Princess Anne vacation rentals

We found 13 vacation rentals — enter your dates for availability

Welcome to Princess Anne, where charming cottages meet stunning riverfront views, creating an inviting atmosphere perfect for family adventures and group getaways. Explore beautiful parks, engage with local culture at the V303 Princess Anne, and savor the scenic delights of nearby Salisbury and Westover. With a variety of cozy accommodations, from modern condos to quaint houses, you’ll enjoy the comfort and convenience of a home-like experience while making unforgettable memories together.

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Find out more about Princess Anne

Why visit Princess Anne

  • Outdoor Adventures: Enjoy family-friendly activities in beautiful parks and stunning nearby islands.
  • Cultural Experiences: Immerse yourself in local culture and visit attractions like the V303 Princess Anne.
  • Scenic Riverfront: Explore the downtown area with picturesque riverfront views, perfect for shopping and dining.
  • Cozy Accommodations: Choose from a range of lodging options, including charming cottages and modern condos.
  • Welcoming Community: Experience friendly encounters in a relaxing atmosphere ideal for budget travelers.

Popular types of accommodation in Princess Anne

Planning a getaway to Princess Anne? The excitement begins with selecting your perfect accommodation. From cozy houses and charming cottages to modern condos, there’s something for everyone. Explore a variety of Princess Anne apartments and homes for rent, complete with detailed floor plans to help you find the ideal space. Get ready for a memorable stay in this delightful destination.

  • Houses: The top choice for visitors in Princess Anne, offering spacious and comfortable stays for families or groups.
  • Cottages: A delightful option for a cozy getaway, perfect for those seeking charm and tranquility.
  • Condos: Ideal for those wanting modern amenities and a bit of luxury, often located near attractions.
  • Cabins: A favorite for nature enthusiasts, providing a rustic escape surrounded by scenic beauty.
  • Apartments: Convenient and budget-friendly, these are great for solo travelers or couples preferring a home-like setting.**

Top attractions in and around Princess Anne

Princess Anne, Maryland is an ideal destination for outdoor family vacations and cultural experiences. Visitors can explore various points of interest, including parks and nearby islands, offering plenty of activities for all ages. Whether you're looking for a relaxing day at the park or a cultural outing, Princess Anne has something to offer every traveler. Don't miss the chance to visit local attractions like the V303 Princess Anne for a memorable experience.

  • Somerset County Library: Located in the heart of Princess Anne, this library offers a welcoming atmosphere perfect for families. Engage in community programs, explore diverse literature, and enjoy cultural events that enrich the local vibe.
  • Delmarva Discovery Center: Situated 11 miles away, this interactive science museum is ideal for families. Discover fascinating exhibits on the region's natural history and culture, making learning fun and engaging for all ages.
  • Ward Museum of Wildfowl Art: Just 12 miles from Princess Anne, this art museum showcases exquisite wildfowl art and celebrates the region's rich cultural heritage, offering a unique perspective on avian artistry.

Things to do recommended for couples

For a romantic getaway in Princess Anne, explore the serene beauty of the Pocomoke River by kayak, enjoy a picnic at the scenic Cypress Park, and take a leisurely stroll through the charming downtown area filled with quaint shops and cozy cafés. It's the perfect setting for couples to reconnect.

Things to do recommended for families

Families can explore the rich history at the Maryland Coastal Bays Program or enjoy outdoor adventures at the nearby Pocomoke River State Park, where fishing and hiking await. Don't miss the local farmers' market for fresh produce and unique crafts.

Things to do recommended for groups

Groups visiting Princess Anne can explore the beautiful Pocomoke River State Park for hiking and kayaking, stroll through the charming downtown area, and enjoy local cuisine at family-owned restaurants. Don’t miss the chance to visit the University of Maryland Eastern Shore for cultural events and activities.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

What do I need to keep in mind when booking a vacation in Princess Anne

When planning your trip—whether you're traveling with a group, your family, or pets, or seeking extended stays—be sure to prioritize your preferences when filtering options. Here are some helpful Vrbo booking tips for you.

