A marina with numerous boats docked at wooden piers under a clear sky.

Find Hotels with a Pool in Eastern Shore, MD

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Check availability on Eastern Shore Hotels with a Pool

Tonight
Aug 29 - Aug 30
Tomorrow
Aug 30 - Aug 31
Next weekend
Sep 4 - Sep 6
In two weeks
Sep 11 - Sep 13

Our 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 IHG
Grasonville
  • Splashy pool escapes by the bay; seasonal swimming paradise with sun-soaked loungers.
$123 nightly
$137 total
Sep 28 - Sep 29
Total with taxes and fees
Holiday Inn Express Annapolis East-Kent Island by IHG

2. Best Western Plus Easton Inn & Suites

Best Western Plus Easton Inn & Suites
Easton
  • Make a splash at this family-friendly hotel with an indoor pool that welcomes guests year-round.
$129 nightly
$142 total
Sep 28 - Sep 29
Total with taxes and fees
Best Western Plus Easton Inn & Suites

3. St Michaels Inn

St Michaels Inn
St. Michaels
  • Seasonal outdoor pool retreat with plush loungers makes summer days in St. Michaels extra delightful.
$87 nightly
$96 total
Sep 8 - Sep 9
Total with taxes and fees
St Michaels Inn

4. Comfort Inn & Suites Cambridge

Comfort Inn & Suites Cambridge
Cambridge
  • Cambridge hotel offers year-round indoor pool and fitness amenities for a refreshing escape.
$114 nightly
$126 total
Sep 7 - Sep 8
Total with taxes and fees
Comfort Inn & Suites Cambridge

5. Fairfield Inn & Suites by Marriott Easton

Fairfield Inn & Suites by Marriott Easton
Easton
  • Dive into saltwater serenity at this Easton hotel with indoor pool and shuttle service.
$135 nightly
$149 total
Sep 3 - Sep 4
Total with taxes and fees
Fairfield Inn & Suites by Marriott Easton

6. Hyatt Place Ocean City / Oceanfront

Hyatt Place Ocean City / Oceanfront
Downtown Ocean City
  • Oceanside pool escape in Maryland features refreshing indoor and seasonal outdoor pool with poolside loungers and bar service.
$118 nightly
$132 total
Sep 17 - Sep 18
Total with taxes and fees
Hyatt Place Ocean City / Oceanfront

7. Princess Royale Oceanfront Resort

Princess Royale Oceanfront Resort
North Ocean City
  • Luxurious indoor pool retreat with beachfront bliss makes this ocean getaway a splash.
$131 nightly
$145 total
Sep 30 - Oct 1
Total with taxes and fees
Princess Royale Oceanfront Resort

8. Fenwick Inn

Fenwick Inn
North Ocean City
  • Dive into resort-style relaxation at this indoor pool oasis just steps from Maryland Beach.
$84 nightly
$95 total
Sep 21 - Sep 22
Total with taxes and fees
Fenwick Inn

9. Grand Hotel Ocean City Oceanfront

Grand Hotel Ocean City Oceanfront
Downtown Ocean City
  • Float in indoor or outdoor pools with oceanfront views in this beach retreat.
$117 nightly
$131 total
Sep 7 - Sep 8
Total with taxes and fees
Grand Hotel Ocean City Oceanfront

10. Carousel Resort Hotel & Condominiums

Carousel Resort Hotel & Condominiums
North Ocean City
  • Splash into seaside bliss with year-round pools and beachfront relaxation at this coastal retreat.
$88 nightly
$98 total
Sep 30 - Oct 1
Total with taxes and fees
Carousel Resort Hotel & Condominiums
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Choose what matters most at hotels with a pool in Eastern Shore

Breakfast included
4 stars
5 stars
Hot tub
Spa

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 IHG
Grasonville
$123 nightly
$137 total
Sep 28 - Sep 29
Total with taxes and fees
Holiday Inn Express Annapolis East-Kent Island by IHG

Best Western Plus Easton Inn & Suites

Best Western Plus Easton Inn & Suites
Easton
$129 nightly
$142 total
Sep 28 - Sep 29
Total with taxes and fees
Best Western Plus Easton Inn & Suites

St Michaels Inn

St Michaels Inn
St. Michaels
$87 nightly
$96 total
Sep 8 - Sep 9
Total with taxes and fees
St Michaels Inn

Best Western Denton Inn

Best Western Denton Inn
Denton
$119 nightly
$132 total
Sep 1 - Sep 2
Total with taxes and fees
Best Western Denton Inn

Comfort Inn & Suites Cambridge

Comfort Inn & Suites Cambridge
Cambridge
$114 nightly
$126 total
Sep 7 - Sep 8
Total with taxes and fees
Comfort Inn & Suites Cambridge

