Princess Anne Vacation Rentals

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Check prices for these dates

Tonight
Jun 23 - Jun 24
Tomorrow
Jun 24 - Jun 25
This weekend
Jun 27 - Jun 29
Next weekend
Jul 4 - Jul 6

Vacation Rentals in Princess Anne

Blufin Bungalows & Marina
On the beach

Blufin Bungalows & Marina

3.0 star property
9.6 out of 10, Exceptional, (136)
"Beautiful place to visit. We stayed here last year as well and each visit has been great."
Blufin Bungalows & Marina
Key West Cottages
Exterior

Key West Cottages

3.0 star property
9.8 out of 10, Exceptional, (390)
"Clean, relaxing we throughly enjoyed our stay!"
Key West Cottages
2BR Waterfront Cottage with the Most Spectacular View of lighthouse!
Pool

2BR Waterfront Cottage with the Most Spectacular View of lighthouse!

9.6 out of 10, Exceptional, (44)
"Lovely , peaceful mini vacation"
2BR Waterfront Cottage with the Most Spectacular View of lighthouse!
Cabin at Holdens Creek on Eastern Shore of VA
Interior

Cabin at Holdens Creek on Eastern Shore of VA

9.6 out of 10, Exceptional, (165)
"I like the fact that we were away from the hustle and bustle. The beaches are near by. And it was an overall great experience. Especially if you like secluded areas "
Cabin at Holdens Creek on Eastern Shore of VA
Strawberry Crossroads
Exterior

Strawberry Crossroads

2.0 star property
8.0 out of 10, Very Good, (1)
"Convenient location to stay if you want to visit Ocean city Maryland. Nothing to do in the camp site. We had a peaceful and relaxing trip. Cabin was comfortable."
Strawberry Crossroads
Waterfront on Marsh Island!
Interior

Waterfront on Marsh Island!

8.8 out of 10, Excellent, (26)
"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!
At the Water's Edge - is there anywhere you'd rather be?!
Interior

At the Water's Edge - is there anywhere you'd rather be?!

10.0 out of 10, Exceptional, (43)
"The property was great and comfy. Had everthing it needed in every way. From top to botyom. Definatley want to book again. Thanks for hosting us. "
At the Water's Edge - is there anywhere you'd rather be?!
Cozy Little Cottage on chincoteague island va.
Property grounds

Cozy Little Cottage on chincoteague island va.

9.6 out of 10, Exceptional, (38)
"Very cute little cottage, perfect amount of space for 2, has just about everything you'd need! Owner is helpful as well. Lots of places to eat within 15 mins"
Cozy Little Cottage on chincoteague island va.
Cottage near the Bay
Dining

Cottage near the Bay

8.8 out of 10, Excellent, (35)
"We enjoyed our stay. The host was very responsive to our needs and I appreciate her flexible schedule"
The price is ￥11,833
￥27,409 total
includes taxes & fees
Jun 27 - Jun 28
Cottage near the Bay
NEW PET FRIENDLY LISTING ALERT!!
Smart TV, fireplace

NEW PET FRIENDLY LISTING ALERT!!

9.4 out of 10, Exceptional, (6)
"Lovely home right on the river- fishing to your hearts content Clean, lots to do very peaceful!!! Would definitely come back! Mia is great to work with"
NEW PET FRIENDLY LISTING ALERT!!
Only 5 min to Assateague National Seashore!
TV, DVD player

Only 5 min to Assateague National Seashore!

9.6 out of 10, Exceptional, (16)
"Nice place. "
Only 5 min to Assateague National Seashore!
Historic home on Smith Island w/ dock!
Beach

Historic home on Smith Island w/ dock!

9.6 out of 10, Exceptional, (37)
"This property was perfect for a family of 4. It was very clean, the kitchen was well stocked and the neighbors were amazing and helpful. Visit the arcade by the marina right before sunset!"
Historic home on Smith Island w/ dock!
Only 5 min. from the Beach!
Beach

Only 5 min. from the Beach!

8.6 out of 10, Excellent, (26)
"Great time. Nice accomodations, easy access. Beautiful area."
The price is ￥22,754
￥37,474 total
includes taxes & fees
Jul 6 - Jul 7
Only 5 min. from the Beach!
The purple door at the bay.
Beach nearby

The purple door at the bay.

