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

This weekend
Jun 12 - Jun 14
Next weekend
Jun 19 - Jun 21

Where to stay in Shady Side?

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, (917 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
Jun 14 - Jun 15
Quality Inn Grasonville near Kent Island
Reception

Kent Island Resort

Kent Island Resort
3.5 star property
Stevensville
9.2 out of 10, Wonderful, (142 reviews)
The price is $153
$204 total
includes taxes & fees
Jun 10 - Jun 11
Kent Island Resort
Indoor pool

Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
2.5 star property
Grasonville
8.0 out of 10, Very Good, (1,009 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 $110
$122 total
includes taxes & fees
Jul 6 - Jul 7
Best Western Kent Narrows Inn
Exterior

Knapps Narrows Marina & Inn

Knapps Narrows Marina & Inn
3.0 star property
Sherwood
9.4 out of 10, Exceptional, (386 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
Jun 10 - Jun 11
Knapps Narrows Marina & Inn
Front of property

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 $128
$141 total
includes taxes & fees
Jun 16 - Jun 17
St Michaels Inn
Outdoor wedding area

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 $161
$208 total
includes taxes & fees
Jun 15 - Jun 16
Rod 'N' Reel Resort
Exterior

Microtel Inn & Suites by Wyndham Gambrills

Microtel Inn & Suites by Wyndham Gambrills
2.0 star property
Gambrills
9.2 out of 10, Wonderful, (1,100 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 $102
$116 total
includes taxes & fees
Jun 21 - Jun 22
Microtel Inn & Suites by Wyndham Gambrills
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, (1,001 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 $134
$149 total
includes taxes & fees
Jun 15 - Jun 16
Holiday Inn Express Annapolis East-Kent Island by IHG
Lobby

Candlewood Suites Annapolis by IHG

Candlewood Suites Annapolis by IHG
2.5 star property
Annapolis
9.0 out of 10, Wonderful, (263 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 $93
$111 total
includes taxes & fees
Jun 21 - Jun 22
Candlewood Suites Annapolis by IHG
Front of property

Anchored Inn at Hidden Harbour Marina

Anchored Inn at Hidden Harbour Marina
2.5 star property
Deale
9.4 out of 10, Exceptional, (487 reviews)
The price is $269
$307 total
includes taxes & fees
Jun 10 - Jun 11
Anchored Inn at Hidden Harbour Marina
Basic Single Room | Bathroom | Towels

Rips Country Inn

Rips Country Inn
2.5 star property
Bowie
6.6 out of 10, (68 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 $81
$92 total
includes taxes & fees
Jun 10 - Jun 11
Rips Country Inn
Lobby

Country Inn & Suites by Radisson, Annapolis, MD

Country Inn & Suites by Radisson, Annapolis, MD
3.0 star property
Annapolis
9.0 out of 10, Wonderful, (1,036 reviews)
Enjoy serene accommodations with an indoor pool and hot tub just 10 minutes from U.S. Naval Academy. This hotel offers complimentary breakfast, WiFi, and parking near Annapolis Bowl and Westfield Mall, earning praise for its helpful staff and quiet atmosphere.
The price is $97
$110 total
includes taxes & fees
Jun 21 - Jun 22
Country Inn & Suites by Radisson, Annapolis, MD
Seasonal outdoor pool, pool umbrellas, sun loungers

The Inn at Tacaro Estate

The Inn at Tacaro Estate
5.0 star property
Tracys Landing
9.6 out of 10, Exceptional, (15 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 $330
$376 total
includes taxes & fees
Jun 11 - Jun 12
The Inn at Tacaro Estate
Lobby

Hilton Garden Inn Annapolis

Hilton Garden Inn Annapolis
3.0 star property
Annapolis
8.2 out of 10, Very Good, (1,005 reviews)
The price is $103
$117 total
includes taxes & fees
Jul 6 - Jul 7
Hilton Garden Inn Annapolis
Dinner served

Comfort Inn Conference Center

Comfort Inn Conference Center
2.5 star property
Bowie
9.2 out of 10, Wonderful, (1,009 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 $104
$117 total
includes taxes & fees
Jul 6 - Jul 7
Comfort Inn Conference Center
Dining

Best Western Annapolis

Best Western Annapolis
2.5 star property
Annapolis
7.8 out of 10, Good, (1,009 reviews)
The price is $83
$94 total
includes taxes & fees
Jun 14 - Jun 15
Best Western Annapolis
Front of property

The Wildset

The Wildset
2.5 star property
Downtown St. Michaels
9.8 out of 10, Exceptional, (455 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
Jul 6 - Jul 7
The Wildset
Reception

DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis
4.0 star property
Annapolis
8.6 out of 10, Excellent, (1,014 reviews)
Just a 5-minute drive from U.S. Naval Academy, this hotel offers a 24-hour fitness center and Ports of Call restaurant. Annapolis Harbor Center and Westfield Mall are nearby, with free WiFi and parking for your convenience.
The price is $103
$118 total
includes taxes & fees
Jun 10 - Jun 11
DoubleTree by Hilton Hotel Annapolis
Exterior

Wylder Tilghman Island

Wylder Tilghman Island
2.0 star property
Tilghman
9.0 out of 10, Wonderful, (97 reviews)
The price is $332
$415 total
includes taxes & fees
Jun 11 - Jun 12
Wylder Tilghman Island
Meeting facility

Historic Inns of Annapolis

Historic Inns of Annapolis
3.5 star property
Historic District
9.0 out of 10, Wonderful, (1,868 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 $115
$165 total
includes taxes & fees
Jun 15 - Jun 16
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.
View all properties

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.
See properties

Learn more about Shady Side

Shady Side is well-known for its attractions such as Shadyside Park and Northern Chesapeake Bay.

See all hotels in Shady Side
Aerial view of Annapolis capital city of Maryland state with expensive waterside properties along the Chesapeake Bay, state capital building and naval academy, dreamy blue sky

Check out reviews of Shady Side hotels guests love

Comfort Inn Conference Center

Comfort Inn Conference Center

4/10 Poor
"They’ve been maintaining it but they need major upgrades"
Delena 3-night trip
Posted less than an hour ago
Comfort Inn Conference Center

Frequently asked questions

What hotels do travelers like in Shady Side?
Guests like Historic Inns of Annapolis, Annapolis Waterfront Hotel, Autograph Collection and DoubleTree by Hilton Hotel Annapolis.
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 12 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.