Fairfield Inn & Suites by Marriott Easton

Fairfield Inn & Suites by Marriott Easton
Easton
$135 nightly
$149 total
Sep 3 - Sep 4
Total with taxes and fees
Fairfield Inn & Suites by Marriott Easton

Hyatt Place Ocean City / Oceanfront

Hyatt Place Ocean City / Oceanfront
Downtown Ocean City
$118 nightly
$132 total
Sep 17 - Sep 18
Total with taxes and fees
Hyatt Place Ocean City / Oceanfront

Fenwick Inn

Fenwick Inn
North Ocean City
$84 nightly
$95 total
Sep 21 - Sep 22
Total with taxes and fees
Fenwick Inn

Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
Grasonville
$100 nightly
$111 total
Sep 28 - Sep 29
Total with taxes and fees
Quality Inn Grasonville near Kent Island

Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay
Cambridge
$254 nightly
$288 total
Sep 29 - Sep 30
Total with taxes and fees
Hyatt Regency Chesapeake Bay
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4-star hotels with pools in Eastern Shore

Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay
Cambridge
$254 nightly
$288 total
Sep 29 - Sep 30
Total with taxes and fees
Hyatt Regency Chesapeake Bay

The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club
Stevensville
$240 nightly
$267 total
Sep 28 - Sep 29
Total with taxes and fees
The Inn at Chesapeake Bay Beach Club

DoubleTree by Hilton Ocean City Oceanfront

DoubleTree by Hilton Ocean City Oceanfront
Midtown Ocean City
$171 nightly
$192 total
Sep 7 - Sep 8
Total with taxes and fees
DoubleTree by Hilton Ocean City Oceanfront

Hilton Ocean City Oceanfront Suites

Hilton Ocean City Oceanfront Suites
Midtown Ocean City
$205 nightly
$230 total
Sep 30 - Oct 1
Total with taxes and fees
Hilton Ocean City Oceanfront Suites

The Oaks Waterfront

The Oaks Waterfront
Easton
$440 nightly
$484 total
Sep 2 - Sep 3
Total with taxes and fees
The Oaks Waterfront
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 Eastern Shore Hotel Reviews

Plim Plaza Hotel

Plim Plaza Hotel

8/10 Good
"The property definitely needs an update. We have stayed there multiple times and like the location, the pool and the pool bar. The front porch is great. The chain and deadbolt on our door didn’t work. You couldn’t set the AC to one temperature. The carpets in the whole building look like they haven’t been cleaned in years. It needs a big renovation."
Linda 4-night trip
Posted 2 hours ago
Plim Plaza Hotel
Castle in the Sand

Castle in the Sand

10/10 Excellent
"Absolutely amazing place, with two restaurants on site, being mere feet from the ocean, and the gorgeous pool. There was zero reason to leave the property. More like a resort than a hotel. Plan to make castle in the sand an annual tradition for my family!!"
Nicole 3-night trip
Posted 3 hours ago
Castle in the Sand
Coastal Palms Inn & Suites

Coastal Palms Inn & Suites

8/10 Good
"I would like a more variable breakfast and they should offer a better coffee."
Johana 3-night trip
Posted 3 hours ago
Coastal Palms Inn & Suites
Grand Hotel Ocean City Oceanfront

Grand Hotel Ocean City Oceanfront

10/10 Excellent
"The ocean view room was nice and is a must have. Accessibility to the boardwalk was great! It would’ve been nice if the hotel was a little more modern. Nevertheless we had a great time in Ocean City, Maryland and will be returning next year!"
Angela 3-night trip
Posted 3 hours ago
Grand Hotel Ocean City Oceanfront
Days Inn by Wyndham Ocean City Oceanfront

Days Inn by Wyndham Ocean City Oceanfront

10/10 Excellent
"Clean room, very short walk to the beach"
Shannon 2-night trip
Posted 7 hours ago
Days Inn by Wyndham Ocean City Oceanfront
Ashore Oceanfront Hotel by Marriott

Ashore Oceanfront Hotel by Marriott

10/10 Excellent
"Clean hotel, super easy parking, free umbrella and beach chairs. Friendly staff. We'll be back!"
PAUL 5-night trip
Posted 7 hours ago
Ashore Oceanfront Hotel by Marriott
Tidelands Caribbean Hotel and Suites

Tidelands Caribbean Hotel and Suites

10/10 Excellent
"Very clean and convenient right on the boardwalk. Recommend"
Edward 3-night trip
Posted 8 hours ago
Tidelands Caribbean Hotel and Suites
Crystal Beach Hotel

Crystal Beach Hotel

10/10 Excellent
"above being fantastic not my first time wont be our last"
Dolly 4-night trip
Posted 9 hours ago
Crystal Beach Hotel
Bonita Beach Hotel

Bonita Beach Hotel

10/10 Excellent
"Very well kept hotel clean"
Melvin 2-night trip
Posted 1 day ago
Bonita Beach Hotel

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