Hot Shady Side Cottage Rates
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Featured Cottages in Shady Side
Amazing views, short walks to great dining!
Relaxing Waterfront Cottage Near St Michaels, Maryland
Firefly Cottage at the Cape, community beach, Hot tub, USNA games, Holidays,
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
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
NEW LISTING! Waterfront cottage, hot tub, fire pit, gated community, pier, kayak
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 | 57 Cottages |
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Lowest Price | AU$154 |
Highest Price | AU$334 |
Popular accommodation | Amazing views, short walks to great dining!, Relaxing Waterfront Cottage Near St Michaels, Maryland, Firefly Cottage at the Cape, community beach, Hot tub, USNA games, Holidays, , 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, Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA, John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!, Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town, NEW LISTING! Waterfront cottage, hot tub, fire pit, gated community, pier, kayak |
Popular Cottages in 2025
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More accommodations in Shady Side
Top trending hotels in Shady Side
Crowne Plaza Annapolis, an IHG Hotel
La Quinta Inn & Suites by Wyndham DC Metro Capital Beltway
Graduate by Hilton Annapolis
Historic Inns of Annapolis
More ways to explore Shady Side
Top picks
**Terms and Conditions apply.
^Subject to availability and chosen travel dates.