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Browse Select Royal Oak Cottages

Relaxing Waterfront Cottage Near St Michaels, Maryland
Exterior

Relaxing Waterfront Cottage Near St Michaels, Maryland

9.8 out of 10, Exceptional, (226)
"We had a lovely stay here.Place was VERY clean.Visited St. Michael’s and relaxed on the porch & pier.It met our expectations."
Relaxing Waterfront Cottage Near St Michaels, Maryland
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
Exterior

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

9.6 out of 10, Exceptional, (122)
"This was a cute historic house very close to all shops and restaurants. Location could not be better. It could use a thorough cleaning and the shower is pretty rustic. But overall a good place to stay."
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE
Exterior

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

10.0 out of 10, Exceptional, (7)
"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
Waterfront property with private boat ramp and new dock!
Outdoor dining

Waterfront property with private boat ramp and new dock!

9.4 out of 10, Exceptional, (13)
"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!
"Point of View" Waterfront cottage with panoramic views on Tilghman Island
Exterior

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

10.0 out of 10, Exceptional, (11)
"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
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)
Outdoor dining

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

10.0 out of 10, Exceptional, (7)
"Perfect house for a long weekend. Clean, cozy and great communication with Maxine. Would definitely stay here again when I return to Cambridge. "
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Exterior

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

9.8 out of 10, Exceptional, (184)
"This house has the perfect location to explore the town. We stayed in this house for the St. Michael’s Running Festival and it couldn’t have been better. The location was so close to the start/finish lines and there were so many restaurants within a few minutes walk. "
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Quick walk to the beach! Fire pit, Corn hole, Games & More!
Property grounds

Quick walk to the beach! Fire pit, Corn hole, Games & More!

10.0 out of 10, Exceptional, (2)
"We loved EVERYTHING about this place. Right next to the beach, great restaurants and shops. Could not have been better service. "
Quick walk to the beach! Fire pit, Corn hole, Games & More!
Accessible, Screened-in porch, Sauna, Fire Pit, Dog Friendly
Exterior

Accessible, Screened-in porch, Sauna, Fire Pit, Dog Friendly

10.0 out of 10, Exceptional, (51)
"Beautiful home with LOTS of attention to detail. The backyard was a beautiful oasis and we LOVED the “swing bed” on the screened-in porch. Mark and Karen add lots of fine touches to make your stay special. Plenty of room for two, cozy for four, and comfortable for four legged friends with the fenced in back yard. Quiet and private with a short 10 minute drive to town. Can’t wait to return!"
Accessible, Screened-in porch, Sauna, Fire Pit, Dog Friendly
Family and Pet-Friendly, Waterfront with Pier
Exterior

Family and Pet-Friendly, Waterfront with Pier

10.0 out of 10, Exceptional, (253)
"What a wonderful area on the water. The proprietors were such friendly and accommodating people. The apartment was clean and well stocked. They had a wide range of activities on the property. It was wonderful being able to sit near the water and enjoy my friend’s company. I highly recommend this welcoming place. "
Family and Pet-Friendly, Waterfront with Pier
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
Outdoor dining

Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA

10.0 out of 10, Exceptional, (214)
"Great views and location. Well furnished and very comfortable. We will definitely be staying here again. "
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
Exterior

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

9.6 out of 10, Exceptional, (142)
"A lovely cottage to stay in. Lots of old world charm and location is unbeatable when want to stay in St. Michaels"
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
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, (118)
"The house and location was perfect for a girls weekend with my mom and 2 daughters! The 1/2 bathrooms in each bedroom were nice to have upstairs!"
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
Chesapeake Cottage
Exterior

Chesapeake Cottage

10.0 out of 10, Exceptional, (2)
"Outstanding accommodations in an extraordinary neighborhood!! Many near by options for dining and outdoor activities!! Highly recommended!! "
Chesapeake Cottage
Adorable Beach Cottage w/ Hot Tub & Tropical Bar!
Interior

Adorable Beach Cottage w/ Hot Tub & Tropical Bar!

3.0 star property
8.0 out of 10, Very good, (2)
"The water is well water and it stinks, water treatment could improve that. This is more in the woods than beachy. In a rundown area. Get some Damprid to cut down on musty smell. Cute decor."
Adorable Beach Cottage w/ Hot Tub & Tropical Bar!
Watrfnt Cottage @ChesapeakeParadise Kayaks/Dogs OK
Exterior

Watrfnt Cottage @ChesapeakeParadise Kayaks/Dogs OK

9.8 out of 10, Exceptional, (82)
"The cottage was a wonderful place for me and my kids to stay. I really appreciate the thoughtfulness of the owner. We would definitely stay here again."
Watrfnt Cottage @ChesapeakeParadise Kayaks/Dogs OK
Private waterfront cottage with pool on Church Creek
Property grounds

Private waterfront cottage with pool on Church Creek

10.0 out of 10, Exceptional, (62)
"Very clean, comfortable, and cozy property with gorgeous view of the water. Would definitely stay here again. Just wish we spent more time on the property this stay, but obligations in Fishing Creek kept us away most of the time. Thank you for sharing your lovely cottage!!"
Private waterfront cottage with pool on Church Creek
North Beach Cottage - Walk to Chesapeake Bay
Exterior

North Beach Cottage - Walk to Chesapeake Bay

10.0 out of 10, Exceptional, (37)
"The house was beautiful with everything you could need. We were out all day so didn’t get to use the house much except for sleeping. The bed was super comfortable."
North Beach Cottage - Walk to Chesapeake Bay
Charming Waterfront Cottage Retreat near St. Michaels
Exterior

Charming Waterfront Cottage Retreat near St. Michaels

10.0 out of 10, Exceptional, (7)
"Great weekend get away if you’re just looking for some peace and quiet with some great scenery. The kitchen was immaculate and everything was as listed."
Charming Waterfront Cottage Retreat near St. Michaels
Cedar Point 6.5 Acre Waterfront Family Retreat With Pool And Sandy Beach!
Outdoor spa tub

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

10.0 out of 10, Exceptional, (88)
"Beautiful property in a great location!"
Cedar Point 6.5 Acre Waterfront Family Retreat With Pool And Sandy Beach!
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 Royal Oak Hotel Reviews

Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay

10/10 Excellent
"Very relaxing and everyone was very nice and helpful. "
Kirk 2-night trip
Posted 1 day ago
Hyatt Regency Chesapeake Bay