Aerial view of Princess Anne, Maryland with marshlands and waterways at sunset

Princess Anne Holiday Rentals

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Check prices for these dates

In two weeks
26 Jun - 28 Jun
In two months
7 Aug - 9 Aug
In three months
4 Sept - 6 Sept
In four months
2 Oct - 4 Oct

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, (266 reviews)
"Loved everything about our stay"
United States
Elizabeth
The price is HK$1,655
HK$2,299 total
includes taxes & fees
15 Jun - 16 Jun
Blufin Bungalows & Marina
Interior

Cottage near the Bay

Cottage near the Bay
Crisfield
8.8 out of 10, Excellent, (55 reviews)
"Cottage was exactly as listed. Great value"
United States
Tom B.
The price is HK$635
HK$1,462 total
includes taxes & fees
16 Jun - 17 Jun
Cottage near the Bay
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$815
HK$2,121 total
includes taxes & fees
25 Jun - 26 Jun
6 Mi to Salisbury: Forest-view Sanctuary!
1 bedroom, premium bedding, individually decorated

Key West Cottages

Key West Cottages
3.0 star property
Downtown Chincoteague
9.8 out of 10, Exceptional, (577 reviews)
"Great place to stay on the island"
United States
Wilmer
The price is HK$2,406
HK$2,702 total
includes taxes & fees
14 Jun - 15 Jun
Key West Cottages
2 bedrooms, individually decorated, individually furnished

Salisbury Riverfront Lofts

Salisbury Riverfront Lofts
3.0 star property
Salisbury
9.2 out of 10, Wonderful, (25 reviews)
"It was a great stay nice comfortable place "
United States
Adam
The price is HK$662
HK$2,109 total
includes taxes & fees
15 Jun - 16 Jun
Salisbury Riverfront Lofts
Beach

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, (1 review)
"Helpful host, clean house, peaceful location! "
United States
Jennifer P.
The price is HK$862
HK$1,919 total
includes taxes & fees
19 Jun - 20 Jun
Tangier Escape, great place get away from it all on Deal Island, MD.
Outdoor dining

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 HK$729
HK$2,114 total
includes taxes & fees
25 Jun - 26 Jun
6 Mi to Salisbury: Forest-View Sanctuary!
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, (20 reviews)
"Property was nice and clean"
United States
Luke S.
The price is HK$737
HK$1,618 total
includes taxes & fees
16 Jun - 17 Jun
Stylish 2 bedroom 1 bath with riverfront views close to dining and downtown
TV, DVD player

The purple door at the bay.

The purple door at the bay.
Captain's Cove
9.4 out of 10, Exceptional, (56 reviews)
"Price and location was the primary reason the purple door works for us!"
United States
Patrick O.
The price is HK$1,234
HK$3,531 total
includes taxes & fees
14 Jun - 15 Jun
The purple door at the bay.
Fridge, microwave, oven, stovetop

Deal Island Bay Cottage

Deal Island Bay Cottage
Deal Island
9.6 out of 10, Exceptional, (59 reviews)
"We got every year and stay here, it’s great! "
United States
Margaret H.
The price is HK$1,121
HK$2,044 total
includes taxes & fees
15 Jun - 16 Jun
Deal Island Bay Cottage
Exterior

Salisbury Hideaway

Salisbury Hideaway
Salisbury
10.0 out of 10, Exceptional, (21 reviews)
"Had a wonderful time house had everything you would need for a stay located right in the heart of Salisbury. Will definitely be going back to stay in this particular house. Thank you"
United States
Bryan M.
The price is HK$1,199
HK$2,866 total
includes taxes & fees
1 Jul - 2 Jul
Salisbury Hideaway
Fridge, microwave, oven, stovetop

Cozy Barn Loft: Country Views & Central to Beaches

Cozy Barn Loft: Country Views & Central to Beaches
Pocomoke City
10.0 out of 10, Exceptional, (20 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 HK$1,051
HK$2,090 total
includes taxes & fees
24 Jun - 25 Jun
Cozy Barn Loft: Country Views & Central to Beaches
Interior

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 HK$2,390
HK$4,703 total
includes taxes & fees
11 Jul - 12 Jul
2 Mi to Downtown: Tranquil Abode in Chincoteague!
Smart TV, books, offices

Salisbury Cottage

Salisbury Cottage
Salisbury
10.0 out of 10, Exceptional, (38 reviews)
"My family and I had a great stay was a comfy and safe space to relax and enjoy our Halloween weekend would definitely recommend!"
United States
Mackenzie N.
The price is HK$1,591
HK$3,339 total
includes taxes & fees
16 Jun - 17 Jun
Salisbury Cottage
Interior

3-bedroom townhome in tranquil Delmar with WiFi, AC. Relax and unwind

3-bedroom townhome in tranquil Delmar with WiFi, AC. Relax and unwind
Delmar
10.0 out of 10, Exceptional, (10 reviews)
"This was a great place to stay, highly recommend."
United States
Brian M.
3-bedroom townhome in tranquil Delmar with WiFi, AC. Relax and unwind
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, (44 reviews)
"It was family & friends that needed a get away and we really Enjoy the area"
United States
Lori D.
The price is HK$1,661
HK$4,198 total
includes taxes & fees
5 Jul - 6 Jul
Great Water Views in quiet pet-friendly location facing lighthouse. Large Yard
Interior

2 Mi to Downtown: Tranquil Abode in Chincoteague!

2 Mi to Downtown: Tranquil Abode in Chincoteague!
Up the Neck
10.0 out of 10, Exceptional, (6 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 HK$2,131
HK$4,772 total
includes taxes & fees
11 Jul - 12 Jul
2 Mi to Downtown: Tranquil Abode in Chincoteague!
Terrace/patio

Cozy 2-bedroom house in Chincoteague

Cozy 2-bedroom house in Chincoteague
Deep Hole
The price is HK$1,566
HK$2,700 total
includes taxes & fees
17 Jun - 18 Jun
Cozy 2-bedroom house in Chincoteague
Exterior

Assateague Inn 106 by Seaside Vacations & Sales

Assateague Inn 106 by Seaside Vacations & Sales
Chincoteague Island
9.8 out of 10, Exceptional, (6 reviews)
"Cute rooms in close proximity to several restaurants. "
United States
Sandy G.
Assateague Inn 106 by Seaside Vacations & Sales
Pool

Deck & EV Charger: Coastal Retreat 1 Mi to Marina

Deck & EV Charger: Coastal Retreat 1 Mi to Marina
Captain's Cove
The price is HK$2,139
HK$5,088 total
includes taxes & fees
14 Jun - 15 Jun
Deck & EV Charger: Coastal Retreat 1 Mi to Marina
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

Marina Bay Hotel & Suites, an Ascend Collection Hotel

Marina Bay Hotel & Suites, an Ascend Collection Hotel

10/10 Excellent
"Due to the bridge being closed for many hours onto the island I was offered another night's stay at a discounted rate. I really appreciated that. I was originally staying for only 1 night and was going to be driving home the next day. I wasn't in my room until 3:15 am due to the closure. It sure was nice to be able to get some time to rest before continuing on home! The room was very clean and the bed was comfortable. Their pool looked very refreshing but I didn't take advantage of it this time. The only down side is that there isn't a waterfront view which I would have preferred. My room was completely blocked by the building next door."
Patricia 1-night trip
Posted 6 hours ago
Marina Bay Hotel & Suites, an Ascend Collection Hotel

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 Smart 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 Ballards Island 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.