Find Hotels with a Pool in Shady Side, MD

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Check availability on Shady Side Hotels with a Pool

Tonight
3 Dec - 4 Dec
Tomorrow
4 Dec - 5 Dec
This weekend
5 Dec - 7 Dec
Next weekend
12 Dec - 14 Dec

Top Shady Side Hotels with a Pool

Front of property
The Oaks Waterfront

The Oaks Waterfront

4.0 star property
Easton
10.0 out of 10, Exceptional, (41)
"Loved the Oaks! Fabulous accommodations and excellent staff"
United States
Barbara
The price is AED 1,517
AED 1,669 total
includes taxes & fees
4 Dec - 5 Dec
The Oaks Waterfront
Seasonal outdoor pool, open 10:00 AM to 7:00 PM, pool umbrellas
St Michaels Inn

St Michaels Inn

2.5 star property
St. Michaels
8.2 out of 10, Very Good, (1001)
"clean and comfy, friendly staff"
United States
Tamara
The price is AED 384
AED 422 total
includes taxes & fees
4 Dec - 5 Dec
St Michaels Inn
Outdoor pool
Inn at Perry Cabin

Inn at Perry Cabin

5.0 star property
St. Michaels
9.6 out of 10, Exceptional, (370)
"Friendly and attentive staff, good cleaning services"
United States
Nathan
The price is AED 1,322
AED 1,600 total
includes taxes & fees
7 Dec - 8 Dec
Inn at Perry Cabin
Porch
Parsonage Inn

Parsonage Inn

3.5 star property
St. Michaels
9.2 out of 10, Wonderful, (130)
"Hosts were wonderful, breakfast was delicious, everything was walkable "
United States
Nathaly
The price is AED 735
AED 808 total
includes taxes & fees
1 Jan - 2 January 2026
Parsonage Inn
Exterior
George Brooks House B&B

George Brooks House B&B

3.0 star property
St. Michaels
8.6 out of 10, Excellent, (65)
"Gorgeous quaint historic house. Friendly owner, close to town "
United States
Christopher
The price is AED 562
AED 618 total
includes taxes & fees
1 Jan - 2 January 2026
George Brooks House B&B
Lobby
Quality Inn

Quality Inn

2.5 star property
Grasonville
7.8 out of 10, Good, (858)
"room was nice breakfast was good and the staff was very friendly and helpful. "
United States
Esai
The price is AED 312
AED 347 total
includes taxes & fees
7 Dec - 8 Dec
Quality Inn
Indoor pool, open 5 AM to 11 PM, sun loungers
Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina

3.0 star property
Grasonville
9.0 out of 10, Wonderful, (1001)
"Easy parking and check in. Conveniently located within walking distance of some great seafood restaurants. Always an enjoyable stay"
United States
Roberta
The price is AED 379
AED 421 total
includes taxes & fees
21 Dec - 22 Dec
Hilton Garden Inn Kent Island Marina
Seasonal outdoor pool, open 9 AM to 9 PM, pool umbrellas, sun loungers
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, (929)
"nice, clean, up to date, budget friendly hotel"
United States
mike
The price is AED 291
AED 323 total
includes taxes & fees
7 Dec - 8 Dec
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, (1001)
"Our room was clean, smelled great, and the breakfast was good with many options."
United States
Eric
The price is AED 308
AED 342 total
includes taxes & fees
10 Dec - 11 Dec
Best Western Kent Narrows Inn
Indoor pool, sun loungers
Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina

3.0 star property
Grasonville
9.4 out of 10, Exceptional, (668)
"Great view, good ambiance all around"
United States
Dianne
The price is AED 426
AED 473 total
includes taxes & fees
7 Dec - 8 Dec
Hyatt Place Kent Narrows & 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.
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Top Shady Side Hotel Reviews

DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

10/10 Excellent
"Great Hotel, Amazing location, very clean, everyone is friendly and helpful. Always recommend staying here if you are in Annapolis"
Tatiana 2-night trip
Posted 1 day ago
DoubleTree by Hilton Hotel Annapolis

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Frequently asked questions

What are some accommodations with pools in Shady Side?
DoubleTree by Hilton Hotel Largo/Washington DC: Hotel located near Northwest Stadium. Features free self parking, an indoor pool, and a 24-hour fitness center. Crowne Plaza Annapolis by IHG: Hotel located near U.S. Naval Academy. Offers free self parking, an indoor pool, and complimentary wireless internet access. DoubleTree by Hilton Hotel Annapolis: Hotel located near Northwest Stadium. Offers buffet, an indoor pool, and free self parking. Historic Inns of Annapolis: Hotel located near Northwest Stadium. Features a snack bar/deli, a seasonal outdoor pool, and buffet. Comfort Inn Largo-Washington DC East: Offers buffet, a seasonal outdoor pool, and complimentary wireless internet access.
What is there to see and do in Shady Side?
Surround yourself with nature at Shadyside Park and Northern Chesapeake Bay. Discover sights such as Chesapeake Bay, Captain Avery Museum, and Franklin Point State Park during your stay.
When is the best time to book a hotel with a pool in Shady Side?
You may want to consider an accommodation with an outdoor swimming pool if you will be visiting Shady Side in the warmest months of July, August, or June when the average temp is 75°F. Lodging with an indoor pool may be what you want if you are visiting during the coldest months of January, February, or December when the average temp is 40°F.