Princess Anne Vacation Rentals

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

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

Tonight
Nov 22 - Nov 23
Tomorrow
Nov 23 - Nov 24
Next weekend
Nov 28 - Nov 30
In two weeks
Dec 5 - Dec 7

Vacation Rentals in Princess Anne

Exterior
Key West Cottages

Key West Cottages

3.0 star property
Downtown Chincoteague
9.8 out of 10, Exceptional, (481)
"Great place to stay!"
United States
Paul
$88 nightly
The price is $99
Dec 22 - Dec 23
Total with taxes and fees
Key West Cottages
House (3 Bedrooms) | Front of property
6 Mi to Salisbury: Forest-view Sanctuary!

6 Mi to Salisbury: Forest-view Sanctuary!

3.0 star property
Parsonsburg
$214 nightly
The price is $239
Nov 24 - Nov 25
Total with taxes and fees
6 Mi to Salisbury: Forest-view Sanctuary!
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)
"It was a great stay nice comfortable place "
United States
Adam
$245 nightly
The price is $264
Nov 30 - Dec 1
Total with taxes and fees
Salisbury Riverfront Lofts
Outdoor dining
"The 3 Sisters" Ivy's Cottage-Adorable In Town Cottage Near Historic Main Street

"The 3 Sisters" Ivy's Cottage-Adorable In Town Cottage Near Historic Main Street

Downtown Chincoteague
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.
$260 nightly
The price is $292
Nov 23 - Nov 24
Total with taxes and fees
"The 3 Sisters" Ivy's Cottage-Adorable In Town Cottage Near Historic Main Street
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.
$243 nightly
The price is $272
Nov 23 - Nov 24
Total with taxes and fees
Chincoteague Island House "Sir Whelk-A-Lot" Kayaks Included! Downtown Location!
Fridge, microwave, oven, stovetop
Walk to Restaurants & Attractions-Linens Included! Book your Beach Vacation Now!

Walk to Restaurants & Attractions-Linens Included! Book your Beach Vacation Now!

2.0 star property
Deep Hole
10.0 out of 10, Exceptional, (6)
"Great stay. Great host. Very clean place. Couldn’t of asked for a better host and house ! "
United States
James E.
$220 nightly
The price is $247
Nov 24 - Nov 25
Total with taxes and fees
Walk to Restaurants & Attractions-Linens Included! Book your Beach Vacation Now!
Fridge, microwave, oven, stovetop
Deal Island Bay Cottage

Deal Island Bay Cottage

Deal Island
9.6 out of 10, Exceptional, (57)
"We got every year and stay here, it’s great! "
United States
Margaret H.
$248 nightly
The price is $263
Nov 24 - Nov 25
Total with taxes and fees
Deal Island Bay Cottage
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)
"It was family & friends that needed a get away and we really Enjoy the area"
United States
Lori D.
$358 nightly
The price is $402
Nov 23 - Nov 24
Total with taxes and fees
Great Water Views in quiet pet-friendly location facing lighthouse. Large Yard
Dining
Cottage near the Bay

Cottage near the Bay

Crisfield
8.8 out of 10, Excellent, (51)
"We had a great time! Everything went smoothly from beginning to end! We would definitely stay here again. "
United States
Jennifer J.
$178 nightly
The price is $189
Nov 23 - Nov 24
Total with taxes and fees
Cottage near the Bay
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)
"The Property was very well-maintained and accommodating, with most everything you could need. This made the stay much simpler and more enjoyable. The dock and kayaks were a great addition to the fun. "
United States
Randy A.
$377 nightly
The price is $416
Nov 23 - Nov 24
Total with taxes and fees
Modern Waterfront Retreat- Panoramic Bay Views, Kayaks, Pools & Resort Amenities
Interior
Only 5 min. from the Beach!

Only 5 min. from the Beach!

