Hot Shady Side Bed & Breakfast Rates

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Featured B&B in Shady Side

George Brooks House B&B

George Brooks House B&B

3 out of 5
24500 Rolles Range Road, St. Michaels, MD
The price is AU$395 per night from 12 Aug to 13 Aug
AU$395
12 Aug - 13 Aug
includes taxes & fees
When you stay at George Brooks House B&B in St. Michaels, you'll be within a 5-minute drive of Chesapeake Bay Maritime Museum.
George Brooks House B&B
Flag House Inn

Flag House Inn

3.5 out of 5
26 Randall St, Annapolis, MD
The price is AU$244 per night from 12 Aug to 13 Aug
AU$244
12 Aug - 13 Aug
includes taxes & fees
With a stay at Flag House Inn, you'll be centrally located in Annapolis, steps from U.S. Naval Academy and Annapolis City Dock.
Flag House Inn
The Oaks Waterfront

The Oaks Waterfront

4 out of 5
25876 Royal Oak Road, Royal Oak, Easton, MD
The price is AU$697 per night from 14 Aug to 15 Aug
AU$697
14 Aug - 15 Aug
includes taxes & fees
Located in Easton, The Oaks Waterfront is on the waterfront, a 5-minute drive from Saint Michaels Village and 6 minutes from St. Michaels Winery.
The Oaks Waterfront
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Laurel Grove Inn on the South

Laurel Grove Inn on the South

3.5 out of 5
2881 South Have Road, Annapolis, MD
With a stay at Laurel Grove Inn on the South in Annapolis, you'll be within a 15-minute drive of U.S. Naval Academy and Broad Creek Marsh.
Laurel Grove Inn on the South
The Inn at Tacaro Estate

The Inn at Tacaro Estate

5 out of 5
6220 Town Point Rd, Tracys Landing, MD
Fully refundableReserve now, pay when you stay
The price is AU$570 per night from 12 Aug to 13 Aug
AU$570
12 Aug - 13 Aug
includes taxes & fees
Located in Tracys Landing, The Inn at Tacaro Estate is in a rural location, within a 15-minute drive of Upper Yough River and Bayside History Museum.
The Inn at Tacaro Estate
Legacy Villa

Legacy Villa

4 out of 5
12605 Brooke Lane, Upper Marlboro, MD
The price is AU$491 per night from 12 Aug to 13 Aug
AU$491
12 Aug - 13 Aug
includes taxes & fees
Located in Upper Marlboro, Legacy Villa is within a 15-minute drive of Show Place Arena and Patuxent River.
Legacy Villa
Parsonage Inn

Parsonage Inn

3.5 out of 5
210 North Talbot Street, St. Michaels, MD
The price is AU$386 per night from 12 Aug to 13 Aug
AU$386
12 Aug - 13 Aug
includes taxes & fees
With a stay at Parsonage Inn in St. Michaels, you'll be in the historical district, within a 15-minute walk of Chesapeake Bay Maritime Museum and St. Michaels ...
Parsonage Inn
Inn at Horn Point

Inn at Horn Point

3 out of 5
534 Burnside Street, Annapolis, MD
The price is AU$601 per night from 12 Aug to 13 Aug
AU$601
12 Aug - 13 Aug
includes taxes & fees
In the heart of Annapolis, Inn at Horn Point is within a 5-minute drive of Annapolis Maritime Museum and Annapolis City Dock.
Inn at Horn Point
Black Walnut Point Inn

Black Walnut Point Inn

3.5 out of 5
4417 Black Walnut Point Road, Tilghman, MD
Located in Tilghman, Black Walnut Point Inn is by the sea, a 4-minute drive from Tilghman Watermen’s Museum and 6 minutes from Talbot County Library Tilghman ...
Black Walnut Point Inn
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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.

B&Bs in Shady Side

We know why you’re here. You forgot something, though we’re not sure what. A birthday or an anniversary, maybe. And this time, a bouquet of fresh flowers and a homemade breakfast in bed aren’t going to cut it. You’re determined your special someone is going to feel like the centre of the universe on whatever special day you have coming up—that’s where lastminute.com.au comes in, and that’s also where Shady Side B&B accommodation comes in.

You can’t go wrong with a romantic getaway to a bed and breakfast. It’s the stuff of poetry, novels, and of course, any good rom-com. You can snuggle under the covers all morning if you like, although the delicious aromas of a home-cooked breakfast are likely to get you out of bed. Even a cheap B&B will have a delectable morning meal included—and you don’t have to make it yourself. After all, that’s kind of the whole point. Add in a boutique feel and the charming Shady Side vibes, and you’ll get why B&Bs are great for couples, families, and even your doggo. Yes, pet-friendly B&Bs are a thing, and although we can’t guarantee the dog will get his own breakfast, you’re more than happy to share, aren’t you?

Hey, if you’re gonna stay in a B and B in Shady Side, you want it to be awesome, don’t you? Well then, check out lastminute.com.au and get to planning. We’ve got everything from luxury to budget bed & breakfasts, and our great prices leave you plenty of cash to splash in Shady Side. No need to thank us—we know how great we are.

Shady Side B&B essential information

Accommodation
11 B&B
Lowest Price
AU$244
Highest Price
AU$697
Popular accommodation
George Brooks House B&B, Flag House Inn, The Oaks Waterfront, Laurel Grove Inn on the South, The Inn at Tacaro Estate, Legacy Villa, Parsonage Inn, Inn at Horn Point, Black Walnut Point Inn

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.