Find Hotels with a Pool in Eastern Shore, MD

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

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
2.5 star property
Grasonville
9.2 out of 10, Wonderful, (1,002 reviews)
  • cleanliness
    Splashy pool escapes by the bay; seasonal swimming paradise with sun-soaked loungers.
The price is AED 349
AED 387 total
includes taxes & fees
6 Dec - 7 Dec
Holiday Inn Express Annapolis East-Kent Island by IHG

2. Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
3.0 star property
Grasonville
9.4 out of 10, Exceptional, (856 reviews)
  • cleanliness
    Scenic waters beckon at this island escape with a relaxing indoor pool and waterfront deck for breathtaking sunset views.
The price is AED 493
AED 547 total
includes taxes & fees
15 Nov - 16 Nov
Hyatt Place Kent Narrows & Marina

3. Comfort Inn & Suites Cambridge

Comfort Inn & Suites Cambridge
2.5 star property
Cambridge
8.4 out of 10, Very good, (925 reviews)
  • cleanliness
    Cambridge hotel offers year-round indoor pool and fitness amenities for a refreshing escape.
The price is AED 417
AED 463 total
includes taxes & fees
22 Nov - 23 Nov
Comfort Inn & Suites Cambridge

4. Hyatt Regency Chesapeake Bay

Hyatt Regency Chesapeake Bay
4.0 star property
Cambridge
8.8 out of 10, Excellent, (1,005 reviews)
  • cleanliness
    Aquatic paradise awaits with 2 outdoor pools, indoor pool, and waterslide offering year-round relaxation at this riverside resort.
The price is AED 531
AED 707 total
includes taxes & fees
23 Nov - 24 Nov
Hyatt Regency Chesapeake Bay

5. Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
2.5 star property
Grasonville
8.0 out of 10, Very good, (1,002 reviews)
  • cleanliness
    Aquatic bliss awaits at this central hotel, with a rejuvenating indoor pool and hot tub sanctuary.
The price is AED 330
AED 366 total
includes taxes & fees
15 Nov - 16 Nov
Best Western Kent Narrows Inn

6. Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina
3.0 star property
Grasonville
8.8 out of 10, Excellent, (1,002 reviews)
  • cleanliness
    Dive into ultimate bay views with serene indoor pool sessions at this waterfront hotel.
The price is AED 440
AED 488 total
includes taxes & fees
18 Nov - 19 Nov
Hilton Garden Inn Kent Island Marina

7. The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club
4.0 star property
Stevensville
9.4 out of 10, Exceptional, (512 reviews)
  • cleanliness
    Dive into summer luxury at this Eastern Shore retreat with a seasonal outdoor pool and personalized spa services.
The price is AED 665
AED 832 total
includes taxes & fees
9 Dec - 10 Dec
The Inn at Chesapeake Bay Beach Club

8. Fairfield Inn & Suites by Marriott Easton

Fairfield Inn & Suites by Marriott Easton
3.0 star property
Easton
9.6 out of 10, Exceptional, (396 reviews)
  • cleanliness
    Dive into saltwater serenity at this Easton hotel with indoor pool and shuttle service.
The price is AED 465
AED 512 total
includes taxes & fees
15 Nov - 16 Nov
Fairfield Inn & Suites by Marriott Easton

9. Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
2.5 star property
Grasonville
7.8 out of 10, Good, (1,000 reviews)
  • cleanliness
    Take a dip anytime, day or night, in this hotel's seasonal outdoor pool near Chesapeake Bay.
The price is AED 308
AED 342 total
includes taxes & fees
29 Nov - 30 Nov
Quality Inn Grasonville near Kent Island

10. Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
2.5 star property
Chestertown
8.6 out of 10, Excellent, (998 reviews)
  • cleanliness
    Dive into the seasonal outdoor pool with comfortable loungers and umbrellas at this refreshing hotel retreat in Chestertown.
The price is AED 361
AED 401 total
includes taxes & fees
6 Dec - 7 Dec
Comfort Inn & Suites Chestertown
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.

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

Top Eastern Shore Hotel Reviews

Explore a world of travel with Expedia