What are the top rated Cottage Rentals in Woolford?

There are a lot of options in Woolford. If you plan on staying in the Woolford area, consider making a reservation for a few nights at one of these properties as these have been rated the top Cottage Rentals in Woolford: <a href="/property/waterfront-family-retreat-with-pool-on-7-acres/HA-3211512883" class="class="static-page-link"">Waterfront Family Retreat with Pool on 7+ acres!</a> <a href="/property/waterfront-getaway-with-dock/HA-3212852851" class="class="static-page-link"">Waterfront Getaway with Dock</a> <a href="/property/endless-summer-waterfront-on-the-chesapeake-bay/HA-3214218261" class="class="static-page-link"">&#34;Endless Summer&#34; Waterfront on the Chesapeake Bay!</a> <a href="/property/chesapeake-waterfront-7bd-5ba-beach-pool-pets-dock/HA-121219957" class="class="static-page-link"">Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock</a> <a href="/property/amazing-views-waterfront-3-bedroom-home-in-madison-with-a-190-foot-pier/HA-3214399934" class="class="static-page-link"">Amazing views waterfront 3-bedroom home in Madison with a 190 foot pier!</a> <a href="/property/the-blue-heron-spacious-waterfront-eastern-shore-getaway-with-kayaks/HA-3213492799" class="class="static-page-link"">The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks</a> <a href="/property/chesapeake-waterfront-7br-5ba-beach-pool-dock/BC-14171561" class="class="static-page-link"">Chesapeake Waterfront - 7BR 5BA - Beach Pool Dock</a> <a href="/property/2br-riverfront-retreat-on-61-acres-with-270-degrees-of-waterfront-private-pool/HA-3215009300" class="class="static-page-link"">2BR Riverfront Retreat on 61 acres with 270 degrees of waterfront/private Pool</a> <a href="/property/a-beautiful-waterfront-retreat-for-family-gatherings/HA-3211709270" class="class="static-page-link"">A Beautiful Waterfront Retreat for Family Gatherings!</a> <a href="/property/farmhouse-charm-woolford-studio-apt-w-amazing-eastern-shore-sunrise-sunsetsn/HA-3213871962" class="class="static-page-link"">Farmhouse Charm Woolford Studio Apt. w/Amazing Eastern Shore Sunrise &amp; Sunsetsn</a>

How much does it cost to rent a cottage in Woolford?

The average cost for a cottage rental in Woolford is $671 per night. Coffeeshawaii has a wide list of great cottages near Woolford that would suit your needs. There are single and multiple rooms for solo trips or family vacations.

Are there any cottages in Woolford that allow pets?

Yes, here are the top cottage rentals in Woolford that allow you to bring your pet: Cedar Point 6.5 Acre Waterfront Family Retreat With Pool And Sandy Beach! Private waterfront cottage with pool on Church Creek Chesapeake Waterfront- 7bd/5ba, Beach, Pool, Pets, Dock Chesapeake Waterfront - 7BR 5BA - Beach Pool Dock Waterfront Getaway with Dock "Endless Summer" Waterfront on the Chesapeake Bay! <a href="/all/usa/maryland/woolford" class="class="static-page-link"">See all pet-friendly vacation rentals in Woolford on Coffeeshawaii</a>

Do you have any rental cottages in Woolford that are suitable for families?

Most of our listed cottages are suitable for families. Check out the complete list of cottages in Woolford to find one that works for you.

Are there quality cottages in Woolford that have indoor swimming pools?

As of 2026, the data from Coffeeshawaii shows that there are Over 2 private swimming pools or cottages with indoor pools in the Woolford area along with other great amenities.

Woolford Cottage Rentals By Owner

Cedar Point 6.5 Acre Waterfront Family Retreat With Pool And Sandy Beach!

From US $1,090

10.0 (88 Reviews)

Cottage

Cedar Point 6.5 Acre Waterfront Family Retreat With Pool And Sandy Beach!

Air Conditioner
Parking
Pet Friendly

Woolford Cottage Rentals & Holiday Homes

Find the best cottages in Woolford - We found 2 exact matches

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