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
7 Aug - 9 Aug
In two months
18 Sept - 20 Sept
In three months
16 Oct - 18 Oct
In four months
13 Nov - 15 Nov

Our top choices for Princess Anne holiday rentals

2 bedrooms, iron/ironing board (on request), free WiFi

Salisbury Riverfront Lofts

Salisbury Riverfront Lofts
3.0 star property
Salisbury
9.4 out of 10, Exceptional, (26 reviews)
"It was a great stay nice comfortable place "
United States
Adam
The price is HK$662
HK$2,111 total
includes taxes & fees
23 Jul - 24 Jul
Salisbury Riverfront Lofts
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
9.8 out of 10, Exceptional, (21 reviews)
"First time using VRBO and it was more than inexpected"
United States
Robert J.
The price is HK$941
HK$1,897 total
includes taxes & fees
27 Jul - 28 Jul
Stylish 2 bedroom 1 bath with riverfront views close to dining and downtown
Exterior

Salisbury Hideaway

Salisbury Hideaway
Salisbury
10.0 out of 10, Exceptional, (22 reviews)
"Perfect for our weekend away watching college softball!!!"
United States
Michelle S.
The price is HK$1,278
HK$2,967 total
includes taxes & fees
12 Aug - 13 Aug
Salisbury Hideaway
Interior

Cottage near the Bay

Cottage near the Bay
Crisfield
8.6 out of 10, Excellent, (58 reviews)
"Quiet area, the place needs to be cleaned, bedding changed, redo the bathroom"
United States
Pamela
The price is HK$706
HK$1,562 total
includes taxes & fees
11 Aug - 12 Aug
Cottage near the Bay
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$1,928 total
includes taxes & fees
3 Aug - 4 Aug
Tangier Escape, great place get away from it all on Deal Island, MD.
Coffee/tea maker, fridge, microwave, oven

Deal Island Bay Cottage

Deal Island Bay Cottage
Deal Island
9.6 out of 10, Exceptional, (60 reviews)
"We got every year and stay here, it’s great! "
United States
Margaret H.
The price is HK$1,122
HK$2,045 total
includes taxes & fees
4 Aug - 5 Aug
Deal Island Bay Cottage
Coffee/tea maker, fridge, microwave, oven

Cozy Barn Loft: Country Views & Central to Beaches

Cozy Barn Loft: Country Views & Central to Beaches
Pocomoke City
10.0 out of 10, Exceptional, (21 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$2,100 total
includes taxes & fees
2 Aug - 3 Aug
Cozy Barn Loft: Country Views & Central to Beaches
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$1,035
HK$2,126 total
includes taxes & fees
9 Aug - 10 Aug
6 Mi to Salisbury: Forest-view Sanctuary!
Smart TV, offices

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 HK$698
HK$1,947 total
includes taxes & fees
23 Jul - 24 Jul
Spacious Riverfront Loft Close to Downtown and Dining
Smart TV, offices

Salisbury Cottage

Salisbury Cottage
Salisbury
10.0 out of 10, Exceptional, (39 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 HK$1,647
HK$3,408 total
includes taxes & fees
18 Aug - 19 Aug
Salisbury Cottage
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$2,138 total
includes taxes & fees
9 Aug - 10 Aug
6 Mi to Salisbury: Forest-View Sanctuary!
Coffee/tea maker, fridge, microwave, oven

Retro Hipster: Close to downtown, dining and fun

Retro Hipster: Close to downtown, dining and fun
Salisbury
9.0 out of 10, Wonderful, (18 reviews)
"Nice large, bright kitchen, each room has a bathroom! Nice river view, many shops within walking distance and good coffee and breakfast right diwnstairs! Loved the funky, whimsical decor too."
United States
Joan
The price is HK$839
HK$1,814 total
includes taxes & fees
27 Jul - 28 Jul
Retro Hipster: Close to downtown, dining and fun
Exterior

Pet-Friendly Smith Island Cottage w/ Golf Cart!

