Westover holiday lettings

We found 58 holiday rentals — enter your dates for availability

Discover a selection of 6 homes and other holiday rentals in Westover that are perfect for your trip. Whether you’re travelling with friends, family or even pets, holiday rentals have the amenities that you expect for your stay, which might include Wi-Fi and a washer and dryer. Whatever you're looking for, you'll be sure to find a property to rent to meet everyone's needs, including a place that is accessible or non-smoking.

Find spaces that suit your style

Why visit Westover

  • Outdoor Adventures: Westover offers an abundance of outdoor activities, perfect for adventure seekers and nature lovers alike.
  • Coastal Charm: Enjoy stunning sea views and relaxing days at picturesque beaches, ideal for a tranquil getaway.
  • Historical Experiences: Explore local historic colleges and engage with the rich cultural heritage of the area.
  • Family-Friendly Attractions: Visit nearby beach houses and coastal attractions that ensure fun for all ages.
  • Variety of Accommodations: Choose from private vacation homes, charming cottages, or modern condos for a perfect stay.

Popular types of accommodation in Westover

Planning a getaway to Westover? You're in for a treat! Discover the charm of Houses, delightful Cottages, and modern Condos. Whether you're dreaming of a beach house in Westover or near Milford, we’ve got you covered. Enjoy the local favourites like the Beach House Pub and unwind at the Beach House at Milford. Your perfect holiday accommodation awaits!

  • Houses: The top choice for visitors to Westover, offering spacious and comfortable lodgings ideal for families or groups.
  • Cottages: A delightful option, these quaint abodes provide a warm and homely atmosphere, perfect for a peaceful retreat.
  • Condos: A popular selection, condos offer modern amenities and often come with stunning views, ideal for a convenient stay.
  • Cabins: For those seeking a rustic experience, cabins provide a charming escape into nature.
  • Apartments: A versatile choice, apartments are suitable for both short and long stays, offering the comforts of home.**

Top attractions in and around Westover

Westover, Maryland, is perfect for an outdoor and adventure holiday, offering a blend of historical and cultural experiences. Visitors can explore local points of interest such as historic colleges, scenic islands, and engaging science museums. Families will enjoy activities that include visiting nearby beach houses and other coastal attractions, ensuring a memorable getaway filled with fun and exploration.

  • University of Maryland Eastern Shore: This historic college boasts a rich cultural atmosphere, offering a glimpse into the educational heritage of the region, located 3.7km from Westover.
  • Delmarva Discovery Center: A family-friendly science museum that immerses visitors in local ecology and history, situated 5.0km from Westover, making it an engaging experience for all ages.
  • Coventry Parish Ruins: Nestled within Westover, these historic ruins provide a fascinating insight into the area's past, surrounded by a serene cultural landscape.

Things to do recommended for couples

For a romantic getaway in Westover, visit Bordeleau Winery, located 6.8km away. Indulge in exquisite wines while soaking up the charming atmosphere. Enjoy a delightful experience filled with romance and entertainment vibes, perfect for couples seeking a memorable outing.

Things to do recommended for families

Families will have a fantastic time at the Hytche Athletic Center, just 3.7km from Westover, enjoying various sports activities. For a more relaxed vibe, Pemberton Historical Park, located 13.7km away, offers a serene escape, while Coco's Funhouse, 11.2km away, promises adventure and fun for all.

Things to do recommended for groups

Enjoy a fantastic group outing at Great Hope Golf Course in Westover, or venture slightly further to Nassawango Golf Course, 8.1km away, and Nutter's Crossing Golf Club, 9.9km distant. Each offers an excellent outdoor sports atmosphere for a memorable experience.

What do I need to keep in mind when booking a vacation in 'Westover

If you're travelling with a group, family, pets, or planning an extended stay, it's important to use the right filters to match your priorities. Here are some helpful booking tips for Vrbo.

