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

Princess Anne Vacation Rentals

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Our top choices for Princess Anne vacation rentals

1. Salisbury Riverfront Lofts

Salisbury Riverfront Lofts
3.0 star property
Salisbury
9.4 out of 10, Exceptional, (27 reviews)
"Excellent choice for the price, recommended for larger groups."
United States
Marcos
The price is CA $92
CA $353 total
includes taxes & fees
Nov 13 - Nov 14
Salisbury Riverfront Lofts

2. Stylish 2 bedroom 1 bath with riverfront views close to dining and downtown

Stylish 2 bedroom 1 bath with riverfront views close to dining and downtown
Salisbury
9.8 out of 10, Exceptional, (25 reviews)
"Great location with plenty of space to relax."
United States
Doug R.
The price is CA $107
CA $264 total
includes taxes & fees
Oct 18 - Oct 19
Stylish 2 bedroom 1 bath with riverfront views close to dining and downtown

3. Salisbury Cottage

Salisbury Cottage
Salisbury
10.0 out of 10, Exceptional, (40 reviews)
"Super convenient to campus and everything was clean and worked perfectly. Overall, a great stay and met all of our expectations."
United States
Matthew B.
The price is CA $223
CA $525 total
includes taxes & fees
Nov 3 - Nov 4
Salisbury Cottage

4. 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 CA $256
CA $562 total
includes taxes & fees
Nov 2 - Nov 3
Salisbury Hideaway

5. 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 CA $157
CA $354 total
includes taxes & fees
Oct 19 - Oct 20
Tangier Escape, great place get away from it all on Deal Island, MD.

6. Cottage near the Bay

Cottage near the Bay
Crisfield
8.6 out of 10, Excellent, (63 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 CA $115
CA $267 total
includes taxes & fees
Oct 15 - Oct 16
Cottage near the Bay

7. Retro Hipster: Close to downtown, dining and fun

Retro Hipster: Close to downtown, dining and fun
Salisbury
9.2 out of 10, Wonderful, (20 reviews)
"Great alternative to a hotel!"
United States
Courtney L.
The price is CA $103
CA $269 total
includes taxes & fees
Nov 1 - Nov 2
Retro Hipster: Close to downtown, dining and fun

8. Deal Island Bay Cottage

Deal Island Bay Cottage
Deal Island
9.6 out of 10, Exceptional, (62 reviews)
"We loved this place! We were in town for baseball. It is very nice and has all the comforts of home. Kitchen big and well equipped, house was clean and very well furnished. Nice bathrooms and a lovely screened in back porch. It is very near a beautiful beach on the bay that has some of the most beautiful sunsets you will ever see. We really enjoyed this perk!! Prompt communication and everything was as described. I highly recommend this rental!!"
United States
Harold B.
The price is CA $199
CA $370 total
includes taxes & fees
Oct 15 - Oct 16
Deal Island Bay Cottage

9. Deluxe corner apartment with riverfront views close to dining and downtown

Deluxe corner apartment with riverfront views close to dining and downtown
Salisbury
8.8 out of 10, Excellent, (6 reviews)
"Lovely apartment in the heart of Salisbury. Ckean, well appointed, and comfortable. "
United States
Gretel S.
The price is CA $117
CA $344 total
includes taxes & fees
Oct 14 - Oct 15
Deluxe corner apartment with riverfront views close to dining and downtown

10. Spacious Riverfront Loft Close to Downtown and Dining

Spacious Riverfront Loft Close to Downtown and Dining
Salisbury
9.0 out of 10, Wonderful, (13 reviews)
"Great location, great restaurants below the loft."
United States
Pamela F.
The price is CA $103
CA $327 total
includes taxes & fees
Nov 1 - Nov 2
Spacious Riverfront Loft Close to Downtown and Dining

11. 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 CA $334
CA $462 total
includes taxes & fees
Oct 16 - Oct 17
Entire Private Home • Sleeps 6 • Prime Salisbury Location

12. Key West Cottages

Key West Cottages
3.0 star property
Downtown Chincoteague
9.8 out of 10, Exceptional, (658 reviews)
"First time here and we absolutely loved it."
United States
Melissa
The price is CA $276
CA $310 total
includes taxes & fees
Oct 14 - Oct 15
Key West Cottages

