Princess Anne Holiday Rentals

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Holiday Rentals in Princess Anne

Our top choices for Princess Anne holiday rentals

Key West Cottages

3.0 star property
9.8 out of 10, Exceptional, (438)
"Great place to stay!"
Key West Cottages

Blufin Bungalows & Marina

3.0 star property
9.6 out of 10, Exceptional, (169)
"excellent place to stay on the water"
Blufin Bungalows & Marina

Strawberry Crossroads

2.0 star property
8.8 out of 10, Excellent, (6)
"My family really enjoyed the stay, its close enough drive to ocean city while being out of the way. Even after having a double booking issue the property owner made it work for us all. The kids were begging us to stay longer it was so peaceful!"
Strawberry Crossroads

NEW PET FRIENDLY LISTING ALERT!!

9.4 out of 10, Exceptional, (16)
"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!!

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

9.6 out of 10, Exceptional, (42)
"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 AU$622
includes taxes & fees
3 Sept - 4 Sept
Great Water Views in quiet pet-friendly location facing lighthouse. Large Yard

The purple door at the bay.

9.2 out of 10, Wonderful, (51)
"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 It was good enough for us to relax and cook but a slight bit expensive for its outdated condition though."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 AU$697
includes taxes & fees
14 Sept - 15 Sept
The purple door at the bay.

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

9.6 out of 10, Exceptional, (48)
"Lovely , peaceful mini vacation"
2BR Waterfront Cottage with the Most Spectacular View of lighthouse!

Waterfront on Marsh Island!

8.8 out of 10, Excellent, (33)
"Visiting Chincoteague "
Waterfront on Marsh Island!

Cabin at Holdens Creek on Eastern Shore of VA

9.6 out of 10, Exceptional, (177)
"Beautiful cabin situated at the back of a farm, very peaceful. Very spacious and inviting. Only a half hour to Chincoteague and an hour to Ocean City. Nice porch with a swing and 2 chairs to sit out in the morning with a cup of coffee (coffee maker provided). We loved having a pool table for our evening entertainment. Only thing we didn't like was the very tiny kitchen, absolutely no counter space at all :( "
Cabin at Holdens Creek on Eastern Shore of VA

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

10.0 out of 10, Exceptional, (55)
"Thank you so much for letting us stay at your house. The location was perfect for walking to restaurants and shops. Did a day at the wildlife refuge and spent some time on the beach. Plan to come back and enjoy another stay. "
The price is AU$425
includes taxes & fees
30 Sept - 1 Oct
Chincoteague Island House "Sir Whelk-A-Lot" Kayaks Included! Downtown Location!

1BR Waterfront cottage with a view of the wild Chincoteague ponies!

9.6 out of 10, Exceptional, (13)
"3 night stay for our anniversary, beautiful view had a relaxing time! "
1BR Waterfront cottage with a view of the wild Chincoteague ponies!

Historic home on Smith Island w/ dock!

9.6 out of 10, Exceptional, (45)
"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!

Make fabulous Vacation Memories at Family Tides Vacation Rental on Chincoteague

9.8 out of 10, Exceptional, (50)
"Great location and property for a peaceful and tranquil getaway."
Make fabulous Vacation Memories at Family Tides Vacation Rental on Chincoteague

Quaint Cottages Near Everything on Beach Road

9.4 out of 10, Exceptional, (39)
"Location, location, location"
Quaint Cottages Near Everything on Beach Road

Cottage near the Bay

9.0 out of 10, Wonderful, (43)
"great, peaceful "
The price is AU$292
includes taxes & fees
2 Sept - 3 Sept
Cottage near the Bay

The Brass Crab - Check in/out any day!

10.0 out of 10, Exceptional, (151)
"The Brass Crab is the perfect family place to stay. Thank you for all the extras."
The Brass Crab - Check in/out any day!

Only 5 min to Assateague National Seashore!

9.6 out of 10, Exceptional, (18)
"Nice place. "
The price is AU$318
includes taxes & fees
30 Sept - 1 Oct
Only 5 min to Assateague National Seashore!

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

10.0 out of 10, Exceptional, (48)
"Great property! Very clean"
At the Water's Edge - is there anywhere you'd rather be?!

5 minutes to Assateague National Seashore!

8.8 out of 10, Excellent, (17)
"The condo was perfect for my girlfriend and I, very private location and nice boardwalk by the creek"
The price is AU$318
includes taxes & fees
30 Sept - 1 Oct
5 minutes to Assateague National Seashore!

Salisbury Riverfront Lofts

3.0 star property
9.2 out of 10, Wonderful, (22)
"Very nice place clean & roomy."
The price is AU$384
includes taxes & fees
2 Sept - 3 Sept
Salisbury Riverfront Lofts
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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Top Princess Anne Hotel Reviews

Find out more about Princess Anne

Find out more about Princess Anne

Everything you need to know about Princess Anne holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Princess Anne holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Princess Anne holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Princess Anne holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Princess Anne. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Princess Anne holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Princess Anne holiday rentals we have selected for you start as low as AU$292 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Princess Anne rentals

At Expedia, we put the best Princess Anne holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Princess Anne rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Princess Anne holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Princess Anne. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find a holiday rental in Princess Anne?

Yes, there are holiday rentals close to the most popular sights in Princess Anne, or you can select a more secluded option if you're looking for a relaxing stay. Our travellers 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 holiday rentals that Princess Anne has to offer?

Blufin Bungalows & Marina: This holiday home rental outside of 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.

What can I see and do in Princess Anne?

Manokin Park and Wellington State Wildlife Management Area are a couple of lovely local spots to get outside and enjoy nature. Somerset County Library and Princess Anne Town Hall are other places to visit while you're in town.

What are holiday rentals like in Princess Anne?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Princess Anne. Holiday rentals feature extras such as patios, hot tubs and fire pits so you'll feel right at home. If you're concerned about cleanliness, holiday rentals can provide a sense of seclusion away from public hotel lifts and busy lobbies while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular choice for family trips.