Bayside holiday lettings

We found 8,948 holiday rentals — enter your dates for availability

Discover a selection of 56 homes, 10 villas and holiday rentals in Bayside that are perfect for your trip. Holiday homes provide the best amenities for your family, friends or furry companion, such as a hot tub and a washer and dryer. At the end of the day, you'll find a property to rent that has what everyone needs, including accessible or non-smoking choices.

Holiday rentals with weekly discounts - Bayside

Showing deals for:31 Jul - 7 Aug

Image gallery for Ocean Pines Chalet

Living area
9.8 out of 10, Exceptional, (10 reviews)
Exceptional
(10 reviews)

Ocean Pines Chalet

Berlin

7% off
Price is £5,184
for 7 nights, 1 home
£741 per night
includes taxes & fees
Ocean Pines Chalet

Find spaces that suit your style

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Why visit Bayside

  • Stunning beaches: Bayside boasts beautiful sandy shores perfect for sunbathing and water activities, ideal for relaxation and adventure.
  • Amusement parks: Enjoy thrilling rides and family-friendly attractions at nearby amusement parks, offering fun for all ages.
  • Charming local eateries: Savor the delightful flavours of trendy restaurants and cafes, showcasing fresh, local cuisine.
  • Outdoor activities: Explore scenic landscapes through hiking, cycling, and water sports, perfect for nature enthusiasts.
  • Welcoming community: Experience the friendly atmosphere of Bayside, making it a perfect destination for couples and families alike.

Popular types of accommodation in Bayside

If you're contemplating a getaway to Bayside, look no further for the ideal accommodation. Our most sought-after options include houses, stylish condos, and comfortable apartments. Whether you're exploring Bayside rentals or the nearby Selbyville vacation rentals, we ensure a delightful stay. Experience the charm of Bayside resort and discover the perfect vacation rentals tailored to your needs.

  • Houses: The most sought-after choice for visitors to Bayside, offering spacious and comfortable stays ideal for families, friends, or couples.
  • Condos: A favourite among travellers, these modern accommodations provide convenient amenities and often stunning views.
  • Apartments: A practical option that offers self-catering facilities for those looking for a homely atmosphere.
  • Cottages: Quaint and charming, these properties provide a delightful escape with a touch of rustic charm.
  • Villas: Luxurious and spacious, perfect for those who desire a lavish getaway with ample room.**

Top attractions near Bayside

Bayside, Delaware, is an ideal destination for outdoor enthusiasts, couples, and sports lovers alike. Visitors can explore beautiful beaches and vibrant amusement parks, while also enjoying various cultural experiences. This charming locale offers a delightful blend of leisure and excitement, ensuring memorable moments for all types of travellers seeking relaxation or adventure.

  • Maryland Beach: This tranquil beach, located 2.5km from Bayside, offers a serene escape with its sun-kissed sands and refreshing sea breezes, perfect for sunbathing, swimming, or leisurely strolls along the shore.
  • Roland E. Powell Convention Center: Situated 4.3km away, this versatile venue hosts a variety of events and conferences, providing a professional atmosphere with modern facilities, ideal for networking and exhibitions.
  • Jolly Roger Amusement Park: Only 4.3km from Bayside, this vibrant amusement park is a family-friendly destination filled with thrilling rides, games, and outdoor adventures, ensuring a fun-filled day for all ages.

Things to do recommended for couples

If you're seeking romance in Bayside, you're in for a treat! Enjoy thrilling water sports at Shark's Cove Marina, challenge each other at the mini-golf at Golf Down Under, or savour exquisite wines at Costa Ventosa Vineyard and Winery. Perfect for creating unforgettable memories together!

Things to do recommended for families

Families visiting Bayside can unwind at Northside Park, just 2.5km away, offering wellness and relaxation. Enjoy thrilling adventures at Thunder Lagoon Waterpark, 1.9km away, or have fun ice skating at Carousel Ice Skating Rink, also 2.5km distant, perfect for family entertainment.

Things to do recommended for groups

Groups visiting Bayside can enjoy a round of golf at Bayside Resort Golf Club, indulge in craft spirits at Seacrets Distilling Company, and shop at Montego Bay Shopping Center for a delightful mix of entertainment and family fun, all within a short distance from the area.

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

If you’re travelling with a group, family, pets, or seeking longer stays, be sure to use the appropriate filters to match your priorities. Here are some helpful Vrbo booking tips for you.

