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, (567 reviews)
"Great place to stay on the island"
United States
Wilmer
The price is CA $410
CA $461 total
includes taxes & fees
Jun 9 - Jun 10
Key West Cottages

Blufin Bungalows & Marina

Blufin Bungalows & Marina
3.0 star property
Down the Marsh
9.6 out of 10, Exceptional, (258 reviews)
"Loved everything about our stay"
United States
Elizabeth
The price is CA $355
CA $477 total
includes taxes & fees
Jun 4 - Jun 5
Blufin Bungalows & Marina

Cottage near the Bay

Cottage near the Bay
Crisfield
8.8 out of 10, Excellent, (54 reviews)
"Property was exactly as pictured, Crystal is very prompt if contacted & very accomdating to questions. If you are looking in ng for some quiet peacefulness yet close to the water, or nearby towns & attractions & travel with your dog this is the perfect spot! My dogs were very content & I had no worries as to if they would be bothered by distractions because there are no distractions, it was a vacation for them as well as cottage is on a quiet street & it was very nice to sit outside wuth them &...
United States
Shelley
The price is CA $112
CA $259 total
includes taxes & fees
May 30 - May 31
Cottage near the Bay

Greenbackville Retreat w/ Deck: 1 Mi to Marina!

Greenbackville Retreat w/ Deck: 1 Mi to Marina!
3.0 star property
Captain's Cove
The price is CA $338
CA $786 total
includes taxes & fees
May 31 - Jun 1
Greenbackville Retreat w/ Deck: 1 Mi to Marina!

Waterfront Bungalow on Chincoteague Bay (VA)! - Waterfront Bungalow with Two Bedrooms

Waterfront Bungalow on Chincoteague Bay (VA)! - Waterfront Bungalow with Two Bedrooms
Down the Marsh
9.8 out of 10, Exceptional, (29 reviews)
"Great place to rent"
United States
Hazel T.
Waterfront Bungalow on Chincoteague Bay (VA)! - Waterfront Bungalow with Two Bedrooms

Salisbury Cottage

Salisbury Cottage
Salisbury
10.0 out of 10, Exceptional, (38 reviews)
"My family and I had a great stay was a comfy and safe space to relax and enjoy our Halloween weekend would definitely recommend!"
United States
Mackenzie N.
The price is CA $236
CA $532 total
includes taxes & fees
Jun 1 - Jun 2
Salisbury Cottage

Pet-friendly creekside cottage w/ backyard

Pet-friendly creekside cottage w/ backyard
Up the Neck
9.4 out of 10, Exceptional, (137 reviews)
"House was exactly as advertised. Everything worked as expected. This house is one of the few in this town that offered linens, a big selling point for us."
United States
Kato A.
The price is CA $366
CA $628 total
includes taxes & fees
Jun 3 - Jun 4
Pet-friendly creekside cottage w/ backyard

Bayfront Modern Retreat • Panoramic Views, Dock, Kayak, Pools & Resort Amenities

Bayfront Modern Retreat • Panoramic Views, Dock, Kayak, Pools & Resort Amenities
Captain's Cove
9.8 out of 10, Exceptional, (66 reviews)
"What a stunning view and super welcoming host!! We loved our stay and especially enjoyed the kayaks and bikes, great welcome kit of toiletries and kitchen supplies, very comfortable beds and soft sheets, outdoor space to watch the stars, and quiet, peaceful neighborhood. "
United States
l h.
The price is CA $118
CA $502 total
includes taxes & fees
May 31 - Jun 1
Bayfront Modern Retreat • Panoramic Views, Dock, Kayak, Pools & Resort Amenities

Salisbury Riverfront Lofts

Salisbury Riverfront Lofts
3.0 star property
Salisbury
9.2 out of 10, Wonderful, (25 reviews)
"It was a great stay nice comfortable place "
United States
Adam
The price is CA $97
CA $349 total
includes taxes & fees
Jun 1 - Jun 2
Salisbury Riverfront Lofts

Salisbury Hideaway

Salisbury Hideaway
Salisbury
10.0 out of 10, Exceptional, (21 reviews)
"Had a wonderful time house had everything you would need for a stay located right in the heart of Salisbury. Will definitely be going back to stay in this particular house. Thank you"
United States
Bryan M.
The price is CA $179
CA $465 total
includes taxes & fees
Jun 1 - Jun 2
Salisbury Hideaway