Chincoteague Island
9.2 out of 10, Wonderful, (30)
"Enjoyed our stay. Clean, comfortable, and tastefully decorated. Perfect set up with privacy between the two rooms. Would definitely recommend and stay again!"
United States
Kristina E.
$183 nightly
The price is $191
Nov 24 - Nov 25
Total with taxes and fees
Only 5 min. from the Beach!
Dining
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)
"It was seamless. Would stay here again."
United States
Joe C.
$223 nightly
The price is $234
Dec 1 - Dec 2
Total with taxes and fees
Deluxe corner apartment with riverfront views close to dining and downtown
Terrace/patio
Assateague Inn 104 by Seaside Vacations & Sales

Assateague Inn 104 by Seaside Vacations & Sales

Chincoteague Island
9.6 out of 10, Exceptional, (21)
"Stay at Assateague Inn was clean, comfy, cozy, and convenient. "
United States
Anonymous traveler
$183 nightly
The price is $191
Nov 24 - Nov 25
Total with taxes and fees
Assateague Inn 104 by Seaside Vacations & Sales
Fridge, microwave, oven, stovetop
Salisbury Cottage

Salisbury Cottage

Salisbury
10.0 out of 10, Exceptional, (32)
"This property was very convenient to everything we needed. It was clean and well equipped and the hosts could not have been nicer or more attentive. We would definitely stay there again. Thank you for a wonderful stay."
United States
Deborah D.
$296 nightly
The price is $330
Nov 23 - Nov 24
Total with taxes and fees
Salisbury Cottage
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, (22)
"Loved that it was right on the bay. "
United States
Debra
$119 nightly
The price is $134
Nov 30 - Dec 1
Total with taxes and fees
Waterfront Bungalow on Chincoteague Bay (VA)! - Waterfront Bungalow with Two Bedrooms
TV
Quaint house in small town of Snow Hill, MD.Centrally located to 3 local beaches

Quaint house in small town of Snow Hill, MD.Centrally located to 3 local beaches

2.0 star property
Snow Hill
10.0 out of 10, Exceptional, (1)
"Just a quick overnight stay but truly enjoyed home. It was clean, comfortable and quiet. Communication with host was easy with quick response and easy to understand instructions. Would definitely recommend and return! "
United States
Lois T.
$172 nightly
The price is $191
Nov 23 - Nov 24
Total with taxes and fees
Quaint house in small town of Snow Hill, MD.Centrally located to 3 local beaches
Terrace/patio
The purple door at the bay.

The purple door at the bay.

Captain's Cove
9.2 out of 10, Wonderful, (54)
"Price and location was the primary reason the purple door works for us!"
United States
Patrick O.
$409 nightly
The price is $451
Nov 23 - Nov 24
Total with taxes and fees
The purple door at the bay.
Fridge, microwave, oven, stovetop
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)
"Went for a guys trip and enjoyed it "
United States
John W.
$330 nightly
The price is $371
Nov 23 - Nov 24
Total with taxes and fees
Chincoteague Island Home- "Blue Tide Townhome" Kayaks Included!
Interior
Cottage w Private Creek, Sunroom, Fire Pit, & WiFi

Cottage w Private Creek, Sunroom, Fire Pit, & WiFi

Up the Neck
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.
$319 nightly
The price is $348
Nov 24 - Nov 25
Total with taxes and fees
Cottage w Private Creek, Sunroom, Fire Pit, & WiFi
Beach
Tangier Escape, great place get away from it all on Deal Island, MD.

Tangier Escape, great place get away from it all on Deal Island, MD.

Deal Island Historic District
$194 nightly
The price is $206
Dec 1 - Dec 2
Total with taxes and fees
Tangier Escape, great place get away from it all on Deal Island, MD.
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

Black Friday Sale

Limited-time deals: Save up to 50% on select hotels.
Book now
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

Best Western Plus Pocomoke City

Best Western Plus Pocomoke City

10/10 Excellent
"Friendly staff clean rooms."
Timothy 1-night trip
Posted 22 hours ago
Best Western Plus Pocomoke City

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 $99 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?

Mount Vernon Beach and Manokin Park 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.