A sunset over a lake with a dock and a small settlement.

Princess Anne Vacation Rentals

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Our top choices for Princess Anne vacation rentals

Key West Cottages

Key West Cottages
3.0 star property
Downtown Chincoteague
9.8 out of 10, Exceptional, (596 reviews)
"Beautiful family friendly place. Great pool. Great location."
United States
KRYSTLE
The price is CA $434
CA $488 total
includes taxes & fees
Aug 4 - Aug 5
Key West Cottages

Blufin Bungalows & Marina

Blufin Bungalows & Marina
3.0 star property
Down the Marsh
9.6 out of 10, Exceptional, (287 reviews)
"Excellent place to stay would definitely come again. Checking in was seem less and the staff very helpful"
United States
Jared
Blufin Bungalows & Marina

2 Mi to Downtown: Tranquil Abode in Chincoteague!

2 Mi to Downtown: Tranquil Abode in Chincoteague!
3.0 star property
Up the Neck
2 Mi to Downtown: Tranquil Abode in Chincoteague!

Pet-friendly creekside cottage w/ backyard

Pet-friendly creekside cottage w/ backyard
Up the Neck
9.4 out of 10, Exceptional, (138 reviews)
"Awesome two night stay! Highly recommend! "
United States
Dorothy D.
The price is CA $546
CA $873 total
includes taxes & fees
Aug 11 - Aug 12
Pet-friendly creekside cottage w/ backyard

Salisbury Riverfront Lofts

Salisbury Riverfront Lofts
3.0 star property
Salisbury
9.4 out of 10, Exceptional, (26 reviews)
"It was a great stay nice comfortable place "
United States
Adam
The price is CA $107
CA $367 total
includes taxes & fees
Jul 15 - Jul 16
Salisbury Riverfront Lofts

Cottage near the Bay

Cottage near the Bay
Crisfield
8.6 out of 10, Excellent, (58 reviews)
"Quiet area, the place needs to be cleaned, bedding changed, redo the bathroom"
United States
Pamela
The price is CA $115
CA $266 total
includes taxes & fees
Jul 26 - Jul 27
Cottage near the Bay

Stylish 2 bedroom 1 bath with riverfront views close to dining and downtown

Stylish 2 bedroom 1 bath with riverfront views close to dining and downtown
Salisbury
9.8 out of 10, Exceptional, (21 reviews)
"The loft apartment was unique, comfortable with everything we needed. It’s an easy walk to downtown and quick easy access to driving. Everything about check in and check out was transparent and easy. Heat was a little noisy, but didn’t hinder us. We’ll likely make this a regular stay."
United States
Eric & Marcy C.
The price is CA $130
CA $292 total
includes taxes & fees
Jul 19 - Jul 20
Stylish 2 bedroom 1 bath with riverfront views close to dining and downtown

Riverside Lodge Bed & Breakfast on the Honga River UNIT C

Riverside Lodge Bed & Breakfast on the Honga River UNIT C
Fishing Creek
10.0 out of 10, Exceptional, (11 reviews)
"Peggy and Gary are the perfect hosts: welcoming, friendly, attentive and respectful of your preferences. Wonderful views of the Bay and River via the lodge -- including the cupola -- and walking around the majestic property."
United States
Thomas S.
The price is CA $382
CA $461 total
includes taxes & fees
Jul 15 - Jul 16
Riverside Lodge Bed & Breakfast on the Honga River UNIT C

Deal Island Bay Cottage

Deal Island Bay Cottage
Deal Island
9.6 out of 10, Exceptional, (60 reviews)
"We got every year and stay here, it’s great! "
United States
Margaret H.
The price is CA $203
CA $372 total
includes taxes & fees
Jul 16 - Jul 17
Deal Island Bay Cottage

Assateague Inn 213 by Seaside Vacations & Sales

Assateague Inn 213 by Seaside Vacations & Sales
Chincoteague Island
9.4 out of 10, Exceptional, (34 reviews)
"Everything was as it was stated. Clean, neat and stocked with essentials. Cozy and comfortable. Quiet and peaceful. Loved the island and will be coming back. "
United States
Kera S.
The price is CA $228
CA $381 total
includes taxes & fees
Jul 26 - Jul 27
Assateague Inn 213 by Seaside Vacations & Sales