  • Traveling to Princess Anne with a group: Think about how many bedrooms you'll require, along with features like a complete kitchen or outdoor areas for group gatherings. Luckily, you can easily filter for these options and more on Vrbo.
  • Traveling to Princess Anne with young kids: Traveling with young kids can be quite demanding. It's important to prioritize their comfort and safety, along with suitable amenities like a private swimming pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Princess Anne: For many families, a vacation wouldn't be the same without their furry companions. If this resonates with you, consider exploring Vrbo properties that welcome pets. Many of these pet-friendly accommodations offer amenities like food bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Princess Anne: If you’re in search of vacation rentals that offer discounts for month-long stays, you’ve come to the perfect spot. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don't forget to include options like a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay in and around Princess Anne

Discover the charm of Princess Anne, Maryland, where outdoor adventures and cultural experiences await. Enjoy riverfront views while exploring the downtown area, perfect for shopping and dining. This family-friendly destination offers a relaxing atmosphere, making it ideal for budget travelers seeking friendly encounters and memorable excursions. Venture into nearby regions to enhance your experience with even more picturesque landscapes and welcoming communities.

  • Salisbury: Located 12 miles from Princess Anne, Salisbury is a vibrant city known for its rich mix of outdoor activities and family-friendly experiences. Visitors can enjoy a leisurely stroll along the scenic boardwalk, explore the local education hubs, or catch an exciting event at the arena entertainment facility. Notable attractions include the picturesque esplanade and historic college university, making Salisbury an ideal destination for history buffs and nature lovers alike.
  • Westover: Just 6 miles from Princess Anne, Westover is a charming city that offers visitors a delightful blend of outdoor adventures and stunning beach scenery. The area features a range of recreational areas perfect for family outings, along with convenient shopping centers for a little retail therapy. Highlights include the beautiful bay and a relaxing beach, as well as urban parks where you can unwind and soak in the local ambiance.
  • Mount Vernon: Nestled within the area of Princess Anne, Mount Vernon is a quaint village that invites travelers to immerse themselves in nature. The village is perfect for outdoor enthusiasts, offering activities like mini golf and educational experiences. Nature lovers will appreciate the nearby bay, serene lake, and peaceful nature reserve, making it an excellent spot for enjoying the great outdoors while taking in breathtaking views and a tranquil atmosphere.

Best time to go to Princess Anne

If you're planning a trip to Princess Anne, it's a good idea to check both the weather and property rates. The warmest month is July. Peak season runs in April and June to July, while off-peak times, like November to January tend to have fewer bookings and better deals.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January37.4°F (3.0°C)Light RainMostly SunnySlightly LowAverage
February39.9°F (4.4°C)Light RainMostly SunnyAverageSlightly Low
March45.9°F (7.7°C)Light RainMostly SunnyAverageSlightly Low
April55.8°F (13.2°C)Light RainMostly SunnySlightly HighAverage
May64.6°F (18.1°C)Light RainMostly SunnyAverageAverage
June73.2°F (22.9°C)Light RainMostly SunnySlightly HighSlightly High
July78.3°F (25.7°C)Light RainMostly SunnySlightly HighSlightly High
August76.6°F (24.8°C)Light RainMostly SunnyAverageSlightly High
September71.2°F (21.8°C)Light RainMostly SunnyAverageAverage
October61.5°F (16.4°C)Light RainMostly SunnyAverageAverage
November50.0°F (10.0°C)Light RainMostly SunnySlightly LowAverage
December43.2°F (6.2°C)Light RainMostly SunnySlightly LowSlightly Low

Booking with Vrbo is a breeze

Looking to save on your next trip? Consider being flexible with your travel dates, as prices can fluctuate. Additionally, extending your stay often results in significant savings. To discover the ideal Vrbo property that fits your budget, utilize our filters to search by price, location, and type of vacation rental.

Vrbo Trips: Planning made easy

Vrbo’s Trip Board provides a convenient platform for you to create new travel plans, manage your existing bookings, or review your reservations. You can easily find your saved or booked properties organized into categories such as Potential, Upcoming, or Current Trips. To check out the Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

The beachside setting of Princess Anne is ready to explore

The beaches and other outdoor surroundings create an inviting atmosphere in Princess Anne. This romantic city is known for its seafood restaurants, shopping and university setting. If you need more space to accommodate a family vacation or friends trip, rental homes often come with separate dining areas and spacious living rooms.

