Princess Anne Vacation Rentals

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Vacation Rentals in Princess Anne

Key West Cottages
3.0 star property
9.8 out of 10, Exceptional, 242 reviews
"Wonderful! Will be back again!"
The price is $251
$282 total
includes taxes & fees
Jun 6 - Jun 7
Key West Cottages
Blufin Bungalows & Marina
3.0 star property
Blufin Bungalows & Marina
Cozy Little Cottage on chincoteague island va.
9.2 out of 10, Wonderful, 19 reviews
"Accurate listing, small cottage but had everything we needed. We rode the Pony Express one night to dinner which was easy - we picked it up only a few steps from the house. Thanks for a great weekend."
Cozy Little Cottage on chincoteague island va.
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Island Breeze Cottage w/ screened porch. Water view! Quiet location!
9.8 out of 10, Exceptional, 259 reviews
"Tiny, but perfect for 2 people. The screened in porch was a huge bonus, we spent alot of time out there in the comfy hammock chairs without having to worry about bugs. The listing is misleading with the "water view" though. Its close to the water but theres a row of houses between that blocks the view. Overall great stay, easy check-in, quiet neighborhood. We would definitely come back"
Island Breeze Cottage w/ screened porch. Water view! Quiet location!
Waterfront on Marsh Island!
9.2 out of 10, Wonderful, 7 reviews
"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
9.6 out of 10, Exceptional, 38 reviews
"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
Quaint Cottages Near Everything on Beach Road
9.6 out of 10, Exceptional, 25 reviews
"Quiet neighborhood. Conveniently close to the refuge and restaurants."
Quaint Cottages Near Everything on Beach Road
SeaLaVie!!!
10.0 out of 10, Exceptional, 23 reviews
"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!!!
Chincoteague Island House "Sir Whelk-A-Lot" Bikes/Kayaks Included! DT Location!
10.0 out of 10, Exceptional, 28 reviews
"The house is a character in itself, loved the stay."
Chincoteague Island House "Sir Whelk-A-Lot" Bikes/Kayaks Included! DT Location!
Only 5 min. from the Beach!
8.8 out of 10, Excellent, 8 reviews
"Clean, two room, 2.bathroom with 2 fridges. Felt safe there. Walk to bars and restaurants. Mini golf nearby. We were happy to find a coffee pot, not Keurig. Air fryer was a nice touch but we didn't use it. We took the saltwater pony boat tour with Henry - well worth it. Got some amazing pictures. Bring binoculars for birdwatching."
Only 5 min. from the Beach!
Cabin at Holdens Creek on Eastern Shore of VA
9.6 out of 10, Exceptional, 145 reviews
"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
5 minutes to Assateague National Seashore!
9.2 out of 10, Wonderful, 5 reviews
"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!
The Hideaway Cottage
10.0 out of 10, Exceptional, 68 reviews
"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
Beautiful Bayfront with Sanctuary Private Beach
9.2 out of 10, Wonderful, 10 reviews
"House was exactly as advertised and expected. Would stay agian for sure"
The price is $239
$396 total
includes taxes & fees
Jun 9 - Jun 10
Beautiful Bayfront with Sanctuary Private Beach
Only 5 min to Assateague National Seashore!
9.2 out of 10, Wonderful, 5 reviews
"It was a little difficult to find, but in a quiet area. Bedroom MAY be warm in summer because the AC is only in the living room/ kitchen area. The heat worked very well, but the thermostats were very inaccurate. 50F was closer to 75-80. Even my freezing wife was very warm"
The price is $154
$257 total
includes taxes & fees
Jun 16 - Jun 17
Only 5 min to Assateague National Seashore!
Cottage near the Bay
9.0 out of 10, Wonderful, 13 reviews
"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 $90
$198 total
includes taxes & fees
Jun 6 - Jun 7
Cottage near the Bay
Waterfront 3 bedroom condo. Spring is here!
10.0 out of 10, Exceptional, 20 reviews
"Very relaxing time. The condo was beautiful"
Waterfront 3 bedroom condo. Spring is here!
Tranquil Shores - Relaxation With a Water View!
9.8 out of 10, Exceptional, 116 reviews
"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!
Small cottage for those little getaways
10.0 out of 10, Exceptional, 89 reviews
"Enjoyed our time great bang for the buck."
Small cottage for those little getaways
Salisbury Riverfront Lofts
3.0 star property
9.4 out of 10, Exceptional, 13 reviews
"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 $80
$264 total
includes taxes & fees
Jun 6 - Jun 7
Salisbury Riverfront Lofts
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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.

Princess Anne Vacation Rental Travel Info

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, 550 reviews
"I enjoyed my stay here. I arrived @ 10:30 am and check in was 2pm so happy that they let me check in @ 11am. Drove from new york for the crab and cruise event. My room was clean towels smelled great. I absolutely enjoyed my stay. Thank u guys for being so nice 💓 "
The price is $90
$100 total
includes taxes & fees
Jun 6 - Jun 7
Econo Lodge Princess Anne
Best Western Salisbury Plaza
2.5 star property
6.2 out of 10, 612 reviews
"Nice property. Check in and check out was easy. The parking is gated so there was plenty of room. Room was clean. "
The price is $96
$108 total
includes taxes & fees
Jun 16 - Jun 17
Best Western Salisbury Plaza
Comfort Suites Chincoteague Island Bayfront Resort
2.5 star property
9.6 out of 10, Exceptional, 1,004 reviews
"Lovely view, clean, recently updated, comfortable bed. I would suggest improved pillows."
The price is $169
$191 total
includes taxes & fees
Jun 6 - Jun 7
Comfort Suites Chincoteague Island Bayfront Resort
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.

Everything you need to know about Princess Anne vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Princess Anne vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Princess Anne vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Princess Anne vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Princess Anne. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Princess Anne in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $80 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Princess Anne rentals

At Expedia, we put the best Princess Anne vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Princess Anne rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Princess Anne vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Princess Anne. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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 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 vacation rentals are there in Princess Anne?

Expedia has 3 vacation 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 larger area.

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.

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