Assateageue Inn 104 by Seaside Vacations & Sales

Assateageue Inn 104 by Seaside Vacations & Sales
Chincoteague Island
9.4 out of 10, Exceptional, (29 reviews)
"Had a great stay! Place was very clean and host was great a communication."
United States
Jen G.
Assateageue Inn 104 by Seaside Vacations & Sales

Salisbury Hideaway

Salisbury Hideaway
Salisbury
10.0 out of 10, Exceptional, (22 reviews)
"Perfect for our weekend away watching college softball!!!"
United States
Michelle S.
The price is CA $234
CA $537 total
includes taxes & fees
Jul 19 - Jul 20
Salisbury Hideaway

'the Bayside Escape' Remote Chesapeake Bay Estate

'the Bayside Escape' Remote Chesapeake Bay Estate
3.0 star property
Fishing Creek
The price is CA $645
CA $1,293 total
includes taxes & fees
Jul 29 - Jul 30
'the Bayside Escape' Remote Chesapeake Bay Estate

Riverside Lodge Bed & Breakfast on the Honga River UNIT E

Riverside Lodge Bed & Breakfast on the Honga River UNIT E
Fishing Creek
10.0 out of 10, Exceptional, (1 review)
The price is CA $382
CA $461 total
includes taxes & fees
Jul 17 - Jul 18
Riverside Lodge Bed & Breakfast on the Honga River UNIT E

Summer is here on Smith Island! Come out and enjoy a great season on the Bay

Summer is here on Smith Island! Come out and enjoy a great season on the Bay
Smith Island
9.8 out of 10, Exceptional, (15 reviews)
"Visiting with locals, fresh steamed crabs, simply enjoying the quiet island life"
United States
Samantha J.
The price is CA $318
CA $508 total
includes taxes & fees
Jul 25 - Jul 26
Summer is here on Smith Island! Come out and enjoy a great season on the Bay

Bayfront Modern Retreat • Dock, Kayaks, Views

Bayfront Modern Retreat • Dock, Kayaks, Views
Captain's Cove
9.8 out of 10, Exceptional, (66 reviews)
"We absolutely love staying here! "
United States
Maggie G.
The price is CA $442
CA $1,035 total
includes taxes & fees
Jul 21 - Jul 22
Bayfront Modern Retreat • Dock, Kayaks, Views

2 Mi to Downtown: Tranquil Abode in Chincoteague!

2 Mi to Downtown: Tranquil Abode in Chincoteague!
Up the Neck
10.0 out of 10, Exceptional, (6 reviews)
"My experience was beyond perfect! The house and yard was perfect. The house was so cozy and had everything we needed. I loved the little game room."
United States
Katlyn
2 Mi to Downtown: Tranquil Abode in Chincoteague!

Salisbury Cottage

Salisbury Cottage
Salisbury
10.0 out of 10, Exceptional, (39 reviews)
"Super convenient to campus and everything was clean and worked perfectly. Overall, a great stay and met all of our expectations."
United States
Matthew B.
The price is CA $379
CA $713 total
includes taxes & fees
Aug 11 - Aug 12
Salisbury Cottage

Cozy 2-bedroom house in Chincoteague

Cozy 2-bedroom house in Chincoteague
Deep Hole
10.0 out of 10, Exceptional, (3 reviews)
"Very nice and well designed property. As soon as you open the door, you can tell that a lot of love and dedication came into designing this beautiful little cottage.Done with taste. Well located, away from the busy beach town center, yet very close to the main street (Maddox Street) and to the National Park where the beach is located.It will be our to-go-to place in the Island."
United States
Jean-Charles G.
The price is CA $294
CA $515 total
includes taxes & fees
Aug 12 - Aug 13
Cozy 2-bedroom house in Chincoteague

Saltwater Serenity Waterfront Cottage

Saltwater Serenity Waterfront Cottage
Deal Island Historic District
Saltwater Serenity Waterfront Cottage
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

Find out more about Princess Anne

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation 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 or room. 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 vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . 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 . 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 vacation rental 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 vacation 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 short-term rentals, that won’t be hard to do.

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Frequently asked questions

Can I find a vacation rental in Princess Anne?

Yes, you can find vacation rentals in Princess Anne close to Ella Fitzgerald Performing Arts Center, or you can choose a more remote option if you're looking for extra privacy while you relax. 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.

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?

Monie Island and Manokin Park are a couple of lovely local spots to get outside and enjoy nature. Somerset County Library and Hytche athletic Center 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.