Whaleyville holiday rentals

We found 290 holiday rentals — enter your dates for availability
Discover a selection of holiday rentals in Whaleyville that are perfect for your trip. Holiday rentals provide the best amenities for you and your friends, family or even pets, such as parking and a pool. You'll be able to choose a property to rent that has what everyone needs, including places that are non-smoking or accessible.

Holiday rentals with weekly discounts – Whaleyville

Showing deals for:25 Dec - 1 Jan

Upstairs kitchen/dinete
Terrace/patio
Upstairs living room
Upstairs sunroom
Exceptional
(73 reviews)

FAIRWAY TO HEAVEN: GOLF course views and BEACH parking pass

Berlin

5% off
AU$2,280
for 7 nights, 1 apartment
AU$326 per night
includes taxes & fees
FAIRWAY TO HEAVEN: GOLF course views and BEACH parking pass
Marina
Living area
Living area
Living area
Exceptional
(10 reviews)

Ocean Pines Chalet

Berlin

6% off
AU$4,382
for 7 nights, 1 home
AU$626 per night
includes taxes & fees
Ocean Pines Chalet
Living area
Room
Terrace/patio
Interior
Exceptional
(44 reviews)

Ocean Pines Retreat with Beach Club

Berlin

8% off
AU$3,400
for 7 nights, 1 home
AU$486 per night
includes taxes & fees
Ocean Pines Retreat with Beach Club
Front Entrance
Exterior
Loft
Terrace/patio
Exceptional
(18 reviews)

Summer Breeze - Waterfront Cottage For Rent

Berlin

8% off
AU$4,173
for 7 nights, 1 home
AU$596 per night
includes taxes & fees
Summer Breeze - Waterfront Cottage For Rent
Dining room for 8; doors can close for privacy in sitting room
Larger couch and ottoman, open to kitchen
There are 5 community pools available to guests for a daily fee
Kitchen remodel completed Fall 2024
Exceptional
(31 reviews)

Private and pet-friendly, with game room and upgraded kitchen

Berlin

7% off
AU$2,481
for 7 nights, 1 home
AU$354 per night
includes taxes & fees
Private and pet-friendly, with game room and upgraded kitchen
Exterior
Pool
Property grounds
Room
Exceptional
(5 reviews)

Cozy house in Ocean pines, only 10 mins away from Ocean City.

Berlin

8% off
AU$3,814
for 7 nights, 1 home
AU$545 per night
includes taxes & fees
Cozy house in Ocean pines, only 10 mins away from Ocean City.
Property grounds
Sunset at the Yacht Club
Yacht Club
Sports Core Indoor Pool
Exceptional
(11 reviews)

Coastal Oasis in Ocean Pines

Berlin

8% off
AU$2,861
for 7 nights, 1 home
AU$409 per night
includes taxes & fees
Coastal Oasis in Ocean Pines

  • 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

Find the perfect holiday rental for your Whaleyville getaway

Learn about the unique charm of Whaleyville with a stay in a holiday home rental. This city has something for everyone. 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 Whaleyville

Do you want to find things to do during your stay? Venture out of your cosy holiday rental and check out everything that makes Whaleyville a one-of-a-kind holiday spot. Here are some of the top attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Frontier Town Water Park and Golf (11.1 mi / 17.8 km)
  • Bayside Resort Golf Club (11.3 mi / 18.2 km)
  • Jolly Roger Amusement Park (12.5 mi / 20.1 km)
  • Trimper's Rides (12.6 mi / 20.2 km)
  • Jolly Roger at the Pier (12.7 mi / 20.4 km)
  • Carousel Ice Skating Rink (13.5 mi / 21.7 km)

Exploring the natural features in Whaleyville

Whether you're looking for adventure or just want to appreciate the scenery, Whaleyville is a great place to get out in nature. Here are a few of the area's most enchanting natural features, all within 30 miles (48.2 km) of the city centre:

  • Ocean City Beach (12.7 mi / 20.5 km)
  • Inlet Park (12.5 mi / 20.2 km)
  • Ocean City Inlet (12.6 mi / 20.3 km)
  • Northside Park (13.4 mi / 21.6 km)
  • Maryland Beach (14.1 mi / 22.7 km)
  • Fenwick Island Beach (15.5 mi / 25 km)

Transport options to and around Whaleyville

Fly into Ocean City, MD (OCE-Ocean City Municipal), the closest airport, located 11.6 mi (18.7 km) from the city centre. If you're unable to find a flight that fits your schedule, you could book a flight to Salisbury, MD (SBY-Salisbury - Ocean City Wicomico Regional), which is 12.2 mi (19.7 km) away.

