Princess Anne Holiday Rentals

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Check prices for these dates

In two weeks
31 Oct - 2 Nov
In one month
14 Nov - 16 Nov
In two months
12 Dec - 14 Dec
In three months
9 Jan - 11 Jan

Holiday Rentals in Princess Anne

Exterior
Key West Cottages
Key West Cottages
3.0 star property
9.8 out of 10, Exceptional, (467)
"Great place to stay!"
Key West Cottages
Exterior
Blufin Bungalows & Marina
Blufin Bungalows & Marina
3.0 star property
9.6 out of 10, Exceptional, (195)
"Absolutely loved it here. Very helpful and friendly staff. Will Absolutely stay again."
Blufin Bungalows & Marina
Pool
1BR Waterfront cottage with a view of the wild Chincoteague ponies!
1BR Waterfront cottage with a view of the wild Chincoteague ponies!
9.6 out of 10, Exceptional, (14)
"3 night stay for our anniversary, beautiful view had a relaxing time! "
1BR Waterfront cottage with a view of the wild Chincoteague ponies!
Beach
2BR Waterfront Cottage with the Most Spectacular View of lighthouse!
2BR Waterfront Cottage with the Most Spectacular View of lighthouse!
9.6 out of 10, Exceptional, (52)
"Very nice and clean and directly at the water. Well equipped and beautiful view and close to everything. Perfect place for a peaceful getaway to explore beautiful Chincoteague. "
2BR Waterfront Cottage with the Most Spectacular View of lighthouse!
Fridge, microwave, oven, stovetop
Chincoteague Island House "Sir Whelk-A-Lot" Kayaks Included! Downtown Location!
Chincoteague Island House "Sir Whelk-A-Lot" Kayaks Included! Downtown Location!
10.0 out of 10, Exceptional, (60)
"Property was as described. Walking distance to cute town.15 min drive to beach. Nice for families or couples."
The price is HK$910
HK$2,218 total
includes taxes & fees
27 Oct - 28 Oct
Chincoteague Island House "Sir Whelk-A-Lot" Kayaks Included! Downtown Location!
Exterior
Strawberry Crossroads
Strawberry Crossroads
2.0 star property
9.0 out of 10, Wonderful, (7)
"Quiet clean cabin off the beaten path!! Absolutely amazing place if you want something more private and rustic!!"
Strawberry Crossroads
Interior
Waterfront on Marsh Island!
Waterfront on Marsh Island!
8.4 out of 10, Very good, (38)
"The location is close to everything, but secluded and quiet for when you just want to relax. We loved the closed in porch where we sat for hours on end talking and watching the water. We really felt comfortable and at home. "
Waterfront on Marsh Island!
Exterior
Great Water Views in quiet pet-friendly location facing lighthouse. Large Yard
Great Water Views in quiet pet-friendly location facing lighthouse. Large Yard
9.6 out of 10, Exceptional, (42)
"Such a great location. You can see the ponies with binoculars from the lovely screened porch.This was close enough to the park and restaurants but far enough for a nice quiet getaway. "
The price is HK$816
HK$3,108 total
includes taxes & fees
17 Oct - 18 Oct
Great Water Views in quiet pet-friendly location facing lighthouse. Large Yard
Beach nearby
The Hideaway Cottage
The Hideaway Cottage
9.8 out of 10, Exceptional, (98)
"Just right for what we needed."
The Hideaway Cottage
Interior
At the Water's Edge - is there anywhere you'd rather be?!
At the Water's Edge - is there anywhere you'd rather be?!
10.0 out of 10, Exceptional, (53)
"My son, daughter in law and other family members "
At the Water's Edge - is there anywhere you'd rather be?!
Interior
Cabin at Holdens Creek on Eastern Shore of VA
Cabin at Holdens Creek on Eastern Shore of VA
9.6 out of 10, Exceptional, (180)
"Beautiful, clean, quaint cabin.....only 25 minutes from Chincoteague island. Highly recommend. Thanks so much for the amazing place to stay!!!!"
Cabin at Holdens Creek on Eastern Shore of VA
