Princess Anne Vacation Rentals

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

Check prices for these dates

In two weeks
Nov 28 - Nov 30
In two months
Jan 9 - Jan 11
In three months
Feb 6 - Feb 8
In four months
Mar 6 - Mar 8

Vacation Rentals in Princess Anne

Exterior
Key West Cottages

Key West Cottages

3.0 star property
Downtown Chincoteague
9.8 out of 10, Exceptional, (480)
"Amazing place for vacation "
United States
carla
$131 nightly
The price is $148
Dec 1 - Dec 2
Total with taxes and fees
Key West Cottages
Exterior
Blufin Bungalows & Marina

Blufin Bungalows & Marina

3.0 star property
Down the Marsh
9.6 out of 10, Exceptional, (205)
"yesss amazing stay "
United States
EDA
$169 nightly
The price is $190
Nov 27 - Nov 28
Total with taxes and fees
Blufin Bungalows & Marina
Pool
1BR Waterfront cottage with a view of the wild Chincoteague ponies!

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

Dodge City
9.6 out of 10, Exceptional, (14)
"Wonderful hosts at a beautiful property. The cottage was quaint, safe and clean, just as advertised, and was perfect for a 2 day quiet get away. The overall property is well cared for and provides for a warm sense of community for the guests. "
United States
Carol P.
1BR Waterfront cottage with a view of the wild Chincoteague ponies!
Beach
2BR Waterfront Cottage with the Most Spectacular View of lighthouse!

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

Dodge City
9.6 out of 10, Exceptional, (52)
"What a perfect location! Loved sitting on the dock with feet in the water watching the horses and lighthouse"
United States
Coleen T.
2BR Waterfront Cottage with the Most Spectacular View of lighthouse!
Fridge, microwave, oven, stovetop
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, (64)
"We absolutely loved the location of the property - so walkable and bikeable to so many fun things, and nestled in a neighborhood with a great vibe. Easy communication with the host when we needed it, too. "
United States
Kimberley M.
$233 nightly
The price is $261
Nov 16 - Nov 17
Total with taxes and fees
Chincoteague Island House "Sir Whelk-A-Lot" Kayaks Included! Downtown Location!
Exterior
Strawberry Crossroads

Strawberry Crossroads

2.0 star property
Pittsville
9.0 out of 10, Wonderful, (7)
"My family really enjoyed the stay, its close enough drive to ocean city while being out of the way. Even after having a double booking issue the property owner made it work for us all. The kids were begging us to stay longer it was so peaceful!"
United States
Samuel
Strawberry Crossroads
Interior
At the Water's Edge - is there anywhere you'd rather be?!

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

Chincoteague Island
10.0 out of 10, Exceptional, (53)
"The condominium was exceptional. It was immaculately clean, well-appointed, and ideally located. The layout was perfectly suited for three adults, offering ample space.We particularly appreciated the peacefulness of the island setting, while still enjoying easy access to all that the town had to offer.We unanimously agreed that we would be pleased to stay there again in the future and would absolutely recommend the property to family and friends. It is truly an outstanding accommodation."
United States
Wanda H.
At the Water's Edge - is there anywhere you'd rather be?!
Interior
Cabin at Holdens Creek on Eastern Shore of VA

Cabin at Holdens Creek on Eastern Shore of VA

Temperanceville
9.6 out of 10, Exceptional, (180)
"Beautiful place and nice and quiet. We loved it."
United States
Jon L.
Cabin at Holdens Creek on Eastern Shore of VA
Fridge, microwave, oven, stovetop
Coastal Daze Cottage on Famous Chincoteague Island! Come see the wild ponies!

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

Downtown Chincoteague
10.0 out of 10, Exceptional, (17)
"Great location and property. Owner was kind and communicative. The playground next to the house was a bonus for my kids!"
United States
Zahra G.
Coastal Daze Cottage on Famous Chincoteague Island! Come see the wild ponies!
Interior
Only 5 min. from the Beach!

Only 5 min. from the Beach!

Chincoteague Island
9.2 out of 10, Wonderful, (29)
"Our 2 bedroom stay was the perfect size. It was right on the corner of the second floor so we felt like we have the balcony to ourselves. The staff was friendly and the communication was great. Will definitely stay again!"
United States
Mallory
$183 nightly
The price is $191
Nov 16 - Nov 17
Total with taxes and fees
Only 5 min. from the Beach!
Outdoor dining
Near Chincoteague & Assateague Island Charming 2-bedroom cottage

Near Chincoteague & Assateague Island Charming 2-bedroom cottage

Saxis
9.4 out of 10, Exceptional, (3)
"Lovely, small but cozy, great place to bond and enjoy good food and drink."
United States
Bob H.
Near Chincoteague & Assateague Island Charming 2-bedroom cottage
Apartment D: Riverfront Grand | In-room dining
Salisbury Riverfront Lofts

Salisbury Riverfront Lofts

3.0 star property
Salisbury
9.4 out of 10, Exceptional, (23)
"Really cute unit. We loved how it was decorated. "
United States
Marianna
$245 nightly
The price is $264
Nov 16 - Nov 17
Total with taxes and fees
Salisbury Riverfront Lofts
Microwave, oven, stovetop, coffee/tea maker
Only 5 min. from the Beach!

Only 5 min. from the Beach!

