Princess Anne Vacation Rentals

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Our top choices for Princess Anne vacation rentals

Blufin Bungalows & Marina

Blufin Bungalows & Marina
3.0 star property
Down the Marsh
9.6 out of 10, Exceptional, (215 reviews)
"Everything at the bungalow was really nice, perfect scenery, nice and clean, check in was real easy. Only one issue, I did not see online where it said you could not fish in front of your bungalow, I only saw the sign when I pulled up to it. I think you should let people know online before you book that there is no fishing. Otherwise I had a great stay. Thank you"
United States
Concella
$134 nightly
The price is $150
Apr 2 - Apr 3
Total with taxes and fees
Blufin Bungalows & Marina

Key West Cottages

Key West Cottages
3.0 star property
Downtown Chincoteague
9.8 out of 10, Exceptional, (532 reviews)
"Great place to stay very clean great location "
United States
Philip
$199 nightly
The price is $224
Mar 31 - Apr 1
Total with taxes and fees
Key West Cottages

6 Mi to Salisbury: Forest-view Sanctuary!

6 Mi to Salisbury: Forest-view Sanctuary!
3.0 star property
Parsonsburg
$230 nightly
The price is $257
Apr 4 - Apr 5
Total with taxes and fees
6 Mi to Salisbury: Forest-view Sanctuary!

Salisbury Riverfront Lofts

Salisbury Riverfront Lofts
3.0 star property
Salisbury
9.4 out of 10, Exceptional, (23 reviews)
"It was a great stay nice comfortable place "
United States
Adam
$242 nightly
The price is $261
Mar 31 - Apr 1
Total with taxes and fees
Salisbury Riverfront Lofts

Deal Island Bay Cottage

Deal Island Bay Cottage
Deal Island
9.6 out of 10, Exceptional, (58 reviews)
"We got every year and stay here, it’s great! "
United States
Margaret H.
$246 nightly
The price is $260
Mar 31 - Apr 1
Total with taxes and fees
Deal Island Bay Cottage

Cottage near the Bay

Cottage near the Bay
Crisfield
8.8 out of 10, Excellent, (53 reviews)
"Great little place "
United States
Eric R.
$176 nightly
The price is $187
Apr 12 - Apr 13
Total with taxes and fees
Cottage near the Bay

Assateague Inn 104 by Seaside Vacations & Sales

Assateague Inn 104 by Seaside Vacations & Sales
Chincoteague Island
9.6 out of 10, Exceptional, (23 reviews)
"Convenient location with everything we needed"
United States
John S.
$181 nightly
The price is $189
Mar 31 - Apr 1
Total with taxes and fees
Assateague Inn 104 by Seaside Vacations & Sales

Cozy creekside cottage w/fire pit & patio

Cozy creekside cottage w/fire pit & patio
Up the Neck
9.4 out of 10, Exceptional, (137 reviews)
"House was exactly as advertised. Everything worked as expected. This house is one of the few in this town that offered linens, a big selling point for us."
United States
Kato A.
$308 nightly
The price is $335
Apr 6 - Apr 7
Total with taxes and fees
Cozy creekside cottage w/fire pit & patio

Stylish 2 bedroom 1 bath with riverfront views close to dining and downtown

Stylish 2 bedroom 1 bath with riverfront views close to dining and downtown
Salisbury
9.6 out of 10, Exceptional, (17 reviews)
"Property was nice and clean"
United States
Luke S.
$175 nightly
The price is $185
Mar 31 - Apr 1
Total with taxes and fees
Stylish 2 bedroom 1 bath with riverfront views close to dining and downtown

The purple door at the bay.

The purple door at the bay.
Captain's Cove
9.2 out of 10, Wonderful, (54 reviews)
"Price and location was the primary reason the purple door works for us!"
United States
Patrick O.
$409 nightly
The price is $451
Mar 30 - Mar 31
Total with taxes and fees
The purple door at the bay.

