Title: Book the Best Sherwood FAMILY FRIENDLY Hotels from CA $126 - Kid-Friendly Hotels in Sherwood, MD | Expedia.ca [Hotels in Sherwood](https://expedia.ca/Sherwood-Hotels.d6034722.Travel-Guide-Hotels)[Vacation Rentals in Sherwood](https://expedia.ca/Sherwood-Vacation-Rentals.d6034722.Travel-Guide-VacationRentals)[Sherwood Car Rentals](https://expedia.ca/Car-Rentals-In-Sherwood.d6034722.Car-Rental-Guide)[Sherwood Vacation Packages](https://expedia.ca/Sherwood.d6034722.Destination-Travel-Guides) ![Default HTG hotel image](https://a.travel-assets.com/travel-assets-manager/bex-affinities/family_friendly.jpeg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Family Hotels in Sherwood, MD from CA $126 ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check availability on Sherwood Family Hotels Tonight [Oct 13 - Oct 14](https://www.expedia.ca/Hotel-Search?regionId=6034722&startDate=2025-10-13&endDate=2025-10-14&adults=2&travelerType=FAMILY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 14 - Oct 15](https://www.expedia.ca/Hotel-Search?regionId=6034722&startDate=2025-10-14&endDate=2025-10-15&adults=2&travelerType=FAMILY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=6034722&startDate=2025-10-17&endDate=2025-10-19&adults=2&travelerType=FAMILY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=6034722&startDate=2025-10-24&endDate=2025-10-26&adults=2&travelerType=FAMILY&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Sherwood Family Hotels ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/11400/11364/fbc96e63.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/1000000/20000/11400/11364/cd0addda.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/20000/11400/11364/97812c41.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 2 Double Beds, Non Smoking](https://images.trvl-media.com/lodging/1000000/20000/11400/11364/16010c68.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Quality Inn Easton 7.6/10 Good (797) "the room was spacious and relaxing. it was nice and very comfortable. I would stay here again" CA $119 CA $131 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Easton-Hotels-Quality-Inn.h11364.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/50000/42100/42068/bf4c0cc1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Boating](https://images.trvl-media.com/lodging/1000000/50000/42100/42068/c1b842f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Boating](https://images.trvl-media.com/lodging/1000000/50000/42100/42068/be7252cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/1000000/50000/42100/42068/e84869d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Historic Inns of Annapolis Historic District 9.0/10 Wonderful (1847) "The hotel was absolutely clean and close to the shops and restaurants. " CA $145 CA $214 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Annapolis-Hotels-Historic-Inns-Of-Annapolis.h42068.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/2000000/1110000/1105600/1105532/fc311cc7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Basic Room, 1 King Bed (Safari Suite (at Tidewater House))](https://images.trvl-media.com/lodging/2000000/1110000/1105600/1105532/17d21ae1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/2000000/1110000/1105600/1105532/1969a1ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Meeting facility](https://images.trvl-media.com/lodging/2000000/1110000/1105600/1105532/e0eae32d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Tidewater Inn Easton 8.8/10 Excellent (832) "Great hotel! Stayed there multiple times." CA $251 CA $276 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Easton-Hotels-The-Tidewater-Inn.h1105532.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/200000/190700/190683/b2a10ae6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 Queen Bed, Non Smoking](https://images.trvl-media.com/lodging/1000000/200000/190700/190683/ead5e21d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/200000/190700/190683/76d50f6c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Business centre](https://images.trvl-media.com/lodging/1000000/200000/190700/190683/48d9bd9b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Quality Inn Grasonville 7.8/10 Good (841) "Great place and great staff" CA $137 CA $152 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Grasonville-Hotels-Quality-Inn.h190683.Hotel-Information) ![Superior Studio Suite | Balcony](https://images.trvl-media.com/lodging/2000000/1060000/1050500/1050433/4803b1f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Marina](https://images.trvl-media.com/lodging/2000000/1060000/1050500/1050433/27bb8cb0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/2000000/1060000/1050500/1050433/4750fa1f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, individually furnished, desk, laptop workspace](https://images.trvl-media.com/lodging/2000000/1060000/1050500/1050433/ad8d4ce2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Rod 'N' Reel Resort Chesapeake Beach 8.4/10 Very good (1001) "Great place to stay." CA $160 CA $206 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Chesapeake-Beach-Hotels-Rod-N-Reel-Resort.h1050433.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/7000000/6850000/6846100/6846089/bedcc35b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Breakfast area](https://images.trvl-media.com/lodging/7000000/6850000/6846100/6846089/3a599b65.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/7000000/6850000/6846100/6846089/ec18bd5a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Business centre](https://images.trvl-media.com/lodging/7000000/6850000/6846100/6846089/66584417.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western Plus Easton Inn & Suites Easton 9.2/10 Wonderful (1002) "Excellent staff, very clean room, good hotel breakfast " CA $167 CA $183 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Easton-Hotels-Best-Western-Plus-Easton-Inn-Suites.h6846089.