1. Chesapeake Bay - Gloucester, VA

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Chesapeake Bay - Gloucester, VA

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Endeavor Point - The pier it awesome even in the snow

Endeavor Point

(2 reviews)

Endeavor Point is a Paradise! Everything about this place is…read moremagnificent, starting with the hostesses, Sophie and Beth. Communication with both was great from booking to leaving. Located by the Patuxent River with a breathtaking view, Endeavor Point, is a ridden gem with campground, private beaches you can swim, a huge fishing pier, and cottages for rentals. From the moment you step onto the grounds of this place you feel your entire body relaxing. It is an amazing experience! I rented a cottage (Mermaid Folly) for the weekend. The place was very well furnished with a fully equipped kitchen, living and dining room furniture, very comfortable beds with soft linens, clean baths with soft towels. In general, the place was very clean, well decorated, and very functional. What I loved the most about the cottage was the balcony with a fantastic view, sitting outside under the tree close to the water, and listening to the waves breaking by the river shore. I also loved my walks in the mornings and afternoons by the breezy beaches and pier watching people fishing, the sunrising, and the sunset. I strongly recommend Endeavor Point if you want to just relax on a visit during the day, if you like camping overnight, or staying in a very comfortable cottage over the weekend.

Warning: stay away, owners are very iffy and unsafe pier and surroundings areas. Owners will accuse…read moreyou of bogus things and put you out, (of course based on race.)

The Chesapeake Inn - Coffee stand, so cute

The Chesapeake Inn

(18 reviews)

$$$

The Chesapeake Inn is a hidden gem in Urbanna, VA. I can't say enough good things about this little…read moreInn. Our room was beautifully appointed with crisp white linens, comfy armchairs, and the cutest decor. It even had a beautiful chandelier and recessed lights. The lobby looked like a showroom for an interior decorator and the grounds are peppered with settees with colorful throw pillows. Everything about this little Inn screams "awesome".

Dog friendly unique inn in the adorable town of Urbanna with great restaurants and the river in…read morewalking distance. Neat town events too that you can check out on Facebook Urbanna sites.. Their rooms are $199/night ($219.50 with taxes).  They do have a two night minimum on weekend. Their rates include everything - many hotels add amenity fees, but they have decided to use simple, predictable pricing so their rates includes their bikes, surreys, kayaks as well as snacks and waters in their rooms and the use of their lobby/living room keurig. They sometimes even have food vendors come to the parking lot. Had a great pizza truck which was awesome to bring pizza back to the room especially since the Italian restaurant shut down during COVID. They have a Farmer's Market, boat and golf cart parade, Oyster Festival, Halloween celebrations, great boutiques with fabulous clothing and unique gifts and wine shops and great prices on antiques to include an awesome flea market. Occasionally live music. Which is the best! They has been limited during COVID but hopefully will start up soon.

Chesapeake Bay - Gloucester, VA - hotels - Updated October 2026

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