Princess Anne Holiday Rentals

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Our top choices for Princess Anne holiday rentals

Cottage in Downtown Chincoteague

Key West Cottages
3.0 star property
9.8 out of 10, Exceptional, (488)
"We love Key West Cottages!"
United States
Jonathan
Key West Cottages
3.0 star property
The price is AU$387
includes taxes & fees
22 Dec - 23 Dec
6 Mi to Salisbury: Forest-view Sanctuary!

Apartment in Salisbury

Salisbury Riverfront Lofts
3.0 star property
9.4 out of 10, Exceptional, (23)
"It was a great stay nice comfortable place "
United States
Adam
The price is AU$374
includes taxes & fees
18 Dec - 19 Dec
Salisbury Riverfront Lofts

Holiday Home in Crisfield

Cottage near the Bay
8.8 out of 10, Excellent, (52)
"Srea was quiet, peaceful, plenty of information provided about the area restaurants, grocery stores, etc. Enjoyed our stay."
United States
Darla J M.
The price is AU$284
includes taxes & fees
20 Dec - 21 Dec
Cottage near the Bay

Cottage in Deal Island

Deal Island Bay Cottage
9.6 out of 10, Exceptional, (58)
"We got every year and stay here, it’s great! "
United States
Margaret H.
The price is AU$398
includes taxes & fees
19 Dec - 20 Dec
Deal Island Bay Cottage
9.6 out of 10, Exceptional, (22)
"Stay at Assateague Inn was clean, comfy, cozy, and convenient. "
United States
Anonymous traveller
The price is AU$287
includes taxes & fees
22 Dec - 23 Dec
Assateague Inn 104 by Seaside Vacations & Sales
9.8 out of 10, Exceptional, (59)
"Nick is an excellent host. The home was so fun for our family to stay in. The view is so beautiful and peaceful. It is even more beautiful in person. Short drive to reach Chincoteague and Assateague. Stocked with everything you need. I walked down the street and got a massage using the info provided in the house. Thanks for a wonderful and beautiful stay. "
United States
Natalie K.
The price is AU$817
includes taxes & fees
19 Dec - 20 Dec
Modern Waterfront Retreat- Panoramic Bay Views, Kayaks, Pools & Resort Amenities

Holiday Home in Salisbury

Salisbury Cottage
10.0 out of 10, Exceptional, (34)
"Very clean, great communication and fabulous location close to SU!"
United States
Anne M.
The price is AU$516
includes taxes & fees
18 Dec - 19 Dec
Salisbury Cottage
9.4 out of 10, Exceptional, (3)
"Check in was easy! A/C units were a bit tricky. Location was great! "
United States
Camille S.
"The 3 Sisters" Ivy's Cottage-Adorable In Town Cottage Near Historic Main Street
10.0 out of 10, Exceptional, (66)
"Great location. The house was perfect for our family. I especially enjoyed the swing on the porch "
United States
pat B.
The price is AU$380
includes taxes & fees
18 Dec - 19 Dec
Chincoteague Island House "Sir Whelk-A-Lot" Kayaks Included! Downtown Location!

Condo in Chincoteague Island

Only 5 min. from the Beach!
9.2 out of 10, Wonderful, (31)
"Great location that was very clean, kid friendly, and good amenities! Liked how close it was to everything, very walkable."
United States
Jeananne K.
The price is AU$291
includes taxes & fees
18 Dec - 19 Dec
Only 5 min. from the Beach!

Holiday Home in Salisbury

Salisbury Hideaway
10.0 out of 10, Exceptional, (19)
"This property was wonderful for our trip to Salisbury for my daughter's travel softball tournament. It was only 30-45 minutes from Ocean City (give or take traffic), and very close to many shopping areas and restaurants. The property itself was very clean and provided many necessities. "
United States
Lisa H.
Salisbury Hideaway
10.0 out of 10, Exceptional, (7)
"Great stay. Great host. Very clean place. Couldn’t of asked for a better host and house ! "
United States
James E.
The price is AU$399
includes taxes & fees
6 Jan - 7 Jan 2026
Walk to Restaurants & Attractions-Linens Included! Book your Beach Vacation Now!
10.0 out of 10, Exceptional, (3)
"Wonderful stay at beautiful homeamazingly"
United States
Jonathan D.
The price is AU$619
includes taxes & fees
12 Jan - 13 Jan 2026
Secluded Waterfront•15mi to Assateague Beach•Fast Wifi•Kayaks•Near Berlin, OC!
10.0 out of 10, Exceptional, (1)
"Helpful host, clean house, peaceful location! "
United States
Jennifer P.
The price is AU$314
includes taxes & fees
6 Jan - 7 Jan 2026
Tangier Escape, great place get away from it all on Deal Island, MD.

Holiday Home in Captain's Cove

The purple door at the bay.
9.2 out of 10, Wonderful, (54)
"Price and location was the primary reason the purple door works for us!"
United States
Patrick O.
The price is AU$682
includes taxes & fees
18 Dec - 19 Dec
The purple door at the bay.
10.0 out of 10, Exceptional, (2)
"The hosts were wonderful, the house is beautiful, access & location was perfect. Next time I'm in the area & this place is avaliable, this is where I want to stay again. I recommend this house if you're in the area!!!Thanks to The Smiths"
United States
Sadat J.
The price is AU$304
includes taxes & fees
17 Jan - 18 Jan 2026
Quaint house in small town of Snow Hill, MD.Centrally located to 3 local beaches

Condo in Chincoteague Island

Only 5 min. from the Beach!
9.4 out of 10, Exceptional, (8)
"Close to everything, quiet, clean"
United States
Eileen D.
The price is AU$321
includes taxes & fees
22 Dec - 23 Dec
Only 5 min. from the Beach!
8.4 out of 10, Very good, (5)
"It was seamless. Would stay here again."
United States
Joe C.
The price is AU$352
includes taxes & fees
9 Jan - 10 Jan 2026
Deluxe corner apartment with riverfront views close to dining and downtown
9.4 out of 10, Exceptional, (137)
"Nice and quiet spot on island, kind of away from the busy parts of island. "
United States
Derek W.
The price is AU$597
includes taxes & fees
13 Jan - 14 Jan 2026
Cottage w Private Creek, Sunroom, Fire Pit, & WiFi
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

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$287 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 close to the most popular sights in Princess Anne, 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.

What can I see and do in Princess Anne?

Manokin Park and Wellington State Wildlife Management Area 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.