Hotels in Shady Side

Free cancellation options if plans change

Earn rewards on every night you stay

Save more with Member Prices

Check prices for these dates

Where to stay in Shady Side?

Best Western Kent Narrows Inn
Best Western Kent Narrows Inn
2.5 star property
Grasonville
8.0 out of 10, Very Good, (1,000 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 CNY677
CNY752 total
includes taxes & fees
Apr 28 - Apr 29
Best Western Kent Narrows Inn
Anchored Inn at Hidden Harbour Marina
Anchored Inn at Hidden Harbour Marina
2.5 star property
Deale
9.4 out of 10, Exceptional, (481 reviews)
The price is CNY1,037
CNY1,182 total
includes taxes & fees
Apr 19 - Apr 20
Anchored Inn at Hidden Harbour Marina
Kent Island Resort
Kent Island Resort
3.5 star property
Stevensville
9.2 out of 10, Wonderful, (137 reviews)
The price is CNY880
CNY1,181 total
includes taxes & fees
Apr 20 - Apr 21
Kent Island Resort
Wylder Tilghman Island
Wylder Tilghman Island
2.0 star property
Tilghman
8.8 out of 10, Excellent, (94 reviews)
The price is CNY835
CNY1,218 total
includes taxes & fees
Apr 27 - Apr 28
Wylder Tilghman Island
Quality Inn Grasonville near Kent Island
Quality Inn Grasonville near Kent Island
2.5 star property
Grasonville
7.8 out of 10, Good, (894 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 CNY725
CNY804 total
includes taxes & fees
Apr 20 - Apr 21
Quality Inn Grasonville near Kent Island
Microtel Inn & Suites by Wyndham Gambrills
Microtel Inn & Suites by Wyndham Gambrills
2.0 star property
Gambrills
9.2 out of 10, Wonderful, (1,064 reviews)
Wake up to complimentary continental breakfast at this Gambrills hotel where clean rooms and attentive staff earn top marks. Free WiFi and parking add value, while nearby attractions like Walden Golf Club provide entertainment options just minutes away.
The price is CNY597
CNY681 total
includes taxes & fees
Apr 26 - Apr 27
Microtel Inn & Suites by Wyndham Gambrills
Rips Country Inn
Rips Country Inn
2.5 star property
Bowie
6.6 out of 10, (66 reviews)
Unwind at this welcoming motel in Bowie with a bar/lounge and restaurant for homestyle meals. Enjoy free WiFi and parking while staying close to Prince George's Stadium and Allen Pond Park. Just a 30-minute drive to Fort Meade.
The price is CNY553
CNY624 total
includes taxes & fees
Apr 20 - Apr 21
Rips Country Inn
Rod 'N' Reel Resort
Rod 'N' Reel Resort
4.0 star property
Chesapeake Beach
8.6 out of 10, Excellent, (1,000 reviews)
The price is CNY985
CNY1,230 total
includes taxes & fees
Apr 23 - Apr 24
Rod 'N' Reel Resort
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, (988 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 CNY791
CNY878 total
includes taxes & fees
Apr 20 - Apr 21
Holiday Inn Express Annapolis East-Kent Island by IHG
Comfort Inn Conference Center
Comfort Inn Conference Center
2.5 star property
Bowie
9.2 out of 10, Wonderful, (1,003 reviews)
Tucked away in Bowie with easy access to shopping and restaurants, this hotel offers a seasonal outdoor pool and 24-hour fitness center. Enjoy American cuisine at Chessies Chesapeake Grill after exploring nearby Prince George's Stadium.
The price is CNY675
CNY763 total
includes taxes & fees
Apr 28 - Apr 29
Comfort Inn Conference Center
Candlewood Suites Annapolis by IHG
Candlewood Suites Annapolis by IHG
2.5 star property
Annapolis
8.8 out of 10, Excellent, (228 reviews)
Just 10 minutes from U.S. Naval Academy, this quiet hotel offers free WiFi and parking for easy exploration. After a day of nearby kayaking or hiking trails, unwind in the 24-hour fitness center. Travelers consistently praise the helpful staff and convenient location.
The price is CNY635
CNY757 total
includes taxes & fees
Apr 26 - Apr 27
Candlewood Suites Annapolis by IHG
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 CNY1,238
CNY1,412 total
includes taxes & fees
Apr 20 - Apr 21
Flag House Inn
The Inn at Tacaro Estate
The Inn at Tacaro Estate
5.0 star property
Tracys Landing
9.4 out of 10, Exceptional, (13 reviews)
Escape to this luxurious B&B offering free breakfast, WiFi, and parking near Upper Yough River. Unwind in the hot tub after exploring local attractions on complimentary bikes, then relax on the terrace amid the estate's peaceful atmosphere.
The price is CNY1,757
CNY2,003 total
includes taxes & fees
Apr 23 - Apr 24
The Inn at Tacaro Estate
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 CNY1,152
CNY1,268 total
includes taxes & fees
Apr 21 - Apr 22
Parsonage Inn
St Michaels Inn
St Michaels Inn
2.5 star property
St. Michaels
8.2 out of 10, Very Good, (1,000 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 CNY882
CNY971 total
includes taxes & fees
Apr 20 - Apr 21
St Michaels Inn
The Wildset
The Wildset
2.5 star property
Downtown St. Michaels
9.8 out of 10, Exceptional, (431 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 CNY1,562
CNY1,868 total
includes taxes & fees
Apr 27 - Apr 28
The Wildset
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 CNY1,602
CNY1,763 total
includes taxes & fees
Apr 19 - Apr 20
The Tilghman Island Inn
Best Western Annapolis
Best Western Annapolis
2.5 star property
Annapolis
7.8 out of 10, Good, (1,001 reviews)
The price is CNY552
CNY630 total
includes taxes & fees
Apr 22 - Apr 23
Best Western Annapolis
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 CNY1,263
CNY1,439 total
includes taxes & fees
Apr 20 - Apr 21
134 Prince - Luxury Boutique Hotel
Hilton Garden Inn Kent Island Marina
Hilton Garden Inn Kent Island Marina
3.0 star property
Grasonville
9.0 out of 10, Wonderful, (1,002 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 CNY889
CNY987 total
includes taxes & fees
Apr 27 - Apr 28
Hilton Garden Inn Kent Island Marina
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.

