A sunset over a lake with a dock and a small settlement.

Princess Anne Vacation Rentals

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Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Princess Anne vacation rentals

A room with a large bed, multiple windows, and a ceiling fan.

1. Salisbury Riverfront Lofts

Salisbury Riverfront Lofts
3.0 star property
Salisbury
9.4 out of 10, Exceptional, (27 reviews)
"Excellent choice for the price, recommended for larger groups."
United States
Marcos
$240 nightly
The price is $258
Oct 12 - Oct 13
Total with taxes and fees
Salisbury Riverfront Lofts
An open door leading to a bedroom with a bed, a nightstand, and a lamp.

2. 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
9.8 out of 10, Exceptional, (25 reviews)
"Great location with plenty of space to relax."
United States
Doug R.
$176 nightly
The price is $186
Oct 18 - Oct 19
Total with taxes and fees
Stylish 2 bedroom 1 bath with riverfront views close to dining and downtown
A living room with a dining area, a TV mounted on the wall, and a ceiling light fixture.

3. Salisbury Cottage

Salisbury Cottage
Salisbury
10.0 out of 10, Exceptional, (40 reviews)
"Super convenient to campus and everything was clean and worked perfectly. Overall, a great stay and met all of our expectations."
United States
Matthew B.
$347 nightly
The price is $368
Nov 3 - Nov 4
Total with taxes and fees
Salisbury Cottage
A single-story house with a front porch, a door, and a mailbox.

4. Salisbury Hideaway

Salisbury Hideaway
Salisbury
10.0 out of 10, Exceptional, (24 reviews)
"Perfect for our weekend away watching college softball!!!"
United States
Michelle S.
$360 nightly
The price is $382
Oct 18 - Oct 19
Total with taxes and fees
Salisbury Hideaway
A sandy beach with footprints, a pier in the distance, and a clear sky.

5. Tangier Escape, great place get away from it all on Deal Island, MD.

Tangier Escape, great place get away from it all on Deal Island, MD.
Deal Island Historic District
10.0 out of 10, Exceptional, (2 reviews)
"Helpful host, clean house, peaceful location! "
United States
Jennifer P.
$232 nightly
The price is $246
Oct 18 - Oct 19
Total with taxes and fees
Tangier Escape, great place get away from it all on Deal Island, MD.
A room with a wooden bench, a lamp, a wicker basket, and a window with sheer curtains.

6. Cottage near the Bay

Cottage near the Bay
Crisfield
8.6 out of 10, Excellent, (63 reviews)
"Nice cottage at the end of a quiet lane, priced reasonably. Host is very accommodating. We had a lovely stay and enjoyed our time in Crisfield."
United States
Karen J.
$176 nightly
The price is $187
Oct 15 - Oct 16
Total with taxes and fees
Cottage near the Bay
A compact kitchen with a checkered floor, a dining table with chairs, and a large wall art piece.

7. Retro Hipster: Close to downtown, dining and fun

Retro Hipster: Close to downtown, dining and fun
Salisbury
9.2 out of 10, Wonderful, (20 reviews)
"Great alternative to a hotel!"
United States
Courtney L.
$179 nightly
The price is $189
Oct 12 - Oct 13
Total with taxes and fees
Retro Hipster: Close to downtown, dining and fun
A modern kitchen with white cabinets, a stainless steel refrigerator, a microwave, and a large island with stools.

8. Deal Island Bay Cottage

Deal Island Bay Cottage
Deal Island
9.6 out of 10, Exceptional, (62 reviews)
"We loved this place! We were in town for baseball. It is very nice and has all the comforts of home. Kitchen big and well equipped, house was clean and very well furnished. Nice bathrooms and a lovely screened in back porch. It is very near a beautiful beach on the bay that has some of the most beautiful sunsets you will ever see. We really enjoyed this perk!! Prompt communication and everything was as described. I highly recommend this rental!!"
United States
Harold B.
$243 nightly
The price is $257
Oct 13 - Oct 14
Total with taxes and fees
Deal Island Bay Cottage
An open doorway leading to a living room with a fireplace, a dining area, and a kitchen visible through an open door.

9. Deluxe corner apartment with riverfront views close to dining and downtown

Deluxe corner apartment with riverfront views close to dining and downtown
Salisbury
8.8 out of 10, Excellent, (6 reviews)
"Lovely apartment in the heart of Salisbury. Ckean, well appointed, and comfortable. "
United States
Gretel S.
$230 nightly
The price is $241
Oct 14 - Oct 15
Total with taxes and fees
Deluxe corner apartment with riverfront views close to dining and downtown
A living room with a patterned rug, a bookshelf, a red sofa, and a fish-shaped wall decoration.

10. Spacious Riverfront Loft Close to Downtown and Dining

Spacious Riverfront Loft Close to Downtown and Dining
Salisbury
9.0 out of 10, Wonderful, (13 reviews)
"Great location, great restaurants below the loft."
United States
Pamela F.
$217 nightly
The price is $227
Oct 19 - Oct 20
Total with taxes and fees
Spacious Riverfront Loft Close to Downtown and Dining
A room with a glass-top coffee table, a white dresser with gold handles, a white door, and a patterned rug.

