Princess Anne Holiday Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
8 May - 10 May
In two months
19 Jun - 21 Jun
In three months
17 Jul - 19 Jul
In four months
14 Aug - 16 Aug

Our top choices for Princess Anne holiday rentals

Exterior

Blufin Bungalows & Marina

Blufin Bungalows & Marina
3.0 star property
Down the Marsh
9.6 out of 10, Exceptional, (227 reviews)
"Everything was great dishes were provided had a stove microwave and full refrigerator and freezer. Even had sponge and soap to wash dishes. Very beautiful view."
United States
Steven
Blufin Bungalows & Marina
1 bedroom, premium bedding, individually decorated

Key West Cottages

Key West Cottages
3.0 star property
Downtown Chincoteague
9.8 out of 10, Exceptional, (542 reviews)
"Great place to stay very clean great location "
United States
Philip
The price is HK$1,406
HK$1,579 total
includes taxes & fees
3 May - 4 May
Key West Cottages
Front of property

6 Mi to Salisbury: Forest-view Sanctuary!

6 Mi to Salisbury: Forest-view Sanctuary!
3.0 star property
Parsonsburg
The price is HK$814
HK$2,119 total
includes taxes & fees
17 May - 18 May
6 Mi to Salisbury: Forest-view Sanctuary!
Smart TV, books

Bayfront Modern Retreat • Panoramic Views, Dock, Kayak, Pools & Resort Amenities

Bayfront Modern Retreat • Panoramic Views, Dock, Kayak, Pools & Resort Amenities
Captain's Cove
9.8 out of 10, Exceptional, (63 reviews)
"What a stunning view and super welcoming host!! We loved our stay and especially enjoyed the kayaks and bikes, great welcome kit of toiletries and kitchen supplies, very comfortable beds and soft sheets, outdoor space to watch the stars, and quiet, peaceful neighborhood. "
United States
l h.
Bayfront Modern Retreat • Panoramic Views, Dock, Kayak, Pools & Resort Amenities
Interior

Cottage near the Bay

Cottage near the Bay
Crisfield
8.8 out of 10, Excellent, (53 reviews)
"Great little place "
United States
Eric R.
The price is HK$634
HK$1,461 total
includes taxes & fees
26 Apr - 27 Apr
Cottage near the Bay
2 bedrooms, individually decorated, individually furnished

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
The price is HK$525
HK$1,956 total
includes taxes & fees
6 May - 7 May
Salisbury Riverfront Lofts
Exterior

The purple door at the bay.

The purple door at the bay.
Captain's Cove
9.2 out of 10, Wonderful, (55 reviews)
"Price and location was the primary reason the purple door works for us!"
United States
Patrick O.
The price is HK$1,233
HK$3,528 total
includes taxes & fees
28 Apr - 29 Apr
The purple door at the bay.
TV, DVD player

Assateague Inn 104 by Seaside Vacations & Sales

Assateague Inn 104 by Seaside Vacations & Sales
Chincoteague Island
9.6 out of 10, Exceptional, (25 reviews)
"Convenient location with everything we needed"
United States
John S.
The price is HK$795
HK$2,051 total
includes taxes & fees
28 Apr - 29 Apr
Assateague Inn 104 by Seaside Vacations & Sales
Fridge, microwave, oven, stovetop

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.
The price is HK$1,092
HK$2,013 total
includes taxes & fees
24 Apr - 25 Apr
Deal Island Bay Cottage
Interior

Pet-friendly creekside cottage w/ backyard

Pet-friendly creekside cottage w/ backyard
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.
The price is HK$1,565
HK$2,919 total
includes taxes & fees
23 Apr - 24 Apr
Pet-friendly creekside cottage w/ backyard
Terrace/patio

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, (28 reviews)
"Loved that it was right on the bay. "
United States
Debra
The price is HK$1,284
HK$1,645 total
includes taxes & fees
22 Apr - 23 Apr
Waterfront Bungalow on Chincoteague Bay (VA)! - Waterfront Bungalow with Two Bedrooms
2 bedrooms, desk, iron/ironing board, travel cot

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, (18 reviews)
"Property was nice and clean"
United States
Luke S.
The price is HK$619
HK$1,494 total
includes taxes & fees
4 May - 5 May
Stylish 2 bedroom 1 bath with riverfront views close to dining and downtown
Interior

