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Featured Cottages in Shady Side

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
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
Eastern Shore Waterside Cottage Near St. Michaels

Eastern Shore Waterside Cottage Near St. Michaels

Neavitt
When you stay at this cottage in Neavitt, you'll be on the waterfront and 3 minutes by foot from Neavitt Park.
Eastern Shore Waterside Cottage Near St. Michaels
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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
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
Waterfront dog-friendly home with beach just mins to Downtown Annapolis

Waterfront dog-friendly home with beach just mins to Downtown Annapolis

Annapolis
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.
Waterfront dog-friendly home with beach just mins to Downtown Annapolis
Premier St. Michaels Cottage - T. Blades House -  Walk to Everything in Town

Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town

St Michaels
With a stay at this cottage in St. Michaels, you'll be just steps from Muskrat Park and St. Michaels Marina.
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
NEW LISTING! Waterfront cottage, hot tub, fire pit, gated community, pier, kayak

NEW LISTING! Waterfront cottage, hot tub, fire pit, gated community, pier, kayak

annapolis
With a stay at this cottage, you'll be centrally located in Annapolis, within a 15-minute drive of U.S. Naval Academy and Annapolis Bowl.
NEW LISTING! Waterfront cottage, hot tub, fire pit, gated community, pier, kayak
Amazing views, short walks to great dining!

Amazing views, short walks to great dining!

Annapolis
With a stay at this cottage in Annapolis (West Annapolis), you'll be within a 5-minute drive of U.S. Naval Academy and Navy-Marine Corps Memorial Stadium.
Amazing views, short walks to great dining!
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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
71 Cottages
Lowest Price
AU$151
Highest Price
AU$608
Popular accommodation
Relaxing Waterfront Cottage Near St Michaels, Maryland, Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch, Eastern Shore Waterside Cottage Near St. Michaels, Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA, Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels, Waterfront dog-friendly home with beach just mins to Downtown Annapolis, Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town, NEW LISTING! Waterfront cottage, hot tub, fire pit, gated community, pier, kayak, Amazing views, short walks to great dining!

Top trending hotels in Shady Side

The Cottage

The Cottage

Shady Side
The price is AU$608 per night from 7 Apr to 8 Apr
AU$608
includes taxes & fees
7 Apr - 8 Apr
Located in Shady Side, this vacation home is within a 5-minute drive of Shadyside Park and Captain Avery Museum.
The Cottage
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 13 Apr to 14 Apr
AU$151
includes taxes & fees
13 Apr - 14 Apr
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 Northwest Stadium ...
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$314 per night from 14 Apr to 15 Apr
AU$314
includes taxes & fees
14 Apr - 15 Apr
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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DoubleTree by Hilton Hotel Largo/Washington DC

DoubleTree by Hilton Hotel Largo/Washington DC

4 out of 5
9100 Basil Court, Upper Marlboro, MD
Fully refundableReserve now, pay when you stay
The price is AU$206 per night from 20 Apr to 21 Apr
AU$206
includes taxes & fees
20 Apr - 21 Apr
When you stay at DoubleTree by Hilton Hotel Largo/Washington DC in Upper Marlboro, you'll be in the business district, a 4-minute drive from Northwest Stadium ...
DoubleTree by Hilton Hotel Largo/Washington DC
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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.