Waterfront Bungalow on Chincoteague Bay (VA)! - Waterfront Bungalow with Two Bedrooms

Waterfront Bungalow on Chincoteague Bay (VA)! - Waterfront Bungalow with Two Bedrooms
Down the Marsh
9.8 out of 10, Exceptional, (27 reviews)
"Loved that it was right on the bay. "
United States
Debra
$186 nightly
The price is $209
Apr 5 - Apr 6
Total with taxes and fees
Waterfront Bungalow on Chincoteague Bay (VA)! - Waterfront Bungalow with Two Bedrooms

Bella's Beach Retreat by Seaside Vacations & Sales

Bella's Beach Retreat by Seaside Vacations & Sales
Chincoteague Island
8.0 out of 10, Very Good, (8 reviews)
"Off season rates are really reasonable- place is as described- good location- good views- would stay again."
United States
Cindy H.
$181 nightly
The price is $189
Mar 31 - Apr 1
Total with taxes and fees
Bella's Beach Retreat by Seaside Vacations & Sales

1 Mi to Resort Marina! Greenbackville Retreat

1 Mi to Resort Marina! Greenbackville Retreat
3.0 star property
Captain's Cove
$319 nightly
The price is $352
Apr 9 - Apr 10
Total with taxes and fees
1 Mi to Resort Marina! Greenbackville Retreat

Historic home on Smith Island w/ dock!

Historic home on Smith Island w/ dock!
Smith Island
9.6 out of 10, Exceptional, (46 reviews)
"Very nice property! Spacious rooms, great host"
United States
Sara L.
$272 nightly
The price is $288
Mar 31 - Apr 1
Total with taxes and fees
Historic home on Smith Island w/ dock!

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

Chincoteague Island House "Sir Whelk-A-Lot" Kayaks Included! Downtown Location!
Downtown Chincoteague
10.0 out of 10, Exceptional, (67 reviews)
"Everything was just perfect! Enjoyed our three day stay! "
United States
Mary C.
$270 nightly
The price is $303
Apr 1 - Apr 2
Total with taxes and fees
Chincoteague Island House "Sir Whelk-A-Lot" Kayaks Included! Downtown Location!

Only 5 min. from the Beach!

Only 5 min. from the Beach!
Chincoteague Island
9.2 out of 10, Wonderful, (31 reviews)
"I liked the location of the Inn on the island. The room(s) were very clean, well furnished and bed was super comfortable. "
United States
Marie E.
$181 nightly
The price is $189
Apr 1 - Apr 2
Total with taxes and fees
Only 5 min. from the Beach!

Only 5 min. from the Beach!

Only 5 min. from the Beach!
Chincoteague Island
9.2 out of 10, Wonderful, (9 reviews)
"Close to everything, quiet, clean"
United States
Eileen D.
$201 nightly
The price is $211
Mar 31 - Apr 1
Total with taxes and fees
Only 5 min. from the Beach!

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

Great Water Views in quiet pet-friendly location facing lighthouse. Large Yard
Birch Town
9.6 out of 10, Exceptional, (42 reviews)
"It was family & friends that needed a get away and we really Enjoy the area"
United States
Lori D.
$358 nightly
The price is $402
Mar 30 - Mar 31
Total with taxes and fees
Great Water Views in quiet pet-friendly location facing lighthouse. Large Yard

Salisbury Cottage

Salisbury Cottage
Salisbury
10.0 out of 10, Exceptional, (35 reviews)
"My family and I had a great stay was a comfy and safe space to relax and enjoy our Halloween weekend would definitely recommend!"
United States
Mackenzie N.
$302 nightly
The price is $320
Mar 30 - Mar 31
Total with taxes and fees
Salisbury Cottage

Come escape to Smith Island for the Spring and enjoy nature, peace and quiet

Come escape to Smith Island for the Spring and enjoy nature, peace and quiet
Smith Island
9.8 out of 10, Exceptional, (15 reviews)
"Excellent property, excellent host. This is a very well-appointed property located very close to the ferry dock. Golf cart, bikes, and kayaks were in great shape. Chris could not have been a more responsive or helpful host."
United States
Timothy S.
$326 nightly
The price is $360
Apr 1 - Apr 2
Total with taxes and fees
Come escape to Smith Island for the Spring and enjoy nature, peace and quiet
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

Everything you need to know about Princess Anne vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Princess Anne vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Princess Anne vacation 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 low season months. For more hustle and bustle, you may prefer to visit Princess Anne in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $150 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Princess Anne rentals

At Expedia, we put the best Princess Anne vacation 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 vacation.

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 vacation rental in Princess Anne?

Yes, you can find vacation rentals in Princess Anne close to Ella Fitzgerald Performing Arts Center, or you can choose a more remote option if you're looking for extra privacy while you relax. 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.

What can I see and do in Princess Anne?

Ballards Island and Monie Island 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 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.