Hot Shady Side Cottage Rates

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Featured Cottages in Shady Side

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
With a stay at this cottage in St. Michaels, you'll be just steps from Muskrat Park and St. Michaels Marina.
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
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
"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
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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
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
Waterfront River Cottage for 2, dog-friendly

Waterfront River Cottage for 2, dog-friendly

Severna Park
Located in Severna Park, this cottage is on the waterfront, within a 10-minute drive of B&A Trail and Severna Park Golf Center.
Waterfront River Cottage for 2, dog-friendly
Enchanting West River Retreat

Enchanting West River Retreat

West River
This cottage is 19.3 mi (31.1 km) from U.S. Naval Academy and 3.5 mi (5.6 km) from Franklin Point State Park.
Enchanting West River Retreat
6 Mi to Dtwn: Family-friendly Home in Annapolis!

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

3 out of 5
Annapolis
With a stay at this cottage in Annapolis, you'll be within a 10-minute drive of U.S. Naval Academy and Broad Creek Marsh.
6 Mi to Dtwn: Family-friendly Home in Annapolis!
Perfect family/friend getaway. Kayaks and bikes provided.Walk to Herrington Harb

Perfect family/friend getaway. Kayaks and bikes provided.Walk to Herrington Harb

North Beach
Located in North Beach, this cottage is on the waterfront, within a 10-minute drive of Bayside History Museum and Upper Yough River.
Perfect family/friend getaway. Kayaks and bikes provided.Walk to Herrington Harb
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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
59 Cottages
Lowest Price
AU$151
Highest Price
AU$311
Popular accommodation
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!, Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch, "Point of View" Waterfront cottage with panoramic views on Tilghman Island, Relaxing Waterfront Cottage Near St Michaels, Maryland, Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA, Waterfront River Cottage for 2, dog-friendly, Enchanting West River Retreat, 6 Mi to Dtwn: Family-friendly Home in Annapolis!, Perfect family/friend getaway. Kayaks and bikes provided.Walk to Herrington Harb

Top trending hotels in Shady Side

La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway

La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway

2.5 out of 5
55 Hampton Park Blvd, Capitol Heights, MD
Fully refundableReserve now, pay when you stay
The price is AU$151 per night from 28 Feb to 1 Mar
AU$151
includes taxes & fees
28 Feb - 1 Mar
Located in Capitol Heights, La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway is connected to a shopping center, a 3-minute drive from FedEx Field and ...
La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway
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$311 per night from 2 Mar to 3 Mar
AU$311
includes taxes & fees
2 Mar - 3 Mar
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
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$273 per night from 16 Mar to 17 Mar
AU$273
includes taxes & fees
16 Mar - 17 Mar
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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The Westin Annapolis

The Westin Annapolis

4 out of 5
100 Westgate Cir, Annapolis, MD
Fully refundableReserve now, pay when you stay
The price is AU$303 per night from 28 Feb to 1 Mar
AU$303
includes taxes & fees
28 Feb - 1 Mar
With a stay at The Westin Annapolis in Annapolis, you'll be in the historical district, within a 5-minute drive of U.S. Naval Academy and People's Brewer Hill ...
The Westin 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.

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^Subject to availability and chosen travel dates.