Princess Anne Holiday Rentals

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Check prices for these dates

In two weeks
19 Dec - 21 Dec
In two months
30 Jan - 1 Feb
In three months
27 Feb - 1 Mar
In four months
27 Mar - 29 Mar

Holiday Rentals in Princess Anne

Exterior
Key West Cottages

Key West Cottages

3.0 star property
Downtown Chincoteague
9.8 out of 10, Exceptional, (485)
"We love Key West Cottages!"
United States
Jonathan
The price is HK$731
HK$821 total
includes taxes & fees
4 Dec - 5 Dec
Key West Cottages
Exterior
Blufin Bungalows & Marina

Blufin Bungalows & Marina

3.0 star property
Down the Marsh
9.6 out of 10, Exceptional, (207)
"yesss amazing stay "
United States
EDA
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!

Dodge City
9.6 out of 10, Exceptional, (14)
"Wonderful hosts at a beautiful property. The cottage was quaint, safe and clean, just as advertised, and was perfect for a 2 day quiet get away. The overall property is well cared for and provides for a warm sense of community for the guests. "
United States
Carol P.
1BR Waterfront cottage with a view of the wild Chincoteague ponies!
Smart TV, DVD player, offices
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, (65)
"Great location. The house was perfect for our family. I especially enjoyed the swing on the porch "
United States
pat B.
The price is HK$666
HK$1,945 total
includes taxes & fees
7 Dec - 8 Dec
Chincoteague Island House "Sir Whelk-A-Lot" Kayaks Included! Downtown Location!
Beach
2BR Waterfront Cottage with the Most Spectacular View of lighthouse!

2BR Waterfront Cottage with the Most Spectacular View of lighthouse!

Dodge City
9.6 out of 10, Exceptional, (52)
"Wonderful property. Very clean, comfortable and has a great view. Awsom host. "
United States
Janet L.
2BR Waterfront Cottage with the Most Spectacular View of lighthouse!
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?!

Chincoteague Island
10.0 out of 10, Exceptional, (53)
"My son, daughter in law and other family members "
United States
Margie O.
At the Water's Edge - is there anywhere you'd rather be?!
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!

Downtown Chincoteague
10.0 out of 10, Exceptional, (19)
"Great host and the house was exactly as described. It provided what we needed for our stay."
United States
Janna M.
Coastal Daze Cottage on Famous Chincoteague Island! Come see the wild ponies!
In-room dining
Salisbury Riverfront Lofts

Salisbury Riverfront Lofts

3.0 star property
Salisbury
9.4 out of 10, Exceptional, (23)
"It was a great stay nice comfortable place "
United States
Adam
The price is HK$561
HK$1,988 total
includes taxes & fees
9 Dec - 10 Dec
Salisbury Riverfront Lofts
Outdoor dining
Near Chincoteague & Assateague Island Charming 2-bedroom cottage

Near Chincoteague & Assateague Island Charming 2-bedroom cottage

Saxis
9.4 out of 10, Exceptional, (3)
"Lovely, small but cozy, great place to bond and enjoy good food and drink."
United States
Bob H.
Near Chincoteague & Assateague Island Charming 2-bedroom cottage
Exterior
Strawberry Crossroads

Strawberry Crossroads

2.0 star property
Pittsville
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!!"
United States
Randolph
Strawberry Crossroads
Microwave, oven, stovetop, coffee/tea maker
Assateague Inn 111 by Seaside Vacations & Sales

Assateague Inn 111 by Seaside Vacations & Sales

Chincoteague Island
8.2 out of 10, Very good, (32)
"It was all we needed. No frills, but in a great location and the pool was wonderful. "
United States
jennifer g.
The price is HK$783
HK$1,486 total
includes taxes & fees
7 Dec - 8 Dec
Assateague Inn 111 by Seaside Vacations & Sales
Terrace/patio
The purple door at the bay.

The purple door at the bay.

