Find Family Hotels in Sherwood, MD

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Our top choices for Sherwood family-friendly hotels

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, (939)
"It was very comfortable and clean"
United States
Maria
The price is NT$2,741
NT$3,043 total
includes taxes & fees
Jan 1 - 2026/1/2
Holiday Inn Express Annapolis East-Kent Island by IHG

Rod 'N' Reel Resort

Rod 'N' Reel Resort
4.0 star property
Chesapeake Beach
8.4 out of 10, Very Good, (1002)
"This place is extremely impressive!!! The room was clean, the view was AMAZING, and the staff were friendly. This is our new spot. Even the guy at the gift shop was really helpful and cool. "
United States
Stacy
The price is NT$2,868
NT$3,814 total
includes taxes & fees
Jan 2 - 2026/1/3
Rod 'N' Reel Resort

Best Western Annapolis

Best Western Annapolis
2.5 star property
Annapolis
7.8 out of 10, Good, (1000)
"Best Western provided a clean comfortable room for our stay at Annapolis. There was plentiful parking and the staff was courteous and helpful. The breakfast was adequate and centrally located. I would definitely recommends this establishment"
United States
Charles
The price is NT$2,098
NT$2,392 total
includes taxes & fees
Jan 10 - 2026/1/11
Best Western Annapolis

Quality Inn

Quality Inn
2.5 star property
Easton
7.6 out of 10, Good, (828)
"Everything was clean; staff friendly; breakfast great"
United States
Richard
The price is NT$2,678
NT$2,946 total
includes taxes & fees
Dec 31 - 2026/1/1
Quality Inn

Best Western Plus Easton Inn & Suites

Best Western Plus Easton Inn & Suites
2.5 star property
Easton
9.2 out of 10, Wonderful, (1002)
"Spacious room, friendly staff, nice bathroom. Everyone is very accommodating."
United States
DONNA
The price is NT$3,749
NT$4,124 total
includes taxes & fees
Dec 25 - Dec 26
Best Western Plus Easton Inn & Suites

Quality Inn Grasonville near Kent Island

Quality Inn Grasonville near Kent Island
2.5 star property
Grasonville
7.8 out of 10, Good, (863)
"room was nice breakfast was good and the staff was very friendly and helpful. "
United States
Esai
The price is NT$2,662
NT$2,955 total
includes taxes & fees
Jan 19 - 2026/1/20
Quality Inn Grasonville near Kent Island

Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
3.0 star property
Grasonville
9.6 out of 10, Exceptional, (678)
"Great view, good ambiance all around"
United States
Dianne
The price is NT$3,655
NT$4,057 total
includes taxes & fees
Jan 19 - 2026/1/20
Hyatt Place Kent Narrows & Marina

The Tidewater Inn

The Tidewater Inn
3.0 star property
Easton
8.8 out of 10, Excellent, (842)
"Friendly staff, spotless room, great location. "
United States
Steven
The price is NT$5,640
NT$6,204 total
includes taxes & fees
Jan 4 - 2026/1/5
The Tidewater Inn

DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis
4.0 star property
Annapolis
8.6 out of 10, Excellent, (1002)
"Great stay "
United States
Jose Miguel
The price is NT$2,351
NT$2,680 total
includes taxes & fees
Jan 4 - 2026/1/5
DoubleTree by Hilton Hotel Annapolis

Hampton Inn Easton

Hampton Inn Easton
2.5 star property
Easton
9.0 out of 10, Wonderful, (553)
"all excellent with kudos to staff and the breakfast cook."
United States
JOSEPH
The price is NT$3,806
NT$4,186 total
includes taxes & fees
Jan 22 - 2026/1/23
Hampton Inn Easton
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.

Top Sherwood Hotel Reviews

Frequently asked questions

What's Sherwood like for family-friendly vacations?
You might want to consider the welcoming destination of Sherwood if you've been thinking about a trip for the whole family. The island setting, sailing, and restaurants are just some of the things that make this an attractive family vacation spot. Arrange a flight into Easton, MD (ESN-Easton - Newnam), which is located 14.1 mi (22.7 km) from the city center.
When's the best time to book a family-friendly vacation in Sherwood?
The hottest months are usually July and August with an average temp of 75°F, while the coldest months are January and February with an average of 41°F. Average annual precipitation for Sherwood is 53 inches.
What's there to see and do with your family in Sherwood?
While you are visiting Sherwood, you and the family might want to check out some interesting spots such as Knapp's Narrows Marina & Inn, St. Michaels Marina, and Saint Michaels Village. Make sure you have lots of time for activities like Rod n Reel Charter Fishing and Chesapeake Beach Water Park.

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