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Our top choices for Princess Anne holiday rentals

6 Mi to Salisbury: Forest-view Sanctuary!

6 Mi to Salisbury: Forest-view Sanctuary!
3.0 star property
Parsonsburg
The price is £199
includes taxes & fees
21 May - 22 May
6 Mi to Salisbury: Forest-view Sanctuary!

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
The price is £107
includes taxes & fees
17 May - 18 May
Blufin Bungalows & Marina

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 £141
includes taxes & fees
20 May - 21 May
Cottage near the Bay

Key West Cottages

Key West Cottages
3.0 star property
Downtown Chincoteague
9.8 out of 10, Exceptional, (558 reviews)
"The property is beautiful, well-kept, and clean, and the staff is very helpful and friendly."
United States
Ana
The price is £171
includes taxes & fees
26 May - 27 May
Key West Cottages

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 £135
includes taxes & fees
14 May - 15 May
Retro Hipster: Close to downtown, dining and fun

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 £142
includes taxes & fees
19 May - 20 May
Assateageue Inn 104 by Seaside Vacations & Sales

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 £272
includes taxes & fees
18 May - 19 May
Salisbury Cottage

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 £287
includes taxes & fees
14 May - 15 May
Cozy creekside cottage w/fire pit & patio

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 £301
includes taxes & fees
19 May - 20 May
The purple door at the bay.

Salisbury Riverfront Lofts

Salisbury Riverfront Lofts
3.0 star property
Salisbury
9.2 out of 10, Wonderful, (25 reviews)
"It was a great stay nice comfortable place "
United States
Adam
The price is £180
includes taxes & fees
14 May - 15 May
Salisbury Riverfront Lofts

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 £251
includes taxes & fees
17 May - 18 May
2 Mi to Downtown: Tranquil Abode in Chincoteague!

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 £147
includes taxes & fees
19 May - 20 May
Assateague Inn 100 by Seaside Vacations & Sales

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 £318
includes taxes & fees
16 May - 17 May
Great Water Views in quiet pet-friendly location facing lighthouse. Large Yard

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 £252
includes taxes & fees
28 May - 29 May
Salisbury Hideaway

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 £203
includes taxes & fees
13 Jun - 14 Jun
Deal Island Bay Cottage

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 £329
includes taxes & fees
14 May - 15 May
The Neigh-Neigh - Location! Location! Location!

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 £185
includes taxes & fees
14 May - 15 May
Assateague Inn 102 by Seaside Vacations & Sales

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 £326
includes taxes & fees
28 May - 29 May
Bayfront Modern Retreat • Panoramic Views, Dock, Kayak, Pools & Resort Amenities

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 £234
includes taxes & fees
17 May - 18 May
Chincoteague Island House "Sir Whelk-A-Lot" Kayaks Included! Downtown Location!

Greenbackville Retreat w/ Deck: 1 Mi to Marina!

Greenbackville Retreat w/ Deck: 1 Mi to Marina!
Captain's Cove
The price is £371
includes taxes & fees
14 May - 15 May
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

Find out more about Princess Anne

Everything you need to know about Princess Anne holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Princess Anne holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Princess Anne holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Princess Anne holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Princess Anne holiday rentals we have selected for you start as low as £107 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Princess Anne rentals

At Expedia, we put the best Princess Anne holiday 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 holiday.

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 holiday rental in Princess Anne?

Yes, there are holiday rentals in Princess Anne close to Ella Fitzgerald Performing Arts Center, or you can select a more secluded option if you're looking for a relaxing stay. Our travellers 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 holiday rentals that Princess Anne has to offer?

Blufin Bungalows & Marina: This holiday home rental outside of 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 holiday rentals are there in Princess Anne?

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

What can I see and do in Princess Anne?

Monie Island and Manokin Park 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 holiday rentals like in Princess Anne?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Princess Anne. Holiday rentals feature extras such as patios, hot tubs and fire pits so you'll feel right at home. If you're concerned about cleanliness, holiday rentals can provide a sense of seclusion away from public hotel lifts and busy lobbies while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular choice for family trips.