Princess Anne Vacation Rentals

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Check prices for these dates

In two weeks
May 29 - May 31
In two months
Jul 10 - Jul 12
In three months
Aug 7 - Aug 9
In four months
Sep 4 - Sep 6

Our top choices for Princess Anne vacation rentals

House (3 Bedrooms) | Front of property

6 Mi to Salisbury: Forest-view Sanctuary!

6 Mi to Salisbury: Forest-view Sanctuary!
3.0 star property
Parsonsburg
The price is ￥16,295
￥42,401 total
includes taxes & fees
May 27 - May 28
6 Mi to Salisbury: Forest-view Sanctuary!
Exterior

Blufin Bungalows & Marina

Blufin Bungalows & Marina
3.0 star property
Down the Marsh
9.6 out of 10, Exceptional, (247 reviews)
"My kids and I had a wonderful spring break stay at the bungalows!"
United States
Susan
Blufin Bungalows & Marina
Interior

Cottage near the Bay

Cottage near the Bay
Crisfield
8.8 out of 10, Excellent, (54 reviews)
"Property was exactly as pictured, Crystal is very prompt if contacted & very accomdating to questions. If you are looking in ng for some quiet peacefulness yet close to the water, or nearby towns & attractions & travel with your dog this is the perfect spot! My dogs were very content & I had no worries as to if they would be bothered by distractions because there are no distractions, it was a vacation for them as well as cottage is on a quiet street & it was very nice to sit outside wuth them &...
United States
Shelley
The price is ￥12,732
￥29,325 total
includes taxes & fees
May 17 - May 18
Cottage near the Bay
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, (558 reviews)
"Lovely cottage for our family."
United States
nancy
The price is ￥32,091
￥36,039 total
includes taxes & fees
May 28 - May 29
Key West Cottages
Fridge, microwave, oven, stovetop

Retro Hipster: Close to downtown, dining and fun

Retro Hipster: Close to downtown, dining and fun
Salisbury
9.2 out of 10, Wonderful, (15 reviews)
"Nice large, bright kitchen, each room has a bathroom! Nice river view, many shops within walking distance and good coffee and breakfast right diwnstairs! Loved the funky, whimsical decor too."
United States
Joan
The price is ￥11,160
￥29,193 total
includes taxes & fees
May 18 - May 19
Retro Hipster: Close to downtown, dining and fun
TV, DVD player

Assateageue Inn 104 by Seaside Vacations & Sales

Assateageue Inn 104 by Seaside Vacations & Sales
Chincoteague Island
9.6 out of 10, Exceptional, (25 reviews)
"Convenient location with everything we needed"
United States
John S.
The price is ￥15,908
￥30,224 total
includes taxes & fees
May 17 - May 18
Assateageue Inn 104 by Seaside Vacations & Sales
Smart TV, books, offices

Salisbury Cottage

Salisbury Cottage
Salisbury
10.0 out of 10, Exceptional, (38 reviews)
"My family and I had a great stay was a comfy and safe space to relax and enjoy our Halloween weekend would definitely recommend!"
United States
Mackenzie N.
The price is ￥22,719
￥53,977 total
includes taxes & fees
May 13 - May 14
Salisbury Cottage
Interior

Cozy creekside cottage w/fire pit & patio

Cozy creekside cottage w/fire pit & patio
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 ￥33,661
￥61,078 total
includes taxes & fees
May 13 - May 14
Cozy creekside cottage w/fire pit & patio
Exterior

The purple door at the bay.

The purple door at the bay.
Captain's Cove
9.4 out of 10, Exceptional, (56 reviews)
"Price and location was the primary reason the purple door works for us!"
United States
Patrick O.
The price is ￥24,677
￥70,597 total
includes taxes & fees
May 20 - May 21
The purple door at the bay.
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, (24 reviews)
"It was a great stay nice comfortable place "
United States
Adam
The price is ￥10,542
￥39,254 total
includes taxes & fees
May 13 - May 14
Salisbury Riverfront Lofts
House (3 Bedrooms) | Interior

2 Mi to Downtown: Tranquil Abode in Chincoteague!

2 Mi to Downtown: Tranquil Abode in Chincoteague!
3.0 star property
Up the Neck
The price is ￥11,438
￥53,204 total
includes taxes & fees
May 17 - May 18
2 Mi to Downtown: Tranquil Abode in Chincoteague!
Exterior

