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.
$88 nightly
$97 total
Aug 30 - Aug 31
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.
$121 nightly
$133 total
Sep 20 - Sep 21
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.
$116 nightly
$130 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.
$98 nightly
$109 total
Sep 13 - Sep 14
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
$88 nightly
$97 total
Aug 30 - Aug 31
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
$239 nightly
$265 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
$226 nightly
$253 total
Sep 20 - Sep 21
Total with taxes and fees
Hilton Ocean City Oceanfront Suites

The Oaks Waterfront

The Oaks Waterfront
Easton
$440 nightly
$484 total
Sep 7 - Sep 8
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

Ashore Oceanfront Hotel by Marriott

Ashore Oceanfront Hotel by Marriott

10/10 Excellent
"Our very first stay and won’t be our last. This hotel has been beautifully decorated, is exceptionally clean, and is a wonderful layout. Loved walking directly out on to the beach! And what a fantastic plus…….their very own beach chairs and umbrellas are available to guests. Only two cons: the bed wasn’t very comfortable and there wasn’t a full length mirror in the room. Otherwise, an overall excellent experience. We look forward to visiting again next year."
Michelle 3-night trip
Posted 9 hours ago
Ashore Oceanfront Hotel by Marriott
Castle in the Sand

Castle in the Sand

10/10 Excellent
"Rooms are a bit dated but everything else was great! Very convenient by beach and friendly staff."
Emilyn 1-night trip
Posted 11 hours ago
Castle in the Sand
Grand Hotel Ocean City Oceanfront

Grand Hotel Ocean City Oceanfront

10/10 Excellent
"This was a wonderful hotel with beautiful views of the ocean. The pizza and epic bar and grille were delicious. Everyone at the hotel was amazing and understanding we would definitely stay again. The pool was spacious they clean the rooms everyday. Which was a big change from the first hotel we stayed at it was like night and day difference."
Samantha 2-night trip
Posted 12 hours ago
Grand Hotel Ocean City Oceanfront
Fenwick Inn

Fenwick Inn

10/10 Excellent
"We were happy with how affordable the hotel was while providing all the amenities we needed for a quick beach trip with our 2 young boys."
April 2-night trip
Posted 12 hours ago
Fenwick Inn
Princess Royale Oceanfront Resort

Princess Royale Oceanfront Resort

10/10 Excellent
"We really enjoyed our stay as a family of four with two young kids. The resort is located right on the beach and offers direct access, which was a huge plus for us. Our room appeared to have been recently renovated and was comfortable and well maintained. The staff were very friendly, welcoming, and accommodating throughout our stay. The main area that could use some updating is the pool and its surrounding area. It would also be great to see more activities and entertainment options for young children. Overall, the resort oceanfront view is beautiful, and we had a wonderful experience. We would definitely stay here again!"
Kendy 5-night trip
Posted 13 hours ago
Princess Royale Oceanfront Resort
Bonita Beach Hotel

Bonita Beach Hotel

10/10 Excellent
"Very well kept hotel clean"
Melvin 2-night trip
Posted 16 hours ago
Bonita Beach Hotel
Francis Scott Key Family Resort

Francis Scott Key Family Resort

10/10 Excellent
"We had a wonderful stay and really enjoyed our time here! The property was clean, comfortable, and had plenty of space for our family. It was a great place for us to relax and spend time together. We especially appreciated that it was family-friendly and accommodating for our group. Parking was convenient, and the overall location worked well for everything we wanted to do. The property matched our expectations and helped make our trip and my mom’s 70th birthday celebration even more special. We would definitely consider staying here again and would recommend it to other families looking for a comfortable place to stay."
Michelle 2-night trip
Posted 18 hours ago
Francis Scott Key Family Resort
Plim Plaza Hotel

Plim Plaza Hotel

8/10 Good
"Nice hotel. Loved sitting on the chairs outside."
Sharina 1-night trip
Posted 2 days ago
Plim Plaza Hotel
Coastal Palms Inn & Suites

Coastal Palms Inn & Suites

10/10 Excellent
"Close to the beach, reasonably priced, had everything we needed for a quick and last minute getaway"
Jamie 4-night trip
Posted 2 days ago
Coastal Palms Inn & Suites

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