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Compare 66 Cottages in Wittman with updated reviews, rates, and availability.

Firefly Cottage at the Cape, community beach, Holidays, hot tub USNA games pets
Firefly Cottage at the Cape, community beach, Holidays, hot tub USNA games pets
10.0 out of 10, Exceptional, (75)
"Lovely house and location! Pat and Ken were rapid and personable with every interaction."
Firefly Cottage at the Cape, community beach, Holidays, hot tub USNA games pets
Relaxing Waterfront Cottage Near St Michaels, Maryland
Charming Cottage on a quite creek of the Chesapeake Bay with private pool.
Relaxing Waterfront Cottage Near St Michaels, Maryland
9.8 out of 10, Exceptional, (211)
"The cottage is beautiful and comfy on the inside. We enjoyed the screened porch where I sat for hours reading my book. I must admit it was my first time being in a place where there are no streetlights, and the dark of night is so beautiful. I can never see the stars in the city. A gem. My mother, husband and I really enjoyed our stay. "
Relaxing Waterfront Cottage Near St Michaels, Maryland
The Yellow Cottage on Harness Creek
The Yellow Cottage on Harness Creek
The Yellow Cottage on Harness Creek
10.0 out of 10, Exceptional, (148)
"This was just a super place- right in the water and beautiful… and surprisingly spacious for a cottage. I loved the kitchen farm sink and the sun coming in the morning off the bay. Will definitely love to stay again. The owner was so nice and thought of all the little details!! Thank you!!"
The Yellow Cottage on Harness Creek
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
Front of house from St. Michaels harbor looking across Town Park
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
9.6 out of 10, Exceptional, (107)
"We love staying at the John Bruff house in St. Michaels. The location is great, right in the heart of town! Our family has been staying here for the past few years and we can’t wait to go back!!"
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
Eastern Shore Waterside Cottage Near St. Michaels
wrap around porch with rockers and dining area
Eastern Shore Waterside Cottage Near St. Michaels
10.0 out of 10, Exceptional, (17)
"We had a great stay at this house. We enjoyed using the kayak and paddleboard. (Access to the water is across this street.) We also enjoyed the pool and relaxing on the porch. It was about a 15 minute drive into St Michael’s, where we had excellent meals, went sailing, and enjoyed the cute shops and pretty houses. It was a really nice, relaxing weekend! "
Eastern Shore Waterside Cottage Near St. Michaels
"Point of View" Waterfront cottage with panoramic views on Tilghman Island
Blue heron sunset
"Point of View" Waterfront cottage with panoramic views on Tilghman Island
10.0 out of 10, Exceptional, (5)
"Our stay was amazing! Words cannot say enough! The view is magical. We enjoyed coffee on the porch to watch the sunrise and the crab/oyster boats going in and out. Maria, is a wonderful and very thoughtful host. At her recommendation, we went to the free wine tasting at the General Store at the end of the street. We met several local residents who could not be more kind and fun to talk with. We can't wait to come back and stay again."
"Point of View" Waterfront cottage with panoramic views on Tilghman Island
Artists, writers & creative minds stay and BE INSPIRED AT SIMPLICITY COTTAGE
Exterior
Artists, writers & creative minds stay and BE INSPIRED AT SIMPLICITY COTTAGE
10.0 out of 10, Exceptional, (1)
"If you want to get away from it all, this is the place to be. My wife and I celebrated our 20th wedding Anniversary. Calm and peaceful, nestled right by the Choptank River. The cottage itself was very comfortable. The air conditioner worked great. It was a pleasure staying there and we will probably return next year."
Artists, writers & creative minds stay and BE INSPIRED AT SIMPLICITY COTTAGE
Cozy retreat in peaceful wooded setting. Pet friendly!
Path to cottage
Cozy retreat in peaceful wooded setting. Pet friendly!
2.0 star property
10.0 out of 10, Exceptional, (1)
"Private country setting with a short drive to civilization. Small studio style home easy to get around with open setting. Owners are super friendly and easy to communicate with"
Cozy retreat in peaceful wooded setting. Pet friendly!
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
10.0 out of 10, Exceptional, (198)
"What a lovely hideaway!!! The owners are extremely hospitable and the area is beautiful quaint and close to everything. Thank you for having us!!!"
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
Amazing views, short walks to great dining!
"The design is probably my favorite thing about the place—it’s well thought out and has an excellent flow. I also slept very deeply. Can’t wait to return." Melissa - April 2021
Amazing views, short walks to great dining!
10.0 out of 10, Exceptional, (71)
"Our stay at this Vrbo in Annapolis was nothing short of spectacular! The property is beautifully maintained, offering the perfect blend of comfort and style. The attention to detail was evident, from the cozy living spaces to the well-appointed kitchen that had everything we needed for our stay. The location is unbeatable—close enough to all the attractions, restaurants, and shops make Annapolis the charming city that it is (1.2 miles walk to the Naval Academy), while distanced enough to be a...
Amazing views, short walks to great dining!
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Front of Carpenter St. Cottage
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
9.8 out of 10, Exceptional, (165)
"Great little cottage and plenty of space for our family of 3 to have an end-of-Summer getaway to one of our favorite towns. Prompt and easy communication with the owner, Tom, both before and during our stay. We loved the back porch and were blessed with some cooler temps and were able to enjoy sitting out there. FYI - Den has a door (third bedroom with pull out sofa). We have rented on Carpenter Street before, and the location cannot be beat as far as walkability to everything in town and along...
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
Front and side view of Blades House from Locust St.
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
9.6 out of 10, Exceptional, (130)
"Had a wonderful time. This home was just perfect for us. Great location and charming. Would definitely stay here again"
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
Waterfront property with private boat ramp and new dock!
Exterior
Waterfront property with private boat ramp and new dock!
9.2 out of 10, Wonderful, (5)
"Perfect size for a small family. Nice kitchen and furnishings, very cute. Nice quiet neighborhood setting."
Waterfront property with private boat ramp and new dock!
Cottage at Goose Neck Point
Living area
Cottage at Goose Neck Point
10.0 out of 10, Exceptional, (28)
"We wanted to spend some time on the water and have the ability and access to fishing and kayaks. This property did not disappoint. The cottage had everything we needed, and then some! We were welcomed with a lovely note, snack basket, charcuterie board and bottle of wine. Two bikes were available for use, the fire pit was loaded and ready for an evening fire. Lovely screened in porch facing the water. Friendly neighbors. We loved the area so much that our retirement plans have no included...
Cottage at Goose Neck Point
Eastport Cozy Charmer
Living area
Eastport Cozy Charmer
9.4 out of 10, Exceptional, (3)
"We really enjoyed our stay. We felt very comfortable there, and it worked well for us. Especially liked that there was space to park the boat on the street next to the house."
Eastport Cozy Charmer
Pet-friendly Annapolis Home: Walk to Beach!
Property grounds
Pet-friendly Annapolis Home: Walk to Beach!
3.0 star property
Pet-friendly Annapolis Home: Walk to Beach!
Enchanting West River Retreat
View from property
Enchanting West River Retreat
10.0 out of 10, Exceptional, (5)
"The views are spectacular and the boat dock is lovely..the hospitality was amazing too can’t wait to come back and visit "
Enchanting West River Retreat
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
Front and side of W Melson House
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
9.6 out of 10, Exceptional, (113)
"We love escaping to St Michaels for a change of scenery. These historic properties are great places to disconnect from our normal fast paced lifestyle. We always enjoy that our dogs are able to enjoy our stay. It’s a vacation for them as well. The town is very dog friendly in general. The properties are historic and have their quirks. For us, this adds to the experience and charm of St Michaels. The centralized location is key. "
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
Secluded Waterfront Cottage on 200 acre farm near Queenstown
Property grounds
Secluded Waterfront Cottage on 200 acre farm near Queenstown
10.0 out of 10, Exceptional, (96)
"My family and I had a ball, enjoyed our time on the water and hanging out on the farm. "
Secluded Waterfront Cottage on 200 acre farm near Queenstown
Updated North Beach Cottage: Pet Friendly!
North Beach Vacation Rental | 3BR | 2BA | 1,440 Sq Ft | Stairs Required to Enter
Updated North Beach Cottage: Pet Friendly!
9.8 out of 10, Exceptional, (10)
"We had a great time. Nice place. Within walking distance to small deli/ market. Just wished we wouldn't have had to pay to go to the beach."
Updated North Beach Cottage: Pet Friendly!
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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 Wittman

