Holiday Homes in Princess Anne

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

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

    Search almost a million properties worldwide

Find holiday rentals that suit your style

Check prices for these dates

Our top choices for Princess Anne holiday homes

1. Salisbury Hideaway

Salisbury Hideaway
Salisbury
10.0 out of 10, Exceptional, (24 reviews)
"Perfect for our weekend away watching college softball!!!"
United States
Michelle S.
The price is AU$470
includes taxes & fees
1 Dec - 2 Dec
Salisbury Hideaway

2. Salisbury Cottage

Salisbury Cottage
Salisbury
10.0 out of 10, Exceptional, (40 reviews)
"The property has cute and cozy curb appeal. The interior was attractive and very clean. The location was excellent for our planned events. Host, Ryan, easily accommodated our needs and we plan to check for availability in the future. Thanks Ryan!"
United States
Star R.
The price is AU$520
includes taxes & fees
15 Nov - 16 Nov
Salisbury Cottage

3. 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, (2 reviews)
"Helpful host, clean house, peaceful location! "
United States
Jennifer P.
The price is AU$376
includes taxes & fees
15 Nov - 16 Nov
Tangier Escape, great place get away from it all on Deal Island, MD.

4. Blufin Bungalows & Marina

Blufin Bungalows & Marina
3.0 star property
Down the Marsh
9.6 out of 10, Exceptional, (344 reviews)
"We had a wonderful stay! The bungalow was nice, clean, and peaceful. It was the perfect place to relax and unwind. Would definitely stay again!"
United States
Rebecca
The price is AU$225
includes taxes & fees
15 Dec - 16 Dec
Blufin Bungalows & Marina

5. Cottage near the Bay

Cottage near the Bay
Crisfield
8.6 out of 10, Excellent, (65 reviews)
"Nice cottage at the end of a quiet lane, priced reasonably. Host is very accommodating. We had a lovely stay and enjoyed our time in Crisfield."
United States
Karen J.
The price is AU$265
includes taxes & fees
17 Nov - 18 Nov
Cottage near the Bay

6. 6 Mi to Salisbury: Forest-View Sanctuary!

6 Mi to Salisbury: Forest-View Sanctuary!
Parsonsburg
9.8 out of 10, Exceptional, (6 reviews)
"Awesome place "
United States
Rebecca M.
The price is AU$381
includes taxes & fees
18 Nov - 19 Nov
6 Mi to Salisbury: Forest-View Sanctuary!

7. Entire Private Home • Sleeps 6 • Prime Salisbury Location

Entire Private Home • Sleeps 6 • Prime Salisbury Location
Salisbury
10.0 out of 10, Exceptional, (1 review)
"The stay was great. "
United States
Nathaniel N.
The price is AU$513
includes taxes & fees
23 Nov - 24 Nov
Entire Private Home • Sleeps 6 • Prime Salisbury Location

8. Bayfront Modern Retreat • Dock, Kayaks, Views

Bayfront Modern Retreat • Dock, Kayaks, Views
Captain's Cove
9.8 out of 10, Exceptional, (73 reviews)
"We absolutely love staying here! "
United States
Maggie G.
The price is AU$632
includes taxes & fees
30 Nov - 1 Dec
Bayfront Modern Retreat • Dock, Kayaks, Views

9. 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
9.6 out of 10, Exceptional, (40 reviews)
"Great place to rent"
United States
Hazel T.
Waterfront Bungalow on Chincoteague Bay (VA)! - Waterfront Bungalow with Two Bedrooms

10. 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, (21 reviews)
"This was an amazing property and a wonderful experience from start to finish."
United States
Benjamin G.
The price is AU$567
includes taxes & fees
15 Nov - 16 Nov
Secluded Waterfront•15mi to Assateague Beach•Fast Wifi•Kayaks•Near Berlin, OC!

