Hotels in Shady Side

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Check prices for these dates

Tonight
Apr 24 - Apr 25
Tomorrow
Apr 25 - Apr 26
This weekend
Apr 24 - Apr 26
Next weekend
May 1 - May 3

Where to stay in Shady Side?

Luxury Cottage, 1 Bedroom, Kitchen, River View | Private kitchen
The Oaks Waterfront
The Oaks Waterfront
4.0 star property
Easton
10.0 out of 10, Exceptional, (41 reviews)
Overlooking the water from a rooftop terrace, this charming B&B in Easton offers massage services and seasonal poolside relaxation. Explore nearby Saint Michaels Village after enjoying free breakfast. The garden setting and helpful staff create a memorable Eastern Shore experience.
The price is $489
$538 total
includes taxes & fees
Apr 26 - Apr 27
The Oaks Waterfront
Front of property
St Michaels Inn
St Michaels Inn
2.5 star property
St. Michaels
8.2 out of 10, Very Good, (1,002 reviews)
Escape to this quiet retreat with hiking trails and a garden terrace. Just minutes from Saint Michaels Village and Classic Motor Museum, this hotel offers free breakfast, WiFi and parking. Guests consistently praise the helpful staff and clean accommodations.
The price is $135
$149 total
includes taxes & fees
Apr 26 - Apr 27
St Michaels Inn
Breakfast, lunch, dinner served; ocean views
Inn at Perry Cabin
Inn at Perry Cabin
5.0 star property
Downtown St. Michaels
9.6 out of 10, Exceptional, (380 reviews)
Set along Maryland's Eastern Shore, this luxurious retreat features a marina, golf course, and serene spa treatments. Enjoy cocktails at the poolside bar before savoring locally-inspired cuisine at Stars restaurant. The helpful staff ensures a peaceful waterfront getaway.
The price is $603
$663 total
includes taxes & fees
Apr 30 - May 1
Inn at Perry Cabin
Front of property
The Wildset
The Wildset
2.5 star property
Downtown St. Michaels
9.8 out of 10, Exceptional, (434 reviews)
Soak in the charm of this waterfront getaway near Higgins Yacht Yard and Marina. Enjoy complimentary breakfast before exploring Muskrat Park. After sightseeing, unwind with drinks at the bar or grab a bite at the on-site café.
The price is $229
$274 total
includes taxes & fees
May 5 - May 6
The Wildset
Porch
Parsonage Inn
Parsonage Inn
3.5 star property
Downtown St. Michaels
9.2 out of 10, Wonderful, (133 reviews)
Immerse yourself in small-town charm at this cozy B&B featuring a lovely garden and terrace. Enjoy complimentary full breakfast daily before exploring nearby hiking trails or Perry Cabin Park. Free WiFi and parking complete your Eastern Shore retreat.
The price is $180
$198 total
includes taxes & fees
Apr 26 - Apr 27
Parsonage Inn
Suite, 1 Queen Bed, Non Smoking | In-room safe, iron/ironing board, free WiFi, bed sheets
Quality Inn Grasonville near Kent Island
Quality Inn Grasonville near Kent Island
2.5 star property
Grasonville
7.8 out of 10, Good, (898 reviews)
Discover quiet comfort at this Grasonville hotel with complimentary buffet breakfast, WiFi, and parking. Take a refreshing swim in the seasonal outdoor pool after exploring nearby Chesapeake Bay Environmental Center. Friendly staff and clean rooms await just 50 minutes from BWI Airport.
The price is $106
$118 total
includes taxes & fees
May 18 - May 19
Quality Inn Grasonville near Kent Island
Terrace/patio
Hilton Garden Inn Kent Island Marina
Hilton Garden Inn Kent Island Marina
3.0 star property
Grasonville
9.0 out of 10, Wonderful, (1,001 reviews)
Overlooking the bay in Grasonville, this hotel offers a refreshing indoor pool, restaurant, and bar. Unwind on the terrace after exploring nearby Chesapeake Bay Environmental Center, with convenient room service and in-room microwaves for added comfort.
The price is $130
$145 total
includes taxes & fees
Apr 28 - Apr 29
Hilton Garden Inn Kent Island Marina
Exterior
Holiday Inn Express Annapolis East-Kent Island by IHG
Holiday Inn Express Annapolis East-Kent Island by IHG
2.5 star property
Grasonville
9.2 out of 10, Wonderful, (993 reviews)
Wake up to tranquil Chesapeake Bay vistas at this quiet waterfront retreat. Steps from the scenic bike trail with an inviting seasonal pool for afternoon dips. Complimentary breakfast fuels adventures to nearby Environmental Center and Queenstown Harbor Golf Club.
The price is $110
$122 total
includes taxes & fees
Apr 26 - Apr 27
Holiday Inn Express Annapolis East-Kent Island by IHG
Indoor pool
Best Western Kent Narrows Inn
Best Western Kent Narrows Inn
2.5 star property
Grasonville
8.0 out of 10, Very Good, (1,002 reviews)
Embrace coastal charm at this hotel in Grasonville, where superior rooms frame magical sunset vistas over the water. After exploring nearby walking trails, unwind in the indoor pool, hot tub, or sauna. Free breakfast fuels adventures to local restaurants.
The price is $108
$120 total
includes taxes & fees
May 3 - May 4
Best Western Kent Narrows Inn