Activities and attractions in and around Princess Anne

Do you want to discover top things to see and do in the city? Venture out of your vacation home and check out everything that makes Princess Anne a fun spot to vacation. These are some of the major attractions to see, all within 30 miles (48.2 km) of the city center:

  • Salisbury Zoo (12.4 mi / 20 km)
  • Captain's Cove Golf and Yacht Club (20.6 mi / 33.1 km)
  • Bordeleau Winery (5.5 mi / 8.9 km)
  • Great Hope Golf Course (6.4 mi / 10.3 km)
  • Coco's Funhouse (13.1 mi / 21 km)
  • Nutter's Crossing Golf Club (10.9 mi / 17.5 km)

Exploring the natural features in Princess Anne

Whether you're looking for adventure or just want to take in the scenery, Princess Anne is a great place to spend some time outside. Here are a few of the area's noteworthy features, all within 30 miles (48.2 km) of the city center:

  • Monie Island (9 mi / 14.5 km)
  • Pemberton Historical Park (10.4 mi / 16.8 km)
  • Cypress Park (10.9 mi / 17.5 km)
  • Crab Island (12.4 mi / 19.9 km)
  • Pocomoke River State Park (14.4 mi / 23.2 km)
  • Wellington Beach and Park (17.1 mi / 27.5 km)

Transportation to and around Princess Anne

The nearest airport is in Salisbury, MD (SBY-Salisbury - Ocean City Wicomico Regional), located 13.6 mi (21.8 km) from the city center. If you're unable to find a flight that fits your schedule, you could also fly into Ocean City, MD (OCE-Ocean City Municipal), which is 32 mi (51.5 km) away.

Frequently asked questions

What is the best area to stay in Princess Anne, Maryland, United States of America when booking a vacation rental?
When considering a vacation rental in Princess Anne, Maryland, the downtown area is a fantastic choice. This vibrant neighborhood is characterized by its charming small-town feel and proximity to local attractions. One of the highlights is the University of Maryland Eastern Shore, which not only adds a lively option to the area but also hosts various events and cultural activities throughout the year. Additionally, the nearby Pocomoke River offers beautiful scenery and opportunities for outdoor activities, such as fishing and kayaking, making it a superb spot for nature enthusiasts.

In downtown Princess Anne, you'll find a selection of vacation rentals that cater to different preferences, from cozy cottages to larger homes. This area is also conveniently located for exploring nearby attractions, including the scenic Assateague Island National Seashore, where visitors can enjoy stunning beaches and the famous wild ponies.
How much does it cost to rent a vacation home in Princess Anne?
Prices for vacation rentals in Princess Anne vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Princess Anne to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Princess Anne vacation house rentals?
You can find great discounts on house rentals in Princess Anne on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
What is the most popular type of vacation rental accomodation in Princess Anne?
In Princess Anne, vacation houses are the most popular type of rental, with several available throughout the town. These homes often feature multiple bedrooms, spacious living areas, and fully equipped kitchens, making them ideal for families or groups looking for a comfortable stay. Many of these vacation houses are situated in quiet neighborhoods, providing a peaceful atmosphere close to local attractions. Additionally, there are several apartments and cottages available, which offer a more compact and cozy living space. Apartments often include essential amenities like kitchen facilities and living areas, while cottages provide a charming, rustic feel.
Are there any family house rentals in Princess Anne?
In Princess Anne, Maryland, there are several family-friendly house rentals available, great for those traveling with children. The locale offers a variety of properties that feature spacious living areas, fully equipped kitchens for preparing meals together, and outdoor spaces where kids can play safely. Many homes also include amenities like air conditioning and Wi-Fi, ensuring a comfortable and convenient stay for families.

