Princess Anne Holiday Rentals

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Our top choices for Princess Anne holiday rentals

Key West Cottages

Key West Cottages
3.0 star property
Downtown Chincoteague
9.8 out of 10, Exceptional, (505 reviews)
"Love the resort! "
United States
Hannah
Key West Cottages

6 Mi to Salisbury: Forest-view Sanctuary!

6 Mi to Salisbury: Forest-view Sanctuary!
3.0 star property
Parsonsburg
The price is AU$369
includes taxes & fees
2 Feb - 3 Feb
6 Mi to Salisbury: Forest-view Sanctuary!

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 AU$363
includes taxes & fees
3 Feb - 4 Feb
Salisbury Riverfront Lofts

Modern Waterfront Retreat- Panoramic Bay Views, Kayaks, Pools & Resort Amenities

Modern Waterfront Retreat- Panoramic Bay Views, Kayaks, Pools & Resort Amenities
Captain's Cove
9.8 out of 10, Exceptional, (61 reviews)
"This is a unique home with beautiful views! The amenities were wonderful, the home was so clean, and Nick was great with checking in to make sure everything was good. Would definitely stay here again! "
United States
Kristy C.
The price is AU$607
includes taxes & fees
3 Feb - 4 Feb
Modern Waterfront Retreat- Panoramic Bay Views, Kayaks, Pools & Resort Amenities

Assateague Inn 104 by Seaside Vacations & Sales

Assateague Inn 104 by Seaside Vacations & Sales
Chincoteague Island
9.6 out of 10, Exceptional, (22 reviews)
"This was a great home-base as we trekked around Assateague and Chincoteague on our honeymoon. Very convenient to the Virginia side entrance to Assateague and the kitchen is perfect for breakfast and simple dinners. I was pleased to see the kitchen had everything you could need for basic cooking & there were a variety of drink glasses for both beer & wine!"
United States
Rosalynde V.
The price is AU$274
includes taxes & fees
3 Feb - 4 Feb
Assateague Inn 104 by Seaside Vacations & Sales

Cozy creekside cottage w/fire pit & sunroom

Cozy creekside cottage w/fire pit & sunroom
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 AU$396
includes taxes & fees
2 Feb - 3 Feb
Cozy creekside cottage w/fire pit & sunroom

Salisbury Cottage

Salisbury Cottage
Salisbury
10.0 out of 10, Exceptional, (34 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 AU$484
includes taxes & fees
5 Feb - 6 Feb
Salisbury Cottage

Deluxe corner apartment with riverfront views close to dining and downtown

Deluxe corner apartment with riverfront views close to dining and downtown
Salisbury
8.4 out of 10, Very good, (5 reviews)
"Apartment was cozy and clean. Didn’t have a pet but the location across from a dog park would make it very easy to bring one. Kitchen had all the essentials. Parking lot behind lofts provided enough parking for everyone. Just a short walk to restaurants, shops, and bars. Had no isses being next to Perdue factory, such as noise and smell. "
United States
Jamie M.
The price is AU$326
includes taxes & fees
3 Feb - 4 Feb
Deluxe corner apartment with riverfront views close to dining and downtown

Cottage near the Bay

Cottage near the Bay
Crisfield
8.8 out of 10, Excellent, (52 reviews)
"Great little place "
United States
Eric R.
The price is AU$271
includes taxes & fees
2 Feb - 3 Feb
Cottage near the Bay

Only 5 min. from the Beach!

Only 5 min. from the Beach!
Chincoteague Island
9.2 out of 10, Wonderful, (31 reviews)
"Everything was great. Will stay again "
United States
Richard R.
The price is AU$274
includes taxes & fees
6 Feb - 7 Feb
Only 5 min. from the Beach!

Only 5 min from Assateague National Seashore!

Only 5 min from Assateague National Seashore!
Chincoteague Island
7.4 out of 10, Good, (3 reviews)
"Low-quality furniture. needs to be updated"
United States
Susan E.
The price is AU$274
includes taxes & fees
2 Feb - 3 Feb
Only 5 min from Assateague National Seashore!

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 AU$372
includes taxes & fees
3 Feb - 4 Feb
Deal Island Bay Cottage

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 AU$274
includes taxes & fees
4 Feb - 5 Feb
A Bargain on Chincoteague Island!

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, (66 reviews)
"Perfect trip!"
United States
Alexis A.
The price is AU$392
includes taxes & fees
2 Feb - 3 Feb
Chincoteague Island House "Sir Whelk-A-Lot" Kayaks Included! Downtown Location!

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, (42 reviews)
"It was family & friends that needed a get away and we really Enjoy the area"
United States
Lori D.
The price is AU$561
includes taxes & fees
2 Feb - 3 Feb
Great Water Views in quiet pet-friendly location facing lighthouse. Large Yard

Only 5 min to Assateague National Seashore!

Only 5 min to Assateague National Seashore!
Chincoteague Island
8.0 out of 10, Very good, (6 reviews)
"The property and room were clean and neat. The facility and rooms are older, but all was functional and clean. Very communicative and easy and clear check in and out process! "
United States
Ellen K.
The price is AU$274
includes taxes & fees
3 Feb - 4 Feb
Only 5 min to Assateague National Seashore!

The Neigh-Neigh - Location! Location! Location!

The Neigh-Neigh - Location! Location! Location!
Downtown Chincoteague
10.0 out of 10, Exceptional, (4 reviews)
"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 AU$697
includes taxes & fees
3 Mar - 4 Mar
The Neigh-Neigh - Location! Location! Location!

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, (7 reviews)
"Beautiful home with everything needed for comfort and a great time! Great location for getting to the beach, shopping and dining out. Communication with host was very informative and helpful. Thank you Chip!"
United States
Gil R.
The price is AU$345
includes taxes & fees
2 Feb - 3 Feb
Walk to Restaurants & Attractions-Linens Included! Book your Beach Vacation Now!

Chincoteague Island Home- "Blue Tide Townhome" Kayaks Included!

Chincoteague Island Home- "Blue Tide Townhome" Kayaks Included!
Deep Hole
9.4 out of 10, Exceptional, (13 reviews)
"The home was perfect for our family gathering. "
United States
Beth H.
The price is AU$541
includes taxes & fees
2 Feb - 3 Feb
Chincoteague Island Home- "Blue Tide Townhome" Kayaks Included!

Only 5 min. from the Beach!

Only 5 min. from the Beach!
Chincoteague Island
7.6 out of 10, Good, (4 reviews)
"Nice quiet Inn. Could use some updating. One air conditioner in dining/living area so bedroom was alway quite warm."
United States
Colleen B.
The price is AU$274
includes taxes & fees
2 Feb - 3 Feb
Only 5 min. from the Beach!
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$274 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 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?

Mount Vernon Beach and Ballards Island are a couple of lovely local spots to get outside and enjoy nature. Hytche athletic Center and Somerset County Library 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.