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

Princess Anne Holiday Rentals

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Our top choices for Princess Anne holiday rentals

Key West Cottages

Key West Cottages
3.0 star property
Downtown Chincoteague
9.8 out of 10, Exceptional, (588 reviews)
"We loved it and will be back for sure!"
United States
Jennifer
The price is AU$506
includes taxes & fees
19 July - 20 July
Key West Cottages

Blufin Bungalows & Marina

Blufin Bungalows & Marina
3.0 star property
Down the Marsh
9.6 out of 10, Exceptional, (275 reviews)
"Loved everything about our stay"
United States
Elizabeth
The price is AU$680
includes taxes & fees
1 July - 2 July
Blufin Bungalows & Marina

'the Bayside Escape' Remote Chesapeake Bay Estate

'the Bayside Escape' Remote Chesapeake Bay Estate
3.0 star property
Fishing Creek
The price is AU$1,322
includes taxes & fees
1 July - 2 July
'the Bayside Escape' Remote Chesapeake Bay Estate

Pet-friendly creekside cottage w/ backyard

Pet-friendly creekside cottage w/ backyard
Up the Neck
9.4 out of 10, Exceptional, (138 reviews)
"Awesome two night stay! Highly recommend! "
United States
Dorothy D.
The price is AU$885
includes taxes & fees
12 July - 13 July
Pet-friendly creekside cottage w/ backyard

Bayfront Modern Retreat • Dock, Kayaks, Views

Bayfront Modern Retreat • Dock, Kayaks, Views
Captain's Cove
9.8 out of 10, Exceptional, (66 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 AU$955
includes taxes & fees
6 July - 7 July
Bayfront Modern Retreat • Dock, Kayaks, Views

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$470
includes taxes & fees
3 July - 4 July
Riverside Lodge Bed & Breakfast on the Honga River UNIT C

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 AU$393
includes taxes & fees
30 June - 1 July
Salisbury Riverfront Lofts

Assateageue Inn 104 by Seaside Vacations & Sales

Assateageue Inn 104 by Seaside Vacations & Sales
Chincoteague Island
9.4 out of 10, Exceptional, (29 reviews)
"Convenient location with everything we needed"
United States
John S.
The price is AU$377
includes taxes & fees
15 July - 16 July
Assateageue Inn 104 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, (44 reviews)
"It was family & friends that needed a get away and we really Enjoy the area"
United States
Lori D.
The price is AU$740
includes taxes & fees
10 July - 11 July
Great Water Views in quiet pet-friendly location facing lighthouse. Large Yard

Salisbury Cottage

Salisbury Cottage
Salisbury
10.0 out of 10, Exceptional, (39 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 AU$526
includes taxes & fees
29 June - 30 June
Salisbury Cottage

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$471
includes taxes & fees
27 June - 28 June
Riverside Lodge Bed & Breakfast on the Honga River UNIT E

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 AU$404
includes taxes & fees
13 July - 14 July
Deal Island Bay Cottage

Salisbury Hideaway

Salisbury Hideaway
Salisbury
10.0 out of 10, Exceptional, (21 reviews)
"Perfect for our weekend away watching college softball!!!"
United States
Michelle S.
The price is AU$522
includes taxes & fees
1 July - 2 July
Salisbury Hideaway

Cottage near the Bay

Cottage near the Bay
Crisfield
8.8 out of 10, Excellent, (56 reviews)
"Cottage was exactly as listed. Great value"
United States
Tom B.
The price is AU$273
includes taxes & fees
30 June - 1 July
Cottage near the Bay

Summer is here on Smith Island! Come out and enjoy a great season on the Bay

Summer is here on Smith Island! Come out and enjoy a great season on the Bay
Smith Island
9.8 out of 10, Exceptional, (15 reviews)
"The perfect place to wind down, reconnect with people, culture and a way of life we’ve strayed away from. The house was amazing! The town, the good people and the atmosphere just as much. "
United States
David
The price is AU$515
includes taxes & fees
28 June - 29 June
Summer is here on Smith Island! Come out and enjoy a great season on the Bay

Bella's Beach Retreat by Seaside Vacations & Sales

Bella's Beach Retreat by Seaside Vacations & Sales
Chincoteague Island
8.0 out of 10, Very good, (8 reviews)
"Off season rates are really reasonable- place is as described- good location- good views- would stay again."
United States
Cindy H.
The price is AU$483
includes taxes & fees
17 July - 18 July
Bella's Beach Retreat by Seaside Vacations & Sales

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 AU$492
includes taxes & fees
28 June - 29 June
2 Mi to Downtown: Tranquil Abode in Chincoteague!

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, (10 reviews)
"Really comfortable and relaxing place to stay. Great service from host. "
United States
Roni V.
The price is AU$871
includes taxes & fees
23 July - 24 July
Secluded Waterfront•15mi to Assateague Beach•Fast Wifi•Kayaks•Near Berlin, OC!

2 Mi to Downtown: Tranquil Abode in Chincoteague!

2 Mi to Downtown: Tranquil Abode in Chincoteague!
Up the Neck
10.0 out of 10, Exceptional, (6 reviews)
"My experience was beyond perfect! The house and yard was perfect. The house was so cozy and had everything we needed. I loved the little game room."
United States
Katlyn
The price is AU$706
includes taxes & fees
1 July - 2 July
2 Mi to Downtown: Tranquil Abode in Chincoteague!

The purple door at the bay.

The purple door at the bay.
Captain's Cove
9.2 out of 10, Wonderful, (57 reviews)
"Great place on the water. We caught enough crabs off the dock to have dinner. Relaxing place to take the family and enjoy the seaside. I wish we had more time to enjoy."
United States
Randy R.
The price is AU$674
includes taxes & fees
26 July - 27 July
The purple door at the bay.
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, 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 favourite 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 depend 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 AU$377 per night. Entering your travel dates in the search wizard might find you 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?

Chincoteague Bay RV Resort & Cottages: This holiday home rental outside of Princess Anne has air conditioning and free WiFi to help you feel perfectly comfortable in your new surroundings. Amenities such as a coffee maker and free parking are also available for your convenience.

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.