11. 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, (49 reviews)
"It was family & friends that needed a get away and we really Enjoy the area"
United States
Lori D.
The price is AU$569
includes taxes & fees
17 Nov - 18 Nov
Great Water Views in quiet pet-friendly location facing lighthouse. Large Yard

12. The purple door at the bay.

The purple door at the bay.
Captain's Cove
9.4 out of 10, Exceptional, (69 reviews)
"Great location"
United States
Rick K.
The price is AU$620
includes taxes & fees
18 Nov - 19 Nov
The purple door at the bay.

13. Central Location~Walk 2 Dining! Beach Pass & Gear!

Central Location~Walk 2 Dining! Beach Pass & Gear!
Deep Hole
10.0 out of 10, Exceptional, (11 reviews)
"Excellent space with everything needed!"
United States
Tianna B.
The price is AU$357
includes taxes & fees
16 Nov - 17 Nov
Central Location~Walk 2 Dining! Beach Pass & Gear!

14. 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, (87 reviews)
"Great house and location. Comfortable for a family - the kids really enjoyed the upstairs loft."
United States
Charles G.
The price is AU$412
includes taxes & fees
3 Dec - 4 Dec
Chincoteague Island House "Sir Whelk-A-Lot" Kayaks Included! Downtown Location!

15. Cozy 2-bedroom house in Chincoteague

Cozy 2-bedroom house in Chincoteague
Deep Hole
10.0 out of 10, Exceptional, (7 reviews)
"Ramsey is a great host and provided everything we needed!"
United States
Kendall M.
The price is AU$420
includes taxes & fees
15 Nov - 16 Nov
Cozy 2-bedroom house in Chincoteague

16. The Neigh-Neigh - Location! Location! Location!

The Neigh-Neigh - Location! Location! Location!
Downtown Chincoteague
9.8 out of 10, Exceptional, (7 reviews)
"Very nice place to stay close to town. Charming screened porch, well appointed kitchen, plenty of space for us."
United States
Veronika B.
The price is AU$567
includes taxes & fees
15 Nov - 16 Nov
The Neigh-Neigh - Location! Location! Location!

17. Coastal Retreat - EV Charger - Near Marina & Beaches

Coastal Retreat - EV Charger - Near Marina & Beaches
Captain's Cove
The price is AU$556
includes taxes & fees
28 Nov - 29 Nov
Coastal Retreat - EV Charger - Near Marina & Beaches

18. Come out and enjoy Autumn at the HH Ranch on Smith Island.

Come out and enjoy Autumn at the HH Ranch on Smith Island.
Smith Island
9.8 out of 10, Exceptional, (17 reviews)
"Visiting with locals, fresh steamed crabs, simply enjoying the quiet island life"
United States
Samantha J.
The price is AU$449
includes taxes & fees
30 Nov - 1 Dec
Come out and enjoy Autumn at the HH Ranch on Smith Island.

19. 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 reviews)
"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 AU$456
includes taxes & fees
16 Nov - 17 Nov
Riverside Lodge Bed & Breakfast on the Honga River UNIT C

20. Riverside Lodge Bed & Breakfast on the Honga River UNIT E

Riverside Lodge Bed & Breakfast on the Honga River UNIT E
Fishing Creek
10.0 out of 10, Exceptional, (1 review)
"We stayed Sunday - Wednesday at Riverside Lodge. The Lodge was beautiful. Breakfast was absolutely fantastic and Hooper Island was breath taking. We were able to take a boat ride to tour around the island and grad a little history and enjoy the stories. If you looking for a place to relax and renew... this is the place. "
United States
Robin E.
The price is AU$413
includes taxes & fees
16 Nov - 17 Nov
Riverside Lodge Bed & Breakfast on the Honga River UNIT E
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.

Learn more about Princess Anne

Explore the historic Teackle Mansion with its Federal-style architecture and period furnishings that showcase Eastern Shore heritage. Visit the University of Maryland Eastern Shore campus for cultural events or take a short trip to nearby Salisbury for the Ward Museum of Wildfowl Art.

A sunset over a lake with a dock and a small settlement.