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/120000/117000/116919/a8fad934.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 Bedroom](https://images.trvl-media.com/lodging/1000000/120000/117000/116919/6b94b388.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/1000000/120000/117000/116919/8e62a1db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/120000/117000/116919/2c8e8566.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express Annapolis East-Kent Island by IHG Grasonville 9.2/10 Wonderful (906) "Nice Holiday Inn Express with great water views." CA $167 CA $185 total includes taxes & fees Nov 10 - Nov 11 [](https://www.expedia.ca/Grasonville-Hotels-Holiday-Inn-Express-Annapolis-Kent-Island.h116919.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/2900/2882/ff227afc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily on-the-go breakfast](https://images.trvl-media.com/lodging/1000000/10000/2900/2882/ffc728ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Pool](https://images.trvl-media.com/lodging/1000000/10000/2900/2882/c066e894.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/2900/2882/59d23d5a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western Annapolis Annapolis 7.8/10 Good (1011) "Great place." CA $111 CA $126 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Annapolis-Hotels-Best-Western-Annapolis.h2882.Hotel-Information) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/1000000/10000/2300/2264/540d96d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/10000/2300/2264/a352e55b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/1000000/10000/2300/2264/19a193ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/2300/2264/4538681a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express Easton by IHG Easton 9.0/10 Wonderful (587) "I liked it. Nice staff!" CA $195 CA $214 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Easton-Hotels-Holiday-Inn-Express-Easton.h2264.Hotel-Information) ![View from property](https://images.trvl-media.com/lodging/1000000/10000/900/846/dcb23c20.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/900/846/e94a05fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/10000/900/846/237feb4b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/10000/900/846/ca081b22.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Graduate by Hilton Annapolis Annapolis 9.4/10 Exceptional (1008) "Staff was outstanding!" CA $217 CA $247 total includes taxes & fees Nov 10 - Nov 11 [](https://www.expedia.ca/Annapolis-Hotels-Graduate-By-Hilton-Annapolis.h846.Hotel-Information) 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](https://expedia.ca/Hotel-Search?startDate=2025-10-27&endDate=2025-10-28®ionId=6034722&adults=2&travelerType=family_friendly&sort=RECOMMENDED&openPlayBack=true) ## Top Sherwood Hotel Reviews ![SpringHill Suites by Marriott Annapolis](//images.trvl-media.com/lodging/2000000/1370000/1364100/1364028/80b99d82_y.jpg) ### SpringHill Suites by Marriott Annapolis 10/10 Excellent " Very clean and fresh room The TV screen already had my name on it !" [](https://expedia.ca/Annapolis-Hotels-SpringHill-Suites-By-Marriott-Annapolis.h1364028.Hotel-Information) ![DoubleTree by Hilton Hotel Annapolis](//images.trvl-media.com/lodging/1000000/10000/3100/3040/f77b4116_y.jpg) ### DoubleTree by Hilton Hotel Annapolis 10/10 Excellent "The staff were uniformly attentive and friendly." [](https://expedia.ca/Annapolis-Hotels-DoubleTree-By-Hilton-Hotel-Annapolis.h3040.Hotel-Information) ![Graduate by Hilton Annapolis](//images.trvl-media.com/lodging/1000000/10000/900/846/dcb23c20_y.jpg) ### Graduate by Hilton Annapolis 10/10 Excellent "Spacious room, very clean and comfortable lots of eclectic nautical furniture. We did not have breakfast. Easy parking in and out right in the heart of restaurants, & bars and a short walk to the harbor." [](https://expedia.ca/Annapolis-Hotels-Graduate-By-Hilton-Annapolis.h846.Hotel-Information) ![St Michaels Inn](//images.trvl-media.com/lodging/1000000/20000/10300/10281/6601016b_y.jpg) ### St Michaels Inn 10/10 Excellent "Room was clean, Staff was very friendly and welcoming. " [](https://expedia.ca/St-Michaels-Hotels-St-Michaels-Inn.h10281.Hotel-Information) ![The Westin Annapolis](//images.trvl-media.com/lodging/2000000/1680000/1678800/1678710/w3998h2667x0y0-54f847ff_y.jpg) ### The Westin Annapolis 10/10 Excellent "The hotel is conveniently located near town and the football stadium. The staff were professional, courteous and friendly. " [](https://expedia.ca/Annapolis-Hotels-The-Westin-Annapolis.h1678710.Hotel-Information) ![Historic Inns of Annapolis](//images.trvl-media.com/lodging/1000000/50000/42100/42068/bf4c0cc1_y.jpg) ### Historic Inns of Annapolis 10/10 Excellent "Excellent stay but I never received my wine " [](https://expedia.ca/Annapolis-Hotels-Historic-Inns-Of-Annapolis.h42068.Hotel-Information) ![Hilton Garden Inn Annapolis](//images.trvl-media.com/lodging/2000000/1650000/1641200/1641168/f7bcd5fc_y.jpg) ### Hilton Garden Inn Annapolis 10/10 Excellent "Derek was 👍" [](https://expedia.ca/Annapolis-Hotels-Hilton-Garden-Inn-Annapolis.h1641168.Hotel-Information) ![Best Western Annapolis](//images.trvl-media.com/lodging/1000000/10000/2900/2882/ff227afc_y.jpg) ### Best Western Annapolis 10/10 Excellent "very friendly personel" [](https://expedia.ca/Annapolis-Hotels-Best-Western-Annapolis.h2882.Hotel-Information) ![Crowne Plaza Annapolis by IHG](//images.trvl-media.com/lodging/1000000/10000/7700/7668/6084a9f0_y.jpg) ### Crowne Plaza Annapolis by IHG 10/10 Excellent "Great room." [](https://expedia.ca/Annapolis-Hotels-Crowne-Plaza-Annapolis.h7668.Hotel-Information) ## 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. 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