Find Hotels with a Pool in Shady Side, MD

Check availability on Shady Side Hotels with a Pool

Check prices for these dates

Tonight
Aug 11 - Aug 12
Tomorrow
Aug 12 - Aug 13
This weekend
Aug 15 - Aug 17
Next weekend
Aug 22 - Aug 24

Top Shady Side Hotels with a Pool

The Oaks Waterfront
Front of property

The Oaks Waterfront

4.0 star property
10.0 out of 10, Exceptional, (33)
"Loved the Oaks! Fabulous accommodations and excellent staff"
$459 nightly
The price is $505
Aug 14 - Aug 15
Total includes taxes and fees
The Oaks Waterfront
St Michaels Inn
Front of property

St Michaels Inn

2.5 star property
8.2 out of 10, Very Good, (1005)
"Great spot to be close to town for a modest price. "
$99 nightly
The price is $109
Sep 1 - Sep 2
Total includes taxes and fees
St Michaels Inn
Inn at Perry Cabin
Breakfast, lunch, dinner served; ocean views

Inn at Perry Cabin

5.0 star property
9.6 out of 10, Exceptional, (358)
"Beautiful place to stay."
$629 nightly
The price is $692
Sep 2 - Sep 3
Total includes taxes and fees
Inn at Perry Cabin
Parsonage Inn
Porch

Parsonage Inn

3.5 star property
9.2 out of 10, Wonderful, (129)
"Beautiful Victorian Cottage Home. Outstanding service and breakfast. Wonderful hosts made us feel right @ home!"
$229 nightly
The price is $252
Aug 12 - Aug 13
Total includes taxes and fees
Parsonage Inn
George Brooks House B&B
Exterior

George Brooks House B&B

3.0 star property
8.8 out of 10, Excellent, (61)
"Gorgeous quaint historic house. Friendly owner, close to town "
$234 nightly
The price is $257
Aug 12 - Aug 13
Total includes taxes and fees
George Brooks House B&B
Quality Inn
Suite, 1 Queen Bed, Non Smoking | In-room safe, iron/ironing board, free WiFi, bed sheets

Quality Inn

2.5 star property
7.8 out of 10, Good, (804)
"Conveniently located with overall great value."
$97 nightly
The price is $108
Aug 24 - Aug 25
Total includes taxes and fees
Quality Inn
Hilton Garden Inn Kent Island Marina
Indoor pool, open 5 AM to 11 PM, sun loungers

Hilton Garden Inn Kent Island Marina

3.0 star property
9.0 out of 10, Wonderful, (982)
"Friendly staff, nice environment"
$152 nightly
The price is $169
Sep 1 - Sep 2
Total includes taxes and fees
Hilton Garden Inn Kent Island Marina
Holiday Inn Express Annapolis East-Kent Island by IHG
Seasonal outdoor pool, open 9 AM to 9 PM, pool umbrellas, sun loungers

Holiday Inn Express Annapolis East-Kent Island by IHG

2.5 star property
9.2 out of 10, Wonderful, (880)
"Great stay beautiful view"
$127 nightly
The price is $141
Aug 24 - Aug 25
Total includes taxes and fees
Holiday Inn Express Annapolis East-Kent Island by IHG
Best Western Kent Narrows Inn
Indoor pool

Best Western Kent Narrows Inn

2.5 star property
8.2 out of 10, Very Good, (1008)
"I like the location and how easy it is to get to our room."
$109 nightly
The price is $121
Aug 18 - Aug 19
Total includes taxes and fees
Best Western Kent Narrows Inn
Hyatt Place Kent Narrows & Marina
Indoor pool, sun loungers

Hyatt Place Kent Narrows & Marina

3.0 star property
9.4 out of 10, Exceptional, (604)
"Great place to stay. "
$159 nightly
The price is $176
Aug 21 - Aug 22
Total includes taxes and fees
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.

Top Shady Side Hotel Reviews

SpringHill Suites by Marriott Annapolis

SpringHill Suites by Marriott Annapolis

10/10 Excellent
"Great place"
Patrick 2-night trip
Posted 18 hours ago
SpringHill Suites by Marriott Annapolis

Frequently asked questions

What are some accommodations with pools in Shady Side?
Bay views with kayaks, bikes, fire pit, crabbing and more: Hotel located near Northwest Stadium. Features a snack bar/deli, a seasonal outdoor pool, and buffet. Calloway Drive Retreat | House in Shady Side: Hotel located near Northwest Stadium. Offers buffet, an indoor pool, and free self parking. Peaceful 2-bedroom / 2-bathroom house with WiFi and AC in serene Shady Side: Provides buffet, an indoor pool, and free self parking. Historic Inns of Annapolis: Features buffet, a seasonal outdoor pool, and complimentary wireless internet access. Graduate by Hilton Annapolis: Features a snack bar/deli, an indoor pool, and daily.
What is there to see and do in Shady Side?
The picturesque setting of Shadyside Park showcases the area's natural beauty. Discover sights such as 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.