Princess Anne Vacation Rentals

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Check prices for these dates

In two weeks
Oct 10 - Oct 12
In one month
Oct 24 - Oct 26
In two months
Nov 21 - Nov 23
In three months
Dec 19 - Dec 21

Vacation Rentals in Princess Anne

Our top choices for Princess Anne vacation rentals

Key West Cottages
Exterior

Key West Cottages

3.0 star property
9.8 out of 10, Exceptional, (456)
"Great place to stay!"
Key West Cottages
Blufin Bungalows & Marina
Exterior

Blufin Bungalows & Marina

3.0 star property
9.6 out of 10, Exceptional, (183)
"This was a great vacation experience! Houseboat are so awesome! Chincoteague is beautiful, so much to do! We will be back, will stay a full week, this was one of the best vacation! "
Blufin Bungalows & Marina
Strawberry Crossroads
Exterior

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
Great Water Views in quiet pet-friendly location facing lighthouse. Large Yard
Exterior

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 ￥15,499
￥59,178 total
includes taxes & fees
Sep 29 - Sep 30
Great Water Views in quiet pet-friendly location facing lighthouse. Large Yard
1BR Waterfront cottage with a view of the wild Chincoteague ponies!
Pool

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

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!
Chincoteague Island House "Sir Whelk-A-Lot" Kayaks Included! Downtown Location!
Fridge, microwave, oven, stovetop

Chincoteague Island House "Sir Whelk-A-Lot" Kayaks Included! Downtown Location!

10.0 out of 10, Exceptional, (58)
"Thank you so much for letting us stay at your house. The location was perfect for walking to restaurants and shops. Did a day at the wildlife refuge and spent some time on the beach. Plan to come back and enjoy another stay. "
The price is ￥15,953
￥41,138 total
includes taxes & fees
Sep 29 - Sep 30
Chincoteague Island House "Sir Whelk-A-Lot" Kayaks Included! Downtown Location!
Cottage near the Bay
Dining

Cottage near the Bay

8.8 out of 10, Excellent, (46)
"great, peaceful "
The price is ￥11,956
￥27,538 total
includes taxes & fees
Oct 1 - Oct 2
Cottage near the Bay
Salisbury Riverfront Lofts
Apartment D: Riverfront Grand | In-room dining

Salisbury Riverfront Lofts

3.0 star property
9.2 out of 10, Wonderful, (22)
"Very nice place clean & roomy."
The price is ￥10,043
￥37,021 total
includes taxes & fees
Oct 1 - Oct 2
Salisbury Riverfront Lofts
Waterfront on Marsh Island!
Interior

Waterfront on Marsh Island!

8.4 out of 10, Very Good, (36)
"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!
The Hideaway Cottage
Beach nearby

The Hideaway Cottage

9.8 out of 10, Exceptional, (95)
"Just right for what we needed."
The Hideaway Cottage
NEW PET FRIENDLY LISTING ALERT!!
Smart TV, fireplace

NEW PET FRIENDLY LISTING ALERT!!

9.2 out of 10, Wonderful, (18)
"Very clean, spacious and perfect for a stay with my girlfriend and two dogs! Definitely recommend!"
NEW PET FRIENDLY LISTING ALERT!!
5 minutes to Assateague National Seashore!
Flat-screen TV

5 minutes to Assateague National Seashore!

9.0 out of 10, Wonderful, (20)
"The condo was perfect for my girlfriend and I, very private location and nice boardwalk by the creek"
The price is ￥14,854
￥28,176 total
includes taxes & fees
Sep 29 - Sep 30
5 minutes to Assateague National Seashore!
At the Water's Edge - is there anywhere you'd rather be?!
Interior

At the Water's Edge - is there anywhere you'd rather be?!

10.0 out of 10, Exceptional, (52)
"Great property! Very clean"
At the Water's Edge - is there anywhere you'd rather be?!
Historic home on Smith Island w/ dock!
Beach

Historic home on Smith Island w/ dock!

9.6 out of 10, Exceptional, (45)
"This property was perfect for a family of 4. It was very clean, the kitchen was well stocked and the neighbors were amazing and helpful. Visit the arcade by the marina right before sunset!"
Historic home on Smith Island w/ dock!
The Brass Crab - Check in/out any day!
Fridge, microwave, oven, stovetop

The Brass Crab - Check in/out any day!

10.0 out of 10, Exceptional, (154)
"The Brass Crab is the perfect family place to stay. Thank you for all the extras."
The Brass Crab - Check in/out any day!
Quaint Cottages Near Everything on Beach Road
Exterior

Quaint Cottages Near Everything on Beach Road

9.4 out of 10, Exceptional, (39)
"Location, location, location"
Quaint Cottages Near Everything on Beach Road
Make fabulous Vacation Memories at Family Tides Vacation Rental on Chincoteague
Microwave, dishwasher, coffee/tea maker, cookware/dishes/utensils

Make fabulous Vacation Memories at Family Tides Vacation Rental on Chincoteague

9.8 out of 10, Exceptional, (52)
"Great location and property for a peaceful and tranquil getaway."
Make fabulous Vacation Memories at Family Tides Vacation Rental on Chincoteague
Small cottage for those little getaways
Exterior

Small cottage for those little getaways

10.0 out of 10, Exceptional, (117)
"Great place, cozy and easy to park and get around. "
Small cottage for those little getaways
Cabin at Holdens Creek on Eastern Shore of VA
Interior

Cabin at Holdens Creek on Eastern Shore of VA

9.6 out of 10, Exceptional, (180)
"Thank you for your hospitality!! Your rental property is absolutely amazing! We love cabins and yours made us feel so at home. We are looking forward to visit again!"
Cabin at Holdens Creek on Eastern Shore of VA
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 Salisbury Plaza

Best Western Salisbury Plaza

10/10 Excellent
"Clean room and friendly staff"
Paulo 2-night trip
Posted 5 days ago
Best Western Salisbury Plaza

Find out more about Princess Anne

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:

  • View our selection of featured holiday rentals in Princess Anne
  • Use the map to find apartments and other holiday homes in the Princess Anne neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Princess Anne while they last

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 close to top local attractions in Princess Anne, or you can go with a more secluded option if you're looking for a relaxing stay. 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?

Blufin Bungalows & Marina: This vacation home rental near 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. Princess Anne Town Hall and Somerset County Library 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.