Find Hotels with a Pool in Eastern Shore, MD
Upfront pricingOur total price for your stay includes taxes and fees
Treat yourselfSave 10% or more on over 100,000 hotels worldwide with Member PricesLearn about One Key
Be pickySearch almost a million properties worldwide
Check availability on Eastern Shore Hotels with a Pool
Tonight
Aug 29 - Aug 30Tomorrow
Aug 30 - Aug 31Next weekend
Sep 4 - Sep 6In two weeks
Sep 11 - Sep 13Our 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.
$123 nightly
$137 total
Sep 28 - Sep 29
Total with taxes and fees
2. 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 28 - Sep 29
Total with taxes and fees
3. St Michaels Inn
St Michaels InnSt. 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
4. Comfort Inn & Suites Cambridge
Comfort Inn & Suites CambridgeCambridge
- 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
5. Fairfield Inn & Suites by Marriott Easton
Fairfield Inn & Suites by Marriott EastonEaston
- 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
6. Hyatt Place Ocean City / Oceanfront
Hyatt Place Ocean City / OceanfrontDowntown 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
7. Princess Royale Oceanfront Resort
Princess Royale Oceanfront ResortNorth 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
8. Fenwick Inn
Fenwick InnNorth 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
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
$123 nightly
$137 total
Sep 28 - Sep 29
Total with taxes and fees
$129 nightly
$142 total
Sep 28 - Sep 29
Total with taxes and fees
$88 nightly
$97 total
Aug 30 - Aug 31
Total with taxes and fees
$119 nightly
$132 total
Sep 1 - Sep 2
Total with taxes and fees
$114 nightly
$126 total
Sep 7 - Sep 8
Total with taxes and fees
$135 nightly
$149 total
Sep 3 - Sep 4
Total with taxes and fees
$118 nightly
$132 total
Sep 17 - Sep 18
Total with taxes and fees
$84 nightly
$95 total
Sep 21 - Sep 22
Total with taxes and fees
$100 nightly
$111 total
Sep 28 - Sep 29
Total with taxes and fees
$254 nightly
$288 total
Sep 29 - Sep 30
Total with taxes and fees
4-star hotels with pools in Eastern Shore
$254 nightly
$288 total
Sep 29 - Sep 30
Total with taxes and fees
$239 nightly
$265 total
Sep 28 - Sep 29
Total with taxes and fees
DoubleTree by Hilton Ocean City Oceanfront
DoubleTree by Hilton Ocean City OceanfrontMidtown Ocean City
$171 nightly
$192 total
Sep 7 - Sep 8
Total with taxes and fees
$226 nightly
$253 total
Sep 20 - Sep 21
Total with taxes and fees
$440 nightly
$484 total
Sep 7 - Sep 8
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
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."
Castle in the Sand
10/10 Excellent
"Rooms are a bit dated but everything else was great! Very convenient by beach and friendly staff."
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."
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."
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!"
Bonita Beach Hotel
10/10 Excellent
"Very well kept hotel clean"
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."
Plim Plaza Hotel
8/10 Good
"Nice hotel. Loved sitting on the chairs outside."
