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Compare 511 Vacation Homes in Princess Anne with updated reviews, rates, and availability.

Blufin Bungalows & Marina

3.0 star property
9.4 out of 10, Exceptional, (85)
"Great stay! Our family had a great time!"
Blufin Bungalows & Marina

Cottage near the Bay

8.8 out of 10, Excellent, (28)
"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!"
The price is SAR 338
SAR 744 total
includes taxes & fees
11 Jan - 12 Jan
Cottage near the Bay

Ryokan - Water views, Shared Boat Launch!

9.0 out of 10, Wonderful, (4)
"Our group chose this house because of its beautiful view of the water and wooded area at the rear, and it did not disappoint. The living room and dining area were comfortable and spacious, and the bedrooms and bathrooms were clean and comfortable. We also liked the fact that the two bathrooms were accessible to all guests, instead of having one attached to a master bathroom, as is the case with many rentals. The one problem we ran into was that the heat didn't work, which meant that the indoor...
Ryokan - Water views, Shared Boat Launch!

Cozy Nest - Waterview, Pet Friendly, Screened Porch

10.0 out of 10, Exceptional, (4)
"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 "
Cozy Nest - Waterview, Pet Friendly, Screened Porch

Set Sail to the Rusty Anchor! Your Perfect Getaway on Deal Island, MD

2.0 star property
10.0 out of 10, Exceptional, (2)
"Our stay was perfect. The home was quite lovely and equipped with all amenities. The location was very nice. The bay was only a 2 minute walk at the end of the street. Highly recommend."
Set Sail to the Rusty Anchor! Your Perfect Getaway on Deal Island, MD

Tranquil Shores - Relaxation With a Water View!

9.8 out of 10, Exceptional, (125)
"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."
Tranquil Shores - Relaxation With a Water View!

Oyster Bay Hideaway on Chincoteague Island!

10.0 out of 10, Exceptional, (8)
"It was great!"
Oyster Bay Hideaway on Chincoteague Island!

The Brass Crab - Check in/out any day!

10.0 out of 10, Exceptional, (144)
"It is my birthday weekend and to celebrate I wanted to rent a beach house"
The Brass Crab - Check in/out any day!

Water's Edge on Chincoteague Island!

9.8 out of 10, Exceptional, (18)
"Wonderfully comfortable property conveniently located within walking distance to downtown shops and restaurants. Lots of opportunities to see beautiful sunsets from the porch!"
Water's Edge on Chincoteague Island!

Quaint Chincoteague Island Hideaway w/ 2 Porches!

8.8 out of 10, Excellent, (59)
"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...
Quaint Chincoteague Island Hideaway w/ 2 Porches!

Lily Pad on Chincoteague Island - Lighthouse Views and Pet Friendly!

9.4 out of 10, Exceptional, (43)
"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"
Lily Pad on Chincoteague Island - Lighthouse Views and Pet Friendly!

Miss Agnes - Water Front 3BR home PET FRIENDLY, NO LINENS PROVIDED

9.4 out of 10, Exceptional, (53)
"A bit outdated and neglected. Stairs to bedrooms are very steep."
Miss Agnes - Water Front 3BR home PET FRIENDLY, NO LINENS PROVIDED

Stunning waterfront panoramic view getaway house

10.0 out of 10, Exceptional, (45)
"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. "
The price is SAR 556
SAR 2,004 total
includes taxes & fees
22 Jan - 23 Jan
Stunning waterfront panoramic view getaway house

Duck's Delight - Pet friendly rentals within walking distance to Maddox Blvd!

9.8 out of 10, Exceptional, (121)
"Made a quick trip for a long weekend. House met our expectations and the host was super helpful. "
Duck's Delight - Pet friendly rentals within walking distance to Maddox Blvd!

Pony Paradise - Gaze at Ponies, Walk to the Carnival, and bring your family dog!

10.0 out of 10, Exceptional, (3)
"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...
Pony Paradise - Gaze at Ponies, Walk to the Carnival, and bring your family dog!

Always Sunny - island home. Pet Friendly - Close to Carnival. NO LINENS

8.2 out of 10, Very Good, (18)
"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."
Always Sunny - island home. Pet Friendly - Close to Carnival. NO LINENS

Serendipity on Chincoteague - The perfect getaway!

9.8 out of 10, Exceptional, (6)
"Super cute place! Quiet and well stocked."
Serendipity on Chincoteague - The perfect getaway!

Waterfront Marion Station Retreat w/ Private Dock!

8.6 out of 10, Excellent, (4)
"Home offers breathtaking views of the bay. Plenty of space for two families with children. Would love to come back!"
Waterfront Marion Station Retreat w/ Private Dock!

Waterfront Wonder - Private Pier on the Chincoteague Bay!

9.4 out of 10, Exceptional, (3)
"I recently completed a stay at Waterfront Wonder. There were no problems with Seaside Rentals. The staff were helpful and answered my calls. I rented this place for specific reasons. I needed a first floor bedroom for my 84-year old mother. I needed a place that was pet-friendly for Mom's dog. FYI, yard is not fenced for dogs. And, I wanted a house with a water view, because Mom loves to see the water. The Waterfront Wonder fulfilled my requirements. Additionally, the kitchen was...
Waterfront Wonder - Private Pier on the Chincoteague Bay!

Cottage on the Bay

9.8 out of 10, Exceptional, (6)
"Clean and accommodating host. Has many of the necessities for the home, including washer/dryer , soaps , trash bags , cleaning essentials , plates/bowls/cups, kitchen gadgets , and more. Home feels safe away from predator animals . Couple deers around. Bring insect repellent."
Cottage on the Bay
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other property types in Princess Anne

Key West Cottages

3.0 star property
9.8 out of 10, Exceptional, (313)
"Gorgeous property, very clean, perfect location, quiet, relaxing"
The price is SAR 453
SAR 509 total
includes taxes & fees
9 Feb - 10 Feb
Key West Cottages

Island Breeze Cottage w/ screened porch. Water view! Quiet location!

9.8 out of 10, Exceptional, (275)
"Clean and quiet. Efficient use of space"
Island Breeze Cottage w/ screened porch. Water view! Quiet location!

Waterfront on Marsh Island!

8.8 out of 10, Excellent, (21)
"Small Cozy condo for couples. Very quiet and relaxing with great sunrises and sunsets! Great location with being on the water!"
Waterfront on Marsh Island!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.