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Compare 54 Cottages in Shady Side with updated reviews, rates, and availability.

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, (216)
"Were pleased with the property and surroundings. Very beautiful, ancient trees. Neighborhood was quiet and the river and dock were favorite reading spots. Enjoyed!!!"
Relaxing Waterfront Cottage Near St Michaels, Maryland
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, (112)
"Our stay in St Michael's was wonderful. The location of this property could not be better. Close to marina, parks, restaurants, historic downtown and the maritime museum. We never needed to use our car! Tom is an excellent host. "
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi
Property grounds
Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi
2.0 star property
10.0 out of 10, Exceptional, (5)
"We thoroughly enjoyed our long weekend stay. We spent great time together in the cozy and spacious living room, as well as enjoying the nice waterfront outdoor areas. The house is unique, well equipped, very clean, and with great attention to details in every room. Host was very proactive and responsive in the communication. Canoes and bikes are available, what we enjoyed. Views from the house were wonderful, including a beautiful sunrise. It was a very relaxing family weekend and we can’t wait...
The price is AED 1,649
AED 3,455 total
includes taxes & fees
12 Nov - 13 Nov
Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi
Firefly Cottage at the Cape, community beach, Hot tub USNA, pets, Holidays, Fun
Exterior detail
Firefly Cottage at the Cape, community beach, Hot tub USNA, pets, Holidays, Fun
10.0 out of 10, Exceptional, (79)
"Firefly Cottage is a wonderful cottage! It’s clean, beautifully decorated, has high quality linens & finishes & fabulous outdoor living spaces. Pat & Ken’s hospitality & thoughtfulness helped to make our stay just perfect. "
Firefly Cottage at the Cape, community beach, Hot tub USNA, pets, Holidays, Fun
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, (202)
"This was a lovely home. I especially appreciated how clean and well-stocked it was. Liz and Tom were very responsive and accommodating! This truly added to a wonderful reunion weekend with friends and family. Thank you!"
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
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, (114)
"Waters edge is just a few steps away to sit and watch boats come in and out. So cute and the most amazing artifacts decorating the place made it even more captivating. Short walk to coffee, food and shopping local. The owner was responsive and kind as well as super easy to work with. Will definitely return."
Location, Location, Location! - W Melson House - Beautiful - 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, (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
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, (132)
"Fine stay pretty quiet off season"
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
Serene spot, West River dock, sunsets, the Bay, only 40 min from Alexandria, DC.
Exterior
Serene spot, West River dock, sunsets, the Bay, only 40 min from Alexandria, DC.
9.8 out of 10, Exceptional, (33)
"A beautiful stay on the Chesapeake."
Serene spot, West River dock, sunsets, the Bay, only 40 min from Alexandria, DC.
"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, (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
Corner lot, walk to stadium, USNA, downtown, cafes, shops, free street parking,
Room
Corner lot, walk to stadium, USNA, downtown, cafes, shops, free street parking,
10.0 out of 10, Exceptional, (24)
"Great location and very clean property. Cyndi was responsive and a great host. Would definitely stay again."
Corner lot, walk to stadium, USNA, downtown, cafes, shops, free street parking,
North Beach Cottage - Walk to Chesapeake Bay
North Beach Vacation Rental | 3BR | 2BA | 1,304 Sq Ft | Steps Required to Access
North Beach Cottage - Walk to Chesapeake Bay
10.0 out of 10, Exceptional, (27)
"This little farmhouse is great. Updated and very clean with an unbelievable location just a short walk to the beach. "
North Beach Cottage - Walk to Chesapeake Bay
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!
Amazing views, short walks to great dining!
"The cottage is lovely—vintage charm in perfect combination with the best modern updates. I was comfortable every minute I spent there..." Darcy - June 2021
Amazing views, short walks to great dining!
10.0 out of 10, Exceptional, (72)
"The place is very comfortable and tucked away on the creek with nice water views. The host was accessible but I didn’t need a thing! The screened porch is a wonderful spot to enjoy my scone and tea fresh from the Great Harvest bakery just up the road. The golden sunset was a bonus each evening. "
Amazing views, short walks to great dining!