Assateague Inn 100 by Seaside Vacations & Sales

Assateague Inn 100 by Seaside Vacations & Sales
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 ￥16,499
￥30,918 total
includes taxes & fees
May 18 - May 19
Assateague Inn 100 by Seaside Vacations & Sales
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, (43 reviews)
"It was family & friends that needed a get away and we really Enjoy the area"
United States
Lori D.
The price is ￥21,152
￥68,974 total
includes taxes & fees
May 20 - May 21
Great Water Views in quiet pet-friendly location facing lighthouse. Large Yard
Exterior

Salisbury Hideaway

Salisbury Hideaway
Salisbury
10.0 out of 10, Exceptional, (21 reviews)
"Had a wonderful time house had everything you would need for a stay located right in the heart of Salisbury. Will definitely be going back to stay in this particular house. Thank you"
United States
Bryan M.
The price is ￥20,838
￥51,651 total
includes taxes & fees
May 13 - May 14
Salisbury Hideaway
Fridge, microwave, oven, stovetop

Deal Island Bay Cottage

Deal Island Bay Cottage
Deal Island
9.6 out of 10, Exceptional, (59 reviews)
"We got every year and stay here, it’s great! "
United States
Margaret H.
The price is ￥24,912
￥43,845 total
includes taxes & fees
Jun 3 - Jun 4
Deal Island Bay Cottage
Interior

The Neigh-Neigh - Location! Location! Location!

The Neigh-Neigh - Location! Location! Location!
Downtown Chincoteague
10.0 out of 10, Exceptional, (4 reviews)
"Loved staying at this house…plenty of room for everyone."
United States
ashley b.
The price is ￥22,007
￥71,318 total
includes taxes & fees
May 13 - May 14
The Neigh-Neigh - Location! Location! Location!
Terrace/patio

Assateague Inn 102 by Seaside Vacations & Sales

Assateague Inn 102 by Seaside Vacations & Sales
Downtown Chincoteague
8.6 out of 10, Excellent, (8 reviews)
"The condo was a perfect weekend getaway. Newly renovated and close to the beach. Great location in town. The property managers were all so helpful and had great communication from the very start. Would definitely stay here again!"
United States
Hunter E.
The price is ￥23,084
￥39,227 total
includes taxes & fees
May 13 - May 14
Assateague Inn 102 by Seaside Vacations & Sales
Smart TV, books

Bayfront Modern Retreat • Panoramic Views, Dock, Kayak, Pools & Resort Amenities

Bayfront Modern Retreat • Panoramic Views, Dock, Kayak, Pools & Resort Amenities
Captain's Cove
9.8 out of 10, Exceptional, (64 reviews)
"What a stunning view and super welcoming host!! We loved our stay and especially enjoyed the kayaks and bikes, great welcome kit of toiletries and kitchen supplies, very comfortable beds and soft sheets, outdoor space to watch the stars, and quiet, peaceful neighborhood. "
United States
l h.
The price is ￥22,793
￥69,353 total
includes taxes & fees
May 28 - May 29
Bayfront Modern Retreat • Panoramic Views, Dock, Kayak, Pools & Resort Amenities
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, (70 reviews)
"Everything was just perfect! Enjoyed our three day stay! "
United States
Mary C.
The price is ￥23,267
￥51,996 total
includes taxes & fees
May 17 - May 18
Chincoteague Island House "Sir Whelk-A-Lot" Kayaks Included! Downtown Location!
Pool

Greenbackville Retreat w/ Deck: 1 Mi to Marina!

Greenbackville Retreat w/ Deck: 1 Mi to Marina!
Captain's Cove
The price is ￥25,696
￥80,130 total
includes taxes & fees
May 20 - May 21
Greenbackville Retreat w/ Deck: 1 Mi to Marina!
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

Key West Cottages

Key West Cottages

10/10 Excellent
"The property is beautiful, well-kept, and clean, and the staff is very helpful and friendly."
Ana 2-night trip
Posted 1 hour ago
Key West Cottages

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:

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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 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?

Monie Island and Ballards Island 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.