Assateague Inn 213 by Seaside Vacations & Sales

Assateague Inn 213 by Seaside Vacations & Sales
Chincoteague Island
9.4 out of 10, Exceptional, (34 reviews)
"I liked the location of the Inn on the island. The room(s) were very clean, well furnished and bed was super comfortable. "
United States
Marie E.
The price is CA $151
CA $278 total
includes taxes & fees
May 31 - Jun 1
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, (26 reviews)
"Convenient location with everything we needed"
United States
John S.
The price is CA $164
CA $294 total
includes taxes & fees
May 31 - Jun 1
Assateageue Inn 104 by Seaside Vacations & Sales

Deal Island Bay Cottage

Deal Island Bay Cottage
Deal Island
9.6 out of 10, Exceptional, (59 reviews)
"We got every year and stay here, it’s great! "
United States
Margaret H.
The price is CA $197
CA $363 total
includes taxes & fees
Jun 3 - Jun 4
Deal Island Bay Cottage

6 Mi to Salisbury: Forest-view Sanctuary!

6 Mi to Salisbury: Forest-view Sanctuary!
3.0 star property
Parsonsburg
The price is CA $143
CA $373 total
includes taxes & fees
Jun 3 - Jun 4
6 Mi to Salisbury: Forest-view Sanctuary!

Retro Hipster: Close to downtown, dining and fun

Retro Hipster: Close to downtown, dining and fun
Salisbury
9.2 out of 10, Wonderful, (15 reviews)
"Nice large, bright kitchen, each room has a bathroom! Nice river view, many shops within walking distance and good coffee and breakfast right diwnstairs! Loved the funky, whimsical decor too."
United States
Joan
The price is CA $112
CA $274 total
includes taxes & fees
Jun 1 - Jun 2
Retro Hipster: Close to downtown, dining and fun

Coastal Retreat w/Deck & EV Charger 1 Mi to Marina

Coastal Retreat w/Deck & EV Charger 1 Mi to Marina
Captain's Cove
The price is CA $302
CA $798 total
includes taxes & fees
May 31 - Jun 1
Coastal Retreat w/Deck & EV Charger 1 Mi to Marina

Twinkle Twinkle Little Tarr- Secluded Coastal Retreat Near East Side

Twinkle Twinkle Little Tarr- Secluded Coastal Retreat Near East Side
Chincoteague
The price is CA $636
CA $802 total
includes taxes & fees
Jun 20 - Jun 21
Twinkle Twinkle Little Tarr- Secluded Coastal Retreat Near East Side

Great Water Views in quiet pet-friendly location facing lighthouse. Large Yard

Great Water Views in quiet pet-friendly location facing lighthouse. Large Yard
Birch Town
9.6 out of 10, Exceptional, (43 reviews)
"It was family & friends that needed a get away and we really Enjoy the area"
United States
Lori D.
The price is CA $186
CA $601 total
includes taxes & fees
Jun 2 - Jun 3
Great Water Views in quiet pet-friendly location facing lighthouse. Large Yard

Saltwater Sunrise- 2BR | Pond Front | Close to Park

Saltwater Sunrise- 2BR | Pond Front | Close to Park
Chincoteague
10.0 out of 10, Exceptional, (1 review)
The price is CA $653
CA $820 total
includes taxes & fees
Jun 17 - Jun 18
Saltwater Sunrise- 2BR | Pond Front | Close to Park

Chincoteague Island House "Sir Whelk-A-Lot" Kayaks Included! Downtown Location!

Chincoteague Island House "Sir Whelk-A-Lot" Kayaks Included! Downtown Location!
Downtown Chincoteague
10.0 out of 10, Exceptional, (72 reviews)
"Great communication with the host and the house was very clean, well kept, and as advertised. "
United States
Heather H.
The price is CA $211
CA $466 total
includes taxes & fees
Jun 3 - Jun 4
Chincoteague Island House "Sir Whelk-A-Lot" Kayaks Included! Downtown Location!
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.

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 Princess Anne Town Hall 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.