11. Entire Private Home • Sleeps 6 • Prime Salisbury Location

Entire Private Home • Sleeps 6 • Prime Salisbury Location
Salisbury
10.0 out of 10, Exceptional, (1 review)
"The stay was great. "
United States
Nathaniel N.
$308 nightly
The price is $326
Oct 12 - Oct 13
Total with taxes and fees
Entire Private Home • Sleeps 6 • Prime Salisbury Location
A waterfront house with a balcony, dock, and a view of the water.

12. Key West Cottages

Key West Cottages
3.0 star property
Downtown Chincoteague
9.8 out of 10, Exceptional, (656 reviews)
"Clean, quiet, and convenient."
United States
KYLE
$215 nightly
The price is $242
Oct 12 - Oct 13
Total with taxes and fees
Key West Cottages
Exterior

13. Blufin Bungalows & Marina

Blufin Bungalows & Marina
3.0 star property
Down the Marsh
9.6 out of 10, Exceptional, (335 reviews)
"Superior views of the bay, very dog friendly"
United States
Angela
$242 nightly
The price is $272
Oct 13 - Oct 14
Total with taxes and fees
Blufin Bungalows & Marina
A modern living room with a curved sofa, a small round table, and large windows offering a view of a river and buildings.

14. Bayfront Modern Retreat • Dock, Kayaks, Views

Bayfront Modern Retreat • Dock, Kayaks, Views
Captain's Cove
9.8 out of 10, Exceptional, (70 reviews)
"Overall nice stay!"
United States
Becky S.
$428 nightly
The price is $472
Oct 15 - Oct 16
Total with taxes and fees
Bayfront Modern Retreat • Dock, Kayaks, Views
A sunroom with wicker furniture, large windows, and a view of the water.

15. The purple door at the bay.

The purple door at the bay.
Captain's Cove
9.4 out of 10, Exceptional, (68 reviews)
"Great location"
United States
Rick K.
$420 nightly
The price is $463
Oct 20 - Oct 21
Total with taxes and fees
The purple door at the bay.
A modern living room with a sliding glass door to a deck, a dining area with a table and chairs, and a cozy seating area with a sofa and cushions.

16. Assateageue Inn 104 by Seaside Vacations & Sales

Assateageue Inn 104 by Seaside Vacations & Sales
Chincoteague Island
9.4 out of 10, Exceptional, (35 reviews)
"Our room was clean and ready for our stay. We could walk to some shops, miniature golfing,restaurants."
United States
Paula
$187 nightly
The price is $203
Oct 13 - Oct 14
Total with taxes and fees
Assateageue Inn 104 by Seaside Vacations & Sales
A two-story building with a central entrance and a wooden walkway leading to it.

17. Assateague Inn 203 by Seaside Vacations & Sales

Assateague Inn 203 by Seaside Vacations & Sales
Chincoteague Island
9.2 out of 10, Wonderful, (9 reviews)
"We had a mommy-daughter mini-getaway to celebrate her 9th birthday! The area is very walkable, but also easy to drive and navigate the rest of the island. Our room was clean, as advertised, and the perfect place to relax, eat, and recharge. We loved the pool! The check-in/check-out process was very easy."
United States
Nora T.
$199 nightly
The price is $218
Oct 13 - Oct 14
Total with taxes and fees
Assateague Inn 203 by Seaside Vacations & Sales
A row of white houses by a lake with American flags.

18. Charming 2 Bedroom house in beautiful Smith Island Pet-Friendly

Charming 2 Bedroom house in beautiful Smith Island Pet-Friendly
Smith Island
10.0 out of 10, Exceptional, (2 reviews)
"This is a great place to stay on Smith Island. Easy access to most areas. The Golf cart is also nice to have. The house has everything you need and many extras too! Highly recommend a visit here."
United States
Margaret A.
$326 nightly
The price is $346
Oct 13 - Oct 14
Total with taxes and fees
Charming 2 Bedroom house in beautiful Smith Island Pet-Friendly
A sandy beach with footprints and a person walking.

19. 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, (48 reviews)
"It was family & friends that needed a get away and we really Enjoy the area"
United States
Lori D.
$368 nightly
The price is $413
Oct 12 - Oct 13
Total with taxes and fees
Great Water Views in quiet pet-friendly location facing lighthouse. Large Yard
A marina at sunset with boats docked and buildings in the background.

20. Come out and enjoy Autumn at the HH Ranch on Smith Island.

Come out and enjoy Autumn at the HH Ranch on Smith Island.
Smith Island
9.8 out of 10, Exceptional, (16 reviews)
"Visiting with locals, fresh steamed crabs, simply enjoying the quiet island life"
United States
Samantha J.
$303 nightly
The price is $334
Oct 16 - Oct 17
Total with taxes and fees
Come out and enjoy Autumn at the HH Ranch on Smith 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.
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Top Princess Anne Hotel Reviews

Chincoteague Inn

Chincoteague Inn

10/10 Excellent
"The room we stayed in was clean and recently updated"
Jay 2-night trip
Posted less than an hour ago
Chincoteague Inn

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 $203 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.

Explore a world of travel with Expedia

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.

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?

Manokin Park and Mount Vernon Beach 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.