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Compare 53 Cottages in Gregory Town with updated reviews, rates, and availability.

Rest Ashore, BRAND NEW 2-bedroom cottage in Spanish Wells!FREE golfcart

2.0 star property
10.0 out of 10, Exceptional, (10)
"We really enjoyed our stay. From Brandi picking us up at the dock to take us to the house to April replacing the golf cart flat tire within an hour and we were back in business. We also enjoyed a half day on Tyman Charters. Got along great with the captain."
Rest Ashore, BRAND NEW 2-bedroom cottage in Spanish Wells!FREE golfcart

Pineapple Blues....Big Bang for your Buck

9.6 out of 10, Exceptional, (68)
" Overall, I thought the stay was great; it was peaceful, noise-free, and close to everything."
Pineapple Blues....Big Bang for your Buck

Waterfront Cottage in Spanish Wells' protected harbor

9.8 out of 10, Exceptional, (31)
"Fully equipped great little cottage. 2 very nice bedrooms and baths with space and privacy for more. Located in the historic harbor with a great porch to watch the world go by. Due to an airline issue we needed 3 extra nights at the very last minute and we were graciously accommodated. This was a great space for us and highly recommend Harbor House."
Waterfront Cottage in Spanish Wells' protected harbor

Mainbrace. A Three Bedroom, Two Bath Home Just Steps From The Beach!

10.0 out of 10, Exceptional, (138)
"When we go to Harbor Island we stay at Mainbrace. Won’t stay anywhere else!"
Mainbrace. A Three Bedroom, Two Bath Home Just Steps From The Beach!

TennesSea Shine. Perfect View for Two. Cozy cottage with amazing views.

10.0 out of 10, Exceptional, (42)
"We have been to Spanish Wells three times, and this was the best cozy cottage we have stayed in, yet! Its fresh, clean, and well-appointed with all the kitchen items and beach supplies you need. The porch view is wonderful and it's a quick cart ride into town and nearby beaches. We look forward to staying at Tennessee Sunshine, again!"
TennesSea Shine. Perfect View for Two. Cozy cottage with amazing views.

Sugar Cube: Charming & Artsy 1 bedroom cottage in the heart of Harbour Island

10.0 out of 10, Exceptional, (6)
Sugar Cube: Charming & Artsy 1 bedroom cottage in the heart of Harbour Island

Spectacular Eco Cottage, oceanfront, secret beach

10.0 out of 10, Exceptional, (64)
"The view is spectacular and the waves were beautiful. The cottage was very cozy, has fans and AC (which we barely used) and hammock was a favourite with our kids. Very quick drive to Gregory Town to Unka Gene's restaurant and convenience stores. Loved it!"
Spectacular Eco Cottage, oceanfront, secret beach

Elizabeth on Crown W/ (Complimentary Breakfast at our local Coffee House)

9.6 out of 10, Exceptional, (23)
"Charming house with beautiful and thoughtful decor. Great location and backyard area."
Elizabeth on Crown W/ (Complimentary Breakfast at our local Coffee House)

Palmetto cottage on the beach with perfect views.

10.0 out of 10, Exceptional, (21)
"We absolutely love this property. Very clean, great decor, outstanding location, fantastic back porch looking out to the beautiful Caribbean! Can’t wait to come back again next year!"
Palmetto cottage on the beach with perfect views.

“ShoreTing” oceanfront, secret beach

10.0 out of 10, Exceptional, (23)
"A stunning property with everything you need for a wonderful stay. It’s comfortable, unique and allowed for a truly unplugged four days for my husband and I. Fast internet allowed for a few seamless work calls. Highly recommend and we’ll be back!"
“ShoreTing” oceanfront, secret beach

Paradise Beach Cottage- Newly Renovated 3 Bed/3 Bath Cottage On The Beach

10.0 out of 10, Exceptional, (91)
"Was very pleasant "
Paradise Beach Cottage- Newly Renovated 3 Bed/3 Bath Cottage On The Beach

Sandy & Salty Beach Cottage

10.0 out of 10, Exceptional, (26)
"Sandy & Salty is a perfect place for 2 couples. The view is spectacular and the home has everything you need for a wonderful getaway. The location is close to everything!The beds are comfortable add the kitchen is well stocked. We enjoyed playing the games inside and loved the comfy Adirondack chairs and chaise lounges for the beach. Thank you JoAnne for making us feel at home!Can’t wait to come back!"
Sandy & Salty Beach Cottage

SEAGLASS ,near beach,free golf cart, dishwasher, sup, kayak, sleeps 10

10.0 out of 10, Exceptional, (110)
"We had a great time here. Owner was very responsive to any issues ( including a flat tire on the cart that was promptly repaired). Highly recommend renting here. "
SEAGLASS ,near beach,free golf cart, dishwasher, sup, kayak, sleeps 10

"Sweet Ting" Charming 3-bedroom cottage in Spanish Wells, Just Steps to beach

10.0 out of 10, Exceptional, (2)
"Great property, cleanly kept and maintained "
"Sweet Ting" Charming 3-bedroom cottage in Spanish Wells, Just Steps to beach

Ocean View, Sleeps 8, SUP, Beach Toys

2.0 star property
10.0 out of 10, Exceptional, (15)
"Accommodations were amazing. They have everything. They were super helpful in everything we needed. From the owner to the amazing caretaker of the home. We hope to be able to come back! "
Ocean View, Sleeps 8, SUP, Beach Toys

Beachfront Water's Edge Cottage with pool (newly renovated)

9.8 out of 10, Exceptional, (71)
"Awesome "
Beachfront Water's Edge Cottage with pool (newly renovated)

Watercolor a Charming Island Cottage. 3 Bedroom

7.4 out of 10, Good, (3)
"Great location for walking to local attractions and general store. It is a busy location so expect "
Watercolor a Charming Island Cottage. 3 Bedroom

Mermaids Cove

10.0 out of 10, Exceptional, (57)
"Second time there and the private beach is worth every penny"
Mermaids Cove

Sands of Time is ready for You

9.6 out of 10, Exceptional, (10)
"These guys have always exceeded expectations and super easy to work with. "
Sands of Time is ready for You

WATERFRONT W/POOL, STARFISH

WATERFRONT W/POOL, STARFISH
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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