The Best Eastern Shore Hotels with Pools from $98 - Hotels with indoor pools in Eastern Shore, MD

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

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Our top choices for Eastern Shore hotels with a pool

Seasonal outdoor pool, open 9 AM to 9 PM, pool umbrellas, sun loungers

Holiday Inn Express Annapolis East-Kent Island by IHG

Grasonville

Splashy pool escapes by the bay; seasonal swimming paradise with sun-soaked loungers.

$111 nightly

Aug 3 - Aug 4

Total with taxes and fees

Holiday Inn Express Cambridge by IHG

Cambridge

Splash into relaxation with a rejuvenating indoor pool and hot tub retreat at this Cambridge hotel.

$119 nightly

Aug 20 - Aug 21

Total with taxes and fees

Seasonal outdoor pool, open 10:00 AM to 7:00 PM, pool umbrellas

St Michaels Inn

St. Michaels

Seasonal outdoor pool retreat with plush loungers makes summer days in St. Michaels extra delightful.

$89 nightly

Jul 28 - Jul 29

Total with taxes and fees

Hyatt Place Kent Narrows & Marina

Grasonville

Scenic waters beckon at this island escape with a relaxing indoor pool and waterfront deck for breathtaking sunset views.

$169 nightly

Jul 30 - Jul 31

Total with taxes and fees

Best Western Plus Easton Inn & Suites

Easton

Make a splash at this family-friendly hotel with an indoor pool that welcomes guests year-round.

$139 nightly

Jul 26 - Jul 27

Total with taxes and fees

Comfort Inn & Suites Cambridge

Cambridge

Cambridge hotel offers year-round indoor pool and fitness amenities for a refreshing escape.

$116 nightly

Aug 17 - Aug 18

Total with taxes and fees

Fairfield Inn & Suites by Marriott Easton

Easton

Dive into saltwater serenity at this Easton hotel with indoor pool and shuttle service.

$135 nightly

Aug 2 - Aug 3

Total with taxes and fees

Indoor pool, open 10:00 AM to 10:00 PM, sun loungers

Hampton Inn & Suites Salisbury/Fruitland

Fruitland

Splash into relaxation at this spotless hotel, featuring a sunlit indoor pool and inviting hot tub.

$106 nightly

Aug 16 - Aug 17

Total with taxes and fees

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Choose what matters most at hotels with a pool in Eastern Shore

Breakfast included

4 stars

Hotels with pools and free breakfast in Eastern Shore

Holiday Inn Express Annapolis East-Kent Island by IHG

Grasonville

$111 nightly

Aug 3 - Aug 4

Total with taxes and fees

Best Western Plus Easton Inn & Suites

Easton

$139 nightly

Jul 26 - Jul 27

Total with taxes and fees

Fairfield Inn & Suites by Marriott Easton

Easton

$135 nightly

Aug 2 - Aug 3

Total with taxes and fees

Hilton Garden Inn Kent Island Marina

Grasonville

$147 nightly

Aug 2 - Aug 3

Total with taxes and fees

Hyatt Place Kent Narrows & Marina

Grasonville

$169 nightly

Jul 30 - Jul 31

Total with taxes and fees

Suite, 1 Queen Bed, Non Smoking | In-room safe, iron/ironing board, WiFi (free), bed sheets

Quality Inn Grasonville near Kent Island

Grasonville

$100 nightly

Aug 19 - Aug 20

Total with taxes and fees

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4-star hotels with pools in Eastern Shore

Indoor pool, 2 outdoor pools, pool umbrellas, sun loungers

Hyatt Regency Chesapeake Bay

Cambridge

$296 nightly

Aug 2 - Aug 3

Total with taxes and fees

The Inn at Chesapeake Bay Beach Club

Stevensville

$258 nightly

Aug 23 - Aug 24

Total with taxes and fees

In-room safe, desk, laptop workspace, blackout drapes

DoubleTree by Hilton Ocean City Oceanfront

Midtown Ocean City

$344 nightly

Aug 23 - Aug 24

Total with taxes and fees

Hilton Ocean City Oceanfront Suites

Midtown Ocean City

$531 nightly

Aug 23 - Aug 24

Total with taxes and fees

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Top Eastern Shore Hotel Reviews

Francis Scott Key Family Resort

10/10 Excellent

"The room is dated but clean. Stocked with small amount of dishes and pans. But handy if you wanted to prepare meals. Two of the burners didn’t work though. Full size frig was nice. Since everyone was there to enjoy the beach having somewhere to hang wet bathing suits would be nice. Most people hung them over rails in front of their rooms. But we didn’t have one. They do have vacuum to get sand out of cars and such. Very handy. Have us discount codes for local attractions for staying at resort. Staff was friendly. Eager to help. They were always busy at the front desk. The pool water was a bit cold but nice pools. The arcade was very hot inside. No air conditioning. There are no elevators. The food was good in the attached restaurant. My son loved that they played two movies every night. One at 6 and one at 8:30 totally free with free popcorn and movie recliners to sit in. The shuttle to the ocean was convenient to catch and ran continuously till 10pm. One block walk to ocean and boardwalk from drop off point. Putt Putt was small but fun to play, sand volleyball net with ball, splash pad (we did not use) and Playground available for free. All conveniently located in middle of resort. Im sure there was more stuff to do at resort but we didn’t do. They have a pay laundry centrally located but not at each building. Lots of kids running around great for playmates for a an only child on vacation."

Days Inn by Wyndham Ocean City Oceanfront

10/10 Excellent

"My boyfriend and I booked this hotel last minute and it was the best decision! Hands-down, the nicest hotel I have stayed at in Ocean City with a perfect view of the beach! We loved the location on the boardwalk and direct access to the beach. The staff was very accommodating as we were able to check in early and do a late checkout without paying any additional fees."