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

Princess Anne Holiday Rentals

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Check prices for these dates

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

Our top choices for Princess Anne holiday 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
The price is AU$368
includes taxes & fees
19 Nov - 20 Nov
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.
The price is AU$250
includes taxes & fees
15 Nov - 16 Nov
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
The price is AU$197
includes taxes & fees
30 Nov - 1 Dec
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.
The price is AU$456
includes taxes & fees
29 Nov - 30 Nov
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.
The price is AU$475
includes taxes & fees
11 Nov - 12 Nov
Salisbury Cottage
A marina with boats docked, a bridge in the background, and a clear sky.

6. Deal Island Bay Cottage

Deal Island Bay Cottage
Deal Island
9.6 out of 10, Exceptional, (62 reviews)
"We got every year and stay here, it’s great! "
United States
Margaret H.
The price is AU$342
includes taxes & fees
11 Nov - 12 Nov
Deal Island Bay Cottage
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.
The price is AU$358
includes taxes & fees
11 Nov - 12 Nov
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.
The price is AU$261
includes taxes & fees
23 Nov - 24 Nov
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.
The price is AU$321
includes taxes & fees
22 Nov - 23 Nov
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.
The price is AU$266
includes taxes & fees
16 Nov - 17 Nov
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.
The price is AU$509
includes taxes & fees
23 Nov - 24 Nov
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
The price is AU$392
includes taxes & fees
19 Nov - 20 Nov
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.
The price is AU$322
includes taxes & fees
29 Nov - 30 Nov
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.
The price is AU$380
includes taxes & fees
9 Dec - 10 Dec
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.
The price is AU$596
includes taxes & fees
15 Nov - 16 Nov
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.
The price is AU$280
includes taxes & fees
12 Nov - 13 Nov
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.
The price is AU$606
includes taxes & fees
11 Nov - 12 Nov
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
The price is AU$267
includes taxes & fees
16 Nov - 17 Nov
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
The price is AU$472
includes taxes & fees
12 Nov - 13 Nov
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.
The price is AU$442
includes taxes & fees
13 Nov - 14 Nov
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

Country Inn & Suites by Radisson, Salisbury, MD

Country Inn & Suites by Radisson, Salisbury, MD

8/10 Good
"Having stayed at this hotel quite a few times, my favorite thing about it is the staff. They are always consistent, welcoming, and genuinely friendly, which makes checking in and out a breeze every single visit. That said, the overall experience can be a bit hit-or-miss depending on the room you get, as the layout and condition vary quite a bit from room to room. Across the board, the property's general maintenance could definitely use some attention and updating."
Seth 3-night trip
Posted 15 hours ago
Country Inn & Suites by Radisson, Salisbury, MD

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$182 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 in Princess Anne close to Ella Fitzgerald Performing Arts Center, 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.

How many holiday rentals are there in Princess Anne?

Expedia has 3 holiday 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 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.