Princess Anne Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Holiday Rentals in Princess Anne

Key West Cottages

3.0 star property
9.8 out of 10, Exceptional, (458)
"Great place to stay!"
Key West Cottages

Blufin Bungalows & Marina

3.0 star property
9.6 out of 10, Exceptional, (189)
"Absolutely loved it here. Very helpful and friendly staff. Will Absolutely stay again."
Blufin Bungalows & Marina

Strawberry Crossroads

2.0 star property
9.0 out of 10, Wonderful, (7)
"Quiet clean cabin off the beaten path!! Absolutely amazing place if you want something more private and rustic!!"
Strawberry Crossroads

Great Water Views in quiet pet-friendly location facing lighthouse. Large Yard

9.6 out of 10, Exceptional, (42)
"Such a great location. You can see the ponies with binoculars from the lovely screened porch.This was close enough to the park and restaurants but far enough for a nice quiet getaway. "
The price is NZ$693
includes taxes & fees
30 Sept - 1 Oct
Great Water Views in quiet pet-friendly location facing lighthouse. Large Yard

1BR Waterfront cottage with a view of the wild Chincoteague ponies!

9.6 out of 10, Exceptional, (14)
"3 night stay for our anniversary, beautiful view had a relaxing time! "
1BR Waterfront cottage with a view of the wild Chincoteague ponies!

2BR Waterfront Cottage with the Most Spectacular View of lighthouse!

9.6 out of 10, Exceptional, (52)
"Very nice and clean and directly at the water. Well equipped and beautiful view and close to everything. Perfect place for a peaceful getaway to explore beautiful Chincoteague. "
2BR Waterfront Cottage with the Most Spectacular View of lighthouse!

Chincoteague Island House "Sir Whelk-A-Lot" Kayaks Included! Downtown Location!

10.0 out of 10, Exceptional, (58)
"Thank you so much for letting us stay at your house. The location was perfect for walking to restaurants and shops. Did a day at the wildlife refuge and spent some time on the beach. Plan to come back and enjoy another stay. "
The price is NZ$474
includes taxes & fees
30 Sept - 1 Oct
Chincoteague Island House "Sir Whelk-A-Lot" Kayaks Included! Downtown Location!

5 minutes to Assateague National Seashore!

9.0 out of 10, Wonderful, (20)
"The condo was perfect for my girlfriend and I, very private location and nice boardwalk by the creek"
The price is NZ$331
includes taxes & fees
30 Sept - 1 Oct
5 minutes to Assateague National Seashore!

The Hideaway Cottage

9.8 out of 10, Exceptional, (96)
"Just right for what we needed."
The Hideaway Cottage

Historic home on Smith Island w/ dock!

9.6 out of 10, Exceptional, (45)
"This property was perfect for a family of 4. It was very clean, the kitchen was well stocked and the neighbors were amazing and helpful. Visit the arcade by the marina right before sunset!"
Historic home on Smith Island w/ dock!

Waterfront on Marsh Island!

8.4 out of 10, Very good, (36)
"The location is close to everything, but secluded and quiet for when you just want to relax. We loved the closed in porch where we sat for hours on end talking and watching the water. We really felt comfortable and at home. "
Waterfront on Marsh Island!

The Brass Crab - Check in/out any day!

10.0 out of 10, Exceptional, (154)
"The Brass Crab is the perfect family place to stay. Thank you for all the extras."
The Brass Crab - Check in/out any day!

Cottage near the Bay

8.8 out of 10, Excellent, (48)
"great, peaceful "
The price is NZ$323
includes taxes & fees
1 Oct - 2 Oct
Cottage near the Bay

Make fabulous Vacation Memories at Family Tides Vacation Rental on Chincoteague

9.8 out of 10, Exceptional, (53)
"Great location and property for a peaceful and tranquil getaway."
Make fabulous Vacation Memories at Family Tides Vacation Rental on Chincoteague

At the Water's Edge - is there anywhere you'd rather be?!

10.0 out of 10, Exceptional, (52)
"Property was exactly like it showed in the pictures. There was a loud fan noise in the attic that maintenance was unable to resolve but we still had a great time."
At the Water's Edge - is there anywhere you'd rather be?!

Cabin at Holdens Creek on Eastern Shore of VA

9.6 out of 10, Exceptional, (180)
"Thank you for your hospitality!! Your rental property is absolutely amazing! We love cabins and yours made us feel so at home. We are looking forward to visit again!"
Cabin at Holdens Creek on Eastern Shore of VA

Coastal Daze Cottage on Famous Chincoteague Island! Come see the wild ponies!

10.0 out of 10, Exceptional, (16)
"Great location and property. Owner was kind and communicative. The playground next to the house was a bonus for my kids!"
Coastal Daze Cottage on Famous Chincoteague Island! Come see the wild ponies!

EVENTIDE on Chincoteague Island!

8.6 out of 10, Excellent, (10)
"Great place. Nice location to everything."
EVENTIDE on Chincoteague Island!

Salisbury Riverfront Lofts

3.0 star property
9.2 out of 10, Wonderful, (22)
"Very nice place clean & roomy."
The price is NZ$435
includes taxes & fees
19 Oct - 20 Oct
Salisbury Riverfront Lofts

Near Chincoteague & Assateague Island Charming 2-bedroom cottage

9.0 out of 10, Wonderful, (2)
"very clean and neat, quiet. just what i needed"
Near Chincoteague & Assateague Island Charming 2-bedroom cottage
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Princess Anne Hotel Reviews

Find out more about Princess Anne

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$323 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 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.