Chincoteague Island
8.2 out of 10, Very Good, (32)
"Excellent location, perfect size for two adults. Easy check in/out procedure. Only negative was lots of flies in room when we checked in and no one working front desk we could communicate with."
United States
Isabela D.
$182 nightly
The price is $190
Nov 18 - Nov 19
Total with taxes and fees
Only 5 min. from the Beach!
Exterior
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)
"We came for the beach and blueberry festival! It was close enough to everything and also far enough away from the crowds. Loved the view of the lighthouse and the park"
United States
Melody S.
$358 nightly
The price is $402
Nov 14 - Nov 15
Total with taxes and fees
Great Water Views in quiet pet-friendly location facing lighthouse. Large Yard
Terrace/patio
The purple door at the bay.

The purple door at the bay.

Captain's Cove
9.2 out of 10, Wonderful, (54)
"We had a great week staying in Captains Cove. The house met all our needs and the amenities at the marina were wonderful. Only wish would be that the house had wifi."
United States
Katrina S.
$409 nightly
The price is $451
Nov 17 - Nov 18
Total with taxes and fees
The purple door at the bay.
Terrace/patio
Waterfront Bungalow on Chincoteague Bay (VA)! - Waterfront Bungalow with Two Bedrooms

Waterfront Bungalow on Chincoteague Bay (VA)! - Waterfront Bungalow with Two Bedrooms

Down the Marsh
9.8 out of 10, Exceptional, (21)
"This was an adorable tiny house that looked brand new. It was very clean, the bed was comfortable, the kitchen amenities were all we needed, and the screened in front porch was a great place to eat, play games, and just hang out while overlooking the water. Check in was easy and the people were very friendly and helpful. "
United States
Ashley L.
$181 nightly
The price is $203
Nov 20 - Nov 21
Total with taxes and fees
Waterfront Bungalow on Chincoteague Bay (VA)! - Waterfront Bungalow with Two Bedrooms
Property grounds
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, (59)
"We enjoyed our stay. Our host was very responsive and the community amenities and access to Chincoteague and Assateague are excellent."
United States
Kristen Z.
$420 nightly
The price is $463
Nov 18 - Nov 19
Total with taxes and fees
Modern Waterfront Retreat- Panoramic Bay Views, Kayaks, Pools & Resort Amenities
Smart TV, fireplace
NEW PET FRIENDLY LISTING ALERT!!

NEW PET FRIENDLY LISTING ALERT!!

Chincoteague Island
9.2 out of 10, Wonderful, (19)
"This worked out for my son's family of five, plus one dog. The dog was brother to our dog so they got along well; we put them in portable kennels when we left the house. Refrigerator broke on first night; owner substituted small one for duration of stay. Few curtains for privacy. Plastic chairs needed repairs. An older house listed for sale. New painting and floor made it attractive. Comfortable overall."
United States
David T.
NEW PET FRIENDLY LISTING ALERT!!
Fridge, microwave, oven, stovetop
The Blue Crab - Your Dream Vacation awaits you!

The Blue Crab - Your Dream Vacation awaits you!

2.0 star property
Deep Hole
9.8 out of 10, Exceptional, (14)
"The Blue Crab was perfect for our family vacation. It was beautiful, clean, spacious, and had everything we needed to enjoy our stay. If we come back, we’ll be staying at The Blue Crab again! "
United States
Erin P.
The Blue Crab - Your Dream Vacation awaits you!
Outdoor pool, a heated pool
Historic Whealton House with full access to Waterside Inn facilites

Historic Whealton House with full access to Waterside Inn facilites

Downtown Chincoteague
9.0 out of 10, Wonderful, (34)
"This was the perfect place we were looking for to spend a relaxing Valentine's Day weekend away. Everything was clean and organized when we showed up, and we loved the location. Main Street was so great and had the cutest local shops everywhere you looked. The weather was perfect for enjoying the waterfront view as well. Although we only came to get a relaxing stay away in a new, quaint town, we would definitely come back in the summer to do some more exploring and enjoy the beach :)"
United States
Emily T.
Historic Whealton House with full access to Waterside Inn facilites
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Princess Anne Hotel Reviews

Econo Lodge Princess Anne

Econo Lodge Princess Anne

10/10 Excellent
"Yea"
Chileshe 2-night trip
Posted 3 days ago
Econo Lodge Princess Anne

Find out more about Princess Anne

Everything you need to know about Princess Anne vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Princess Anne vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Princess Anne vacation 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 low season months. For more hustle and bustle, you may prefer to visit Princess Anne in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $148 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Princess Anne rentals

At Expedia, we put the best Princess Anne vacation 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 vacation.

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.

Explore a world of travel with Expedia

Frequently asked questions

Can I find a vacation rental in Princess Anne?

Yes, you can find vacation rentals close to top local attractions in Princess Anne, or you can go with a more secluded option if you're looking for a relaxing stay. Our travelers 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 vacation home rentals in Princess Anne?

Blufin Bungalows & Marina: This vacation home rental near 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 vacation rentals like in Princess Anne?

Vacation rentals are private properties you can stay in for several days or more in Princess Anne. Vacation rentals feature amenities such as patios, hot tubs, and fire pits so you'll feel just like you're staying in your own home. If you're concerned about a clean environment, vacation rentals can offer a sense of safety away from public hotel elevators and busy concierge desks while still allowing you the enjoyment of travel. You'll also find more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a great option for small groups.