Find Family Hotels in Sherwood, MD

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Check availability on Sherwood Family Hotels

Tonight
Dec 27 - Dec 28
Tomorrow
Dec 28 - Dec 29
Next weekend
Jan 2 - Jan 4
In two weeks
Jan 9 - Jan 11

Our top choices for Sherwood family-friendly hotels

Balcony
Rod 'N' Reel Resort

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$2,862
NT$3,805 total
includes taxes & fees
Jan 2 - 2026/1/3
Rod 'N' Reel Resort
Exterior
Holiday Inn Express Annapolis East-Kent Island by IHG

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, (940)
"It was very comfortable and clean"
United States
Maria
The price is NT$2,484
NT$2,757 total
includes taxes & fees
Jan 25 - 2026/1/26
Holiday Inn Express Annapolis East-Kent Island by IHG
Exterior
Quality Inn

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$2,672
NT$2,939 total
includes taxes & fees
Jan 4 - 2026/1/5
Quality Inn
Lobby
Quality Inn Grasonville near Kent Island

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$2,645
NT$2,936 total
includes taxes & fees
Jan 19 - 2026/1/20
Quality Inn Grasonville near Kent Island
In-room safe, individually decorated, individually furnished, desk
Best Western Kent Narrows Inn

Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
2.5 star property
Grasonville
8.0 out of 10, Very Good, (1002)
"Nice place "
United States
Tucker T
The price is NT$2,622
NT$2,911 total
includes taxes & fees
Jan 4 - 2026/1/5
Best Western Kent Narrows Inn
Terrace/patio
Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
3.0 star property
Grasonville
9.6 out of 10, Exceptional, (680)
"The staff are the absolute best. Our room was perfect."
United States
Deborah
The price is NT$3,646
NT$4,047 total
includes taxes & fees
Jan 19 - 2026/1/20
Hyatt Place Kent Narrows & Marina
Terrace/patio
The Tidewater Inn

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$5,627
NT$6,189 total
includes taxes & fees
Jan 1 - 2026/1/2
The Tidewater Inn
Garden
DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis
4.0 star property
Annapolis
8.6 out of 10, Excellent, (1005)
"Great stay "
United States
Jose Miguel
The price is NT$2,346
NT$2,674 total
includes taxes & fees
Jan 4 - 2026/1/5
DoubleTree by Hilton Hotel Annapolis
Lobby
Best Western Plus Easton Inn & Suites

Best Western Plus Easton Inn & Suites

Best Western Plus Easton Inn & Suites
2.5 star property
Easton
9.2 out of 10, Wonderful, (1000)
"Spacious room, friendly staff, nice bathroom. Everyone is very accommodating."
United States
DONNA
The price is NT$3,741
NT$4,115 total
includes taxes & fees
Dec 29 - Dec 30
Best Western Plus Easton Inn & Suites
Property amenity
Fairfield Inn & Suites By Marriott Annapolis

Fairfield Inn & Suites By Marriott Annapolis

Fairfield Inn & Suites By Marriott Annapolis
3.0 star property
Annapolis
9.0 out of 10, Wonderful, (167)
"Beautiful and very modern, breakfast was great"
United States
Dominic
The price is NT$3,458
NT$3,942 total
includes taxes & fees
Jan 1 - 2026/1/2
Fairfield Inn & Suites By Marriott Annapolis
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 properties

Top Sherwood Hotel Reviews

DoubleTree by Hilton Hotel Annapolis

DoubleTree by Hilton Hotel Annapolis

10/10 Excellent
"did not dine in your hotel. "
Stan 5-night trip
Posted 3 days ago
DoubleTree by Hilton Hotel Annapolis

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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