
Vacation rentals in Woolford
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Top-rated vacation rentals in Woolford
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Top guest favorite

Guesthouse in Cambridge
5 out of 5 average rating, 14 reviewsThe Place in Cambridge-Summer is in the Air!
PhilRating, 5 stars1 week ago
Catherine’s place was perfect location for Ironman eagleman. We were able to walk everywhere we needed to go. The place was clean, quiet, and comfortable. Being able to cool off in the pool was great. They were very friendly and I would stay again.
Top guest favorite

Cabin in Church Creek
5 out of 5 average rating, 22 reviewsCharles Creek Cabin
LaurenRating, 5 stars1 week ago
Enjoyable getaway in Blackwater area. The cabin really felt off the grid, and I enjoyed the wide selection of movies and non-internet entertainment. The area is very buggy when we went in early June, I wasn't quite ready for that as Cambridge is not. I liked the feel and would recommend it for anyone looking for quiet and remote feeling, but not challenging to get to.
Top guest favorite

Home in Madison
4.96 out of 5 average rating, 47 reviewsBayfront Gem w/ Amazing Water Views + Pond!
AnneRating, 5 stars3 weeks ago
The house was exactly as pictured--lovely, spacious, and welcoming. Right on the water with absolutely gorgeous views and a calming, peaceful vibe! The kitchen was fantastic and well-appointed with high-end appliances and all the pots/pans/utensils we needed to cook family meals. Beds were super-comfortable. The whole house is fully stocked for a wonderful stay. We loved it! Thank you for sharing your amazing home with us!
Top guest favorite

Place to stay in East New Market
5 out of 5 average rating, 17 reviewsBeautiful Waterfront Getaway on the Choptank River
AmyRating, 5 stars4 days ago
We had a wonderful two-night getaway at this beautiful home! It was perfect for our little family—super clean and incredibly comfortable. Our toddler loved having space to explore, especially with the beach and water just a walk away on the property. There's also so much to do locally that's close to this listing as well (all within 10-20 min drive). Lee and his wife were so friendly and welcoming. We’d come back in a heartbeat! Highly recommend for anyone traveling with kids.

Home in Woolford
4.62 out of 5 average rating, 42 reviewsThe Blue Heron-Spacious Waterfront house w/ kayaks
RhondaRating, 5 stars3 weeks ago
We stayed here with our family for my son‘s wedding. Anne was wonderful when we had questions as we were entertaining some guests for rehearsal dinner party there. Beautiful sunrises super peaceful area. Awesome sunroom screened in porch just can’t beat it. She had games and activities for inside and outand everyone in our family had a blast. We will definitely return again.

Home in Cambridge
4.88 out of 5 average rating, 129 reviewsDorothy's Chesapeake Delight
AnitaRating, 5 stars4 days ago
What a great place to stay and relax. Sitting with your feet in the sand , kayaking , crabbing and fishing . We will definitely boom again .
Top guest favorite

Apartment in Port Republic
4.97 out of 5 average rating, 206 reviewsSerenity Suite on Chesapeake Bay
KristaRating, 5 stars1 week ago
This is our second time staying at this cozy and tranquil retreat—and it won’t be our last. We first came here six months ago for a quiet getaway from the kids, and we liked it so much we knew we’d be back. This time was just as wonderful. The place is spotless, peaceful, and incredibly relaxing. The view of the bay is absolutely stunning—calm, quiet, and the perfect backdrop for unwinding. The hosts are warm and welcoming, and the space has everything you need for a comfortable and refreshing stay. If you’re looking for a serene escape with beautiful scenery and thoughtful touches, this is the place. We’re already planning our next visit.
Top guest favorite

Home in Cambridge
5 out of 5 average rating, 7 reviewsMagical Waterfront Home Dock, Firepit, Family Fun!
EdieRating, 5 stars2 weeks ago
We walked in to Heron’s Rest and were AWESTRUCK by the view! The open floor plan and huge windows take complete advantage of that view. It was gorgeous. In addition, there were many great sitting areas both inside and out, to relax with family and friends, to hide away with a book, or to duck out for a quick meeting. We can be picky about kitchens (we always bring our own necessities) but this kitchen has it all. And we were with old friends who all love to cook. We had so much good food. I know Cambridge has interesting place to eat, but we never left the house. When we did leave the house, we were out on boats. We put a small fishing boat in at the boat ramp at Boyle Park, very close and easy. We also put our own kayaks in the water using the kayak lift on the dock. For me, the best part was swimming every day from the ladder on the dock. It’s not too deep, the bottom is sandy and even in late May the water was not too chilly. Overall, Heron’s Rest was a huge hit!
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- Sandy Point State Park
- National Harbor
- Quiet Waters Park
- Maryland Renaissance Festival
- Flounder Pavilion Beach Front - Sandy Point State Park
- Plantation Lakes Golf and Country Club
- Heritage Shores
- Killens Pond State Park
- Gerry Boyle Park
- Ragged Point Beach
- Six Flags America
- Breezy Point Beach & Campground
- Chesapeake Beach Water Park
- Idlewilde Restoration Project
- Rose Haven Memorial Park
- Bayfront Beach
- Brownies Beach
- Sandyland Beach
- Quiet Waters Dog Beach
- Oxford Beach
- Matapeake Clubhouse and Beach
- Downs Park Dog Beach
- Lane Beach
- North Beach Boardwalk/Beach