Princess Anne Holiday Rentals

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Holiday Rentals in Princess Anne

Key West Cottages
Exterior
Key West Cottages
3.0 star property
9.8 out of 10, Exceptional, (238)
"Not much to say other than it’s a quiet area and everything is new and clean. We hope it stays that way because we liked staying here."
The price is NZ$378
per night
4 Jun - 5 Jun
Key West Cottages
Blufin Bungalows & Marina
Beach
Blufin Bungalows & Marina
3.0 star property
Blufin Bungalows & Marina
Cozy Little Cottage on chincoteague island va.
Property grounds
Cozy Little Cottage on chincoteague island va.
9.0 out of 10, Wonderful, (18)
"This was our second time staying here, with our first being during the summer. The cottage is very clean and overall quite pleasant with a location perfect for bicycling into town and to the beach. However, this cottage really needs heat if it is to be rented during the cooler months. The owner did provide a portable heater at our request, which did warm the place, but was very noisy. Would stay again but only in the warmer weather. "
Cozy Little Cottage on chincoteague island va.
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Island Breeze Cottage w/ screened porch. Water view! Quiet location!
Island Breeze Cottage w/ screened porch. Water view! Quiet location!
9.8 out of 10, Exceptional, (258)
"We loved the cottage. Perfect location to everything on the island. Was within walking distance to the seafood festival and shops. The screened porch was a nice place to enjoy our morning coffee. The cottage had everything we needed. The bed was super comfy. We highly recommend staying there. We are considering a summer visit and hope the cottage is available if we do."
Island Breeze Cottage w/ screened porch. Water view! Quiet location!
Waterfront on Marsh Island!
Outdoor dining
Waterfront on Marsh Island!
9.2 out of 10, Wonderful, (7)
"Such a great island to visit. The Bay view was perfect. Got to see the sunset on our first night. Easy trip onto the Island for dinner at Rope Walk and Bills Steak & Seafood. Both were excellent. The bed was not very comfortable and the AC was not the greatest. Overall a great place to stay for a long weekend."
Waterfront on Marsh Island!
2BR Snug Harbor Waterfront Cottage with the Most Spectacular View of lighthouse
Pool
2BR Snug Harbor Waterfront Cottage with the Most Spectacular View of lighthouse
9.6 out of 10, Exceptional, (38)
"Snug Harbor is simply amazing, and is truly a home away from home. The location is on the water with amazing views of the lighthouse and the poines. There are tiki huts, lawn chairs, etc. for you to enjoy. Basia and Captain John can take you on kayak and boat tours. I highly recommend taking a guided tour as you learn so much history. Our hosts were so committed to us having a great time and went the extra mile so we could see the poines every chance possible. The cottages are comfortable...
2BR Snug Harbor Waterfront Cottage with the Most Spectacular View of lighthouse
SeaLaVie!!!
1 bedroom, iron/ironing board, free WiFi, bed sheets
SeaLaVie!!!
10.0 out of 10, Exceptional, (23)
"This was a convenient nice cottage not far from Maddox and piney island / community boat ramp/kayak launch. Added bonus pet friendly. We had a very nice stay at this location. Easy check in & check out."
SeaLaVie!!!
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, (145)
"We get together once a year, 5 guys, to hang out, catch up, shoot skeet, target shoot and fish. We do this at a different location every year. This location worked out great. It was private, allowed shooting and had enough room to sleep 5. We would use this cabin again!"
Cabin at Holdens Creek on Eastern Shore of VA
The Hideaway Cottage
Beach nearby
The Hideaway Cottage
10.0 out of 10, Exceptional, (68)
"Enjoy Don's cottage - the screened in patio was lovely to enjoy coffee and do some light office work. Kitchen had enough of everything to heat or prepare simple meals. Hot water was plentiful and pressure good in the shower. Bed was comfortable. The area is very quiet at night but during the day there is a small business next door that you do hear light people chatter/deliveries. I would say this location is like a modern cabin - just enough of everything but still feels rustic."
The Hideaway Cottage
Only 5 min. from the Beach!
Beach
Only 5 min. from the Beach!
8.6 out of 10, Excellent, (7)
"The property was fine, however, both doors did not close tightly. I could see daylight through the bottom corner of both doors. The property was full of flies, I kill them every evening and there were 3-6 when I came back the next evening. They were coming in from somewhere, the doors? The property was very clean but I gave 4 stars because the rug in front of the sink was pretty gross. The towel rack was barely attached to the wall."
Only 5 min. from the Beach!
Quaint Cottages Near Everything on Beach Road
Exterior
Quaint Cottages Near Everything on Beach Road
9.6 out of 10, Exceptional, (25)
"Quiet neighborhood. Conveniently close to the refuge and restaurants."
Quaint Cottages Near Everything on Beach Road
Chincoteague Island House "Sir Whelk-A-Lot" Bikes/Kayaks Included! DT Location!
Fridge, microwave, oven, stovetop
Chincoteague Island House "Sir Whelk-A-Lot" Bikes/Kayaks Included! DT Location!
10.0 out of 10, Exceptional, (27)
"The house is a character in itself, loved the stay."
The price is NZ$606
per night
3 Jun - 4 Jun
Chincoteague Island House "Sir Whelk-A-Lot" Bikes/Kayaks Included! DT Location!
Beautiful Bayfront with Sanctuary Private Beach
Outdoor dining
Beautiful Bayfront with Sanctuary Private Beach
9.2 out of 10, Wonderful, (10)
"House was exactly as advertised and expected. Would stay agian for sure"
The price is NZ$647
per night
2 Jun - 3 Jun
Beautiful Bayfront with Sanctuary Private Beach
Small cottage for those little getaways
Exterior
Small cottage for those little getaways
10.0 out of 10, Exceptional, (89)
"Enjoyed our time great bang for the buck."
Small cottage for those little getaways
5 minutes to Assateague National Seashore!
Property grounds
5 minutes to Assateague National Seashore!
9.2 out of 10, Wonderful, (5)
"Our stay this time was in a different room than last December but just as good! The view was great- location was very convenient. Room clean and orderly. Everything as described. It is perfect for my husband and I, has everything we need. The toaster didn’t work and they replaced it immediately. We stayed two extra days! Loved it! Will definitely book again! Thank you!"
5 minutes to Assateague National Seashore!
Tranquil Shores - Relaxation With a Water View!
Property grounds
Tranquil Shores - Relaxation With a Water View!
9.8 out of 10, Exceptional, (116)
"love the house, the location and it is the perfect size. Deck and screened porch are perfect too. Nice neighborhood also. Very clean and comfy. Thank you for allowing well behaved dogs too :)"
Tranquil Shores - Relaxation With a Water View!
Salisbury Riverfront Lofts
Apartment D: Riverfront Grand | Private kitchen
Salisbury Riverfront Lofts
3.0 star property
9.4 out of 10, Exceptional, (13)
"The property itself was beautiful, had a history and well kept. The street to get to the parking lot was flooded for two days."
The price is NZ$293
per night
3 Jun - 4 Jun
Salisbury Riverfront Lofts
Hidden Gem ! Clean & Cozy and Family Friendly !
Pool
Hidden Gem ! Clean & Cozy and Family Friendly !
9.4 out of 10, Exceptional, (50)
"The house is in a very nice community campground! It made me miss camping and the restaurant there is super good and there’s even a crab guy within the park that will cook up your crabs that you buy from him and there’s a launch place for your boat. So many things but not close to many stores, very peaceful and relaxing!!!!"
Hidden Gem ! Clean & Cozy and Family Friendly !
Cottage near the Bay
Private kitchen
Cottage near the Bay
9.0 out of 10, Wonderful, (13)
"Come stay at this wonderful house in lovely Crisfield Maryland. You won't be sorry. The host is fantastic and gets back to you quickly if you have questions. Thank you for everything."
The price is NZ$324
per night
3 Jun - 4 Jun
Cottage near the Bay
Comfortable & pet friendly home with a view of the bay with a golf cart option.
Fridge, microwave, oven, stovetop
Comfortable & pet friendly home with a view of the bay with a golf cart option.
8.0 out of 10, Very good, (1)
"Used the home as base camp for visiting with family who live on the island. Convenient location (although front deck sits right on the road so didn’t feel comfortable sitting out with coffee for the morning sun). Spacious. Modern kitchen and baths. Everything you need."
Comfortable & pet friendly home with a view of the bay with a golf cart option.
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See all available properties in Princess Anne
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.

