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, 249 reviews
"The property is beautiful. It sits right on the bay and the view is amazing. The town is so clean and quiet. The area is family friendly and each establishment felt like you entered an aunt’s home. I absolutely loved it. And they have free EV parking at the resort!"
The price is CA $458
CA $515 total
includes taxes & fees
Jun 24 - Jun 25
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, 20 reviews
"We were cozy and comfortable during our stay at this cabin. It was clean, quaint and well located for our weekend exploring Assateague."
Cozy Little Cottage on chincoteague island va.
Island Breeze Cottage w/ screened porch. Water view! Quiet location!
9.8 out of 10, Exceptional, 261 reviews
"We enjoyed our stay in this tiny house! Spent quiet mornings on the screened porch with coffee and a breeze off the channel. It is a tiny space but perfect for our weekend getaway and we appreciated having more space than most island hotel rooms. If you book in July it should be in walking distance of the Fireman’s Carnival."
Island Breeze Cottage w/ screened porch. Water view! Quiet location!
Waterfront on Marsh Island!
9.2 out of 10, Wonderful, 9 reviews
"Perfect place for just us two. Quiet and sparkling clean, we loved every minute. Hope to be back soon!"
Waterfront on Marsh Island!
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
2BR Snug Harbor Waterfront Cottage with the Most Spectacular View of lighthouse
9.6 out of 10, Exceptional, 39 reviews
"Nice"
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
Only 5 min. from the Beach!
9.0 out of 10, Wonderful, 9 reviews
"Easy to find and access. The dock was enjoyable with wildlife. Tha accommodation was clean and spacious for 3 adults. Nice walking paths to food and fun and shops. Definitely plan to stay again."
The price is CA $338
CA $510 total
includes taxes & fees
Jul 19 - Jul 20
Only 5 min. from the Beach!
SeaLaVie!!!
10.0 out of 10, Exceptional, 24 reviews
"Nice little rental. However, it needs a memory foam mattress. The old spring one has to go!!"
SeaLaVie!!!
Cabin at Holdens Creek on Eastern Shore of VA
9.6 out of 10, Exceptional, 146 reviews
"We rented this cabin to spend a couple of nights to be close to other places we planned to spend time at. The cabin is much bigger than I thought it would be space wise. The kitchen is tiny, only one person can fit in there at a time. It worked well for us, but just know if you plan to make a big meal with lots of prep you will have to utilize the dining room table for that. The ad states there is Satellite TV but for us it didn’t seem to be hooked up, again we weren’t there to spend all day...
Cabin at Holdens Creek on Eastern Shore of VA
5 minutes to Assateague National Seashore!
9.4 out of 10, Exceptional, 6 reviews
"Has everything you need."
5 minutes to Assateague National Seashore!
Chincoteague Island House "Sir Whelk-A-Lot" Bikes/Kayaks Included! DT Location!
10.0 out of 10, Exceptional, 28 reviews
"This Island House meets all expectations for anyone looking for a beach getaway including a couple, couples, or a family. The addition of bikes, kayaks, and everything needed for a day at the beach adds to the value. The house is an easy 5 mile drive or bike ride from the beach and the neighborhood is in an imminently walkable area of town. You will have plenty of walkable options for eating and sightseeing from this house."
Chincoteague Island House "Sir Whelk-A-Lot" Bikes/Kayaks Included! DT Location!
Small cottage for those little getaways
10.0 out of 10, Exceptional, 93 reviews
"Awesome little cottage that was perfect for our family of five! Great location; great host. Would gladly stay here again and again."
Small cottage for those little getaways
Salisbury Riverfront Lofts
3.0 star property
9.4 out of 10, Exceptional, 14 reviews
"Really cute unit. We loved how it was decorated. "
The price is CA $100
CA $352 total
includes taxes & fees
Jun 24 - Jun 25
Salisbury Riverfront Lofts
Only 5 min to Assateague National Seashore!
9.4 out of 10, Exceptional, 6 reviews
"Thoroughly enjoyed our stay! Very clean, close to everything yet off in a natural setting very quiet. Kitchen had everything we needed, ice machine and just really enjoyed our stay. Air/fan wouldn’t turn on and they came very quickly and fixed. Would definitely stay here again, perfect mom and daughter trip!"
Only 5 min to Assateague National Seashore!
Tranquil Shores - Relaxation With a Water View!
9.8 out of 10, Exceptional, 117 reviews
"Best place to stay in Chincoteague !!!!"
Tranquil Shores - Relaxation With a Water View!
Cottage near the Bay
8.8 out of 10, Excellent, 15 reviews
"The owner was quick to respond, informative, and polite. The property did the job we were asking from it by being near by our family, close to the bay, and being pet friendly. I was not impressed by the cleanliness, but it was not out right dirty or unsanitary. You get what you pay for. Over all we were pleased with our stay!"
The price is CA $123
CA $271 total
includes taxes & fees
Jun 24 - Jun 25
Cottage near the Bay
Beautiful Bayfront with Sanctuary Private Beach
9.2 out of 10, Wonderful, 12 reviews
"Nice, relaxing stay!"
The price is CA $341
CA $557 total
includes taxes & fees
Jun 25 - Jun 26
Beautiful Bayfront with Sanctuary Private Beach
Hidden Gem ! Clean & Cozy and Family Friendly !
9.4 out of 10, Exceptional, 50 reviews
"The property lies a couple of streets back from the water front. The drive to the house is via an eclectic variation of trailer homes. The campsite is really quite large. The house was lovely - very clean and spacious. There are three bedrooms, one downstairs powder room and a jack-and-Jill bathroom accessible from the master bedroom and the upstairs hallway. On our day of arrival, we were treated to 2 2-hour training shows, at 3pm and 8pm, from the nearby Naval base, where Hawkeye aircraft...
Hidden Gem ! Clean & Cozy and Family Friendly !
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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, 553 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 CA $123
CA $137 total
includes taxes & fees
Jun 23 - Jun 24
Econo Lodge Princess Anne
Best Western Salisbury Plaza
2.5 star property
6.2 out of 10, 621 reviews
"it was much better than my last visit"
The price is CA $81
CA $91 total
includes taxes & fees
Jun 23 - Jun 24
Best Western Salisbury Plaza
Comfort Suites Chincoteague Island Bayfront Resort
2.5 star property
9.6 out of 10, Exceptional, 1,003 reviews
"Nice rooms, nice grounds, nice pool, nice views, nice staff, nice price. What else do you want? "
The price is CA $324
CA $365 total
includes taxes & fees
Jul 2 - Jul 3
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, cottages, cabins, villas... 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Princess Anne vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Princess Anne vacation rentals we have selected for you start as low as CA $100 per night. Entering your travel dates in the search wizard 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.

Recent reviews of Princess Anne properties
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