Search Woolford Cottage Rentals from CA $201

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Check prices for these dates

Next weekend
Mar 7 - Mar 9
In two weeks
Mar 14 - Mar 16
In one month
Mar 28 - Mar 30
In two months
Apr 25 - Apr 27

Browse Select Woolford Cottages

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

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.
Soul Oasis - home on the Chesapeake Bay
Sun loungers, beach towels

Soul Oasis - home on the Chesapeake Bay

9.8 out of 10, Exceptional, (19)
"Beautiful place, very clean and nicely decorated. The only thing I wish was better was to have a bathroom upstairs and the stairs to be a bit easier to access, they are a bit tricky for those over 50:) nice view too!"
The price is CA $201
CA $427 total
includes taxes & fees
Mar 13 - Mar 14
Soul Oasis - home on the Chesapeake Bay
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
Property grounds

John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!

9.6 out of 10, Exceptional, (113)
"The location couldn't have been more ideal. We were able to walk everywhere...all around town. And there was a beautiful view of the town park and the bay from the house. We were there for Christmas, visiting family, and her house was overflowing, so this was a little home-away-from-home. There were some difficulties. The shower curtain and main bath downstairs needs updating and the kitchen could be better appointed. The stairs to the king bed bedroom are, as others and the owner noted, very...
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Outdoor dining

Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch

9.8 out of 10, Exceptional, (173)
"Great location! Antique furniture in a well maintained beautiful old house. Exactly what we needed."
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
"Point of View" Waterfront cottage with panoramic views on Tilghman Island
Miscellaneous

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

10.0 out of 10, Exceptional, (7)
"“Point of View” waterfront cottage did not disappoint. In fact, it was beyond expectations. Maria’s (the host) personal touches made the cottage feel like home. We used “Point of View” as overflow for a family reunion we were having. It is perfectly situated for easy walking to anything you need or want to do on Tilghman Island. The views from the cottage are amazing. Being on the entrance to Dogwood Harbor provides you with a real time experience of what a waterman’s life is truly all...
"Point of View" Waterfront cottage with panoramic views on Tilghman Island
Relaxing Waterfront Cottage Near St Michaels, Maryland
Exterior

Relaxing Waterfront Cottage Near St Michaels, Maryland

9.8 out of 10, Exceptional, (220)
"This was a winter getaway to a very comfortable house with all the amenities on a quiet tributary of the Chesapeake. A rare vacation for and just what we wanted. Conveniently located near St Michael’s and Easton. Communication was excellent and everything was just as described. Would go back if we get the opportunity. "
Relaxing Waterfront Cottage Near St Michaels, Maryland
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
Marina

Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels

9.6 out of 10, Exceptional, (116)
"This was a quick getaway for my husband, me, and our 2-year-old grandson. The location of this property is perfect! We could walk over to the waterfront and watch the geese or walk into town for shopping and food. We lost power (a fluke) during our stay, and the owner was extremely responsive and easy to contact. We walked to dinner, and it was back on when we returned. Highly recommend!"
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
Waterfront Cottage in Beautiful Hoopers Island
Property grounds

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
Eastern Shore Waterside Cottage Near St. Michaels
Outdoor dining

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
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
Property grounds

Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town

9.6 out of 10, Exceptional, (136)
"The T. Blades house was the perfect choice for a two day quick getaway for my husband and I. The house is not only filled with period charm and character, but has been lovingly and perfectly restored to make it a very comfortable stay. Immaculately clean and furnished. The location is a 5 star, as well. One block to the main street with shops and restaurants, and two blocks in the other direction to the water. Can't wait to go back. Kathleen and John"
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
Delightful Waterfront Cottage on Hoopers Island, MD. 🏝️🦀🎣
Miscellaneous

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. 🏝️🦀🎣
Waterfront, cozy cottage with private pool on 27 acres
Beach nearby

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
The Middle Point Cabin in Saint Michaels
Fridge, microwave, oven, stovetop

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

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
Waterfront property with private boat ramp and new dock!
Outdoor dining

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)
Property grounds

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 at Goose Neck Point
Sun loungers, beach towels

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
Modern Solomons Cottage Rental - Walk to Island!
View from property

Modern Solomons Cottage Rental - Walk to Island!

10.0 out of 10, Exceptional, (9)
"This place was so cute and cozy. Fabulous!"
Modern Solomons Cottage Rental - Walk to Island!
Riverside House w/ Kayaks, Piano & Fireplace
House (5 Bedrooms) | Private kitchen

Riverside House w/ Kayaks, Piano & Fireplace

3.0 star property
Riverside House w/ Kayaks, Piano & Fireplace
Tranquil Port Republic Home w/ Water Views!
Property grounds

Tranquil Port Republic Home w/ Water Views!

3.0 star property
Tranquil Port Republic Home w/ Water Views!
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 Woolford

The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
Interior

The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks

10.0 out of 10, Exceptional, (7)
"This house is huge and has lots of different indoor and outdoor gathering spaces so the kids and adults in our group of three families didn’t have to be on top of each other in one living space the whole time. Big firepit area and huge lawn were great, and we enjoyed the kayaks and canoe. There’s a place to buy fresh crabs, oysters, and shrimp very close by, and the house has everything you need for a crab night. The owner was incredibly responsive and kind."
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
Waterfront Getaway with Dock
Fridge, microwave, oven, stovetop

Waterfront Getaway with Dock

10.0 out of 10, Exceptional, (38)
"Stayed at the rental for a day sandwiched between two nights. Perfect for R&R. "
The price is CA $330
CA $398 total
includes taxes & fees
Mar 1 - Mar 2
Waterfront Getaway with Dock
Cozy Cottage with access to and partially obstructed views of the bay.
Miscellaneous

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.
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.