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Featured Cottages in Shady Side

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

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

Annapolis
With a stay at this cottage in Annapolis (Cape Saint Claire), you'll be within a 15-minute drive of U.S. Naval Academy and Sandy Point State Park.
Firefly Cottage at the Cape, Community beach, Hot tub, USNA, Pets, summer fun!
Relaxing Waterfront Cottage Near St Michaels, Maryland

Relaxing Waterfront Cottage Near St Michaels, Maryland

Wittman
Located in Wittman, this cottage is on the waterfront, within a 15-minute drive of Wittman Park and CL Open Field.
Relaxing Waterfront Cottage Near St Michaels, Maryland
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels

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

St Michaels
With a stay at this cottage in St. Michaels, you'll be just steps from Muskrat Park and St. Michaels Marina.
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
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The Yellow Cottage on Harness Creek

The Yellow Cottage on Harness Creek

Annapolis
With a stay at this cottage in Annapolis (Hillsmere), you'll be within a 15-minute drive of U.S. Naval Academy and Maryland Quiet Waters Park.
The Yellow Cottage on Harness Creek
"Point of View" Waterfront cottage with panoramic views on Tilghman Island

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

Tilghman Island
With a stay at this cottage in Tilghman, you'll be within a 10-minute walk of Kronsberg Park and Talbot County Library Tilghman Branch.
"Point of View" Waterfront cottage with panoramic views on Tilghman Island
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch

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

Saint Michaels
With a stay at this cottage in St. Michaels, you'll be just steps from Higgins Yacht Yard and Marina and St. Michaels Marina.
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Quick walk to the beach! Fire pit, Corn hole, Games & More!

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

North Beach
With a stay at this vacation home in North Beach, you'll be a 4-minute walk from Bayside History Museum and within a 5-minute drive of Chesapeake Beach Water ...
Quick walk to the beach! Fire pit, Corn hole, Games & More!
Accessible, Screened-in porch, Sauna, Fire Pit, Dog Friendly

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

Stevensville
Located in Stevensville, this cottage is a 2-minute drive from Romancoke Wharf County Park and 10 minutes from Matapeake State Park.
Accessible, Screened-in porch, Sauna, Fire Pit, Dog Friendly
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA

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

Edgewater
With a stay at this cottage, you'll be centrally located in Edgewater, within a 15-minute drive of Sand Point Marsh and South River Golf Links.
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
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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.

Shady Side Budget-Friendly Cottage Accommodation

Adulting can be rough. You love your job, and your sweetheart is the best, but next time someone says “think outside the box” or “we’ll park that”, you just might throw a fit. When was the last time you had one of those really deep convos with your person, anyway? It sounds like you need a holiday, and you’ve come to the right place. Budget-friendly cottage accommodation in Shady Side will have you feeling like your SO is the peanut butter to your jelly again in no time.

We’re not here to tell you what you want—we think you already know. You want a spot that’s totally relaxing, but still has plenty of things to do, you know, if you feel like it. You want great scenery, and you want food that’s worthy of your number one hashtag: #nomnom. Cottage getaways to Shady Side definitely fit the bill.

Yes, the scenery is stunning, but on a romantic cottage holiday, it’s what’s inside that counts. Today’s cottages are filled with those little touches of luxury, like fine bath amenities and gourmet kitchens. You know the saying about how the way to someone’s heart is through their stomach? Don’t miss your chance to impress this holiday—even if that just means remembering their favourite wine. (Hey, that still counts!)

Before you can check out entirely, you’ve got a few last bits of adulting to take care of: pick your perfect cheap country cottage in Shady Side, then type up that email to your boss and request your annual leave. We’re sure they’ll understand.

Shady Side Cottages essential information

Accommodation
73 Cottages
Lowest Price
AU$271
Highest Price
AU$271
Popular accommodation
Firefly Cottage at the Cape, Community beach, Hot tub, USNA, Pets, summer fun!, Relaxing Waterfront Cottage Near St Michaels, Maryland, Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels, The Yellow Cottage on Harness Creek, "Point of View" Waterfront cottage with panoramic views on Tilghman Island, Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch, Quick walk to the beach! Fire pit, Corn hole, Games & More!, Accessible, Screened-in porch, Sauna, Fire Pit, Dog Friendly, Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA

Top trending hotels in Shady Side

Bay views with kayaks, bikes, fire pit, crabbing and more

Bay views with kayaks, bikes, fire pit, crabbing and more

Shady Side
With a stay at this vacation home in Shady Side, you'll be within a 5-minute drive of Shadyside Park and Captain Avery Museum.
Bay views with kayaks, bikes, fire pit, crabbing and more
Calloway Drive Retreat | House in Shady Side

Calloway Drive Retreat | House in Shady Side

Shady Side
When you stay at this vacation home in Shady Side, you'll be near the beach and 5 minutes by car from Franklin Point State Park.
Calloway Drive Retreat | House in Shady Side
Historic Inns of Annapolis

Historic Inns of Annapolis

3.5 out of 5
58 State Circle, Annapolis, MD
Fully refundableReserve now, pay when you stay
With a stay at Historic Inns of Annapolis, you'll be centrally located in Annapolis, steps from The Colonial Players and Thurgood Marshall Memorial.
Historic Inns of Annapolis
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Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

4 out of 5
126 West St, Annapolis, MD
Fully refundableReserve now, pay when you stay
The price is AU$271 per night from 17 Aug to 18 Aug
AU$271
17 Aug - 18 Aug
includes taxes & fees
With a stay at Graduate by Hilton Annapolis, you'll be centrally located in Annapolis, within a 5-minute drive of U.S. Naval Academy and Annapolis Civil Rights ...
Graduate by Hilton Annapolis
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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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^Subject to availability and chosen travel dates.