Vacation rentals in Gloucester

Cape Charles cottage, family friendly, in town

Welcome to Cape Charles Cottage in the historic district! We are 6 blocks to the beach and 4 blocks to Mason ave (shops, restaurants). The town is very walkable or golf cartable…you can rent ours! We can host up to 10 guests with 4 bedrooms and a bonus room with a daybed w trundle that pulls to side by side twins. One bedroom has an ensuite bathroom and the others share a hall bath with a tub/shower. Kitchen is fully equipped, fenced yard, outdoor shower,fire pit, grill & shed with beach gear.

Cape Charles Retreat - 2 Blocks from Beach/Town

Welcome to Cape Charles Retreat! Come on up to the porch, grab a lemonade and settle into the porch swing for some much deserved rest and relaxation. Cape Charles Retreat is a beautiful 100+ year old American Foursquare located two blocks from the beach, Central Park, and town! Our home has been restored to preserve much of its original charm while adding modern amenities and outfitted with everything you’ll need for a great beach vacation. So grab your bathing suit and come for a visit!

Riverfront Retreat with PRIVATE POOL and BEACH!!

Welcome to your riverfront retreat. Only a 2 hour drive from DC/RVA, this riverfront cottage has everything you need to get away. After spending time on your private beach, relax in your own pool, before spending the evening relaxing in the screened in porch or by the firepit. Sunny? Take out the kayaks, stand up paddle boards or cornhole. Rainy? The home is furnished with TVs, chromecasts, high speed internet, board games and puzzles. Follow us on IG @riverfront_retreat for more

Summer Camp Tiny Cottage Walk to the beach & shops

At less than 470 sq feet, this 1920s house is super fun & ready to be enjoyed for a couples, friends, and small families! • King sized bed with smart tv on the first floor • Two twin beds in a cozy sleeping loft • Small kitchen with propane stove, Nespresso maker & living space with a smart tv • Patio w/ charcoal grill, solo stove, & dining table • Paddle board & floats Please read through our totally honest disclaimer below!

The Tarryn Elizabeth Unit A

What better way to enjoy a getaway or family vacation than on a peaceful quiet island where the beach is clean and spacious and some of best fishing and crabbing in the world! Rent a four wheeler and drive on the beach 24/7 or lounge on the porch and soak in the sun, and not to mention the unlimited hi speed Internet with smart TVs in all 3 rooms for all your relaxing needs if you should choose to stay in the home!

Fantastic Getaway

You need to see this fully furnished, stunning guest house located along the historic section of Chesapeake Ave. Wake-up to breathtaking views of the Chesapeake Bay. Great fishing, crabbing, sailing, bike trails, kayaking and more. Enjoy herons, osprey, dolphins and other wildlife. Centrally located to shopping, casinos, restaurants and public beaches!

Nicebay Getaway

Discover this cozy Cape Charles haven near beach & bay. Golf, biking, kayaking, fishing - all at your doorstep. Charming golf cart community, stunning sunsets & nature trails await. Relax in comfort after outdoor adventures. Days in the sun and on the bay make the most unforgettable coastal getaway! null.

White Heron Cottage

Find yourself feeling cozy at this charming and peaceful home. Centrally located 15 minutes from our lovely little town and 45 minutes to Williamsburg, VA. Several public beaches are close by. Owners are proud Super Host who specialize in attention to detail and making sure guest have a great stay.

Pleasant House by the beach

Home away from home. Relax with the whole family at this peaceful place to stay. 3 bedrooms, 2 baths house. Beautiful, updated kitchen to cook in and drink your morning coffee. Walking distance to the Chesapeake Bay. Restaurants and brewery nearby. You will truly feel like you're on vacation here.