Princess Anne Holiday Rentals

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Holiday Rentals in Princess Anne

Key West Cottages

3.0 star property
9.8 out of 10, Exceptional, (309)
"It’s really nice, clean, and new. We have a toddler, so for families with little kids, this is a great place to stay (especially enough space for little kids to walk around! The deck is a big plus!) The communication could be better on how to checkin and checkout but it was easy to figure out. Not much around, highly recommend to bring your own food/cook. "
The price is AU$219
includes taxes & fees
19 Jan - 20 Jan
Key West Cottages

Island Breeze Cottage w/ screened porch. Water view! Quiet location!

9.8 out of 10, Exceptional, (275)
"Clean and quiet. Efficient use of space"
Island Breeze Cottage w/ screened porch. Water view! Quiet location!

Waterfront on Marsh Island!

8.8 out of 10, Excellent, (21)
"Small Cozy condo for couples. Very quiet and relaxing with great sunrises and sunsets! Great location with being on the water!"
Waterfront on Marsh Island!

Cozy Little Cottage on chincoteague island va.

9.4 out of 10, Exceptional, (36)
"The cottage is as described. There is no stove but it truly didn’t matter. Bed is very compfy. Shower is clean and hot. Quit neighborhood. The screened in porch is the best! Coffee and reading in the rockers. The cottage is close to everything !Thank you Don. We loved our stay."
Cozy Little Cottage on chincoteague island va.

Only 5 min. from the Beach!

9.0 out of 10, Wonderful, (19)
"We were pleased with what we found! The space was exactly as advertised and we really liked the fact that the bedroom was completely separate from the kitchenette and second bed. The two bathrooms we also great since it was my wife and I, our daughter and her best friend. The separate space for the adults was super! The cost of the room per night was very reasonable for it being the off season. "
The price is AU$306
includes taxes & fees
5 Jan - 6 Jan
Only 5 min. from the Beach!

Blufin Bungalows & Marina

3.0 star property
9.4 out of 10, Exceptional, (85)
"Great stay! Our family had a great time!"
Blufin Bungalows & Marina

2BR Snug Harbor Waterfront Cottage with the Most Spectacular View of lighthouse

9.6 out of 10, Exceptional, (43)
"Wonderful property and great location. Would love to stay in cabin 5 again. Had everything we needed. Management was friendly and always available."
2BR Snug Harbor Waterfront Cottage with the Most Spectacular View of lighthouse

Cabin at Holdens Creek on Eastern Shore of VA

9.6 out of 10, Exceptional, (159)
"Cozy quiet and warm.. Great getaway from a busy life"
Cabin at Holdens Creek on Eastern Shore of VA

Deal Island Bay Cottage

9.6 out of 10, Exceptional, (55)
"We got every year and stay here, it’s great! "
The price is AU$375
includes taxes & fees
15 Jan - 16 Jan
Deal Island Bay Cottage

SeaLaVie!!!

9.8 out of 10, Exceptional, (38)
"Loved it. It was clean and just a lovely quaint cabin. Just enough for us to enjoy each others company. Would recommend this place to my other friends and family. Thank you to the wonderful host for a beautiful Christmas with our kids! "
SeaLaVie!!!

Tranquil Shores - Relaxation With a Water View!

9.8 out of 10, Exceptional, (124)
"This is a cute house in a beautiful location. We were very comfortable. I was a little taken aback at having to pay extra for linens and towels but everything else was excellent. Communication with the host was great."
Tranquil Shores - Relaxation With a Water View!

Historic Family Vacation Home with Golf Cart

9.6 out of 10, Exceptional, (5)
"A great stay with the family and friends plenty of room for the seven of us. The kitchen was good to cook, enjoyed the espresso machine. "
Historic Family Vacation Home with Golf Cart

The Hideaway Cottage

9.8 out of 10, Exceptional, (79)
"Has what you need. It is cozy. Close to town and the beach. Third time staying here. Love it. "
The Hideaway Cottage

Small cottage for those little getaways

10.0 out of 10, Exceptional, (105)
"Very cozy cottage tucked off the road great check-in experience place was clean easy parking will definitely go back again"
Small cottage for those little getaways

Hidden Gem! Clean & Cozy and Family Friendly!

9.6 out of 10, Exceptional, (54)
"Overall our stay here was great. The house was clean, and the furniture and beds were comfortable. The rooms are spacious. The only negatives for us were the very low water pressure in the shower, and having to park under a pine tree that dropped needles and sap all over our cars. All my interactions with the owner were great. "
Hidden Gem! Clean & Cozy and Family Friendly!

Only 5 min to Assateague National Seashore!

9.4 out of 10, Exceptional, (11)
"I have been staying at the Assateague Inn in Chincoteague for the last 7 Years! It is an annual Fall trip that I look forward to every year. This years visit did not disappoint. The apartment was exceptionally clean, modern, and had all of the comforts of home. The bed was very comfortable, and there was even a Wine Cooler!"
The price is AU$306
includes taxes & fees
5 Jan - 6 Jan
Only 5 min to Assateague National Seashore!

Oyster Bay Hideaway on Chincoteague Island!

10.0 out of 10, Exceptional, (8)
"It was great!"
Oyster Bay Hideaway on Chincoteague Island!

Chincoteague Island House "Sir Whelk-A-Lot" Bikes/Kayaks Included! DT Location!

10.0 out of 10, Exceptional, (37)
"We went for a quick weekend getaway to Chincoteague. Great location and comfortable stay. Hosts were very prompt with responses to emails. No problems whatsoever. Everything we needed. Thanks for the use of your home. "
The price is AU$467
includes taxes & fees
5 Jan - 6 Jan
Chincoteague Island House "Sir Whelk-A-Lot" Bikes/Kayaks Included! DT Location!

Salisbury Riverfront Lofts

3.0 star property
9.2 out of 10, Wonderful, (20)
"Great spot and well appointed. Great communicator. HVAC loud and might consider brighter bulbs in lamps. "
The price is AU$405
includes taxes & fees
17 Jan - 18 Jan
Salisbury Riverfront Lofts

Quaint Cottages Near Everything on Beach Road

9.4 out of 10, Exceptional, (36)
"We booked this at the very last minute so we could clean out our father’s home (he passed the week before). It was perfect for our needs. One caution…the grass has tiny little burrs that stick to socks and flip flops. Nothing to do about them but if you have a dog, check their paws. We were even able to add an additional night easily when the clean out took longer than we expected. I would recommend!"
Quaint Cottages Near Everything on Beach Road
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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Other types of properties in Princess Anne you may be interested in

Econo Lodge Princess Anne

2.0 star property
6.6 out of 10, (583)
"Nothing"
The price is AU$152
includes taxes & fees
5 Jan - 6 Jan
Econo Lodge Princess Anne

Courtyard by Marriott Salisbury

3.0 star property
8.6 out of 10, Excellent, (866)
"T"
The price is AU$177
includes taxes & fees
7 Jan - 8 Jan
Courtyard by Marriott Salisbury

Key West Cottages

3.0 star property
9.8 out of 10, Exceptional, (309)
"It’s really nice, clean, and new. We have a toddler, so for families with little kids, this is a great place to stay (especially enough space for little kids to walk around! The deck is a big plus!) The communication could be better on how to checkin and checkout but it was easy to figure out. Not much around, highly recommend to bring your own food/cook. "
The price is AU$219
includes taxes & fees
19 Jan - 20 Jan
Key West Cottages
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.

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.

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?

Mount Vernon Park and Ballards Island are a couple of lovely local spots to get outside and enjoy nature. Hytche athletic Center and Corbin Memorial Library 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.