Coastal Palms Inn & Suites
10/10 Excellent
"Close to the beach, reasonably priced, had everything we needed for a quick and last minute getaway"
Explore a world of travel with Expedia
- Hotels with a View in Eastern Shore
- Historic Hotels in Maryland
- Oceanfront Hotels in Maryland
- Hotel Wedding Venues Hotels in Annapolis
- Hotels with a Swim-up Bar in Maryland
- Hotels with Bars in Eastern Shore
- Quiet Resorts & in Annapolis
- Hotels with a Lazy River in Maryland
- Waterpark Hotels in Maryland
- Extended Stay Hotels in Eastern Shore
- Hotels with Tennis Courts in Anchorage
- Non-Smoking Hotels in Annapolis
- Winery Hotels in Eastern Shore
- Romantic Hotels in Eastern Shore
- Cheap Hotels in Baltimore
- Hotels with Fireplaces in Maryland
- Hotels with Room Service in Maryland
- Honeymoon Resorts & in Eastern Shore
- Hotels with Bars in Annapolis
- Family Hotels in Annapolis
- Hotels with a View in Maryland
- Quiet Resorts & in Maryland
- Hotels with Tennis Courts in Eastern Shore
- Hotels with Childcare in Eastern Shore
- Hotels with Hot Tubs in Eastern Shore
- Hotels with an Indoor Pool in Eastern Shore
- Adults Only Resorts & in Eastern Shore
- Boutique Hotels in Eastern Shore
- Hotels with a Pool in Annapolis
- Hotels with Connecting Rooms in Eastern Shore
- Hotels with a Lazy River in Eastern Shore
- Hotels with Fireplaces in Eastern Shore
- Cheap Hotels in Easton
- Cheap Hotels in Washington
- Hotels on the River in Eastern Shore
- Hotels with Childcare in Maryland
- Historic Hotels in Annapolis
- Gay friendly Hotels in Annapolis
- Golf Hotels in Eastern Shore
- Historic Hotels in Eastern Shore
- Resorts & Hotels with Spas in Eastern Shore
- Golf Hotels in Maryland
- Pet-Friendly Hotels in Easton
- Hotels with Laundry Facilities in Maryland
- Hotels with Free Airport Shuttle in Eastern Shore
- Hotels with Room Service in Eastern Shore
- Beach Hotels in Annapolis
- Hotels with Connecting Rooms in Annapolis
- Hotels with Free Parking in Maryland
- Hotels with Early Check-in in Maryland
- Ski Hotels in Maryland
- Hotels with Waterslides in Eastern Shore
- Hotel Wedding Venues Hotels in Maryland
- Boutique Hotels in Maryland
- Quiet Resorts & in Eastern Shore
- Golf Hotels in Annapolis
- Hotels with Waterslides in Maryland
- Hotels with Restaurants in Eastern Shore
- Hotels with Connecting Rooms in Maryland
- Hotels with Free Breakfast in Maryland
- Casino Hotels in Eastern Shore
- Hotels with a Swim-up Bar in Eastern Shore
- Hotel Wedding Venues Hotels in Eastern Shore
- Honeymoon Resorts & in Maryland
- Hotels with Kitchenettes in Annapolis
- Beach Hotels in Eastern Shore
- Boutique Hotels in Annapolis
- Oceanfront Hotels in Eastern Shore
- Hotels with Balconies in Annapolis
- Hotels with Hot Tubs in Maryland
- Hotels with Free Parking in Annapolis
- Hotels with Early Check-in in Eastern Shore
- Hotels with a Pool in Maryland
- Romantic Hotels in Annapolis
- Gay friendly Hotels in Eastern Shore
- Hotels with Suites in Eastern Shore
- Hotels with Restaurants in Annapolis
- Fishing Resorts & in Maryland
- Honeymoon Resorts & in Annapolis
- Hotels with Fireplaces in Annapolis
- Luxury Hotels in Eastern Shore
- Hotels with Restaurants in Maryland
- Hotels with Early Check-in in Annapolis
- Fishing Resorts & in Eastern Shore
- Hotels with an Outdoor Pool in Maryland
- Pet-Friendly Hotels in Eastern Shore
- All-Inclusive Resorts in Maryland
- Family Hotels in Eastern Shore
- Oceanfront Hotels in Annapolis
- Hotels with Hot Tubs in Annapolis
- Hotels with Free Airport Shuttle in Annapolis
- All-Inclusive Resorts in Annapolis
- Hotels with a Gym in Annapolis
- Hotels with an Outdoor Pool in Eastern Shore
- Hotels with Free Breakfast in Annapolis
- Cheap Hotels in Eastern Shore
- Hotels on the River in Maryland
- Waterpark Hotels in Eastern Shore
- Hotels with Laundry Facilities in Annapolis
- Hotels with Kitchenettes in Eastern Shore