The Yellow Cottage on Harness Creek
The Yellow Cottage on Harness Creek
The Yellow Cottage on Harness Creek
10.0 out of 10, Exceptional, (154)
"Great cottage along a quiet road in a private setting. This is just what my family was looking for to escape the busy weekend in Annapolis. Will not hesitate to schedule future stays at this home."
The Yellow Cottage on Harness Creek
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, (168)
"We went to St. Michael’s for a wedding. The cottage was great. Very charming. The location was perfect. We could walk everywhere. We had great communication with the host. He was very accommodating. We will stay there again. "
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
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!
10.0 out of 10, Exceptional, (11)
"We came into town over the weekend for a family funeral. The house was perfect. So cute and clean. Location is great. House has everything you need and comfy beds. Would definitely stay here again."
Updated North Beach Cottage: Pet Friendly!
The Middle Point Cabin in Saint Michaels
Living area
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
Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.
Living area
Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.
10.0 out of 10, Exceptional, (40)
"Nice place to stay for work trip. "
The price is AED 514
AED 1,063 total
includes taxes & fees
10 Nov - 11 Nov
Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.
NEW LISTING! Waterfront cottage, hot tub, fire pit, gated community, pier, kayak
Regularly cleaned and maintained hot tub perfect for cool nights
NEW LISTING! Waterfront cottage, hot tub, fire pit, gated community, pier, kayak
9.8 out of 10, Exceptional, (20)
"This cottage sits in an amazing peaceful location on the water and was an oasis for 5 girlfriends to spend several days together and explore Annapolis. We thoroughly enjoyed the spaces, had plenty of room for all of us to stay. The staircase is a bit off-putting if you are trying to carry anything downstairs but it is very easy to navigate otherwise for 5 50-70 year olds without mobility issues. And you can also go outside and walk down the stairs instead if needed. The beds and seating were...
NEW LISTING! Waterfront cottage, hot tub, fire pit, gated community, pier, kayak
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 Shady Side

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Miscellaneous
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
10.0 out of 10, Exceptional, (20)
"Our group had an amazing time staying on this property. There are many areas inside the house as well as outside the house where you can gather with family and friends. It was very quick and easy to order Ubers/lyfts to the downtow Annapolis area whenever we needed. The house is also convientely located near a small shaping center less than a mile away. We would highly recommend this property!"
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Directly Across from Gate One & Steps from the Waterfront
Private rear courtyard
Directly Across from Gate One & Steps from the Waterfront
10.0 out of 10, Exceptional, (200)
"Incredible location! The process was easy and the house completely suited our needs! We would definitely stay again!"
Directly Across from Gate One & Steps from the Waterfront
Charming Annapolis WaterVIEW Home
3 covered balconies, a ground floor patio, and ceramic and propane grills.
Charming Annapolis WaterVIEW Home
9.6 out of 10, Exceptional, (48)
"This house was perfect for our group of friends especially with infants. Easy check in, comfortable beds and room for pack and plays. Water view is amazing. Definitely worth the rent and would be interested in coming back!"
Charming Annapolis WaterVIEW Home
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 Shady Side cost?
Prices for cottages in Shady Side range between AED 514 and AED 1,649 per night. No matter your budget, you’ll find the perfect place to touch base with nature. These prices were 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.
Why book your cottage in Shady Side with Expedia?
Expedia has some great cottages in Shady Side, so start packing your bags for a memorable vacation on nature’s doorstep. If you’re sticking to a budget, choose how much you’re willing to spend and the preferred star rating of your property. Or, use our filters to search for cottages with a pool or free WiFi. We’ll help you find the right digs whatever your trip looks like.
How can I find cheap cottages in Shady Side?
Expedia can help you easily track down cheap cottages in Shady Side. To reserve a terrific stay in just a few clicks, simply use our handy filter tool to tailor your search results by budget, star rating and amenities.