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

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

Our top choices for Princess Anne vacation rentals

Key West Cottages

Key West Cottages
3.0 star property
Downtown Chincoteague
9.8 out of 10, Exceptional, (492)
"What an absolute wonderful place. Staff were so friendly and the cottages were amazing very clean. We would definitely stay here again."
United States
julie
$111 nightly
The price is $125
Dec 30 - Dec 31
Total with taxes and fees
Key West Cottages

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
$250 nightly
The price is $269
Jan 12 - Jan 13, 2026
Total with taxes and fees
Salisbury Riverfront Lofts

6 Mi to Salisbury: Forest-view Sanctuary!

6 Mi to Salisbury: Forest-view Sanctuary!
3.0 star property
Parsonsburg
$230 nightly
The price is $257
Dec 30 - Dec 31
Total with taxes and fees
6 Mi to Salisbury: Forest-view Sanctuary!

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, (7)
"Great stay. Great host. Very clean place. Couldn’t of asked for a better host and house ! "
United States
James E.
$225 nightly
The price is $252
Jan 6 - Jan 7, 2026
Total with taxes and fees
Walk to Restaurants & Attractions-Linens Included! Book your Beach Vacation Now!

Cottage near the Bay

Cottage near the Bay
Crisfield
8.8 out of 10, Excellent, (52)
"Great little place "
United States
Eric R.
$177 nightly
The price is $188
Jan 4 - Jan 5, 2026
Total with taxes and fees
Cottage near the Bay

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, (2)
"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.
$189 nightly
The price is $209
Jan 3 - Jan 4, 2026
Total with taxes and fees
Quaint house in small town of Snow Hill, MD.Centrally located to 3 local beaches

Only 5 min. from the Beach!

Only 5 min. from the Beach!
Chincoteague Island
9.2 out of 10, Wonderful, (31)
"Great location that was very clean, kid friendly, and good amenities! Liked how close it was to everything, very walkable."
United States
Jeananne K.
$183 nightly
The price is $191
Jan 4 - Jan 5, 2026
Total with taxes and fees
Only 5 min. from the Beach!

Riverside Lodge Bed & Breakfast on the Honga River UNIT C

Riverside Lodge Bed & Breakfast on the Honga River UNIT C
Fishing Creek
10.0 out of 10, Exceptional, (11)
"Peggy and Gary are the perfect hosts: welcoming, friendly, attentive and respectful of your preferences. Wonderful views of the Bay and River via the lodge -- including the cupola -- and walking around the majestic property."
United States
Thomas S.
$309 nightly
The price is $328
Dec 30 - Dec 31
Total with taxes and fees
Riverside Lodge Bed & Breakfast on the Honga River UNIT C

Cozy cottage w/creekside fire pit & grill

Cozy cottage w/creekside fire pit & grill
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.
$342 nightly
The price is $373
Jan 5 - Jan 6, 2026
Total with taxes and fees
Cozy cottage w/creekside fire pit & grill

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)
"Wonderful location. Walking distance to shops and restaurants and sunsets. Hosts were responsive and helpful. Check in and checkout were seamless."
United States
imelda s.
$274 nightly
The price is $308
Dec 30 - Dec 31
Total with taxes and fees
Chincoteague Island House "Sir Whelk-A-Lot" Kayaks Included! Downtown Location!

Secluded Waterfront•15mi to Assateague Beach•Fast Wifi•Kayaks•Near Berlin, OC!

Secluded Waterfront•15mi to Assateague Beach•Fast Wifi•Kayaks•Near Berlin, OC!
Newark
10.0 out of 10, Exceptional, (3)
"Wonderful stay at beautiful homeamazingly"
United States
Jonathan D.
$366 nightly
The price is $406
Jan 12 - Jan 13, 2026
Total with taxes and fees
Secluded Waterfront•15mi to Assateague Beach•Fast Wifi•Kayaks•Near Berlin, OC!

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
Jan 7 - Jan 8, 2026
Total with taxes and fees
Great Water Views in quiet pet-friendly location facing lighthouse. Large Yard

3-bedroom townhome in tranquil Delmar with WiFi, AC. Relax and unwind

3-bedroom townhome in tranquil Delmar with WiFi, AC. Relax and unwind
Delmar
10.0 out of 10, Exceptional, (8)
"Clean and comfortable. Great communication. "
United States
Paul R.
$650 nightly
The price is $689
Dec 31 - Jan 1, 2026
Total with taxes and fees
3-bedroom townhome in tranquil Delmar with WiFi, AC. Relax and unwind

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.
$377 nightly
The price is $423
Dec 30 - Dec 31
Total with taxes and fees
Chincoteague Island Home- "Blue Tide Townhome" Kayaks Included!

Only 5 minutes to Assateague National Seashore!

Only 5 minutes to Assateague National Seashore!
Chincoteague
8.8 out of 10, Excellent, (10)
"Quiet area and close to all attractions. Very fast response with any questions before and during stay. Would recommend!"
United States
Sue S.
$183 nightly
The price is $191
Jan 4 - Jan 5, 2026
Total with taxes and fees
Only 5 minutes 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)
"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.
$336 nightly
The price is $377
Jan 12 - Jan 13, 2026
Total with taxes and fees
The Neigh-Neigh - Location! Location! Location!

A Bargain on Chincoteague Island!

A Bargain on Chincoteague Island!
Chincoteague Island
8.8 out of 10, Excellent, (3)
"Overall the place was nice enough for the cost. "
United States
Stacey S.
$183 nightly
The price is $191
Jan 4 - Jan 5, 2026
Total with taxes and fees
A Bargain on Chincoteague Island!

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
10.0 out of 10, Exceptional, (1)
"Helpful host, clean house, peaceful location! "
United States
Jennifer P.
$194 nightly
The price is $206
Jan 6 - Jan 7, 2026
Total with taxes and fees
Tangier Escape, great place get away from it all on Deal Island, MD.

Deal Island Bay Cottage

Deal Island Bay Cottage
Deal Island
9.6 out of 10, Exceptional, (58)
"We got every year and stay here, it’s great! "
United States
Margaret H.
$246 nightly
The price is $261
Jan 1 - Jan 2, 2026
Total with taxes and fees
Deal Island Bay Cottage

Only 5 min from Assateague National Seashore!

Only 5 min from Assateague National Seashore!
Chincoteague Island
7.4 out of 10, Good, (3)
"Low-quality furniture. needs to be updated"
United States
Susan E.
$183 nightly
The price is $191
Jan 4 - Jan 5, 2026
Total with taxes and fees
Only 5 min from Assateague National Seashore!
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

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 $125 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.

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 Smart 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.