Princess Anne Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Feb 27 - Mar 1
In two months
Apr 10 - Apr 12
In three months
May 8 - May 10
In four months
Jun 5 - Jun 7

Our top choices for Princess Anne vacation rentals

Palm Cottage | 1 bedroom, premium bedding, individually decorated

Key West Cottages

Key West Cottages
3.0 star property
Downtown Chincoteague
9.8 out of 10, Exceptional, (508 reviews)
"Love the resort! "
United States
Hannah
Key West Cottages
Apartment D: Riverfront Grand | 2 bedrooms, individually decorated, individually furnished

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 ￥10,877
￥39,446 total
includes taxes & fees
Feb 24 - Feb 25
Salisbury Riverfront Lofts
Interior

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 ￥12,648
￥29,131 total
includes taxes & fees
Feb 20 - Feb 21
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, (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 ￥9,978
￥66,810 total
includes taxes & fees
Feb 11 - Feb 12
Modern Waterfront Retreat- Panoramic Bay Views, Kayaks, Pools & Resort Amenities
Exterior

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 ￥15,713
￥29,806 total
includes taxes & fees
Feb 18 - Feb 19
Only 5 min from Assateague National Seashore!
Exterior

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 ￥15,713
￥29,980 total
includes taxes & fees
Feb 11 - Feb 12
Only 5 min to Assateague National Seashore!
Exterior

Only 5 minutes to Assateague National Seashore!

Only 5 minutes to Assateague National Seashore!
Chincoteague
8.8 out of 10, Excellent, (10 reviews)
"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 ￥15,713
￥29,980 total
includes taxes & fees
Feb 22 - Feb 23
Only 5 minutes to Assateague National Seashore!
Beach nearby, sun loungers

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)
"Everything was just perfect! Enjoyed our three day stay! "
United States
Mary C.
The price is ￥17,567
￥44,631 total
includes taxes & fees
Feb 11 - Feb 12
Chincoteague Island House "Sir Whelk-A-Lot" Kayaks Included! Downtown Location!
Exterior

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 ￥14,857
￥39,108 total
includes taxes & fees
Feb 11 - Feb 12
Walk to Restaurants & Attractions-Linens Included! Book your Beach Vacation Now!
Exterior

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 ￥15,713
￥29,806 total
includes taxes & fees
Feb 18 - Feb 19
A Bargain on Chincoteague Island!
Exterior

Blufin Bungalows & Marina

Blufin Bungalows & Marina
3.0 star property
Down the Marsh
9.6 out of 10, Exceptional, (210 reviews)
"yesss amazing stay "
United States
EDA
Blufin Bungalows & Marina
Fridge, microwave, oven, stovetop

Cozy Barn Loft: Country Views & Central to Beaches

Cozy Barn Loft: Country Views & Central to Beaches
Pocomoke City
10.0 out of 10, Exceptional, (19 reviews)
"Very clean and cozy home, they had all the necessary things we needed for our stay and we will certainly be staying there again if it’s available during our next visit. "
United States
Ryan B.
The price is ￥20,940
￥41,817 total
includes taxes & fees
Feb 24 - Feb 25
Cozy Barn Loft: Country Views & Central to Beaches
Interior

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
Snow Hill
10.0 out of 10, Exceptional, (3 reviews)
"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 ￥20,378
￥32,792 total
includes taxes & fees
Feb 11 - Feb 12
Quaint house in small town of Snow Hill, MD.Centrally located to 3 local beaches
Beach nearby

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 ￥16,396
￥62,427 total
includes taxes & fees
Feb 18 - Feb 19
Great Water Views in quiet pet-friendly location facing lighthouse. Large Yard
Exterior

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 ￥15,713
￥29,980 total
includes taxes & fees
Feb 12 - Feb 13
Only 5 min. from the Beach!
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, (25 reviews)
"Loved that it was right on the bay. "
United States
Debra
The price is ￥18,709
￥24,542 total
includes taxes & fees
Feb 12 - Feb 13
Waterfront Bungalow on Chincoteague Bay (VA)! - Waterfront Bungalow with Two Bedrooms
Exterior

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.
Only 5 min. from the Beach!
Interior

Cozy cottage w/creekside fire pit & pet‑friendly

Cozy cottage w/creekside fire pit & pet‑friendly
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 ￥21,274
￥45,596 total
includes taxes & fees
Feb 11 - Feb 12
Cozy cottage w/creekside fire pit & pet‑friendly
Interior

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 ￥15,615
￥63,130 total
includes taxes & fees
Feb 24 - Feb 25
The Neigh-Neigh - Location! Location! Location!
Exterior

Salisbury Hideaway

Salisbury Hideaway
Salisbury
10.0 out of 10, Exceptional, (20 reviews)
"This property was wonderful for our trip to Salisbury for my daughter's travel softball tournament. It was only 30-45 minutes from Ocean City (give or take traffic), and very close to many shopping areas and restaurants. The property itself was very clean and provided many necessities. "
United States
Lisa H.
The price is ￥19,987
￥50,171 total
includes taxes & fees
Mar 10 - Mar 11
Salisbury Hideaway
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

Hampton Inn & Suites Chincoteague Waterfront

Hampton Inn & Suites Chincoteague Waterfront

10/10 Excellent
"Clean and comfortable rooms and beds. Staff was great. Location was scenic"
Margie 1-night trip
Posted 23 hours ago
Hampton Inn & Suites Chincoteague Waterfront

Find out more about Princess Anne

Search for holiday rentals in Princess Anne on Expedia! You can easily find your home rentals, villas, holiday apartments in Princess Anne using one of the methods below:

  • View our selection of featured holiday rentals in Princess Anne
  • Use the map to find apartments and other holiday homes in the Princess Anne neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Princess Anne while they last

Look no further and take a look at our great range of rental properties in Princess Anne!

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.