Princess Anne holiday rentals

We found 11 holiday rentals — enter your dates for availability
Scroll through and select from holiday rentals in Princess Anne to find one that's perfect for your trip. Whether you’re staying in a holiday home with friends, family or even just your pets, you'll find the best amenities for hanging out with the people that matter most, which might include Wi-Fi and a hot tub. Whatever you're looking for, you'll find a property to rent for everyone's needs, including a place that is accessible or non-smoking.

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

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 holiday or a trip with friends, rental homes often come with separate dining areas and spacious living rooms.

Activities and attractions in and around Princess Anne

Are you hoping to find things to do during your stay? Venture out of your holiday home and check out everything that Princess Anne has to offer. These are some of the top attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Bordeleau Winery (5.5 mi / 8.9 km)
  • Salisbury Zoo (12.4 mi / 20 km)
  • Captain's Cove Golf and Yacht Club (20.6 mi / 33.1 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 fun outdoor activities or just want to spend some time taking in the scenery, you'll be sure to find the perfect setting for your holiday in Princess Anne. Here are some of the area’s most stunning features, all within 30 miles (48.2 km) of the city centre:

  • Pemberton Historical Park (10.4 mi / 16.8 km)
  • Crab Island (12.4 mi / 19.9 km)
  • Pocomoke River State Park (14.4 mi / 23.2 km)
  • Smith Island (23.3 mi / 37.5 km)
  • Blackwater National Wildlife Refuge (27.7 mi / 44.6 km)
  • Mount Vernon Beach (8.4 mi / 13.5 km)

Transport 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 centre. If you're unable to find a flight that fits your schedule, you can also fly into Ocean City, MD (OCE-Ocean City Municipal), which is 32 mi (51.5 km) away.

Frequently asked questions

What is the most popular type of holiday rental accomodation in Princess Anne?
In Princess Anne, holiday houses are the most popular type of holiday rental, with several options available throughout the area. These properties typically offer spacious rooms, featuring multiple bedrooms, fully equipped kitchens, and comfortable living areas, making them ideal for families or groups. Additionally, there are several cottages and apartments that provide a more intimate setting for travellers looking for a cosy getaway. Many of these rentals include amenities such as outdoor seating areas and easy access to local attractions, allowing guests to enjoy the charm of this quaint town while having a comfortable base to return to after exploring the sights.
Are there any family house rentals in Princess Anne?
In Princess Anne, Maryland, there are several family-friendly house rentals available, making it an ideal spot for families looking for a memorable getaway. Many of these homes are situated near the charming downtown area, providing easy access to local shops and eateries. Visitors will find properties that boast spacious living areas, fully equipped kitchens for convenient meal preparation, and outdoor spaces where children can play and enjoy the fresh air.Additionally, the nearby deals of the Pocomoke River and the scenic landscapes of the Eastern Shore offer opportunities for outdoor activities such as kayaking and fishing. Families can also explore the historic sites and parks in the vicinity, ensuring a fun and enriching experience for all ages.
Are there pet-friendly house rentals in Princess Anne?
In Princess Anne, there are several pet-friendly house rentals available, making it a great choice for travellers looking to bring their furry companions along. Many of these properties offer a range of amenities, such as spacious living areas, fully equipped kitchens, and outdoor spaces where pets can enjoy the fresh air.The area is conveniently located near the beautiful Pocomoke River, which provides opportunities for leisurely walks and nature exploration. Nearby parks and natural reserves also cater to pet owners, offering scenic trails and open spaces.
Are there any remote work holiday rentals in Princess Anne?
In Princess Anne, Maryland, there are several remote work holiday rentals available, with around 12 options to choose from. These accommodations cater specifically to those looking to maintain their work commitments while enjoying a change of scenery. Many properties offer amenities such as dedicated laptop workspaces, free Wi-Fi both in rooms and in public areas, and comfortable desks designed for productivity.The town itself provides a peaceful setting, with proximity to local attractions like the University of Maryland Eastern Shore and the serene waters of the Pocomoke River. For those seeking a blend of work and leisure, the area offers a charming environment with ample opportunities for outdoor activities and exploring the natural beauty of the Eastern Shore. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Princess Anne?
In Princess Anne, holiday rentals typically feature a variety of amenities that enhance the comfort and convenience of stays. Most properties include a fully equipped kitchen, allowing guests to prepare their own meals, along with essential appliances like a blender. Many rentals also offer outdoor spaces such as decks or patios, as well as balconies that provide lovely views and a place to relax. For those needing to work or study during their stay, a desk is commonly available.
When is the best time to visit Princess Anne for a holiday rental?
The best time to visit Princess Anne for a holiday rental is during the peak summer season, which spans from June to August. This vibrant period draws travellers, as the warm weather creates superb conditions for exploring the nearby Assateague Island National Seashore and enjoying outdoor activities such as kayaking and hiking.July is particularly popular, with temperatures typically ranging from 20 to 30 degrees Celsius, making it a comfortable month for beach outings, picnics, and local festivals. The lively option during this time is enhanced by a variety of events and activities, ensuring plenty of options for entertainment and engagement.For those looking to save while still enjoying the charm of this lovely area, consider visiting in December. This quieter month offers a unique perspective of Princess Anne, allowing you to appreciate its serene beauty and local culture without the summer crowds. The mild winter climate provides a different but equally enjoyable experience, superb for leisurely walks and exploring the quaint town.Ultimately, your ideal time to visit will depend on whether you prefer the energy of the bustling summer season or the peacefulness of the off-peak months.
What are the top attractions in Princess Anne?
In Princess Anne, visitors can explore a variety of attractions that highlight the area's unique charm and natural beauty. The historic downtown area features quaint shops and local eateries, great for a leisurely stroll. One of the main attractions is the University of Maryland Eastern Shore, where visitors can appreciate the beautiful campus and possibly catch events or exhibitions.Nature enthusiasts will enjoy the nearby Pocomoke River State Park, which offers opportunities for hiking, canoeing, and wildlife observation amidst scenic landscapes. Additionally, the nearby Chesapeake Bay provides a lovely backdrop for fishing and boating activities. For those interested in history, the nearby town of Snow Hill offers a glimpse into the region's past with its historical sites and museums.
Are all fees included in the Princess Anne holiday homes prices shown on Stayz?
Stayz 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.
Are there any Princess Anne holiday homes with parking?
Stayz offers a wide selection of holiday homes in Princess Anne with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details 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.
Are there any discounts for Princess Anne holiday homes?
You can find great discounts on holiday homes in Princess Anne on Stayz, 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.
Can I change or cancel my Princess Anne holiday home booking on Stayz?
To find Princess Anne holiday rentals with free cancellation, just use Stayz'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". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Princess Anne?
A long-stay holiday home in Princess Anne is the best way to experience local living. Plus, you can make the most of long-stay discounts. 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.
Can I plan a group trip on Stayz?
Stayz's Trip Planner makes organising 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 favourites, and build the perfect itinerary together.
How early should I book a Princess Anne holiday home?
Book your Princess Anne holiday home 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 Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Princess Anne?
Prices for holiday homes 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 travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Princess Anne to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, 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.
Why should I join Stayz as a host?
Joining Stayz as a host opens the door to a global community of travellers 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, Stayz makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

More holiday ideas