  • Traveling to Bayside with a group: Think about how many bedrooms you'll require, along with features like a fully equipped kitchen or outdoor areas for group gatherings. Thankfully, you can easily filter for all these options and more on Vrbo.
  • Traveling to Bayside with young kids: Travelling with young children can be quite demanding. It's essential to prioritise 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 Bayside: For many families, a holiday isn't truly fulfilling without their furry companion by their side. If this resonates with you, explore Vrbo properties that welcome pets. The majority of pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Bayside: If you're seeking holiday rentals with discounts for stays of a month or more, you've come to the right place. By using the appropriate filters, you'll be able to effortlessly discover and save on monthly rentals. Don’t forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay in and around Bayside

Bayside offers a charming escape with its welcoming waterfront community, perfect for a relaxing Delaware beach getaway. Explore nearby towns for a blend of family-friendly activities and scenic spots, ideal for outdoor adventures or romantic retreats. Enjoy the friendly atmosphere and trendy local eateries as you soak in the coastal beauty and unwind in this delightful oceanfront haven.

  • Sun Ridge: Sun Ridge is a charming neighbourhood located near Bayside, known for its outdoor and sporting experiences. Visitors flock here for an array of activities, including golf at the well-maintained golf course and leisurely strolls along the picturesque boardwalk. The local landmarks, such as the family-friendly beach and scenic esplanade, provide the perfect backdrop for a romantic getaway or an active holiday. Whether you're looking to play a round of golf or soak up the sun on the beach, Sun Ridge offers something for everyone.
  • The Commons: The Commons is another delightful neighbourhood situated around Bayside, highly regarded for its outdoor and sporting opportunities. This area features beautiful golf courses and expansive green spaces, making it an ideal location for outdoor enthusiasts. With nearby attractions like the beach, family beach, and tranquil lake, The Commons invites visitors to indulge in both relaxation and adventure. Couples and families alike will find plenty of activities to enjoy, from picnics by the lake to rounds of golf.
  • Keenwick Sound: Located a mere 559m from Bayside, Keenwick Sound is a vibrant neighbourhood that offers a perfect blend of outdoor, sporting, and beach experiences. Golf enthusiasts can take advantage of the golf course, while leisurely walks along the boardwalk provide stunning views and a sense of tranquillity. With attractions such as the family beach and esplanade close by, Keenwick Sound is an ideal spot for visitors seeking a sun-soaked escape, whether it’s a day at the beach or a round of golf with friends.

Best time to go to Bayside

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

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January37.9°F (3.3°C)Light RainMostly SunnyLowSlightly Low
February39.7°F (4.3°C)Light RainMostly SunnyLowSlightly Low
March44.8°F (7.1°C)Light RainMostly SunnyAverageSlightly Low
April53.8°F (12.1°C)Light RainMostly SunnyAverageAverage
May62.4°F (16.9°C)Light RainMostly SunnyAverageAverage
June71.4°F (21.9°C)Light RainMostly SunnyHighSlightly High
July77.2°F (25.1°C)Light RainMostly SunnyHighSlightly High
August76.1°F (24.5°C)Light RainMostly SunnyHighSlightly High
September71.2°F (21.8°C)Light RainMostly SunnyAverageAverage
October62.2°F (16.8°C)Light RainMostly SunnyAverageAverage
November51.3°F (10.7°C)Light RainMostly SunnyAverageAverage
December44.2°F (6.8°C)Light RainMostly SunnyLowAverage

Booking with Vrbo is simple

Are you hoping to save on your upcoming trip? It might be worth considering some flexibility with your travel dates, as prices can vary. Additionally, opting for a longer stay often leads to significant savings. To discover the perfect Vrbo property that fits your budget, utilise our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Effortless planning

Vrbo's pioneering Trip Board offers you a dedicated space to craft new journeys, pick up from where you last stopped, or view and arrange your travel plans. You can now easily access properties you've previously saved and booked under Potential, Upcoming, or Current Trips. To explore Trip Boards, simply visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

Choose a holiday rental for your Bayside getaway

Learn about the unique charm of Bayside with a stay in a holiday home rental. This city has something for everyone. If you're looking for accommodation options with space to entertain friends and family, HomeAway has plenty of options to choose from. Many rental homes offer full kitchens and laundry facilities, perfect for big groups.

