
Holiday houses in Princess Anne
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Top-rated holiday rentals in Princess Anne
Guests agree: these stays are highly rated for location, cleanliness and more.
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Popular amenities for Princess Anne holiday rentals
Other great holiday rentals in Princess Anne

Cottage in Deal Island
4.64 out of 5 average rating, 236 reviewsDeal Island Bay Cottage - Maryland
AshRating, 5 stars1 week ago
Great location. Very rural, quiet neighborhood, very responsive host.

Home in Salisbury
4.85 out of 5 average rating, 131 reviewsHighbanks House
RobertRating, 5 stars2 weeks ago
We stayed here for the Eagleman 70.3 and found the HighBanks house exactly what we needed and wanted. A secluded property where our families could relax and enjoy some time together. Parisa send us the information we needed and was very accommodating to us. We enjoyed staying at the HighBanks house and would recommend to others as well.

Home in Eden
5 out of 5 average rating, 3 reviewsCountry House on Wicomico Creek
AshleyRating, 5 stars4 days ago
Our stay was absolutely amazing. The house was stunning and comfortable, definitely hands down one of my favorites places I have stayed. The kitchen had everything I could need and such great quality cookware. The beds were so comfortable and cozy. The farm was peaceful, beautiful and so enjoyable to look at. The hosts were so nice. I honestly didn’t want to leave definitely Would love to stay again.
Top Guest favourite

Cabin in Westover
5 out of 5 average rating, 45 reviewsChalet Style Home, private country setting
AprilRating, 5 stars4 months ago
I recently stayed at Crooked Elm and was thoroughly impressed. The place was impeccably clean, and the attention to detail was evident in every corner. The host's responsiveness was top-notch! One feature that stood out was the guest binder. It was incredibly detailed, providing clear instructions on everything from using the fireplaces to local attractions and dining recommendations. This made it easy to settle in and feel at home. It had everything we needed for a cozy stay! Overall, my stay at Crooked Elm was delightful, and I highly recommend it to anyone looking for a cozy, well-managed retreat.
Guest favourite

Home in Westover
5 out of 5 average rating, 17 reviewsRumbley Retreat
JesseRating, 5 stars3 days ago
Hope is amazing and very responsive to all questions we had. This is a great place to stay and I highly recommend it. Great host beautiful surroundings.
Top Guest favourite

Farm stay in Westover
5 out of 5 average rating, 58 reviewsThe Homestead at Sugar Water Manor Farm Stay
JakeRating, 5 stars1 month ago
This place is great! We had such a wonderful time staying on the farm. Our kids loved watching the animals, helping the crew collect eggs from the hens and ducks, and the amazing breakfasts delivered every morning and smores over the fire every night. We'll be back for sure!
Guest favourite

Home in Salisbury
4.99 out of 5 average rating, 71 reviewsLuxe Zen Retreat
CadeRating, 5 stars1 week ago
Came to stay for a wedding. Could tell the home was newly renovated and very clean. Great place to stay.
Guest favourite

Home in Quantico
4.98 out of 5 average rating, 103 reviewsOne of a kind waterfront home with private dock
ZoeyRating, 5 stars4 weeks ago
This was one of my favorite stays so far! The location was quiet and peaceful with beautiful views all around. The dock in the backyard was nice, my dogs loved the fenced in yard and big yard to the side of the house. The house was clean and the bed was super comfortable. I can’t wait to come back! 😊
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- Ocean City Beach
- Assateague Island National Seashore
- Ocean City Boardwalk
- Dewey Beach Access
- Jolly Roger Amusement Park
- Towers Beach
- Northside Park
- Bayside Resort Golf Club
- Jolly Roger at the Pier
- Assateague Beach
- Delaware Seashore State Park
- Poodle Beach
- Snead Beach
- Peninsula Golf & Country Club
- Whiskey Beach
- Heritage Shores
- Plantation Lakes Golf and Country Club
- Baywood Greens Golf Maintenance
- Bear Trap Dunes
- Gerry Boyle Park
- Nassau Valley Vineyards
- Gordons Pond State Park Area
- Fenwick Island State Park Beach
- Trimper Rides of Ocean City