Other types of properties in Princess Anne you may be interested in

Econo Lodge Princess Anne
Room, 1 King Bed, Accessible, Non Smoking
Econo Lodge Princess Anne
2.0 star property
6.6 out of 10, (549)
"Stay was good"
The price is NZ$163
per night
2 Jun - 3 Jun
Econo Lodge Princess Anne
Comfort Suites Chincoteague Island Bayfront Resort
Indoor pool, outdoor pool, pool umbrellas, pool loungers
Comfort Suites Chincoteague Island Bayfront Resort
2.5 star property
9.6 out of 10, Exceptional, (1002)
"Lovely view, clean, recently updated, comfortable bed. I would suggest improved pillows."
The price is NZ$366
per night
3 Jun - 4 Jun
Comfort Suites Chincoteague Island Bayfront Resort
Waterside Inn
Seasonal outdoor pool
Waterside Inn
2.0 star property
8.8 out of 10, Excellent, (1004)
"I have stayed here several times and never disappointed. Room is comfortable with a nice view of the water. Very quiet. Breakfast is hot and packed up to take to the room or eat outside. Pool is clean and has late hours at night. "
The price is NZ$231
per night
2 Jun - 3 Jun
Waterside Inn
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Princess Anne holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Princess Anne. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Princess Anne. Seeing all the best attractions is bound to make you fall in love with Princess Anne. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Princess Anne short-term rentals, that won’t be hard to do.

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 has 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.

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?

While exploring the area, visit family-friendly sights like Delmarva Discovery Center, or get outside and enjoy nature at Pocomoke River State Park. University of Maryland Eastern Shore and Hytche athletic Center are a couple of places you'll find in the wider area.

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.

Recent reviews of Princess Anne properties
Expedia verified reviews

Key West Cottages

Key West Cottages

5/5 Excellent
"Not much to say other than it’s a quiet area and everything is new and clean. We hope it stays that way because we liked staying here."
A verified traveller stayed at Key West Cottages
Posted 1 day ago
Key West Cottages