house!! Clean, comfortable, and inviting. Close to Falmouth to get the ferry, close to Hyannis for dinner. Several great restaurants nearby! "
Totally Renovated Central AC Dog Friendly Near Golf

Walking to the beach. Bars and Restaurants.

9.6 out of 10, Exceptional, (5)
"Our group included l, my husband & I and our daughter, her husband, their two kids, boys aged 3&5. The place was spotless - completely clean and filled with amenities! Ample parking and truly happy to pick some party up at the airport! Absolute “ Service with a smile."
Walking to the beach. Bars and Restaurants.

Maushop Property - First Time Available

10.0 out of 10, Exceptional, (42)
"Great spot, we loved it!"
Maushop Property - First Time Available

Your Oasis Awaits

9.6 out of 10, Exceptional, (42)
"We had a great stay. Nice and close to the beach so my mid 80’s mom could even walk back and forth. and the raw bar on property was the perfect place for an easy meal. Would happily stay again."
Your Oasis Awaits

Cozy cottage 3/4 mile from Oak Bluffs harbor

9.8 out of 10, Exceptional, (47)
"Stayed here with 3 friends as we were running the marathon. Better than the photos! So cute, everything was thoughtfully set up, we had anything we needed and having a washer dryer was a huge bonus! Flexible check in as well. Secluded, but easily walkable to many great places to eat and shop. Would 100% stay here again, highly recommend."
Cozy cottage 3/4 mile from Oak Bluffs harbor

Gorgeous Spacious Victorian Cape Cod Beach View Retreat

10.0 out of 10, Exceptional, (14)
Gorgeous Spacious Victorian Cape Cod Beach View Retreat

Quaint,,,Quiet..up island feel yet a short walk to town and harbor

9.8 out of 10, Exceptional, (92)
"Awesome, fun place. Has everything you need for a great Vineyard stay!"
Quaint,,,Quiet..up island feel yet a short walk to town and harbor

Lambert's Cove Beach Getaway - NEW LISTING Private Beach Access!

10.0 out of 10, Exceptional, (62)
"The most magical place, thank you for the prefect stay."
Lambert's Cove Beach Getaway - NEW LISTING Private Beach Access!

By the Water - Steps to the Beach - 4Br, AC, Views of Vineyard Sound

9.8 out of 10, Exceptional, (23)
"We had a great week staying at this property. It's well maintained and had plenty of room for a family getaway to the Cape. Steps away from the beach, this property is well taken care of and had everything we needed for a comfortable stay. This would be our first choice for any future trips to the Cape."
By the Water - Steps to the Beach - 4Br, AC, Views of Vineyard Sound

Expansive Cape Cod Family Retreat

10.0 out of 10, Exceptional, (8)
"House was amazing for our large group! Exactly as advertised and Edward was very communicative throughout our stay."
Expansive Cape Cod Family Retreat

West Falmouth Cottage in the Heart of This Historic Village.

10.0 out of 10, Exceptional, (53)
"Great location, comfortable and perfect for my family of four. "
West Falmouth Cottage in the Heart of This Historic Village.

Secluded Guest House overlooking Menemsha Pond. Dogs welcome + Lvl2 EV charger.

10.0 out of 10, Exceptional, (53)
"We were in town for a wedding in Chilmark and the property was exactly what we needed!"
Secluded Guest House overlooking Menemsha Pond. Dogs welcome + Lvl2 EV charger.
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Chappaquiddick Island Hotel Reviews