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
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

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, (27 reviews)
"Excellent choice for the price, recommended for larger groups."
United States
Marcos
The price is AU$348
includes taxes & fees
27 Oct - 28 Oct
Salisbury Riverfront Lofts
A living room with a dining area, a TV mounted on the wall, and a ceiling light fixture.

2. 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.
The price is AU$490
includes taxes & fees
27 Oct - 28 Oct
Salisbury Cottage
A single-story house with a front porch, a door, and a mailbox.

3. Salisbury Hideaway

Salisbury Hideaway
Salisbury
10.0 out of 10, Exceptional, (23 reviews)
"Perfect for our weekend away watching college softball!!!"
United States
Michelle S.
The price is AU$450
includes taxes & fees
4 Oct - 5 Oct
Salisbury Hideaway
A sandy beach with footprints, a pier in the distance, and a clear sky.

4. 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$354
includes taxes & fees
27 Oct - 28 Oct
Tangier Escape, great place get away from it all on Deal Island, MD.
An open door leading to a bedroom with a bed, a nightstand, and a lamp.

5. 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$259
includes taxes & fees
27 Oct - 28 Oct
Stylish 2 bedroom 1 bath with riverfront views close to dining and downtown
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)
"Quiet area, the place needs to be cleaned, bedding changed, redo the bathroom"
United States
Pamela
The price is AU$259
includes taxes & fees
27 Sept - 28 Sept
Cottage near the Bay
A kitchen with a farmhouse sign, a clock, and a refrigerator.

7. Cozy Barn Loft: Country Views & Central to Beaches

Cozy Barn Loft: Country Views & Central to Beaches
Pocomoke City
10.0 out of 10, Exceptional, (23 reviews)
"Very clean and cozy home, they had all the necessary things we needed for our stay and we will certainly be staying there again if it’s available during our next visit. "
United States
Ryan B.
The price is AU$387
includes taxes & fees
27 Sept - 28 Sept
Cozy Barn Loft: Country Views & Central to Beaches

8. Blufin Bungalows & Marina

Blufin Bungalows & Marina
3.0 star property
Down the Marsh
9.6 out of 10, Exceptional, (330 reviews)
"Superior views of the bay, very dog friendly"
United States
Angela
The price is AU$323
includes taxes & fees
13 Oct - 14 Oct
Blufin Bungalows & Marina
A modern kitchen with white cabinets, a stainless steel refrigerator, a microwave, and a large island with stools.

9. Deal Island Bay Cottage

Deal Island Bay Cottage
Deal Island
9.6 out of 10, Exceptional, (61 reviews)
"We were there for our granddaughter's wrestling tournament in Salisbury. House was excellent, quiet and clean. Beautiful home. Thank you."
United States
Christopher M.
The price is AU$373
includes taxes & fees
27 Sept - 28 Sept
Deal Island Bay Cottage
A covered porch with white wooden walls and large windows. There are two rocking chairs with floral cushions and a small table with a chair.

10. 2 Mi to Downtown: Tranquil Abode in Chincoteague!

2 Mi to Downtown: Tranquil Abode in Chincoteague!
3.0 star property
Up the Neck
The price is AU$487
includes taxes & fees
30 Sept - 1 Oct
2 Mi to Downtown: Tranquil Abode in Chincoteague!
A compact kitchen with a checkered floor, a dining table with chairs, and a large wall art piece.

11. 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
6 Oct - 7 Oct
Retro Hipster: Close to downtown, dining and fun
An open doorway leading to a living room with a fireplace, a dining area, and a kitchen visible through an open door.

12. 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$330
includes taxes & fees
14 Oct - 15 Oct
Deluxe corner apartment with riverfront views close to dining and downtown
A sunroom with wicker furniture, large windows, and a view of the water.

13. The purple door at the bay.

The purple door at the bay.
Captain's Cove
9.4 out of 10, Exceptional, (67 reviews)
"Everything was just perfect. I will be back. This time for a long stay. My entire family loves the place. Thanks Kelly."
United States
Francis
The price is AU$624
includes taxes & fees
27 Sept - 28 Sept
The purple door at the bay.
A living room with a patterned rug, a bookshelf, a red sofa, and a fish-shaped wall decoration.

14. 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$324
includes taxes & fees
14 Oct - 15 Oct
Spacious Riverfront Loft Close to Downtown and Dining
A waterfront house with a balcony, dock, and a view of the water.

15. Key West Cottages

Key West Cottages
3.0 star property
Downtown Chincoteague
9.8 out of 10, Exceptional, (647 reviews)
"Excellent place to stay. Clean, convenient, comfortable."
United States
Debra
The price is AU$323
includes taxes & fees
18 Oct - 19 Oct
Key West Cottages
A modern living room with a curved sofa, a small round table, and large windows offering a view of a river and buildings.

16. Bayfront Modern Retreat • Dock, Kayaks, Views

Bayfront Modern Retreat • Dock, Kayaks, Views
Captain's Cove
9.8 out of 10, Exceptional, (68 reviews)
"Overall nice stay!"
United States
Becky S.
The price is AU$671
includes taxes & fees
27 Sept - 28 Sept
Bayfront Modern Retreat • Dock, Kayaks, Views
A sandy beach with footprints and a person walking.

17. 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.
The price is AU$573
includes taxes & fees
27 Sept - 28 Sept
Great Water Views in quiet pet-friendly location facing lighthouse. Large Yard
A two-story building with a central entrance and a wooden walkway leading to it.

18. Assateague Inn 111 by Seaside Vacations & Sales

Assateague Inn 111 by Seaside Vacations & Sales
Chincoteague Island
8.4 out of 10, Very good, (37 reviews)
"The location was central with a deck out on the marsh, which was lovely. The pool seemed well kept and was nice. It was clean and the communication with the hosts was quite good. The smart TVs didn’t really work and could only work with live tv. No apps worked. Overall, though, would stay again."
United States
Erin
The price is AU$278
includes taxes & fees
28 Sept - 29 Sept
Assateague Inn 111 by Seaside Vacations & Sales
A room with a glass-top coffee table, a white dresser with gold handles, a white door, and a patterned rug.

19. 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$456
includes taxes & fees
27 Sept - 28 Sept
Entire Private Home • Sleeps 6 • Prime Salisbury Location
A covered porch with white wooden walls and large windows. There are two rocking chairs with floral cushions and a small table with a chair.

20. 2 Mi to Downtown: Tranquil Abode in Chincoteague!

2 Mi to Downtown: Tranquil Abode in Chincoteague!
Up the Neck
9.8 out of 10, Exceptional, (9 reviews)
"My experience was beyond perfect! The house and yard was perfect. The house was so cozy and had everything we needed. I loved the little game room."
United States
Katlyn
The price is AU$493
includes taxes & fees
30 Sept - 1 Oct
2 Mi to Downtown: Tranquil Abode in Chincoteague!
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

Waterside Inn

Waterside Inn

8/10 Good
"have stayed here several times over the years and have always enjoyed our stay. the front desk people are always kind and helpful. the rooms are always clean the beds comfortable, and you have great views from the balcony. the problem is no ramp up to the office so if you have limited mobility such as i that is a major problem. also no rooms have handicap accessible tubs. we do love staying here but as i get older the issues with my mobility may not allow it."
LAWRENCE 3-night trip
Posted 7 hours ago
Waterside Inn

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$275 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?

Mount Vernon Beach and Manokin Park are a couple of lovely local spots to get outside and enjoy nature. Princess Anne Town Hall and Teackle Mansion 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.