9.4 out of 10, Exceptional, (42)
"Property was slightly run down and had no driveway (just grass). It was in a great neighborhood with a beautiful view. We had to take the trash 15 minutes south when leaving (in the opposite direction of home for us). It was good enough for us to relax and cook but a slight bit expensive for its outdated condition though."
The price is ￥23,009
￥65,341 total
includes taxes & fees
Jul 2 - Jul 3
The purple door at the bay.
Chincoteague Island House "Sir Whelk-A-Lot" Kayaks Included! Downtown Location!
Fridge, microwave, oven, stovetop

Chincoteague Island House "Sir Whelk-A-Lot" Kayaks Included! Downtown Location!

10.0 out of 10, Exceptional, (50)
"Hi we stayed at the beach house and loved it. Easy booking process, great host, great accommodations and location was perfect!"
Chincoteague Island House "Sir Whelk-A-Lot" Kayaks Included! Downtown Location!
Pet-Friendly Smith Island Cottage w/ Golf Cart!
Miscellaneous

Pet-Friendly Smith Island Cottage w/ Golf Cart!

10.0 out of 10, Exceptional, (15)
"great but high tide problems to limit activity"
Pet-Friendly Smith Island Cottage w/ Golf Cart!
The Mermaid Lounge on Chincoteague island!
Terrace/patio

The Mermaid Lounge on Chincoteague island!

10.0 out of 10, Exceptional, (2)
"We had a wonderful time just relaxing and enjoying the area. The property was perfect for our family needs. The neighbors were lovely. Amenities were just what we needed. The neighborhood is quiet, but very close to everything. Some things are within walking distance such as kayaks and tours of the bay. Nice front porch. We went to the last night of the Fireman’s carnival. Small town America does still exist. We did not need a pool as planned on beaching it. The community park is very close by...
The Mermaid Lounge on Chincoteague island!
Water's Edge on Chincoteague Island!
Property grounds

Water's Edge on Chincoteague Island!

9.8 out of 10, Exceptional, (24)
"Great services.. And great place and location!"
Water's Edge on Chincoteague Island!
Salty Sailor - 2BR , close to Memorial Park Pet friendly LINENS AND TOWELS
Exterior

Salty Sailor - 2BR , close to Memorial Park Pet friendly LINENS AND TOWELS

6.8 out of 10, (12)
"The Salty Sailor was an excellent, affordable, and pet friendly rental. Nice location on ridge rd next to Mr Baldys which is a must to try if you stay here. The rooms are a bit older but maintained well. I didn’t experience any of the conditions that were listed in the other reviews here. We would certainly stay here again."
Salty Sailor - 2BR , close to Memorial Park Pet friendly LINENS AND TOWELS
Great Water Views in quiet pet-friendly location facing lighthouse. Large Yard
Dining

Great Water Views in quiet pet-friendly location facing lighthouse. Large Yard

9.6 out of 10, Exceptional, (38)
"We enjoyed our stay at Waterside. Location was perfect and host was very responsive to questions. A great rental for a few friends and/or family."
The price is ￥21,475
￥66,608 total
includes taxes & fees
Jun 25 - Jun 26
Great Water Views in quiet pet-friendly location facing lighthouse. Large Yard
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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Frequently asked questions

Can I find a vacation rental in Princess Anne?

Yes, you can find vacation rentals close to top local attractions in Princess Anne, or you can go with a more secluded option if you're looking for a relaxing stay. Our travelers say Princess Anne has a good selection of restaurants. Make sure you have time to check out the beaches and shopping during your trip.

What are some of the best vacation home rentals in Princess Anne?

Blufin Bungalows & Marina: This vacation home rental near Princess Anne is on the beach and equipped with free WiFi and a TV to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a full-sized fridge, a stovetop, and a microwave.

How many vacation rentals are there in Princess Anne?

Expedia has 3 vacation rentals for your stay in Princess Anne.

What can I see and do in Princess Anne?

Monie Island and Manokin Park are a couple of lovely local spots to get outside and enjoy nature. Hytche athletic Center and Somerset County Library are other places to visit while you're in town.

What are vacation rentals like in Princess Anne?

Vacation rentals are private properties you can stay in for several days or more in Princess Anne. Vacation rentals feature amenities such as patios, hot tubs, and fire pits so you'll feel just like you're staying in your own home. If you're concerned about a clean environment, vacation rentals can offer a sense of safety away from public hotel elevators and busy concierge desks while still allowing you the enjoyment of travel. You'll also find more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a great option for small groups.