13. Blufin Bungalows & Marina

Blufin Bungalows & Marina
3.0 star property
Down the Marsh
9.6 out of 10, Exceptional, (338 reviews)
"It was so fun to be sleeping right on the water."
United States
Marissa
Blufin Bungalows & Marina

14. Bayfront Modern Retreat • Dock, Kayaks, Views

Bayfront Modern Retreat • Dock, Kayaks, Views
Captain's Cove
9.8 out of 10, Exceptional, (70 reviews)
"Overall nice stay!"
United States
Becky S.
The price is CA $147
CA $658 total
includes taxes & fees
Oct 15 - Oct 16
Bayfront Modern Retreat • Dock, Kayaks, Views

15. The purple door at the bay.

The purple door at the bay.
Captain's Cove
9.4 out of 10, Exceptional, (68 reviews)
"Great location"
United States
Rick K.
The price is CA $238
CA $661 total
includes taxes & fees
Oct 20 - Oct 21
The purple door at the bay.

16. Assateageue Inn 104 by Seaside Vacations & Sales

Assateageue Inn 104 by Seaside Vacations & Sales
Chincoteague Island
9.4 out of 10, Exceptional, (35 reviews)
"Our room was clean and ready for our stay. We could walk to some shops, miniature golfing,restaurants."
United States
Paula
The price is CA $148
CA $289 total
includes taxes & fees
Oct 14 - Oct 15
Assateageue Inn 104 by Seaside Vacations & Sales

17. Assateague Inn 203 by Seaside Vacations & Sales

Assateague Inn 203 by Seaside Vacations & Sales
Chincoteague Island
9.2 out of 10, Wonderful, (9 reviews)
"We had a mommy-daughter mini-getaway to celebrate her 9th birthday! The area is very walkable, but also easy to drive and navigate the rest of the island. Our room was clean, as advertised, and the perfect place to relax, eat, and recharge. We loved the pool! The check-in/check-out process was very easy."
United States
Nora T.
The price is CA $163
CA $307 total
includes taxes & fees
Oct 14 - Oct 15
Assateague Inn 203 by Seaside Vacations & Sales

18. Charming 2 Bedroom house in beautiful Smith Island Pet-Friendly

Charming 2 Bedroom house in beautiful Smith Island Pet-Friendly
Smith Island
9.4 out of 10, Exceptional, (3 reviews)
"This is a great place to stay on Smith Island. Easy access to most areas. The Golf cart is also nice to have. The house has everything you need and many extras too! Highly recommend a visit here."
United States
Margaret A.
The price is CA $329
CA $556 total
includes taxes & fees
Oct 14 - Oct 15
Charming 2 Bedroom house in beautiful Smith Island Pet-Friendly

19. 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, (48 reviews)
"It was family & friends that needed a get away and we really Enjoy the area"
United States
Lori D.
The price is CA $170
CA $588 total
includes taxes & fees
Oct 16 - Oct 17
Great Water Views in quiet pet-friendly location facing lighthouse. Large Yard

20. 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, (16 reviews)
"Visiting with locals, fresh steamed crabs, simply enjoying the quiet island life"
United States
Samantha J.
The price is CA $285
CA $475 total
includes taxes & fees
Oct 16 - Oct 17
Come out and enjoy Autumn at the HH Ranch on Smith Island.
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.
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Top Princess Anne Hotel Reviews

Find out more about Princess Anne

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Princess Anne. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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Frequently asked questions

Can I find a vacation rental in Princess Anne?

Yes, you can find vacation rentals in Princess Anne close to Ella Fitzgerald Performing Arts Center, or you can choose a more remote option if you're looking for extra privacy while you relax. 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.

How many vacation rentals are there in Princess Anne?

Expedia has 3 vacation rentals for your stay in Princess Anne.

What can I see and do in Princess Anne?

Manokin Park and Mount Vernon Beach are a couple of lovely local spots to get outside and enjoy nature. Hytche athletic Center and Somerset County Library 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.