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
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

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, (29 reviews)
"Amazing experience"
United States
Chad
$242 nightly
The price is $261
Nov 15 - Nov 16
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.
$167 nightly
The price is $177
Nov 15 - Nov 16
Total with taxes and fees
Stylish 2 bedroom 1 bath with riverfront views close to dining and downtown
A waterfront house with a balcony, dock, and a view of the water.

3. Key West Cottages

Key West Cottages
3.0 star property
Downtown Chincoteague
9.8 out of 10, Exceptional, (674 reviews)
"First time here and we absolutely loved it."
United States
Melissa
$134 nightly
The price is $151
Nov 30 - Dec 1
Total with taxes and fees
Key West Cottages
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.
$320 nightly
The price is $339
Nov 12 - Nov 13
Total with taxes and fees
Salisbury Hideaway
A living room with a dining area, a TV mounted on the wall, and a ceiling light fixture.

5. Salisbury Cottage

Salisbury Cottage
Salisbury
10.0 out of 10, Exceptional, (40 reviews)
"The property has cute and cozy curb appeal. The interior was attractive and very clean. The location was excellent for our planned events. Host, Ryan, easily accommodated our needs and we plan to check for availability in the future. Thanks Ryan!"
United States
Star R.
$310 nightly
The price is $329
Nov 12 - Nov 13
Total with taxes and fees
Salisbury Cottage
A modern kitchen with white cabinets, a stainless steel refrigerator, a microwave, and a large island with stools.

6. Deal Island Bay Cabin

Deal Island Bay Cabin
Deal Island
9.6 out of 10, Exceptional, (62 reviews)
"We got every year and stay here, it’s great! "
United States
Margaret H.
$223 nightly
The price is $236
Nov 12 - Nov 13
Total with taxes and fees
Deal Island Bay Cabin
A hallway with a framed artwork of a bird, a wooden entertainment unit with a TV, and a dining area with a bar stool.

7. 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.
$233 nightly
The price is $247
Nov 12 - Nov 13
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.

8. Cottage near the Bay

Cottage near the Bay
Crisfield
8.6 out of 10, Excellent, (65 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.
$168 nightly
The price is $178
Nov 17 - Nov 18
Total with taxes and fees
Cottage near the Bay
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.
$218 nightly
The price is $229
Nov 15 - Nov 16
Total with taxes and fees
Deluxe corner apartment with riverfront views close to dining and downtown
A calm river with a white fire hydrant and buildings in the background.

10. 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.
$173 nightly
The price is $183
Nov 16 - Nov 17
Total with taxes and fees
Retro Hipster: Close to downtown, dining and fun
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.
$337 nightly
The price is $357
Nov 23 - Nov 24
Total with taxes and fees
Entire Private Home • Sleeps 6 • Prime Salisbury Location
Front of property

12. 6 Mi to Salisbury: Forest-view Sanctuary!

6 Mi to Salisbury: Forest-view Sanctuary!
3.0 star property
Parsonsburg
$242 nightly
The price is $271
Nov 18 - Nov 19
Total with taxes and fees
6 Mi to Salisbury: Forest-view Sanctuary!
A calm waterfront with a row of buildings, a white fire hydrant, and a clear sky.

13. 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.
$210 nightly
The price is $220
Nov 15 - Nov 16
Total with taxes and fees
Spacious Riverfront Loft Close to Downtown and Dining
Parsonsburg Vacation Rental | 3BR | 2BA | 1,482 Sq Ft | 4 Steps Required

14. 6 Mi to Salisbury: Forest-View Sanctuary!

6 Mi to Salisbury: Forest-View Sanctuary!
Parsonsburg
9.8 out of 10, Exceptional, (6 reviews)
"Awesome place "
United States
Rebecca M.
$234 nightly
The price is $261
Nov 18 - Nov 19
Total with taxes and fees
6 Mi to Salisbury: Forest-View Sanctuary!
An outdoor seating area with a view of a waterfront during sunset.

15. Bayfront Modern Retreat • Dock, Kayaks, Views

Bayfront Modern Retreat • Dock, Kayaks, Views
Captain's Cove
9.8 out of 10, Exceptional, (73 reviews)
"We absolutely love staying here! "
United States
Maggie G.
$377 nightly
The price is $403
Nov 15 - Nov 16
Total with taxes and fees
Bayfront Modern Retreat • Dock, Kayaks, Views
A two-story building with a central entrance and a wooden walkway leading to it.

16. Assateague Inn 103 by Seaside Vacations & Sales

Assateague Inn 103 by Seaside Vacations & Sales
Chincoteague Island
8.0 out of 10, Very good, (6 reviews)
"The property and room were clean and neat. The facility and rooms are older, but all was functional and clean. Very communicative and easy and clear check in and out process! "
United States
Ellen K.
$177 nightly
The price is $192
Nov 12 - Nov 13
Total with taxes and fees
Assateague Inn 103 by Seaside Vacations & Sales
A sunroom with wicker furniture, large windows, and a view of the water.

17. The purple door at the bay.

The purple door at the bay.
Captain's Cove
9.4 out of 10, Exceptional, (69 reviews)
"Great location"
United States
Rick K.
$389 nightly
The price is $429
Nov 18 - Nov 19
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.

18. 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
$170 nightly
The price is $184
Nov 16 - Nov 17
Total with taxes and fees
Assateageue Inn 104 by Seaside Vacations & Sales
A covered porch with wicker chairs and a view of the outdoors.

19. Pet-friendly creekside cottage w/ backyard

Pet-friendly creekside cottage w/ backyard
Up the Neck
9.4 out of 10, Exceptional, (141 reviews)
"The house was very clean and tidy when we arrived. We appreciated having our linens supplied, the very clear house manual with all instructions and clear communication on how to access the house. We also liked how the host checked in to see how we were doing and if we had any needs. This house was also pet friendly."
United States
Christine
$318 nightly
The price is $345
Nov 12 - Nov 13
Total with taxes and fees
Pet-friendly creekside cottage w/ backyard
A wooden deck with white railings, a door with a wreath, and two wicker chairs.

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, (17 reviews)
"Visiting with locals, fresh steamed crabs, simply enjoying the quiet island life"
United States
Samantha J.
$275 nightly
The price is $305
Nov 30 - Dec 1
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

The Reserve Inn

The Reserve Inn

8/10 Good
"The room was clean and, with very few choices for that area, the stay was fine."
Jordan 1-night trip
Posted 16 hours ago
The Reserve 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 $125 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.