  • Traveling to Westover with a group: Think about how many bedrooms will be necessary, along with features like a fully equipped kitchen or outdoor areas for group gatherings. Thankfully, you can easily apply filters for all these options and more on Vrbo.
  • Traveling to Westover with young kids: Travelling with young children can indeed present its challenges. It's essential to prioritise their comfort and safety, along with ensuring access to suitable amenities, like a private swimming pool. Additionally, it's wise to think about how close you are to attractions that are family-friendly.
  • Taking your pets with you to Westover: For many families, a holiday isn’t truly fulfilling without their beloved pet by their side. If this resonates with you, explore Vrbo properties that welcome pets. Most of these pet-friendly accommodations offer feeding bowls and beds, ensuring that every member of the family feels at home.
  • Planning for a long term stay visiting Westover: If you’re in search of holiday rentals offering discounts for stays of a month or more, you’ve come to the perfect spot. By applying the appropriate filter, you can effortlessly discover and save on monthly rentals. Don’t forget to include features such as a parking space, a well-equipped kitchen, or a private pool in your search criteria as well.

Where to stay in and around Westover

Westover, Maryland, offers a delightful blend of outdoor adventures and coastal charm. Enjoy the picturesque beach and stunning sea views, perfect for a relaxing getaway. Nearby, Milford and Isle of Wight provide charming experiences for families and those seeking a tranquil escape. With its historical vibes and family-friendly atmosphere, Westover is an ideal destination for both budget-conscious travellers and those looking for a secluded retreat.

  • Princess Anne: Situated a mere 3.7km from Westover, Princess Anne is a charming city steeped in culture and history. It offers an engaging atmosphere for families and outdoor enthusiasts alike, with attractions such as the historic college university and nearby beaches. Stroll along the boardwalk or indulge in retail therapy at the local shopping centre. With its blend of educational and recreational experiences, Princess Anne serves as a delightful base for exploring the surrounding area.
  • Rehobeth: Nestled close to Westover, Rehobeth is a picturesque village known for its outdoor charm and family-friendly environment. Visitors flock to its stunning beach and vibrant esplanade, perfect for a leisurely day out. The boardwalk beckons with recreational areas and inviting shops, making it an ideal spot for couples seeking a romantic getaway or families looking for fun. Whether you're sunbathing on the beach or exploring local boutiques, Rehobeth promises a refreshing escape.
  • Frenchtown-Rumbly: This lively village near Westover is a haven for adventure seekers and entertainment lovers. With attractions like a mini golf course and a water park, Frenchtown-Rumbly offers a perfect blend of excitement and relaxation. Nature enthusiasts will appreciate the nearby nature reserve and scenic beaches, while the iconic bridge adds to the village's charm. Whether you're looking for thrilling activities or a tranquil day in nature, Frenchtown-Rumbly caters to all tastes.

Best time to go to Westover

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

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January37.2°F (2.9°C)Light RainMostly SunnyModerately LowAverage
February39.9°F (4.4°C)Light RainMostly SunnyModerately LowSlightly Low
March45.9°F (7.7°C)Light RainMostly SunnyAverageSlightly Low
April55.8°F (13.2°C)Light RainMostly SunnyAverageAverage
May64.6°F (18.1°C)Light RainMostly SunnyAverageAverage
June73.2°F (22.9°C)Light RainMostly SunnyModerately HighSlightly High
July78.3°F (25.7°C)Light RainMostly SunnyModerately 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
November50.2°F (10.1°C)Light RainMostly SunnyModerately LowAverage
December43.0°F (6.1°C)Light RainMostly SunnyModerately HighSlightly Low

Booking with Vrbo is simple

Are you hoping to cut costs on your upcoming holiday? It might be worth being flexible with your travel dates, as prices can vary quite a bit. Additionally, opting for a longer stay often leads to significant savings. To help you discover the perfect Vrbo property that fits your budget, take advantage of our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Effortless planning

Vrbo’s Trip Board offers you a user-friendly platform to plan new journeys, seamlessly resume previous ones, or manage your travel arrangements. You can easily find your saved or booked properties sorted into categories such as Potential, Upcoming, or Current Trips. To begin exploring the benefits of Trip Boards, please visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

Head to the historical city of Westover

Enjoy the history and other features of Westover. One of the city's many top draws is its golfing. Many of our holiday rentals offer full kitchens, spacious living quarters and sometimes even a hot tub—perfect for a relaxing getaway.

