Eastern Shore Hotel Guide - Family Friendly Hotels in Eastern Shore, Maryland
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11 Sept - 13 SeptOur top choices for Eastern Shore family-friendly hotels
1. Best Western Plus Easton Inn & Suites
Best Western Plus Easton Inn & SuitesEaston
- Family-friendly getaway with indoor pool offers fun activities, free breakfast, and comfortable spaces for all ages.
€122
includes taxes & fees
4 Oct - 5 Oct
2. Holiday Inn Express Annapolis East-Kent Island by IHG
Holiday Inn Express Annapolis East-Kent Island by IHGGrasonville
- Family-friendly fun on the Kent Island escape—enjoy the seasonal outdoor pool, hiking trails, and beautiful views of Chesapeake Bay.
€114
includes taxes & fees
5 Oct - 6 Oct
3. The Tidewater Inn
The Tidewater InnEaston
- Family getaway enchantment awaits with premium entertainment, requested kitchen essentials, and nearby outdoor adventures.
€179
includes taxes & fees
7 Sept - 8 Sept
€109
includes taxes & fees
10 Sept - 11 Sept
5. Fairfield Inn & Suites by Marriott Easton
Fairfield Inn & Suites by Marriott EastonEaston
- Family fun escape at Fairfield Inn Easton with indoor saltwater pool, complimentary breakfast, and convenient location.
€128
includes taxes & fees
13 Sept - 14 Sept
6. Best Western Denton Inn
Best Western Denton InnDenton
- Family-friendly pool oasis near Martinak State Park offers cool splashes and free perks for the whole gang.
€113
includes taxes & fees
7 Sept - 8 Sept
7. Comfort Inn & Suites Chestertown
Comfort Inn & Suites ChestertownChestertown
- Splash into seasonal fun with the family near Washington College, where kids love the outdoor pool and premium entertainment options.
€99
includes taxes & fees
4 Oct - 5 Oct
€84
includes taxes & fees
29 Sept - 30 Sept
View all properties
Family-friendly hotels with free breakfast in Eastern Shore
€122
includes taxes & fees
4 Oct - 5 Oct
Holiday Inn Express Annapolis East-Kent Island by IHG
Holiday Inn Express Annapolis East-Kent Island by IHGGrasonville
€114
includes taxes & fees
5 Oct - 6 Oct
La Quinta Inn & Suites by Wyndham Newark - Elkton
La Quinta Inn & Suites by Wyndham Newark - ElktonElkton
€96
includes taxes & fees
7 Sept - 8 Sept
€145
includes taxes & fees
5 Oct - 6 Oct
€128
includes taxes & fees
13 Sept - 14 Sept
€109
includes taxes & fees
10 Sept - 11 Sept
€113
includes taxes & fees
7 Sept - 8 Sept
€139
includes taxes & fees
6 Sept - 7 Sept
€99
includes taxes & fees
4 Oct - 5 Oct
Family-friendly hotels with pools in Eastern Shore
Holiday Inn Express Annapolis East-Kent Island by IHG
Holiday Inn Express Annapolis East-Kent Island by IHGGrasonville
€114
includes taxes & fees
5 Oct - 6 Oct
€84
includes taxes & fees
29 Sept - 30 Sept
€122
includes taxes & fees
4 Oct - 5 Oct
€145
includes taxes & fees
5 Oct - 6 Oct
€119
includes taxes & fees
4 Oct - 5 Oct
€128
includes taxes & fees
13 Sept - 14 Sept
€109
includes taxes & fees
10 Sept - 11 Sept
€113
includes taxes & fees
7 Sept - 8 Sept
€134
includes taxes & fees
4 Oct - 5 Oct
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
Tidelands Caribbean Hotel and Suites
8/10 Good
"The room was clean. The AC worked great. It was in a great location . Staff was helpful but I didn’t like that when they cleaned the room they didn’t change the sheets and I know because they still had sand in them. The pool was roof top which is fine but no working umbrellas they were 2 broken down ones held up with shoelaces and rope to keep them open"
Fenwick Inn
10/10 Excellent
"Entire hotel is exceptionally well kept and clean. Vista rooftop is excellent."
Holiday Inn & Suites Ocean City by IHG
10/10 Excellent
"Staff was very pleasant. Room very clean, the only thing i was a little disappointed was with the shower pressure. Otherwise, I was very satisfied with my stay and recommend this hotel for a nice family stay!"
Quality Inn Oceanfront
10/10 Excellent
"I‘ve stayed there many times before and the staff and accommodations were great"
Princess Royale Oceanfront Resort
8/10 Good
"Two bedroom condo is perfect for families especially with the ocean front view. Great location."
Bonita Beach Hotel
8/10 Good
"We were able to check-in 2 hours early, which was nice. The carpet in the room wasn't as clean as we hoped, but overall we had a nice stay."
Grand Hotel Ocean City Oceanfront
10/10 Excellent
"2nd year staying there ,coming back next year!!"
Crystal Beach Hotel
8/10 Good
"You pay extra for more than 2 adults. Do not be honest on your people staying. The more people entered increases the rate and they do not increase the key cards or towels, linens, etc. non smoking rooms, balcony, etc — completely understand — have a smoking area with benches to sit and relax!!"
Plim Plaza Hotel
10/10 Excellent
"The hotel was great but the restaurants weren't. They shorted us 3 crabs and left the clams off the meal. When asked about it they said they were out of clams and they would put 3 more crabs in for us.if your paying 140 for a meal you would think they'd te1ll you they were out of stuff when your ordering. Went to get some breakfast sandwiches for us and the waiter said I had to order from the bar. I waited 10 minutes and was totally ignored. No customers but me. So I got some sandwiches elsewhere."
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