Pet-Friendly Smith Island Cottage w/ Golf Cart!
Ewell
10.0 out of 10, Exceptional, (22 reviews)
"Enjoyed Smith Island , great place to stay, friendly people, loved the golf cart a real plus! Flies and mosquitoes were terrible, restaurant food was just OK! Make sure you get food and supplies before coming! "
United States
richard a. g.
Pet-Friendly Smith Island Cottage w/ Golf Cart!
Interior

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 HK$2,039
HK$2,801 total
includes taxes & fees
4 Aug - 5 Aug
Entire Private Home • Sleeps 6 • Prime Salisbury Location
Outdoor pool

Charming camper within Trails End ChinoteagueBay Resort in Horntown VA

Charming camper within Trails End ChinoteagueBay Resort in Horntown VA
Horntown
10.0 out of 10, Exceptional, (3 reviews)
"My stay was an absolute joy! Very easy to check in and out and the hosts are wonderful! Beautiful outdoor setup! The kids loved it and the beach was a short distance away. Highly recommend!"
United States
Stephanie P.
The price is HK$953
HK$1,224 total
includes taxes & fees
4 Aug - 5 Aug
Charming camper within Trails End ChinoteagueBay Resort in Horntown VA
Exterior

Blufin Bungalows & Marina

Blufin Bungalows & Marina
3.0 star property
Down the Marsh
9.6 out of 10, Exceptional, (289 reviews)
"Excellent place to stay would definitely come again. Checking in was seem less and the staff very helpful"
United States
Jared
The price is HK$2,392
HK$3,127 total
includes taxes & fees
26 Jul - 27 Jul
Blufin Bungalows & Marina
TV, DVD player

The purple door at the bay.

The purple door at the bay.
Captain's Cove
9.4 out of 10, Exceptional, (62 reviews)
"This is a great property with a great view of the bay. It's tucked away in a quiet little neighborhood in a nice and friendly community. Chincoteague is close by and it's not too far from Assateague. The property management team is excellent. They were extremely responsive to our questions and requests. They were patient with all our questions. Kelly was fantastic. The best hosts I've had."
United States
A Shabeen J.
The price is HK$1,372
HK$3,710 total
includes taxes & fees
8 Aug - 9 Aug
The purple door at the bay.
Interior

Pet-friendly Smith Island Cottage w/ Golf Cart!

Pet-friendly Smith Island Cottage w/ Golf Cart!
3.0 star property
Smith Island
10.0 out of 10, Exceptional, (1 review)
"We had a lovely 2 night stay. The owners and host were wonderful. We were so happy to have use of the golf cart and bicycles. The cottage is adorable with beautiful touches all around."
United States
Karl
Pet-friendly Smith Island Cottage w/ Golf Cart!
Smart TV, books, offices

Bayfront Modern Retreat • Dock, Kayaks, Views

Bayfront Modern Retreat • Dock, Kayaks, Views
Captain's Cove
9.8 out of 10, Exceptional, (66 reviews)
"We absolutely love staying here! "
United States
Maggie G.
The price is HK$1,713
HK$4,811 total
includes taxes & fees
26 Jul - 27 Jul
Bayfront Modern Retreat • Dock, Kayaks, Views
1 bedroom, premium bedding, laptop workspace, soundproofing

Key West Cottages

Key West Cottages
3.0 star property
Downtown Chincoteague
9.8 out of 10, Exceptional, (602 reviews)
"Beautiful family friendly place. Great pool. Great location."
United States
KRYSTLE
The price is HK$2,407
HK$2,703 total
includes taxes & fees
6 Aug - 7 Aug
Key West Cottages
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

10/10 Excellent
"Beautiful hotel. Especially the roses!! Access to the dock was a nice surprise. Great, quiet hotel."
Sheri 1-night trip
Posted 1 day ago
Waterside Inn

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?

Manokin Park and Monie Island are a couple of lovely local spots to get outside and enjoy nature. Somerset County Library and Hytche athletic Center 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.