Vacation Homes in Woolford
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Featured Vacation Homes in Woolford

Spacious 6-Bedroom Solomons Island Retreat • Walk to Waterfront & Shops

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

NEW! Gorgeous Waterfront Estate with Saltwater pool, beach and dock

The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks

Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife

2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!

Shewell's A-Frame on Mill Creek

Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier

Discover tranquility near Calvert Cliffs

Midcentury Modern Lake House, gorgeous views, deck, 4-bedrooms in Lusby/Solomons

Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space.

Heart of Tilghman Island | Pet Friendly | Perfect for Weddings Guests & Families
Top trending hotels in Woolford

Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock
Vacation Rentals in Woolford
What kind of vacation do you want in Woolford? The answer to that question will help you choose the right lodging for your stay. The wise wanderer knows that a vacation rental is an essential part of the traveling experience. It’s more than just a place to crash at night—it’s where you wake up in the morning, where you lounge when you’re not exploring, and it’s the starting point for all your adventures. No matter what type of vacation homes strike your fancy, Travelocity has something in Woolford that will speak to you.
Do you want a fully equipped kitchen so you can exercise your culinary mastery and impress your travel buddies? How about a romantic terrace for your anniversary trip? Have you always wished to fall asleep to the sound of waves crashing on the shore? One of our vacation home rentals is bound to add that extra magic to your trip. In fact, we’ve got plenty of options lined up just for you in Woolford, including luxury vacation rentals. On a budget? We can work with your funds and still give you a great place to sleep at night.
Take a look at what we have on offer. You’ll find rentals close to the big tourist draws, as well as rentals that keep you away from the crowd. Consider vacation rentals a little off the beaten path where you can live like a local and discover hidden gems that never make it to the tourist sites. Book through Travelocity and start your getaway today.
Woolford Vacation Homes essential information
Accommodation | 254 Vacation Homes |
|---|---|
Lowest Price | CA $153 |
Highest Price | CA $822 |
Popular accommodation | Spacious 6-Bedroom Solomons Island Retreat • Walk to Waterfront & Shops, Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina, NEW! Gorgeous Waterfront Estate with Saltwater pool, beach and dock, The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks, Downtown St. Michaels | Walk to Shops, Restaurants and Nightlife, 2 blocks from Bay! Community beach! Boat launch! Kayak! Hike! Fossil Hunt!, Shewell's A-Frame on Mill Creek, Stunning Chesapeake view from almost ever room, private 15 home community beach, fossils, 450 pier, Discover tranquility near Calvert Cliffs , Midcentury Modern Lake House, gorgeous views, deck, 4-bedrooms in Lusby/Solomons, Kick back and enjoy the Chesapeake & this 3-bedroom, relaxing, stylish space., Heart of Tilghman Island | Pet Friendly | Perfect for Weddings Guests & Families |





