Holiday houses in Woolford

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Popular amenities for Woolford holiday rentals

Other great holiday rentals in Woolford

Top Guest favourite
Guesthouse in Cambridge
5 out of 5 average rating, 14 reviews

The 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 favourite
Home in Piney Point
5 out of 5 average rating, 18 reviews

Waterfront Studio | Bikes & Kayaks | Beach Access

LeslieRating, 5 stars6 days ago
May and my partner wanted to get away for the weekend for some rest and relaxation. This is the perfect place. It’s peaceful private. The water is awesome. I will definitely stay there again. Earl was awesome and giving instructions and making sure that we had everything we needed this is a true diamond in the rough. I don’t say that often Thank you very much. 🥂👏👍🏽
Top Guest favourite
Home in Madison
4.96 out of 5 average rating, 47 reviews

Bayfront 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 favourite
Place to stay in East New Market
4.94 out of 5 average rating, 18 reviews

Beautiful Waterfront Getaway on the Choptank River

AmyRating, 5 stars6 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 reviews

The 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, 130 reviews

Dorothy's Chesapeake Delight

AnitaRating, 5 stars6 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 favourite
Home in Cambridge
4.94 out of 5 average rating, 17 reviews

Peaceful Waterfront Home with Pool and Pier

KarenRating, 5 starstoday
Our favorite Airbnb stay! Every aspect of this house was well executed & thoughtful. Fantastic layout of the house allowed our family to be as connected as we wanted yet had private places to retreat. The pool was perfect and the dock had everything you could ask for with fishing and crabbing. The kitchen was stocked with anything you would possibly need. Very quiet and calm location, yet near to grocery and restaurants. We couldn’t have asked for a better vacation spot. Mindy was awesome and available for any questions that we had. We are so grateful for this great family vacation spot!
Top Guest favourite
Apartment in Port Republic
4.97 out of 5 average rating, 206 reviews

Serenity 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.

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  2. United States
  3. Maryland
  4. Dorchester County
  5. Woolford