Sightseeing in and around Westover

Do you want to discover top things to see and do in the area? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that makes Westover a fun spot to go on holiday. These are some of the most popular attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Nutter's Crossing Golf Club (16 mi / 25.7 km)
  • Captain's Cove Golf and Yacht Club (17.8 mi / 28.7 km)
  • Salisbury Zoo (17.9 mi / 28.7 km)
  • Coco's Funhouse (18.5 mi / 29.7 km)
  • Bordeleau Winery (10.9 mi / 17.6 km)
  • Great Hope Golf Course (0.8 mi / 1.2 km)

Exploring the natural landscape of Westover

Whether you're an adventurous traveller or just want to spend some time taking in the scenery, Westover is a great spot to appreciate mother nature. These are some of the area's most enchanting natural features, all within 30 miles (48.2 km) of the city centre:

  • Rock Island (12.6 mi / 20.3 km)
  • Jersey Island (13.7 mi / 22 km)
  • Big Island (13.8 mi / 22.2 km)
  • Pocomoke River State Park (14.6 mi / 23.5 km)
  • Pemberton Historical Park (16.1 mi / 25.9 km)
  • City Park Picnic Island (17.9 mi / 28.8 km)

Travelling to and around Westover

The nearest airport is in Salisbury, MD (SBY-Salisbury - Ocean City Wicomico Regional), located 18.5 mi (29.7 km) from the city centre. If you're unable to find a flight that fits your schedule, you could book a flight to Ocean City, MD (OCE-Ocean City Municipal), which is 34.5 mi (55.6 km) away.

Frequently asked questions

What is the best area to stay in Westover when booking a holiday rental?
When considering a holiday rental in Westover, Maryland, the nearby area of Princess Anne is a fantastic option. This charming town offers a quaint atmosphere with a variety of properties ranging from cosy cottages to spacious family homes. Princess Anne is known for its close-knit community feel and beautiful surroundings, making it an inviting choice for visitors.

One of the top attractions in Princess Anne is the University of Maryland Eastern Shore, which boasts lovely campus grounds and often hosts cultural events. Additionally, the nearby Pocomoke River State Park is a wonderful spot for nature enthusiasts, offering hiking trails and opportunities for kayaking, superb for a day of outdoor adventure.

Another appealing neighbourhood is Crisfield, located just a short drive away. Crisfield is famous for its seafood, particularly its crab dishes, and visitors can enjoy a meal at local eateries while taking in views of the waterfront. The town also features the J. Millard Tawes Museum, which provides insight into the region's maritime history and culture.
How much does it cost to rent a holiday home in Westover?
Prices for holiday rentals in Westover 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 Westover 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 Westover holiday house rentals?
You can find great discounts on house rentals in Westover 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.
Where are the best areas for renting a beach house in Westover?
For renting a beach house in Westover, the nearby areas along the Eastern Shore of Maryland offer some appealing options. Specifically, the coastal towns of Ocean City and Assateague Island are great choices, providing easy access to sandy beaches and vibrant seaside activities. In Ocean City, beachfront properties often come with amenities such as private balconies, outdoor pools, and direct beach access, making them ideal for families or groups seeking a lively beach experience.

Assateague Island, known for its stunning natural beauty and wild ponies, offers a more tranquil setting for those looking to unwind. Beach houses here frequently include features like outdoor grills, spacious decks, and proximity to nature trails, superb for enjoying a more relaxed beach holiday. Travellers can expect to find properties that allow for easy exploration of the island's pristine landscapes, with some homes situated just a short walk from the beach.

