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Compare 512 Vacation Homes in Princess Anne with updated reviews, rates, and availability.

"Great stay! Our family had a great time!"

"Our stay at the Cottage near the Bay was fantastic and exactly what my family needed. The host went above and beyond to communicate with us and make our stay excellent. The cottage was very clean, cozy, and a welcome escape. When we come back to Crisfield we won't be staying anywhere else, as long as it isn't already booked!"

AED 732 total

includes taxes & fees

24 Dec - 25 Dec

Quaint home-like atmosphere for your vacation. Your home away from home!

"Made a quick trip for a long weekend. House met our expectations and the host was super helpful. "

"We loved the cozyness of this location and the view from the bedroom upstairs was just breathtaking. No better place to open the windows and enjoy theocean breeze and the "

"Thank you for allowing us to use you beautiful home for our stay. The location was perfect for us and our fur babies. The home was well stocked and very clean. If I could offer a suggestion it would be a reminder that your home is set up for maximum of 12 guest, but you offer one small TV and sitting room that accomdates only 6 people comfortably for the entire home, Most guest are looking for a place for everyone to gather together to talk or watch TV. I would suggest a large TV in your...

"This is a cute house in a beautiful location. We were very comfortable. I was a little taken aback at having to pay extra for linens and towels but everything else was excellent. Communication with the host was great."

Welcome to Oyster Bay Hideaway in the heart of Chincoteague Island.

"It was great!"

Welcome to Water's Edge perched on the Chincoteague Bay - Water Access and a Boat Slip!

"Wonderfully comfortable property conveniently located within walking distance to downtown shops and restaurants. Lots of opportunities to see beautiful sunsets from the porch!"

Chincoteague Island Vacation Rental | 3BR | 2BA | 1,280 Sq Ft

"The location is great. The space was comfortable and had everything we needed, plus extras. The rear porch was heavily utilized for morning coffee watching wildlife over the water (lots of birds, deer, and a visit from a muskrat) and evening relaxing. We crabbed and fished off the little dock, enjoyed home cooked meals and naps on the hammock. This home is not new. It’s not fancy. It’s exactly as advertised. If you’re looking for bells and whistles, stay elsewhere and pay more. If you want a...

Lily Pad has lovely Views of the Assateague Lighthouse!

"Great place for the price. 10/10 stay. Only small complaint is that the patio furniture, fridge, and radiators are older and have visible rust damage (but still work fine) and the floors were dirty when we arrived"

"A bit outdated and neglected. Stairs to bedrooms are very steep."

Ready to feel those 'East Side Breezes'?

"The place was perfect for the four of us. Plenty of room, very comfortable and quiet but close to anything we wanted to do on Chincoteague. Thank you for a wonderful stay and we look forward to coming back again :)"

"My husband and I along with two cats found ourselves homeless for a few days between selling one home and getting the keys to our forever home located in captains cove. Nick made the transition possible and easy. The home is beautifully decorated and quite interesting. Sunrise from the living room with a cup of tea was the best way to start my day. "

AED 1,868 total

includes taxes & fees

22 Jan - 23 January 2025

"We had a really lovely stay at Pony Paradise. Clean, comfortable, cozy. House comes with a linen package and I’m always weary of the sheets/towels a place offers but theirs were really nice! I will say that the beds are quite small but we made do for our short stay. Check in time at 4pm is rough- even a 3pm would be helpful but again, you make it work. Overall, the place itself was great and I would definitely rebook! The property management was easy to get in touch with and...

"The harbor checking stated 2 queen beds, but one was a king. Also misleading weather linnens & towels are included or need to bring your own. Everything else was great!’"

"I suspect the owner is paying someone to clean the property between visits. The owner is getting ripped off. There were huge dust bunnies in every corner and the front porch is where spiders come for their annual convention. The house itself could be cute and cozy if it were cared for. Location is good. Close to town, easy bike ride to beach."

"Super cute place! Quiet and well stocked."

"This property was exactly what we were looking for our family vacation. Location on the water, the amenities were above and beyond, comfortable beds, and land as far as you could see. The fishing and crabbing was exceptional for all ages. The kids loved crabbing, new to us, caught some turtles as well, all released back. Paddle boarding and kayaking on morning water (like glass), was on the daily. There is a perfect fire pit area to enjoy. The large open concept home is perfect for the...

Marion Station Vacation Rental | 3BR | 3BA | 2,660 Sq Ft | Step-Free Entry

"Home offers breathtaking views of the bay. Plenty of space for two families with children. Would love to come back!"

"Great location, restaurants and stores are within walking distance. the beach and museums are a short drive. We were there during the pony swim so that was a good experience. The house met our needs as a family of 9."