Outdoor dining
Near Chincoteague & Assateague Island Charming 2-bedroom cottage
Near Chincoteague & Assateague Island Charming 2-bedroom cottage
9.4 out of 10, Exceptional, (3)
"Lovely, small but cozy, great place to bond and enjoy good food and drink."
Near Chincoteague & Assateague Island Charming 2-bedroom cottage
Property grounds
Cozy Little Cottage on chincoteague island va.
Cozy Little Cottage on chincoteague island va.
9.6 out of 10, Exceptional, (49)
"Was the best little house we love "
Cozy Little Cottage on chincoteague island va.
Fridge, microwave, oven, stovetop
Coastal Daze Cottage on Famous Chincoteague Island! Come see the wild ponies!
Coastal Daze Cottage on Famous Chincoteague Island! Come see the wild ponies!
10.0 out of 10, Exceptional, (16)
"Great location and property. Owner was kind and communicative. The playground next to the house was a bonus for my kids!"
Coastal Daze Cottage on Famous Chincoteague Island! Come see the wild ponies!
Fridge, microwave, oven, stovetop
The Brass Crab - Check in/out any day!
The Brass Crab - Check in/out any day!
10.0 out of 10, Exceptional, (154)
"This is a lovely place to stay with a nice amount of space indoors and a sweet back yard with plenty for the kids to do."
The Brass Crab - Check in/out any day!
Dining
Cottage near the Bay
Cottage near the Bay
8.8 out of 10, Excellent, (49)
"great, peaceful "
The price is HK$630
HK$1,467 total
includes taxes & fees
18 Oct - 19 Oct
Cottage near the Bay
Terrace/patio
Waterfront Bungalow on Chincoteague Bay (VA)! - Waterfront Bungalow with Two Bedrooms
Waterfront Bungalow on Chincoteague Bay (VA)! - Waterfront Bungalow with Two Bedrooms
9.8 out of 10, Exceptional, (20)
"Loved that it was right on the bay. "
The price is HK$1,236
HK$1,563 total
includes taxes & fees
26 Oct - 27 Oct
Waterfront Bungalow on Chincoteague Bay (VA)! - Waterfront Bungalow with Two Bedrooms
In-room dining
Salisbury Riverfront Lofts
Salisbury Riverfront Lofts
3.0 star property
9.2 out of 10, Wonderful, (22)
"Very nice place clean & roomy."
The price is HK$542
HK$1,964 total
includes taxes & fees
16 Oct - 17 Oct
Salisbury Riverfront Lofts
Smart TV, video games, DVD player, books
Sunset Bay Villas at Chincoteague Island Virginia - direct water front
Sunset Bay Villas at Chincoteague Island Virginia - direct water front
9.8 out of 10, Exceptional, (128)
"Great place with excellent views! Check in was effortless and the condo was one of the cleanest I’ve seen. This was our first time visiting Chincoteague and we will definitely be back!"
Sunset Bay Villas at Chincoteague Island Virginia - direct water front
Microwave, oven, stovetop, coffee/tea maker
Only 5 min. from the Beach!
Only 5 min. from the Beach!
8.4 out of 10, Very good, (31)
"Excellent location, perfect size for two adults. Easy check in/out procedure. Only negative was lots of flies in room when we checked in and no one working front desk we could communicate with."
The price is HK$782
HK$1,475 total
includes taxes & fees
20 Oct - 21 Oct
Only 5 min. from the Beach!
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

Best Western Plus Pocomoke City

Best Western Plus Pocomoke City

10/10 Excellent
"The breakfast was good and the customer service from the staff was great and helpful "
Isaiah 2-night trip
Posted 3 days ago
Best Western Plus Pocomoke City

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 holiday rental in Princess Anne?

Yes, there are holiday rentals close to the most popular sights in Princess Anne, 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.

What can I see and do in Princess Anne?

Manokin Park and Wellington State Wildlife Management Area 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.