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Check prices for these dates

Compare 61 Cottages in Taylors Island with updated reviews, rates, and availability.

Soul Oasis - home on the Chesapeake Bay

9.8 out of 10, Exceptional, (20)
"."
The price is SAR 521
SAR 1,098 total
includes taxes & fees
1 May - 2 May
Soul Oasis - home on the Chesapeake Bay

Cozy Cottage with access to and partially obstructed views of the bay.

9.4 out of 10, Exceptional, (18)
"My wife and I stayed two nights to visit family. Cottage was as described, very roomy and comfortable. Great location. Host was very kind. Only dislike was smell from oil heat, I've never had oil heat and not sure if that is normal."
Cozy Cottage with access to and partially obstructed views of the bay.

Waterfront Cottage in Beautiful Hoopers Island

10.0 out of 10, Exceptional, (66)
"the Hoopers Island area is amazingly wild and beautiful. we loved the Harriet Tubman visitors center just a short trip away, and the Blackwater Refuge just incredibly beautiful. the winter birds! we learned so much about the history and culture of the lower islands.the house is more cabin style, smaller than we anticipated, but we got used to that. it was full-on winter weather and wind, so we couldn't kayak as we'd hoped, and the coast was mostly rocks so hard to walk along. it's a place for...
Waterfront Cottage in Beautiful Hoopers Island

Family and Pet-Friendly, Waterfront with Pier

10.0 out of 10, Exceptional, (244)
"The only thing I can say is that the online listing really doesn’t do justice to how amazingly stunning Rob & Clarissa’s place is. My family and I decided last minute that we wanted to spend a weekend on the bay. I never expected it to be so beautiful! We got there late in the evening and we were speechless when we woke up to the most beautiful view of the water. My son had an amazing time between playing in the loft or in the playhouse outside, kayaking, and paddle boating. My parents “settled”...
Family and Pet-Friendly, Waterfront with Pier

Eastern Shore Waterside Cottage Near St. Michaels

10.0 out of 10, Exceptional, (19)
"Had a great visit. House was perfect and the area is absolutely gorgeous"
Eastern Shore Waterside Cottage Near St. Michaels

Block to Beach! Fossil Hunting, Hot Tub, Coffee Bar, Screened Deck, 1hr to DC

10.0 out of 10, Exceptional, (14)
"It was very clean and not cluttered. I felt it had all the essentials, however, lacked closet space in the bed-rooms. Definitely would stay there again."
Block to Beach! Fossil Hunting, Hot Tub, Coffee Bar, Screened Deck, 1hr to DC

North Beach Cottage - Walk to Chesapeake Bay

10.0 out of 10, Exceptional, (30)
"Our family was in town to attend the promotion in the air force of a nephew at Ft. McNair. Close to everything. Beautiful house prefect for us. Enjoyed walking the boardwalk. Would highly recommend this property. Excellent communication with the host. "
North Beach Cottage - Walk to Chesapeake Bay

Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE

10.0 out of 10, Exceptional, (3)
"Lovely little rustic cottage full of charm.We arrived over Thanksgiving,the off season was wonderful thank s again"
Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE

Cedar Point 6.5 Acre Waterfront Family Retreat With Pool And Sandy Beach!

10.0 out of 10, Exceptional, (88)
"Wonderful. "
Cedar Point 6.5 Acre Waterfront Family Retreat With Pool And Sandy Beach!

Delightful Waterfront Cottage on Hoopers Island, MD. 🏝️🦀🎣

10.0 out of 10, Exceptional, (47)
"The views of the bay are magnificent, sunrise and sunset. The property is spotless. Toby and Kim, the hosts, could not be more accommodating. "
Delightful Waterfront Cottage on Hoopers Island, MD. 🏝️🦀🎣

Private waterfront cottage with pool on Church Creek

10.0 out of 10, Exceptional, (61)
"This was one of the most beautiful spots I've seen. Kayaking was wonderful! Couch was very uncomfortable. And many maybe put off to find they must put everything in a box to keep away from rodents. And I just took my garbage home as we didn't have time to dump at an off site location on vacation. I would still book again as it was the most peaceful, charming and secluded place to truly relax!"
Private waterfront cottage with pool on Church Creek

Waterfront, cozy cottage with private pool on 27 acres

9.8 out of 10, Exceptional, (87)
"We had a wonderful time overlooking the water and swimming in the refreshing pool while enjoying easy access to downtown Cambridge and Blackwater NW Refuge."
Waterfront, cozy cottage with private pool on 27 acres

