Hot Shady Side Cottage Rates

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Featured Cottages in Shady Side

Relaxing Waterfront Cottage Near St Michaels, Maryland

Relaxing Waterfront Cottage Near St Michaels, Maryland

Wittman MD
Located in Wittman, this cottage is on the waterfront, within a 15-minute drive of Wittman Park and CL Open Field.
Opens in a new windowRelaxing Waterfront Cottage Near St Michaels, Maryland
"Point of View" Waterfront cottage with panoramic views on Tilghman Island

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

Tilghman Island MD
With a stay at this cottage in Tilghman, you'll be within a 10-minute walk of Chesapeake Bay and Kronsberg Park.
Opens in a new window"Point of View" Waterfront cottage with panoramic views on Tilghman Island
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels

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

St Michaels MD
With a stay at this cottage in St. Michaels (Downtown St. Michaels), you'll be steps from Muskrat Park and St. Michaels Marina.
Opens in a new windowLocation, Location, Location! - W Melson House - Beautiful - In Town St Michaels
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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 MD
With a stay at this cottage in St. Michaels (Downtown St. Michaels), you'll be steps from Higgins Yacht Yard and Marina and St. Michaels Marina.
Opens in a new windowCarpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!

John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!

Saint Michaels MD
With a stay at this cottage in St. Michaels (Downtown St. Michaels), you'll be steps from Muskrat Park and St. Michaels Marina.
Opens in a new windowJohn Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
Serene spot, West River dock, sunsets, the Bay, only 40 min from Alexandria, DC.

Serene spot, West River dock, sunsets, the Bay, only 40 min from Alexandria, DC.

West River MD
This cottage is 19.1 mi (30.8 km) from U.S. Naval Academy and 3.3 mi (5.2 km) from Franklin Point State Park.
Opens in a new windowSerene spot, West River dock, sunsets, the Bay, only 40 min from Alexandria, DC.
Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.

Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.

Owings MD
With a stay at this cottage in Owings, you'll be on a river, a 3-minute walk from Fridays Creek Winery and a 4-minute drive from Patuxent River.
Opens in a new windowRelaxing, peaceful house in Calvert County, Md close to beach towns and DC.
 Artists, writers & creative minds  IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE

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

Tilghman Island MD
With a stay at this cottage in Tilghman, you'll be on the waterfront, within a 5-minute drive of Chesapeake Bay and Northern Chesapeake Bay.
Opens in a new window Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE
Beachfront Home Minutes to Downtown Annapolis Dogs OK

Beachfront Home Minutes to Downtown Annapolis Dogs OK

Annapolis MD
When you stay at this cottage in Annapolis, you'll be on the beach, within a 10-minute walk of Annapolis Sailing School and Annapolis Landing Marina.
Opens in a new windowBeachfront Home Minutes to Downtown Annapolis Dogs OK
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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
76 Cottages
Lowest Price
AU$139
Highest Price
AU$241
Popular accommodation
Relaxing Waterfront Cottage Near St Michaels, Maryland, "Point of View" Waterfront cottage with panoramic views on Tilghman Island, Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels, Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch, John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!, Serene spot, West River dock, sunsets, the Bay, only 40 min from Alexandria, DC., Relaxing, peaceful house in Calvert County, Md close to beach towns and DC., Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE, Beachfront Home Minutes to Downtown Annapolis Dogs OK

Top trending hotels in Shady Side

Comfort Inn Largo-Washington DC East

Comfort Inn Largo-Washington DC East

3 out of 5
9421 Largo Drive West Upper Marlboro MD
Fully refundable
The price is AU$139 per night from 25 May to 26 May
AU$139
25 May - 26 May
includes taxes & fees
With a stay at Comfort Inn Largo-Washington DC East in Upper Marlboro, you'll be 2.1 mi (3.3 km) from Northwest Stadium and 10.9 mi (17.6 km) from University ...
Opens in a new windowComfort Inn Largo-Washington DC East
La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway

La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway

3 out of 5
55 Hampton Park Blvd Capitol Heights MD
Fully refundableReserve now, pay when you stay
The price is AU$141 per night from 17 May to 18 May
AU$141
17 May - 18 May
includes taxes & fees
With a stay at La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway in Capitol Heights, you'll be 2 mi (3.2 km) from Northwest Stadium and 9.3 mi (15 km) ...
Opens in a new windowLa Quinta Inn & Suites by Wyndham DC Metro Capital Beltway
DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

4 out of 5
210 Holiday Court Annapolis MD
Fully refundableReserve now, pay when you stay
The price is AU$179 per night from 31 May to 1 June
AU$179
31 May - 1 June
includes taxes & fees
With a stay at DoubleTree by Hilton Hotel Annapolis in Annapolis, you'll be in the business district, within a 5-minute drive of U.S. Naval Academy and The Kunta ...
Opens in a new windowDoubleTree by Hilton Hotel Annapolis
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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
The price is AU$241 per night from 31 May to 1 June
AU$241
31 May - 1 June
includes taxes & fees
With a stay at Historic Inns of Annapolis, you'll be centrally located in Annapolis, steps from The Colonial Players and Thurgood Marshall Memorial.
Opens in a new windowHistoric Inns of Annapolis
Don't see what you're looking for?
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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.

Top Picks

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