In addition to the beach access, both regions boast a variety of local attractions, including restaurants and shops that enhance the holiday experience.
What is the most popular type of holiday rental accomodation in Westover?
In Westover, holiday houses and cottages are the most popular types of holiday rental accommodations, with several options available throughout the area. These rentals typically offer a homely atmosphere, featuring amenities such as fully equipped kitchens, comfortable living spaces, and outdoor areas for relaxation. Many properties are set in tranquil surroundings, ideal for those looking to enjoy the natural beauty of Maryland.
Are there any family house rentals in Westover?
In Westover, Maryland, there are several family-friendly house rentals available. This charming locale offers a variety of spacious homes that cater to families looking for comfort and convenience. Many of these properties include inviting living areas, fully equipped kitchens for preparing meals together, and outdoor spaces great for children to enjoy.

Visitors can also explore nearby attractions, such as the scenic beauty of the Chesapeake Bay and the local parks that provide opportunities for outdoor activities.
Can I rent a holiday home with a pool or hot tub in Westover?
In Westover, Maryland, there are several holiday homes available for rent that feature pools and hot tubs. This charming area provides a peaceful retreat for travellers looking to relax and enjoy the outdoors. Many of these properties come equipped with private pools, hot tubs, spacious outdoor areas, and fully equipped kitchens, ideal for family gatherings or socialising with friends.

The surrounding landscapes offer a serene backdrop, allowing guests to unwind in a tranquil setting. Additionally, the proximity to local attractions and natural beauty enhances the appeal of renting a holiday home in Westover.
Can I find long-stay holiday rentals in Westover?
A long-stay holiday rental in Westover 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 travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there any Westover holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Westover 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 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 Westover?
In Westover, popular rental amenities include fully equipped kitchens, which allow guests to prepare their own meals during their stay. Many properties also feature decks or patios, providing outdoor spaces for relaxation and enjoyment of the surrounding scenery. Onsite parking is commonly available, making it convenient for those travelling with their own vehicles. Additionally, some rentals permit pets, suiting visitors who wish to bring their furry companions along. Many properties may also provide conveniences such as blenders, enhancing the self-catering experience.
When is the best time to visit Westover for a holiday rental?
The peak season for holiday rentals in Westover runs from June to August, with July being the most popular month for visitors. This vibrant time of year welcomes travellers, eager to explore the beautiful surroundings and engage in outdoor activities under the warm sun. The region's lush landscapes are great for hiking, cycling, and enjoying the local parks, making it an ideal choice for those who appreciate nature and adventure.

During these summer months, temperatures typically range from 20 to 30 degrees Celsius, creating comfortable conditions for sightseeing and outdoor fun. You'll find the town buzzing with activity, from festivals to farmers' markets, all of which showcase the local culture and community spirit.

If you're looking for a more affordable time to visit, consider planning your trip in February. While this is the quieter season, it offers a unique charm, with fewer crowds and the opportunity to enjoy the tranquility of Westover. The crisp winter air can be invigorating, great for peaceful walks and enjoying the serene landscapes.

Ultimately, the best time to visit Westover depends on your preferences.
How early should I book a Westover holiday rental?
Book your Westover holiday 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 holiday rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Westover?
In Westover, Maryland, visitors can enjoy a variety of attractions that showcase the natural beauty and local culture. The nearby Blackwater National Wildlife Refuge is a major highlight, offering opportunities for birdwatching, hiking, and enjoying the scenic landscapes of the Eastern Shore. This expansive refuge is home to diverse wildlife, including migratory birds, making it a great spot for nature enthusiasts.

Additionally, the charming town of Westover features local shops and eateries that reflect the community's character. You can explore the historic sites and enjoy the quaint atmosphere while sampling local cuisine. For those interested in outdoor activities, the surrounding areas provide access to beautiful waterways, ideal for kayaking and fishing.
Can I change or cancel my Westover home rental booking on Vrbo?
To find Westover holiday 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 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 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, Vrbo 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 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 Westover holiday 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, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.

Vrbo 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.
Can I plan a group trip on Vrbo?
Vrbo'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 favorites, and build the perfect itinerary together.

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