1 Mi to Resort Marina! Greenbackville Retreat

1 Mi to Resort Marina! Greenbackville Retreat
3.0 star property
Captain's Cove
1 Mi to Resort Marina! Greenbackville Retreat
Beach nearby, sun-loungers

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, (69 reviews)
"Everything was just perfect! Enjoyed our three day stay! "
United States
Mary C.
The price is HK$1,022
HK$2,414 total
includes taxes & fees
27 Apr - 28 Apr
Chincoteague Island House "Sir Whelk-A-Lot" Kayaks Included! Downtown Location!
Beach nearby

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, (43 reviews)
"It was family & friends that needed a get away and we really Enjoy the area"
United States
Lori D.
The price is HK$822
HK$3,131 total
includes taxes & fees
26 Apr - 27 Apr
Great Water Views in quiet pet-friendly location facing lighthouse. Large Yard
Exterior

Only 5 min. from the Beach!

Only 5 min. from the Beach!
Chincoteague Island
9.2 out of 10, Wonderful, (32 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.
The price is HK$795
HK$2,051 total
includes taxes & fees
22 Apr - 23 Apr
Only 5 min. from the Beach!
Exterior

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.
The price is HK$795
HK$2,051 total
includes taxes & fees
29 Apr - 30 Apr
Bella's Beach Retreat by Seaside Vacations & Sales
Exterior

A Bargain on Chincoteague Island!

A Bargain on Chincoteague Island!
Chincoteague Island
8.8 out of 10, Excellent, (3 reviews)
"Overall the place was nice enough for the cost. "
United States
Stacey S.
The price is HK$795
HK$2,051 total
includes taxes & fees
22 Apr - 23 Apr
A Bargain on Chincoteague Island!
Marina

Summer is almost here on Smith Island! Get ready for a great season on the Bay

Summer is almost here on Smith Island! Get ready for a great season on the Bay
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.
The price is HK$1,410
HK$2,327 total
includes taxes & fees
22 Apr - 23 Apr
Summer is almost here on Smith Island! Get ready for a great season on the Bay
Exterior

Walk to Restaurants & Attractions-Linens Included! Book your Beach Vacation Now!

Walk to Restaurants & Attractions-Linens Included! Book your Beach Vacation Now!
Deep Hole
10.0 out of 10, Exceptional, (9 reviews)
"My husband and I stayed here with our two pups for one night, and we truly wish we could have stayed longer. The home is exceptionally clean, cozy, and well-appointed with everything you could need. The beds were very comfortable, and the location is perfect—close to everything in Chincoteague. We’d happily stay here again and highly recommend it!"
United States
Alice J.
The price is HK$776
HK$1,989 total
includes taxes & fees
22 Apr - 23 Apr
Walk to Restaurants & Attractions-Linens Included! Book your Beach Vacation Now!
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Princess Anne Hotel Reviews

Econo Lodge Princess Anne

Econo Lodge Princess Anne

2/10 Terrible
"This has been—without a doubt—one of the worst stays I have ever experienced in my life. If you’re looking for a “real” getaway that feels like something out of a horror movie, then this is the hotel to visit. First, they claim that breakfast is included, but when you arrive, all they offer is coffee in a dirty, unkept area. The pool area is disgusting—it looks like it could be home to the next frog prince or even the source of a future pandemic. In the room, you’ll encounter everything you can imagine: insects like ants and spiders, leaks in the shower, and an air conditioner so loud it makes it impossible to sleep. But out of all these unfortunate experiences, the most absurd situation happened on my last night. Around 9:00 p.m., another guest tried to open my door because they had also been assigned the same room I was already staying in."
Cesar 3-night trip
Posted 12 hours ago
Econo Lodge Princess Anne

Find out more about Princess Anne

Search for holiday rentals in Princess Anne on Expedia! You can easily find your home rentals, villas, holiday apartments in Princess Anne using one of the methods below:

  • View our selection of featured holiday rentals in Princess Anne
  • Use the map to find apartments and other holiday homes in the Princess Anne neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Princess Anne while they last

Look no further and take a look at our great range of rental properties in Princess Anne!

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?

Monie Island and Manokin Park 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 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.