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, (492)
"What an absolute wonderful place. Staff were so friendly and the cottages were amazing very clean. We would definitely stay here again."
United States
julie
Key West Cottages

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 NZ$445
includes taxes & fees
12 Jan - 13 Jan 2026
Salisbury Riverfront Lofts
3.0 star property
The price is NZ$441
includes taxes & fees
31 Dec - 1 Jan 2026
6 Mi to Salisbury: Forest-view Sanctuary!
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 NZ$444
includes taxes & fees
6 Jan - 7 Jan 2026
Walk to Restaurants & Attractions-Linens Included! Book your Beach Vacation Now!

Holiday Home in Crisfield

Cottage near the Bay
8.8 out of 10, Excellent, (52)
"Great little place "
United States
Eric R.
The price is NZ$321
includes taxes & fees
4 Jan - 5 Jan 2026
Cottage near 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 NZ$359
includes taxes & fees
3 Jan - 4 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!
9.2 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 NZ$327
includes taxes & fees
4 Jan - 5 Jan 2026
Only 5 min. from the Beach!
10.0 out of 10, Exceptional, (11)
"Peggy and Gary are the perfect hosts: welcoming, friendly, attentive and respectful of your preferences. Wonderful views of the Bay and River via the lodge -- including the cupola -- and walking around the majestic property."
United States
Thomas S.
The price is NZ$561
includes taxes & fees
30 Dec - 31 Dec
Riverside Lodge Bed & Breakfast on the Honga River UNIT C
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 NZ$664
includes taxes & fees
4 Jan - 5 Jan 2026
Cozy cottage w/creekside fire pit & grill
10.0 out of 10, Exceptional, (66)
"Wonderful location. Walking distance to shops and restaurants and sunsets. Hosts were responsive and helpful. Check in and checkout were seamless."
United States
imelda s.
The price is NZ$544
includes taxes & fees
30 Dec - 31 Dec
Chincoteague Island House "Sir Whelk-A-Lot" Kayaks Included! Downtown Location!
10.0 out of 10, Exceptional, (3)
"Wonderful stay at beautiful homeamazingly"
United States
Jonathan D.
The price is NZ$696
includes taxes & fees
12 Jan - 13 Jan 2026
Secluded Waterfront•15mi to Assateague Beach•Fast Wifi•Kayaks•Near Berlin, OC!
9.6 out of 10, Exceptional, (42)
"It was family & friends that needed a get away and we really Enjoy the area"
United States
Lori D.
The price is NZ$689
includes taxes & fees
7 Jan - 8 Jan 2026
Great Water Views in quiet pet-friendly location facing lighthouse. Large Yard
10.0 out of 10, Exceptional, (8)
"Clean and comfortable. Great communication. "
United States
Paul R.
The price is NZ$1,181
includes taxes & fees
31 Dec - 1 Jan 2026
3-bedroom townhome in tranquil Delmar with WiFi, AC. Relax and unwind
9.4 out of 10, Exceptional, (13)
"Went for a guys trip and enjoyed it "
United States
John W.
Chincoteague Island Home- "Blue Tide Townhome" Kayaks Included!
8.8 out of 10, Excellent, (10)
"Quiet area and close to all attractions. Very fast response with any questions before and during stay. Would recommend!"
United States
Sue S.
The price is NZ$327
includes taxes & fees
4 Jan - 5 Jan 2026
Only 5 minutes to Assateague National Seashore!

Holiday Home in Downtown Chincoteague

The Neigh-Neigh - Location! Location! Location!
10.0 out of 10, Exceptional, (4)
"House was clean, cozy and convenient for our weekend stay on the island. We will be there for the same event next year and will consider booking The Neigh Neigh again depending on who comes next time! Cheers"
United States
Bob S.
The price is NZ$647
includes taxes & fees
23 Jan - 24 Jan 2026
The Neigh-Neigh - Location! Location! Location!

Condo in Chincoteague Island

A Bargain on Chincoteague Island!
8.8 out of 10, Excellent, (3)
"Overall the place was nice enough for the cost. "
United States
Stacey S.
The price is NZ$327
includes taxes & fees
4 Jan - 5 Jan 2026
A Bargain on Chincoteague Island!
10.0 out of 10, Exceptional, (1)
"Helpful host, clean house, peaceful location! "
United States
Jennifer P.
The price is NZ$352
includes taxes & fees
6 Jan - 7 Jan 2026
Tangier Escape, great place get away from it all on Deal Island, MD.

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 NZ$447
includes taxes & fees
1 Jan - 2 Jan 2026
Deal Island Bay Cottage
7.4 out of 10, Good, (3)
"Low-quality furniture. needs to be updated"
United States
Susan E.
The price is NZ$327
includes taxes & fees
4 Jan - 5 Jan 2026
Only 5 min from Assateague National Seashore!
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 favorite 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 depends 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 NZ$327 per night. Entering your travel dates in the search wizard you might find 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.