
Holiday houses in Woolford
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Top-rated holiday rentals in Woolford
Guests agree: these stays are highly rated for location, cleanliness and more.
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Other great holiday rentals in Woolford
Top Guest favourite

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 favourite

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 favourite

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!

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.
Guest favourite

Home in Taylors Island
5 out of 5 average rating, 15 reviewsHolliday House
JamesRating, 5 stars3 weeks ago
nice quiet place to relax and feel right at home

Home in Cambridge
4.88 out of 5 average rating, 129 reviewsDorothy's Chesapeake Delight
AnitaRating, 5 stars3 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

Houseboat in Solomons
5 out of 5 average rating, 72 reviewsIsland Shanty
SherriRating, 5 stars3 weeks ago
Clean, quiet, and convenient. Would stay again!
Top Guest favourite

Cottage in Princess Anne
5 out of 5 average rating, 9 reviewsWaterfront Cottage in Mt. Vernon
JillianRating, 5 stars4 days ago
Had a wonderful stay! The entire family enjoyed the little beach and dock. Our son caught us crabs to eat every day and our daughter was in the water constantly! Very peaceful sitting on the back deck.
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- Sandy Point State Park
- National Harbor
- Quiet Waters Park
- Maryland Renaissance Festival
- Flounder Pavilion Beach Front - Sandy Point State Park
- Heritage Shores
- Killens Pond State Park
- Plantation Lakes Golf and Country Club
- Gerry Boyle Park
- Ragged Point Beach
- Six Flags America
- Breezy Point Beach & Campground
- Chesapeake Beach Water Park
- Idlewilde Restoration Project
- Sandyland Beach
- Rose Haven Memorial Park
- Bayfront Beach
- Brownies Beach
- Quiet Waters Dog Beach
- Oxford Beach
- Matapeake Clubhouse and Beach
- Downs Park Dog Beach
- Piney Point Beach
- Lane Beach