Frequently asked questions

What is the best area to stay in Whaleyville when booking a holiday rental?
When considering a holiday rental in Whaleyville, Maryland, a popular area to stay is in the surrounding neighbourhoods that offer a blend of tranquillity and accessibility to nearby attractions. Just a short drive away, you'll find yourself close to the vibrant resort town of Ocean City, which boasts beautiful beaches and a lively boardwalk, great for enjoying seaside activities and dining.Another appealing area is near Assateague Island, renowned for its stunning natural landscapes and the famous wild horses that roam freely. This location provides a serene atmosphere, ideal for those looking to immerse themselves in nature while still being within reach of Whaleyville's amenities.While Whaleyville itself has a smaller number of holiday rental properties, the nearby regions are well-equipped with a variety of options, ensuring visitors can find something that suits their needs.
What is the most popular type of holiday rental accomodation in Whaleyville?
In Whaleyville, cottages are the most popular type of holiday rental, with several available throughout the area. These charming properties often feature cosy interiors, fully equipped kitchens, and outdoor areas where guests can relax and enjoy the scenic surroundings. Many cottages provide a rustic atmosphere, making them ideal for families or groups seeking a peaceful retreat close to nature.
Are there any family house rentals in Whaleyville?
In Whaleyville, Maryland, there are several family-friendly house rentals available, making it an appealing choice for those looking to enjoy a family getaway. This charming area offers a range of properties, often featuring spacious living rooms, fully equipped kitchens, and outdoor areas for children to play. Many homes also provide amenities such as Wi-Fi, air conditioning, and barbecue facilities.Visitors to Whaleyville can explore nearby attractions, including the tranquil waters of the Assawoman Bay and the bustling excitement of Ocean City, which is just a short drive away. Here, families can enjoy beautiful beaches, amusement parks, and a variety of dining options.
Can I rent a holiday home with a pool or hot tub in Whaleyville?
In Whaleyville, Maryland, there are several holiday homes available for rent that feature pools and hot tubs, making it a lovely choice for those looking to relax and unwind. The area is conveniently located near the popular resort town of Ocean City, providing easy access to beautiful beaches and a variety of attractions.Travellers can expect amenities such as private swimming pools, hot tubs, spacious outdoor areas for entertaining, and fully equipped kitchens for home-cooked meals. Many properties are designed with comfort in mind, offering generous living spaces, air conditioning, and outdoor seating areas.
Are there any remote work holiday rentals in Whaleyville?
In Whaleyville, Maryland, there are several remote work holiday rentals available. This quaint area offers a peaceful retreat while still providing essential amenities for those needing to work remotely. Many properties feature free Wi-Fi in both rooms and public areas, ensuring that you can stay connected during your stay.The surroundings are serene, ideal for focusing on work, yet you are just a short drive from the vibrant setting of nearby Ocean City, where you can enjoy beautiful beaches and local attractions during your downtime. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are popular rental amenities in Whaleyville?
In Whaleyville, popular rental amenities include air conditioning, which ensures a comfortable stay during warmer months. Many properties feature an arcade game room, providing entertainment for families and groups. Travellers can also expect balconies or patios, great for enjoying the scenic surroundings. Kitchens are commonly available, allowing guests to prepare their own meals and dine in. Additionally, some rentals offer onsite mini-golf, adding a fun activity right at your doorstep.
When is the best time to visit Whaleyville for a holiday rental?
The best time to visit Whaleyville for a holiday rental is during the peak season from June to August. This vibrant period attracts families and outdoor enthusiasts eager to soak up the sun and explore the area's natural beauty. With temperatures typically ranging from 20 to 30 degrees Celsius, it's ideal for enjoying beach outings, water sports, and the nearby Assateague Island National Seashore, known for its wild ponies and scenic landscapes.July stands out as the most popular month, with a lively option and a variety of local events, including festivals and outdoor concerts. Visitors can immerse themselves in the community spirit while enjoying the warm weather and numerous recreational activities available in the region.For those looking for a more budget-friendly experience, consider planning your trip in November. This month offers a quieter atmosphere, which is superb for relaxing strolls and enjoying the autumn scenery without the bustling summer crowds. It's a lovely time to appreciate the picturesque landscapes and the charm of Whaleyville at a more leisurely pace.
What are the top attractions in Whaleyville?
In Whaleyville, Maryland, visitors can enjoy a charming small-town atmosphere with access to several attractions nearby. The area is close to the Assawoman Bay, where outdoor enthusiasts can enjoy activities such as kayaking and fishing. Just a short drive away, the bustling resort town of Ocean City offers beautiful beaches, boardwalk attractions, and a variety of dining options.For those interested in nature, the nearby Berlin, a historic town, features quaint shops and eateries, along with the stunning Pocomoke River State Park, which provides opportunities for hiking and wildlife observation. Additionally, the nearby Frontier Town, an old-west themed amusement park, is a fun destination for families looking for entertainment.
Are all fees included in the Whaleyville 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 Whaleyville holiday homes with parking?
Stayz offers a wide selection of holiday homes in Whaleyville 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 Whaleyville holiday homes?
You can find great discounts on holiday homes in Whaleyville 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 Whaleyville holiday home booking on Stayz?
To find Whaleyville 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 Whaleyville?
A long-stay holiday home in Whaleyville 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 Whaleyville holiday home?
Book your Whaleyville 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 Whaleyville?
Prices for holiday homes in Whaleyville 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 Whaleyville 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.

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