Find Hotels with a Pool in Eastern Shore, MD
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Check availability on Eastern Shore Hotels with a Pool
Tonight
Sep 19 - Sep 20Tomorrow
Sep 20 - Sep 21Next weekend
Sep 25 - Sep 27In two weeks
Oct 2 - Oct 4Our top choices for Eastern Shore hotels with a pool
1. Holiday Inn Express Annapolis East-Kent Island by IHG
Holiday Inn Express Annapolis East-Kent Island by IHGGrasonville
- Splashy pool escapes by the bay; seasonal swimming paradise with sun-soaked loungers.
$107 nightly
$119 total
Oct 18 - Oct 19
Total with taxes and fees
2. Baymont by Wyndham Easton
Baymont by Wyndham EastonEaston
- Dive into summer bliss at this quality hotel featuring a seasonal outdoor pool and fitness center.
$98 nightly
$108 total
Sep 27 - Sep 28
Total with taxes and fees
3. Best Western Plus Easton Inn & Suites
Best Western Plus Easton Inn & SuitesEaston
- Make a splash at this family-friendly hotel with an indoor pool that welcomes guests year-round.
$129 nightly
$142 total
Sep 27 - Sep 28
Total with taxes and fees
4. St Michaels Inn
St Michaels InnSt. Michaels
- Seasonal outdoor pool retreat with plush loungers makes summer days in St. Michaels extra delightful.
$89 nightly
$98 total
Oct 20 - Oct 21
Total with taxes and fees
5. Princess Royale Oceanfront Resort
Princess Royale Oceanfront ResortNorth Ocean City
- Luxurious indoor pool retreat with beachfront bliss makes this ocean getaway a splash.
$108 nightly
$119 total
Oct 18 - Oct 19
Total with taxes and fees
6. Fenwick Inn
Fenwick InnNorth Ocean City
- Dive into resort-style relaxation at this indoor pool oasis just steps from Maryland Beach.
$82 nightly
$92 total
Sep 21 - Sep 22
Total with taxes and fees
7. Grand Hotel Ocean City Oceanfront
Grand Hotel Ocean City OceanfrontDowntown Ocean City
- Float in indoor or outdoor pools with oceanfront views in this beach retreat.
$94 nightly
$106 total
Oct 14 - Oct 15
Total with taxes and fees
8. Comfort Inn & Suites Cambridge
Comfort Inn & Suites CambridgeCambridge
- Cambridge hotel offers year-round indoor pool and fitness amenities for a refreshing escape.
$118 nightly
$131 total
Oct 11 - Oct 12
Total with taxes and fees
View all properties
Hotels with pools and free breakfast in Eastern Shore
Holiday Inn Express Annapolis East-Kent Island by IHG
Holiday Inn Express Annapolis East-Kent Island by IHGGrasonville
$107 nightly
$119 total
Oct 18 - Oct 19
Total with taxes and fees
Hampton Inn & Suites Ocean City/Bayfront-Convention Center
Hampton Inn & Suites Ocean City/Bayfront-Convention CenterMidtown Ocean City
$73 nightly
$82 total
Oct 4 - Oct 5
Total with taxes and fees
$82 nightly
$92 total
Sep 21 - Sep 22
Total with taxes and fees
$98 nightly
$108 total
Sep 27 - Sep 28
Total with taxes and fees
$152 nightly
$169 total
Oct 4 - Oct 5
Total with taxes and fees
$89 nightly
$98 total
Oct 20 - Oct 21
Total with taxes and fees
$101 nightly
$113 total
Oct 13 - Oct 14
Total with taxes and fees
DoubleTree by Hilton Ocean City Oceanfront
DoubleTree by Hilton Ocean City OceanfrontMidtown Ocean City
$98 nightly
$109 total
Oct 12 - Oct 13
Total with taxes and fees
$118 nightly
$131 total
Oct 11 - Oct 12
Total with taxes and fees
Gateway Hotel & Suites Ocean City, an Ascend Collection Hotel
Gateway Hotel & Suites Ocean City, an Ascend Collection HotelDowntown Ocean City
$100 nightly
$112 total
Sep 21 - Sep 22
Total with taxes and fees
4-star hotels with pools in Eastern Shore
DoubleTree by Hilton Ocean City Oceanfront
DoubleTree by Hilton Ocean City OceanfrontMidtown Ocean City
$98 nightly
$109 total
Oct 12 - Oct 13
Total with taxes and fees
$260 nightly
$295 total
Oct 13 - Oct 14
Total with taxes and fees
$214 nightly
$238 total
Oct 19 - Oct 20
Total with taxes and fees
$152 nightly
$170 total
Oct 18 - Oct 19
Total with taxes and fees
$489 nightly
$538 total
Sep 23 - Sep 24
Total with taxes and fees
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 propertiesTop Eastern Shore Hotel Reviews
Fenwick Inn
10/10 Excellent
"The room was clean. The housekeeping staff were excellent and helpful. The front desk staff were attentive and pleasant. Good selection of breakfast items. The bed was slightly uncomfortable for me."
Holiday Inn & Suites Ocean City by IHG
10/10 Excellent
"Location was perfect we enjoyed both pools and the outside bar staff was very friendly and the rooms were very spacious and clean we also really enjoyed the large balcony"
Princess Royale Oceanfront Resort
10/10 Excellent
"."
Francis Scott Key Family Resort
10/10 Excellent
"We absolutely love Francis Scott Key Family Resort! We’ve been coming here for over 16 years, and it truly feels like our home away from home. ❤️ My kids have grown up coming here, and even after all these years, they still get excited about every visit. There’s something really special about a place that can continue to bring your family together and create memories year after year. During the summer, we look forward to coming at least once a month. It has become one of our favorite family traditions, and we’ve made so many wonderful memories here over the years. Thank you, Francis Scott Key, for being such a special part of our family’s summers for more than 16 years. We’re already looking forward to our next stay! ❤️🏖️"
Crystal Beach Hotel
10/10 Excellent
"Decent overall and would definitely stay here again"
Quality Inn Oceanfront
8/10 Good
"Met our expectations."
Tidelands Caribbean Hotel and Suites
10/10 Excellent
"As always this is a good place to stay if you just want to get away. The rooms are very large."
Castle in the Sand
8/10 Good
"Nice hotel great patio and bar."
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