Visitors can enjoy nearby attractions such as the University of Maryland Eastern Shore, which provides educational opportunities and beautiful grounds for leisurely strolls. Additionally, the charming small-town atmosphere allows families to explore local shops and eateries, fostering a sense of community.
Can I find long-stay vacation rentals in Princess Anne?
A long-stay vacation rental in Princess Anne is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there pet-friendly house rentals in Princess Anne?
In Princess Anne, several pet-friendly house rentals are available, suiting travelers who wish to bring their furry companions along. Many of these homes offer amenities such as spacious backyards, fully equipped kitchens, and comfortable living spaces, making them great for families or groups. Some properties may also include features like outdoor seating areas and fire pits, enhancing the experience of enjoying the pleasant Maryland weather.

The town is close to various natural attractions, including the nearby Deal Island Wildlife Management Area, which provides opportunities for hiking and exploring nature with pets. Additionally, the surrounding area offers charming local shops and eateries, ensuring that guests have everything they need within reach while enjoying their stay.
Are there any remote work vacation rentals in Princess Anne?
In Princess Anne, Maryland, there are several vacation rentals that cater to remote workers, making it a suitable destination for those looking to blend work and leisure. Many of these properties provide essential amenities such as high-speed Wi-Fi and dedicated workspace areas, ensuring a productive environment. Guests can also enjoy free Wi-Fi in public areas, which is great for those who might want to work outside or in communal settings.

The town's proximity to points of interest, such as the picturesque Pocomoke River and the nearby University of Maryland Eastern Shore, allows for a balance of work and exploration. After a day of remote work, travelers can unwind by taking advantage of the local parks or visiting charming downtown shops and eateries. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Princess Anne vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Princess Anne with parking available—perfect for families or travelers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Princess Anne?
In Princess Anne, popular rental amenities include kitchens, which allow travelers to prepare their own meals, and blenders for those who enjoy making smoothies or other blended drinks. Many vacation rentals also feature decks or patios, providing outdoor spaces to relax and enjoy the pleasant surroundings. Some properties come with balconies, offering lovely views of the area, and desks, which cater to those needing a workspace during their stay.
When is the best time to visit Princess Anne for a vacation rental?
The peak travel season in Princess Anne runs from June to August, making it a vibrant time for visitors seeking sun-soaked days and endless outdoor activities. July stands out as the most popular month, when families flock to enjoy the warm temperatures, typically ranging from the low 70s to mid-80s Fahrenheit. This is an ideal time for beachgoers to bask in the sun or take part in local events and festivals that reflect the region's rich culture.

During these summer months, you can enjoy a variety of activities such as kayaking on the Pocomoke River or exploring the nearby Assateague Island, famous for its wild horses. The lush landscapes and friendly atmosphere make for an unforgettable experience filled with adventure.

If you're looking for a more budget-friendly option, consider planning your visit in December. While it's the low season, this month offers a unique charm with fewer crowds, allowing for a more relaxed exploration of the town's local shops and holiday festivities. Additionally, winter months in Princess Anne can provide a cozy retreat, superb for enjoying quiet walks and the serene beauty of the region.

Ultimately, the best time to visit Princess Anne depends on your travel preferences—whether you thrive on the energy of summer activities or enjoy the tranquil, charming vibe of the off-season.
How early should I book a Princess Anne vacation rental?
Book your Princess Anne vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Princess Anne, Maryland, United States of America?
In Princess Anne, visitors can explore a variety of attractions that highlight the town's charm and history. The University of Maryland Eastern Shore (UMES) offers beautiful grounds and cultural events, making it a focal point for community activities. Nearby, the historic downtown area features quaint shops and local eateries that reflect the town's heritage.

For nature enthusiasts, the nearby Pocomoke River State Park provides opportunities for hiking, fishing, and enjoying scenic views along the river. The park's trails are superb for exploring the natural beauty of the area. Additionally, the town is close to the Assateague Island National Seashore, famous for its wild horses and pristine beaches, offering a great day trip option for those looking to experience the coastal environment.
Can I change or cancel my Princess Anne home rental booking on Vrbo?
To find Princess Anne vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travelers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cozy cabin or a beach condo, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Princess Anne vacation rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations like last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to help resolve problems quickly and effectively.

Vrbo also offers support via live chat through our Help Center, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organizing group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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