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

Princess Anne Vacation Rentals

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Check prices for these dates

In two weeks
Jul 10 - Jul 12
In two months
Aug 21 - Aug 23
In three months
Sep 18 - Sep 20
In four months
Oct 16 - Oct 18

Our top choices for Princess Anne vacation rentals

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, (588 reviews)
"We loved it and will be back for sure!"
United States
Jennifer
The price is ￥52,510
￥58,969 total
includes taxes & fees
Jul 13 - Jul 14
Key West Cottages
Exterior

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 ￥59,537
￥75,941 total
includes taxes & fees
Jul 1 - Jul 2
Blufin Bungalows & Marina
House (6 Bedrooms) | Front of property

'the Bayside Escape' Remote Chesapeake Bay Estate

'the Bayside Escape' Remote Chesapeake Bay Estate
3.0 star property
Fishing Creek
The price is ￥73,753
￥147,752 total
includes taxes & fees
Jul 1 - Jul 2
'the Bayside Escape' Remote Chesapeake Bay Estate
Interior

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 ￥61,888
￥99,813 total
includes taxes & fees
Jul 12 - Jul 13
Pet-friendly creekside cottage w/ backyard
Smart TV, books, offices

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 ￥64,550
￥128,105 total
includes taxes & fees
Jul 8 - Jul 9
Bayfront Modern Retreat • Dock, Kayaks, Views
Exterior

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 ￥43,670
￥52,977 total
includes taxes & fees
Jun 28 - Jun 29
Riverside Lodge Bed & Breakfast on the Honga River UNIT C
Apartment D: Riverfront Grand | 2 bedrooms, individually decorated, individually furnished

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 ￥12,323
￥42,048 total
includes taxes & fees
Jun 29 - Jun 30
Salisbury Riverfront Lofts
TV, DVD player

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 ￥25,131
￥41,938 total
includes taxes & fees
Jul 15 - Jul 16
Assateageue Inn 104 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, (44 reviews)
"It was family & friends that needed a get away and we really Enjoy the area"
United States
Lori D.
The price is ￥29,922
￥80,645 total
includes taxes & fees
Jul 5 - Jul 6
Great Water Views in quiet pet-friendly location facing lighthouse. Large Yard
Smart TV, books, offices

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 ￥26,047
￥60,878 total
includes taxes & fees
Jun 30 - Jul 1
Salisbury Cottage
Exterior

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 ￥43,670
￥52,977 total
includes taxes & fees
Jun 28 - Jun 29
Riverside Lodge Bed & Breakfast on the Honga River UNIT E
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 ￥25,717
￥45,262 total
includes taxes & fees
Jul 13 - Jul 14
Deal Island Bay Cottage
Exterior

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 ￥24,908
￥59,491 total
includes taxes & fees
Jul 1 - Jul 2
Salisbury Hideaway
Interior

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 ￥13,101
￥30,174 total
includes taxes & fees
Jul 1 - Jul 2
Cottage near the Bay
Marina

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 ￥36,392
￥58,196 total
includes taxes & fees
Jun 29 - Jun 30
Summer is here on Smith Island! Come out and enjoy a great season on the Bay
Exterior

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 ￥31,607
￥50,558 total
includes taxes & fees
Jul 17 - Jul 18
Bella's Beach Retreat by Seaside Vacations & Sales
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 ￥29,275
￥69,539 total
includes taxes & fees
Jul 1 - Jul 2
2 Mi to Downtown: Tranquil Abode in Chincoteague!
Exterior

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 ￥45,611
￥100,376 total
includes taxes & fees
Jul 23 - Jul 24
Secluded Waterfront•15mi to Assateague Beach•Fast Wifi•Kayaks•Near Berlin, OC!
Interior

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 ￥17,144
￥63,982 total
includes taxes & fees
Jul 1 - Jul 2
2 Mi to Downtown: Tranquil Abode in Chincoteague!
TV, DVD player

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 ￥25,474
￥72,877 total
includes taxes & fees
Jun 28 - Jun 29
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

Marina Bay Hotel & Suites, an Ascend Collection Hotel

Marina Bay Hotel & Suites, an Ascend Collection Hotel

10/10 Excellent
"Overall pretty good place to stay."
Tiffany 2-night trip
Posted 5 hours ago
Marina Bay Hotel & Suites, an Ascend Collection Hotel

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?

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

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 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 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.