Terrace/patio
Hyatt Place Kent Narrows & Marina
Hyatt Place Kent Narrows & Marina
3.0 star property
Grasonville
9.4 out of 10, Exceptional, (749 reviews)
Experience coastal luxury at this modern Kent Narrows hotel with marina access. A 24-hour fitness center, bar, and café await after exploring nearby Chesapeake Bay Environmental Center. The helpful staff and convenient location make for an exceptional stay.
The price is $179
$199 total
includes taxes & fees
Apr 26 - Apr 27
Hyatt Place Kent Narrows & Marina
Exterior
Knapps Narrows Marina & Inn
Knapps Narrows Marina & Inn
3.0 star property
Sherwood
9.4 out of 10, Exceptional, (380 reviews)
Set on the bay, this Tilghman hotel offers waterfront relaxation with complimentary breakfast and free parking. Explore by kayak or bicycle with onsite rentals, or unwind at the marina. Each room includes convenient refrigerators and microwaves for added comfort.
The price is $150
$165 total
includes taxes & fees
May 3 - May 4
Knapps Narrows Marina & Inn
Exterior
Wylder Tilghman Island
Wylder Tilghman Island
2.0 star property
Tilghman
8.8 out of 10, Excellent, (94 reviews)
The price is $191
$254 total
includes taxes & fees
Apr 30 - May 1
Wylder Tilghman Island
Outdoor banquet area
The Tilghman Island Inn
The Tilghman Island Inn
3.5 star property
Tilghman
9.6 out of 10, Exceptional, (127 reviews)
This waterfront inn on Tilghman Island features a seasonal outdoor pool and welcoming restaurant with bar. Near local marinas, it offers free breakfast, WiFi, and parking. Guests can relax on the terrace or stroll through the garden while experiencing exceptional staff service.
The price is $235
$259 total
includes taxes & fees
Apr 26 - Apr 27
The Tilghman Island Inn
Reception
Kent Island Resort
Kent Island Resort
3.5 star property
Stevensville
9.2 out of 10, Wonderful, (137 reviews)
The price is $136
$185 total
includes taxes & fees
Apr 27 - Apr 28
Kent Island Resort
Front of property - evening/night
The Inn at Chesapeake Bay Beach Club
The Inn at Chesapeake Bay Beach Club
4.0 star property
Stevensville
9.4 out of 10, Exceptional, (448 reviews)
Escape to this serene Chesapeake retreat featuring an outdoor pool and indulgent spa treatments. Just minutes from Northern Chesapeake Bay and Paul Reed Smith Guitars, the hotel offers a cafe, 24-hour fitness center, and attentive staff that guests consistently praise.
The price is $216
$265 total
includes taxes & fees
Apr 26 - Apr 27
The Inn at Chesapeake Bay Beach Club
Outdoor wedding area
Rod 'N' Reel Resort
Rod 'N' Reel Resort
4.0 star property
Chesapeake Beach
8.6 out of 10, Excellent, (1,002 reviews)
The price is $142
$177 total
includes taxes & fees
May 18 - May 19
Rod 'N' Reel Resort
Premium bedding, down comforters, pillowtop beds, in-room safe
Annapolis Waterfront Hotel, Autograph Collection
Annapolis Waterfront Hotel, Autograph Collection
4.0 star property
Historic District
8.8 out of 10, Excellent, (920 reviews)
Wake up to shimmering harbor vistas at this waterfront gem steps from U.S. Naval Academy. After breakfast at Pussers Caribbean Grille, explore nearby Ego Alley or work out in the 24-hour fitness center while luxury yachts drift by.
The price is $209
$238 total
includes taxes & fees
Apr 26 - Apr 27
Annapolis Waterfront Hotel, Autograph Collection
Lobby lounge
Flag House Inn
Flag House Inn
3.5 star property
Historic District
9.2 out of 10, Wonderful, (94 reviews)
Warm B&B located steps from the Naval Academy with free breakfast featuring local cuisine. Enjoy free WiFi while exploring nearby attractions like John Smith House and Annapolis City Dock. Valet parking is also available.
The price is $182
$207 total
includes taxes & fees
Apr 26 - Apr 27
Flag House Inn
Exterior
134 Prince - Luxury Boutique Hotel
134 Prince - Luxury Boutique Hotel
2.5 star property
Annapolis
9.8 out of 10, Exceptional, (34 reviews)
Immerse yourself in Annapolis at this luxury boutique hotel near the City Dock and John Smith House. Enjoy free breakfast featuring local cuisine each morning and complimentary WiFi throughout your stay while exploring Maryland's picturesque capital.
The price is $196
$224 total
includes taxes & fees
Apr 27 - Apr 28
134 Prince - Luxury Boutique Hotel
Meeting facility
Historic Inns of Annapolis
Historic Inns of Annapolis
3.5 star property
Historic District
9.0 out of 10, Wonderful, (1,839 reviews)
Nestled in the heart of Annapolis, this historic hotel offers easy access to the Naval Academy. Unwind in comfortable beds after exploring nearby attractions, or enjoy a drink at the bar. The helpful staff and clean rooms earn high praise from travelers.
The price is $159
$215 total
includes taxes & fees
May 25 - May 26
Historic Inns of Annapolis
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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Top landmarks in Shady Side