Relaxing Waterfront Cottage Near St Michaels, Maryland
Charming Cottage on a quite creek of the Chesapeake Bay with private pool.
Relaxing Waterfront Cottage Near St Michaels, Maryland
9.8 out of 10, Exceptional, (211)
"The cottage is beautiful and comfy on the inside. We enjoyed the screened porch where I sat for hours reading my book. I must admit it was my first time being in a place where there are no streetlights, and the dark of night is so beautiful. I can never see the stars in the city. A gem. My mother, husband and I really enjoyed our stay. "
Relaxing Waterfront Cottage Near St Michaels, Maryland
Rockhold Creek Cottage, Water Front, Vacation Home, Docks
Grill no longer works
Rockhold Creek Cottage, Water Front, Vacation Home, Docks
9.8 out of 10, Exceptional, (83)
"The house was clean and comfortable. Walking distance to a local restaurant. Screened porch was great for watching the sunrise in the morning and the boats coming in and out of harbor "
Rockhold Creek Cottage, Water Front, Vacation Home, Docks
Firefly Cottage at the Cape, community beach, Holidays, hot tub USNA games pets
Firefly Cottage at the Cape, community beach, Holidays, hot tub USNA games pets
10.0 out of 10, Exceptional, (75)
"Lovely house and location! Pat and Ken were rapid and personable with every interaction."
Firefly Cottage at the Cape, community beach, Holidays, hot tub USNA games pets
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

How much do cottages in Wittman cost?
Cottages in Wittman range between and per night. These stays offer a chance to reconnect with nature — at a price you can afford. This price was available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many cottages are there in Wittman?
Get in touch with nature in one of the 66 cottages waiting for you in Wittman. To help you select your ideal stay, take advantage of our filters to search for must-have perks or amenities.
Why book your cottage in Wittman with Expedia?
We think that traveling should be stress-free, so if you’re searching for cottages in Wittman at an affordable price, Expedia has you covered. Keep the budget under control and go for a cheap option far from the rush of the city, or book a luxury cottage to spoil your favorite people.
How can I find cheap cottages in Wittman?
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