Princess Anne Vacation Rentals

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

  • 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

Tonight
Dec 26 - Dec 27
Tomorrow
Dec 27 - Dec 28
This weekend
Dec 26 - Dec 28
Next weekend
Jan 2 - Jan 4

Our top choices for Princess Anne vacation rentals

Exterior
Key West Cottages

Key West Cottages

Key West Cottages
3.0 star property
Downtown Chincoteague
9.8 out of 10, Exceptional, (491)
"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
Key West Cottages
Apartment D: Riverfront Grand | In-room dining
Salisbury Riverfront Lofts

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
The price is ￥11,382
￥40,009 total
includes taxes & fees
Dec 28 - Dec 29
Salisbury Riverfront Lofts
House (3 Bedrooms) | Outdoor dining
6 Mi to Salisbury: Forest-view Sanctuary!

6 Mi to Salisbury: Forest-view Sanctuary!

6 Mi to Salisbury: Forest-view Sanctuary!
3.0 star property
Parsonsburg
The price is ￥14,365
￥40,156 total
includes taxes & fees
Dec 29 - Dec 30
6 Mi to Salisbury: Forest-view Sanctuary!
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!

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.
The price is ￥16,373
￥40,481 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Walk to Restaurants & Attractions-Linens Included! Book your Beach Vacation Now!
Dining
Cottage near the Bay

Cottage near the Bay

Cottage near the Bay
Crisfield
8.8 out of 10, Excellent, (52)
"Could use some fixing here and there which was addressed to owner and handicap accessibility would be great, like a ramp from outside into sunroom entrance. Was very quiet and relaxing, overall had a wonderful stay"
United States
Amy C.
The price is ￥12,647
￥29,129 total
includes taxes & fees
Dec 28 - Dec 29
Cottage near the Bay
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

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.
The price is ￥20,376
￥32,670 total
includes taxes & fees
Jan 3 - Jan 4, 2026
Quaint house in small town of Snow Hill, MD.Centrally located to 3 local beaches
Interior
Only 5 min. from the Beach!

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.
The price is ￥15,712
￥29,452 total
includes taxes & fees
Dec 30 - Dec 31
Only 5 min. from the Beach!
Exterior
Riverside Lodge Bed & Breakfast on the Honga River UNIT C

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.
The price is ￥42,104
￥50,416 total
includes taxes & fees
Jan 26 - Jan 27, 2026
Riverside Lodge Bed & Breakfast on the Honga River UNIT C
Interior
Cozy cottage w/creekside fire pit & grill

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.
The price is ￥34,679
￥62,620 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Cozy cottage w/creekside fire pit & grill
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!

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.
The price is ￥20,376
￥47,257 total
includes taxes & fees
Dec 28 - Dec 29
Chincoteague Island House "Sir Whelk-A-Lot" Kayaks Included! Downtown Location!
Fridge, microwave, oven, stovetop
Secluded Waterfront•15mi to Assateague Beach•Fast Wifi•Kayaks•Near Berlin, OC!

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.
The price is ￥23,733
￥63,606 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Secluded Waterfront•15mi to Assateague Beach•Fast Wifi•Kayaks•Near Berlin, OC!
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

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.
The price is ￥16,395
￥62,775 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Great Water Views in quiet pet-friendly location facing lighthouse. Large Yard
Fridge, microwave, oven, stovetop
3-bedroom townhome in tranquil Delmar with WiFi, AC. Relax and unwind

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.
The price is ￥26,354
￥107,443 total
includes taxes & fees
Jan 25 - Jan 26, 2026
3-bedroom townhome in tranquil Delmar with WiFi, AC. Relax and unwind
Fridge, microwave, oven, stovetop
Chincoteague Island Home- "Blue Tide Townhome" Kayaks Included!

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.
The price is ￥31,228
￥72,243 total
includes taxes & fees
Dec 28 - Dec 29
Chincoteague Island Home- "Blue Tide Townhome" Kayaks Included!
2 bedrooms, internet, bed sheets
Only 5 minutes to Assateague National Seashore!

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.
The price is ￥15,712
￥29,804 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Only 5 minutes to Assateague National Seashore!
Exterior detail
The Neigh-Neigh - Location! Location! Location!

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.
The price is ￥15,614
￥62,775 total
includes taxes & fees
Jan 12 - Jan 13, 2026
The Neigh-Neigh - Location! Location! Location!
Terrace/patio
A Bargain on Chincoteague Island!

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.
The price is ￥15,712
￥29,804 total
includes taxes & fees
Jan 4 - Jan 5, 2026
A Bargain on Chincoteague Island!
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.

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.
The price is ￥14,833
￥32,108 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Tangier Escape, great place get away from it all on Deal Island, MD.
Fridge, microwave, oven, stovetop
Deal Island Bay Cottage

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.
The price is ￥24,826
￥43,694 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Deal Island Bay Cottage
Property grounds
Only 5 min from Assateague National Seashore!

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.
The price is ￥15,712
￥29,804 total
includes taxes & fees
Jan 4 - Jan 5, 2026
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.
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

Best Western Plus Pocomoke City

Best Western Plus Pocomoke City

10/10 Excellent
"Great hotel great customer service "
Lucius 2-night trip
Posted 10 hours ago
Best Western Plus Pocomoke City

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 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.