"Point of View" Waterfront cottage with panoramic views on Tilghman Island

10.0 out of 10, Exceptional, (8)
"The home was so well appointed and walking distance to stores, restaurants, quaint museums and beautiful nature. The host was so friendly and helpful with quick responses. We had high winds and lots of rain, but stayed cozy and warm. What a friendly Island of people!!"
"Point of View" Waterfront cottage with panoramic views on Tilghman Island

Charming Waterfront Cottage Retreat near St. Michaels

10.0 out of 10, Exceptional, (1)
"Our stay at this beautiful cottage was truly unforgettable! The space was clean, cozy, and well-appointed, with every detail carefully considered. Nestled right on the water’s edge, every inch of the house was tastefully decorated and had all the amenities you could ask for. The tasteful decor, fully stocked kitchen, and comfortable bed made us feel right at home from the moment we arrived.The hosts went above and beyond to make this an enjoyable stay, with excellent communication and thoughtful...
Charming Waterfront Cottage Retreat near St. Michaels

Cottage at Goose Neck Point

10.0 out of 10, Exceptional, (31)
"We loved everything about this sweet cottage on the water! The decor was top notch, and so welcoming! We stayed 3 nights, and can’t say enough about this beautiful area of Maryland. Great restaurants, shoppes, and delicious crabs! We also did the ferry ride over to Oxford. Had an amazing time at this property! The host also left some yummy treats, and a bottle of champagne for our anniversary! Can’t wait to come back!"
Cottage at Goose Neck Point

Cottage Located on the Patuxent River!

10.0 out of 10, Exceptional, (38)
"The property and the cottage are just beautiful [very quiet] and incredibly well appointed. The bed is super cozy. There is no kitchen but the coffee station was great to have. Note that the cottage shares the property with the main house. My husband and I enjoyed sitting by the river multiple times during our stay and we really appreciated our hosts’ hospitality and communication. Thank you for the beautiful respite!"
The price is SAR 1,219
SAR 1,479 total
includes taxes & fees
5 Apr - 6 Apr
Cottage Located on the Patuxent River!

Waterfront property with private boat ramp and new dock!

9.6 out of 10, Exceptional, (8)
"Thoroughly enjoyed our stay! Cottage was comfortable and very clean with everything we could have needed! "
Waterfront property with private boat ramp and new dock!

Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)

10.0 out of 10, Exceptional, (2)
"Great little cottage, beautiful scenery, quiet and peaceful. "
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)

Cottage on the Bay

6.0 out of 10, (1)
"This property has some good qualities. For one, it is right on the water, and you have access to three small beaches and good fishing. It was nice to wake up and drink coffee next to the waves. The house was stocked and seemed to have everything we could’ve needed. However, for us, the negatives far outweighed the positives here. Most significantly to me, the property did not mention that the outdoor amenities - the fire pit, grills, and boats - are shared between you and the adjoining property....
Cottage on the Bay

The Middle Point Cabin in Saint Michaels

9.8 out of 10, Exceptional, (48)
"nice property. secluded. clean and comfortable. owners very very responsive. "
The Middle Point Cabin in Saint Michaels
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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Other property types in Taylors Island

Soul Oasis - home on the Chesapeake Bay

9.8 out of 10, Exceptional, (20)
"."
The price is SAR 521
SAR 1,098 total
includes taxes & fees
1 May - 2 May
Soul Oasis - home on the Chesapeake Bay

The Blue Crab Beach House - Free beach passes

10.0 out of 10, Exceptional, (51)
"The Blue Crab Beach House was perfect for my wife and I and our dog. Very comfortable with a great backyard space for our dog. We loved the location - it’s just a short walk to restaurants and the bay. Very enjoyable stay and we hope to return."
The Blue Crab Beach House - Free beach passes

Family and Pet-Friendly, Waterfront with Pier

10.0 out of 10, Exceptional, (244)
"The only thing I can say is that the online listing really doesn’t do justice to how amazingly stunning Rob & Clarissa’s place is. My family and I decided last minute that we wanted to spend a weekend on the bay. I never expected it to be so beautiful! We got there late in the evening and we were speechless when we woke up to the most beautiful view of the water. My son had an amazing time between playing in the loft or in the playhouse outside, kayaking, and paddle boating. My parents “settled”...
Family and Pet-Friendly, Waterfront with Pier
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.

Frequently asked questions

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