Hot Shady Side Bed & Breakfast Rates

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Featured B&B in Shady Side

Flag House Inn

Flag House Inn

3.5 out of 5
26 Randall St, Annapolis, MD
The price is AU$326 per night from 24 Dec to 25 Dec
AU$326
includes taxes & fees
24 Dec - 25 Dec
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
Parsonage Inn

Parsonage Inn

3.5 out of 5
210 North Talbot Street, St. Michaels, MD
The price is AU$317 per night from 6 Jan to 7 Jan
AU$317
includes taxes & fees
6 Jan - 7 Jan 2025
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
The Oaks Waterfront

The Oaks Waterfront

4 out of 5
25876 Royal Oak Road, Royal Oak, Easton, MD
The price is AU$679 per night from 23 Jan to 24 Jan
AU$679
includes taxes & fees
23 Jan - 24 Jan 2025
Located in Easton, The Oaks Waterfront is on the waterfront, within a 10-minute drive of St. Michaels Winery and St. Michaels Museum.
The Oaks Waterfront
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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$282 per night from 6 Jan to 7 Jan
AU$282
includes taxes & fees
6 Jan - 7 Jan 2025
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
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$514 per night from 24 Dec to 25 Dec
AU$514
includes taxes & fees
24 Dec - 25 Dec
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
Black Walnut Point Inn

Black Walnut Point Inn

3.5 out of 5
4417 Black Walnut Point Road, Tilghman, MD
When you stay at Black Walnut Point Inn in Tilghman, you'll be by the sea and within a 5-minute drive of Tilghman Watermen’s Museum.
Black Walnut Point Inn
Inn at Horn Point

Inn at Horn Point

3 out of 5
534 Burnside Street, Annapolis, MD
The price is AU$676 per night from 9 Jan to 10 Jan
AU$676
includes taxes & fees
9 Jan - 10 Jan 2025
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
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 Annapolis Inn

The Annapolis Inn

4 out of 5
144 Prince George St, Annapolis, MD
With a stay at The Annapolis Inn in Annapolis (Historic District), you'll be steps from U.S. Naval Academy and John Smith House.
The Annapolis 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
9 B&B
Lowest Price
AU$154
Highest Price
AU$679
Popular accommodation
Flag House Inn, Parsonage Inn, The Oaks Waterfront, George Brooks House B&B, The Inn at Tacaro Estate, Black Walnut Point Inn, Inn at Horn Point, Laurel Grove Inn on the South, The Annapolis Inn

Top trending hotels in Shady Side

Crowne Plaza Annapolis, an IHG Hotel

Crowne Plaza Annapolis, an IHG Hotel

3.5 out of 5
173 Jennifer Rd, Annapolis, MD
Fully refundable
The price is AU$208 per night from 13 Jan to 14 Jan
AU$208
includes taxes & fees
13 Jan - 14 Jan 2025
Located in Annapolis, Crowne Plaza Annapolis, an IHG Hotel is a 3-minute walk from Westfield Annapolis Mall and 14 minutes by foot from Anne Arundel Medical ...
Crowne Plaza Annapolis, an IHG Hotel
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$154 per night from 2 Jan to 3 Jan
AU$154
includes taxes & fees
2 Jan - 3 Jan 2025
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
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$252 per night from 30 Dec to 31 Dec
AU$252
includes taxes & fees
30 Dec - 31 Dec
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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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$334 per night from 26 Dec to 27 Dec
AU$334
includes taxes & fees
26 Dec - 27 Dec
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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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.