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Browse Select Rock Hall Cottages

Firefly Cottage at the Cape, Community beach, Hot tub, USNA, Pets, summer fun!
Set against a serene backdrop, this house features a beautifully lit facade and a decorative reindeer sculpture on the lawn.

Firefly Cottage at the Cape, Community beach, Hot tub, USNA, Pets, summer fun!

10.0 out of 10, Exceptional, (93)
"We stay at Firefly every time we go to visit our son and his family. It works perfectly for us…an oasis for us, and a fun place for the kids to visit, too. Pat and Ken have been the perfect hosts!"
Firefly Cottage at the Cape, Community beach, Hot tub, USNA, Pets, summer fun!
Relaxing Waterfront Cottage Near St Michaels, Maryland
Situated on a serene grassy area, this charming home features a two-story design with a prominent chimney and a cozy porch with white railings.

Relaxing Waterfront Cottage Near St Michaels, Maryland

9.8 out of 10, Exceptional, (224)
"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
The Heron's Nest at Atlantic Marina
Enjoy the ocean view from this outdoor space with a deck and columned roof.

The Heron's Nest at Atlantic Marina

10.0 out of 10, Exceptional, (301)
"Nice weekend getaway!"
The Heron's Nest at Atlantic Marina
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
Traditional home with a gabled roof and central chimney, set amidst a peaceful grassy lawn and trees.

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

9.6 out of 10, Exceptional, (121)
"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
Secluded Waterfront Cottage on 200 acre farm near Queenstown
Escape to a secluded cabin perched on a hill overlooking a serene body of water, surrounded by lush trees and dense vegetation.

Secluded Waterfront Cottage on 200 acre farm near Queenstown

10.0 out of 10, Exceptional, (103)
"Secluded"
Secluded Waterfront Cottage on 200 acre farm near Queenstown
The Yellow Cottage on Harness Creek
Traditional house with a front porch surrounded by lush gardens and flowering plants.

The Yellow Cottage on Harness Creek

10.0 out of 10, Exceptional, (162)
"Easy checkin/checkout. Cute cottage. Scenic and comfortable."
The Yellow Cottage on Harness Creek
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Enjoy a patio surrounded by lush trees and a well-manicured lawn.

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

9.8 out of 10, Exceptional, (184)
"Great spot for a weekend visit. Second time staying. Great communication with owner. Will stay again"
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Eastern Shore beach cottage get-away
Cozy home with a front porch and bench, surrounded by well-maintained hedges and a sandy area.

Eastern Shore beach cottage get-away

10.0 out of 10, Exceptional, (136)
"This house was the cutest little place right across the street from the beach with a beautiful view. The house was clean and had all the amenities needed for our stay. We would definitely stay there again!"
Eastern Shore beach cottage get-away
Charming, updated 1930's beachfront cottage with stunning sunset views
Interior

Charming, updated 1930's beachfront cottage with stunning sunset views

10.0 out of 10, Exceptional, (1)
"Check in was a breeze. Place was clean. Simply beautiful. Most relaxing place ever. "
Charming, updated 1930's beachfront cottage with stunning sunset views
Accessible, Screened-in porch, Sauna, Fire Pit, Dog Friendly
Relax on the front porch with a bench and two chairs, surrounded by a serene garden and a wooded area.

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

10.0 out of 10, Exceptional, (50)
"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
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
Enjoy al fresco dining and social gatherings on this shaded deck with a grill and comfortable seating.

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

10.0 out of 10, Exceptional, (213)
"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
Secluded Cozy Cottage in Historic Downtown
Stroll along the pathway to an entrance surrounded by lush greenery and a curved brick wall.

Secluded Cozy Cottage in Historic Downtown

9.4 out of 10, Exceptional, (13)
"We had a very lovely stay . This is an excellent location . "
The price is CA $640
CA $1,049 total
includes taxes & fees
Aug 13 - Aug 14
Secluded Cozy Cottage in Historic Downtown
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
Traditional two-story house with a gabled roof and chimney, featuring a front entrance with a door and small porch.

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!
Relax in a serene lakeside setting with two Adirondack chairs.

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, (1)
"The cottage acted as the perfect base for our little weekend getaway with friends. Positioned well on Kent Island, and with plenty of parking for three sedans, it was very easy to get from place to place. The space appeared to be similar to an in-law suite, just big enough to move around while being compact and cozy. Just enough necessities were there at the cottage, including basic condiments in the fridge, cutlery, shower essentials, etc. Overall we were very happy with our stay and would...
Chesapeake Cottage
Take a Water Taxi to Downtown Annapolis from Beachfront home, Dogs OK
Stunning two-story house with a gabled roof and inviting front porch, set amidst a beautifully maintained garden.

Take a Water Taxi to Downtown Annapolis from Beachfront home, Dogs OK

10.0 out of 10, Exceptional, (32)
"Really like this place "
Take a Water Taxi to Downtown Annapolis from Beachfront home, Dogs OK
Peaceful getaway convenient to local amenities including beach, boating & food
Stunning two-story home with a central entrance, flanked by windows and a well-manicured lawn.

Peaceful getaway convenient to local amenities including beach, boating & food

9.8 out of 10, Exceptional, (115)
"Great location and local restaurants. Perfect side for small group to do paper crafting. Would definitely book this place again. "
Peaceful getaway convenient to local amenities including beach, boating & food
Rock Creek Cottage, Waterfront, Serene Views
Terrace/patio

Rock Creek Cottage, Waterfront, Serene Views

10.0 out of 10, Exceptional, (6)
"My husband and I enjoyed our stay. The property was actually quite beautiful. The view was lovely as the home sits on a creek. The home provided everything we needed. Shopping and restaurants were very close. If you need to be in the Baltimore/Annapolis area as we had, this property is perfect."
Rock Creek Cottage, Waterfront, Serene Views
6 Mi to Dtwn: Family-friendly Home in Annapolis!
Stroll up to this charming two-story home with a welcoming front porch and garage, set amidst a beautifully manicured lawn.

6 Mi to Dtwn: Family-friendly Home in Annapolis!

3.0 star property
6 Mi to Dtwn: Family-friendly Home in Annapolis!
Charming Waterfront Cottage Retreat near St. Michaels
Escape to a serene lakeside retreat surrounded by lush greenery and a well-maintained lawn.

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
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 Rock Hall Hotel Reviews

The Westin Annapolis

The Westin Annapolis

10/10 Excellent
"The breakfast was amazing and the restaurant staff made it even better. Al greeted us with a warm smile everyday and the staff were very attentive, making sure our meals and experience was just right. "
Colleen 2-night trip
Posted 6 hours ago
The Westin Annapolis