Top landmarks in Shady Side

Check out reviews of Shady Side hotels guests love

Frequently asked questions

How much does a hotel room cost in Shady Side?
You can choose a great hotel in Shady Side from CNY624 with properties to suit all budgets and needs. If you're after an affordable hotel in Shady Side that meets all of your requirements, set your filters and then sort the results by "Price: low to high".
How can I find deals and earn rewards at Shady Side hotels?
Discover great deals on Shady Side hotel stays with Hotels.com. It's also a good idea to look at hotel prices mid-week or during the low season as you're likely to find off-peak deals. And make sure to check out our last-minute deals on Shady Side hotels.
Can I book Shady Side hotels with free cancellation?
It's easy to book a refundable Shady Side hotel on Hotels.com. Simply filter hotels by "Property cancellation options" and select "Fully refundable property". Many hotels offer free cancellation, so you can receive a refund if you need to cancel. Some hotels do require cancelling more than 24 hours before check-in, so double-check your booking beforehand.
What are some popular hotels in central Shady Side?
If you're looking for hotels in central Shady Side, check out The Inn at Tacaro Estate. Travelers love The Inn at Tacaro Estate for its location, as well as the seasonal outdoor pool, hot tub and free full breakfast this bed & breakfast offers. Arundel on the Bay and Hillsmere are some of the most central neighborhoods for your Shady Side vacation.
What hotels do travelers like in Shady Side?
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.

Keep exploring