Shadyside Park

Shadyside Park is 0.4 mi (0.6 km) from central Shady Side, why not stop by during your stay. Our travelers also like this walkable area for its port and restaurants.If you like Shadyside Park, you'll love Maryland Quiet Waters Park and Ellen O. Moyer Nature Park at Back Creek, both just a short drive away.
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Captain Avery Museum

Captain Avery Museum is 0.5 mi (0.8 km) from central Shady Side, why not stop by during your stay. Why not take a stroll along the port and watch the sunset while you're here? If you want to experience more of the culture Shady Side has to offer, head to Shadyside Park, Triton Beach, and Smithsonian Environmental Research Center.
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Check out reviews of Shady Side hotels guests love

Microtel Inn & Suites by Wyndham Gambrills

Microtel Inn & Suites by Wyndham Gambrills

8/10 Good
"Clean rooms. "
Roberto 4-night trip
Posted 2 hours ago
Microtel Inn & Suites by Wyndham Gambrills

Frequently asked questions

What hotels do travelers like in Shady Side?
Guests like Graduate by Hilton Annapolis, Historic Inns of Annapolis and Hilton Garden Inn Annapolis Downtown.
Can I book a refundable hotel in Shady Side?
If you need the flexibility to change your plans to Shady Side, most properties provide refundable* bookable rates. You can find these accommodations by searching our site and using the "fully refundable" filter to narrow down the results.
Where can I stay in Shady Side if I want a vacation rental instead of a hotel?
If you want to find a good alternative to a hotel, browse our selection of 11 vacation homes.
What will the weather in Shady Side be like during my vacation?
The warmest months in Shady Side are usually July and August with an average temp of 75°F. January and February are the chilliest months when the average temp is 40°F. The rainiest months are July and August.
Why should I book my Shady Side accommodation with Hotels.com?
There are plenty of reasons to book your Shady Side travel with us: our free cancellations on selected hotels gives you the flexibility you're looking for, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™* on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.