Captain's Cove
9.2 out of 10, Wonderful, (54)
"Price and location was the primary reason the purple door works for us!"
United States
Patrick O.
The price is HK$1,226
HK$3,508 total
includes taxes & fees
4 Dec - 5 Dec
The purple door at the bay.
Outdoor dining
Island Retreat by Seaside Vacations & Sales

Island Retreat by Seaside Vacations & Sales

Chincoteague Island
9.0 out of 10, Wonderful, (16)
"Quiet place with everything we needed to be comfortable for our 10th anniversary. We loved it & are looking forward to a return trip."
United States
Anita A.
Island Retreat by Seaside Vacations & Sales
Terrace/patio
Assateague Inn 104 by Seaside Vacations & Sales

Assateague Inn 104 by Seaside Vacations & Sales

Chincoteague Island
9.6 out of 10, Exceptional, (21)
"Stay at Assateague Inn was clean, comfy, cozy, and convenient. "
United States
Anonymous traveller
The price is HK$783
HK$1,486 total
includes taxes & fees
7 Dec - 8 Dec
Assateague Inn 104 by Seaside Vacations & Sales
Fridge, microwave, oven, stovetop
The Blue Crab - Your Dream Vacation awaits you!

The Blue Crab - Your Dream Vacation awaits you!

2.0 star property
Deep Hole
9.8 out of 10, Exceptional, (14)
"The Blue Crab was perfect for our family vacation. It was beautiful, clean, spacious, and had everything we needed to enjoy our stay. If we come back, we’ll be staying at The Blue Crab again! "
United States
Erin P.
The Blue Crab - Your Dream Vacation awaits you!
Interior
Cabin at Holdens Creek on Eastern Shore of VA

Cabin at Holdens Creek on Eastern Shore of VA

Temperanceville
9.6 out of 10, Exceptional, (180)
"We had a wonderful stay!"
United States
Anna-Marie
Cabin at Holdens Creek on Eastern Shore of VA
Terrace/patio
Waterfront Bungalow on Chincoteague Bay (VA)! - Waterfront Bungalow with Two Bedrooms

Waterfront Bungalow on Chincoteague Bay (VA)! - Waterfront Bungalow with Two Bedrooms

Down the Marsh
9.8 out of 10, Exceptional, (22)
"Loved that it was right on the bay. "
United States
Debra
Waterfront Bungalow on Chincoteague Bay (VA)! - Waterfront Bungalow with Two Bedrooms
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

Birch Town
9.6 out of 10, Exceptional, (42)
"It was family & friends that needed a get away and we really Enjoy the area"
United States
Lori D.
The price is HK$817
HK$3,130 total
includes taxes & fees
4 Dec - 5 Dec
Great Water Views in quiet pet-friendly location facing lighthouse. Large Yard
Property grounds
Tranquil Shores - Relaxation With a Water View!

Tranquil Shores - Relaxation With a Water View!

Chincoteague
9.8 out of 10, Exceptional, (138)
"Comfortable rooms with two bathrooms. Beautiful views, especially from upstairs bedroom. Conveniently located near eateries and small shops, and Assateague Island. We love Chincoteague, so this was a very pleasant stay! "
United States
Minette H.
Tranquil Shores - Relaxation With a Water View!
Property grounds
Sunrise - Waterfront home ,lg back waterfront deck. NO LINENS

Sunrise - Waterfront home ,lg back waterfront deck. NO LINENS

Chincoteague
8.0 out of 10, Very good, (23)
"The location of this home is spectacular with a gorgeous view of Oyster Bay. The home is comfortable. However, there were a few small issues, such as the toaster not working and although the amenities listed a grill, it was in the back of a garage behind broken chairs - not easily accessible if even usable. Also, the furniture on the screened in porch was a disappointment for us. All that said, we would return for the location, alone."
United States
Heather C.
Sunrise - Waterfront home ,lg back waterfront deck. NO LINENS
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

Waterside Inn

Waterside Inn

10/10 Excellent
"Nice accommodations for the Holiday with a front row seat for the Sunsets."
Sallie 2-night trip
Posted 2 days ago
Waterside Inn

Find out more about Princess Anne

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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 Mount Vernon Beach 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.