Sightseeing in and around Bayside

Are you looking for top things to see and do in the city? Although it can be tempting to stay in your comfortable holiday rental, you'll want to check out everything that Bayside has to offer. These are some of the major attractions to put on your list, all within 30 miles (48.2 km) of the city centre:

  • Bayside Resort Golf Club (0.5 mi / 0.7 km)
  • Carousel Ice Skating Rink (3.9 mi / 6.3 km)
  • Jolly Roger Amusement Park (7.1 mi / 11.4 km)
  • Jolly Roger at the Pier (9.2 mi / 14.7 km)
  • Trimper's Rides (9.2 mi / 14.8 km)
  • Frontier Town Water Park and Golf (11.7 mi / 18.8 km)

Exploring the natural features in Bayside

Whether you're an outdoor enthusiast or just want to take in the scenery, Bayside is a great place to get outside. These are a few of the area's most enchanting sights, all within 30 miles (48.2 km) of the city centre:

  • Ocean City Beach (9.3 mi / 14.9 km)
  • Northside Park (3.4 mi / 5.5 km)
  • Maryland Beach (3.4 mi / 5.5 km)
  • Fenwick Island Beach (4.6 mi / 7.4 km)
  • Bethany Beach Beaches (6 mi / 9.6 km)
  • Inlet Park (9.3 mi / 14.9 km)

Transport to and around Bayside

Fly into Ocean City, MD (OCE-Ocean City Municipal), the closest airport, located 10.3 mi (16.5 km) from the city centre. If you can't find a flight that works for your travel itinerary, you could book a flight to Georgetown, DE (GED-Sussex County), which is 21 mi (33.8 km) away.

Frequently asked questions

What is the best area to stay in Bayside when booking a holiday rental?
When considering a holiday rental in Bayside, Delaware, the most appealing area to stay in is the community surrounding the Bayside Resort. This charming neighbourhood offers a delightful blend of comfort and recreational opportunities, making it a favourite among visitors. The area boasts a variety of properties, from spacious family homes to more intimate retreats, suiting diverse preferences and group sizes.

One of the standout attractions nearby is the stunning Bayside Golf Club, which not only offers a fantastic golfing experience but also provides beautiful views of the surrounding landscape. Additionally, the area is in close proximity to the scenic beaches of Delaware, where you can enjoy sunbathing, swimming, and a range of water sports.

For those who appreciate nature, the nearby Assawoman Bay offers opportunities for kayaking and birdwatching, making it a splendid spot for outdoor enthusiasts.
How much does it cost to rent a holiday home in Bayside?
Prices for holiday rentals in Bayside 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 Bayside 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 Bayside holiday house rentals?
You can find great discounts on house rentals in Bayside 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.
Can I find long-stay holiday rentals in Bayside?
A long-stay holiday rental in Bayside 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 Bayside holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Bayside 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.
When is the best time to visit Bayside for a holiday rental?
The best time to visit Bayside is during the peak season from June to August, with July being the most popular month. This vibrant period attracts families and beach lovers eager to soak up the sun and enjoy the area's numerous outdoor activities. The warm weather, typically ranging from 20 to 30 degrees Celsius, creates an ideal setting for swimming, kayaking, and exploring the picturesque coastal landscapes.

Visitors during these months can take advantage of the lively option, with plenty of events and activities, including local festivals and outdoor concerts. If you're looking for a convenient and bustling environment, this is an excellent time to experience everything Bayside has to offer.

For those seeking a more budget-friendly option, November presents a quieter alternative. Although it's outside the main tourist season, you can still enjoy the beauty of Bayside with fewer crowds and lower rental prices. Plus, autumn brings charming coastal views and opportunities for peaceful walks along the shore.

Ultimately, your choice will depend on whether you prefer the excitement of summer gatherings or the tranquillity and affordability of a late autumn escape.
How early should I book a Bayside holiday rental?
Book your Bayside 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 Bayside?
In Bayside, Delaware, visitors can enjoy a variety of attractions that highlight the area's natural beauty and recreational opportunities. The Bayside community itself features a stunning golf course that appeals to golf enthusiasts, while the nearby Assawoman Bay offers opportunities for kayaking, paddleboarding, and fishing.

For those who enjoy nature, the Fenwick Island State Park is just a short drive away, providing pristine beaches and scenic walking trails. The park is great for a day out, with options for swimming, sunbathing, and picnicking along the coastline.

Additionally, the nearby town of Fenwick Island boasts charming shops and eateries, making it a lovely spot to explore after a day of outdoor activities. For families, the attractions of Ocean City, Maryland, are within easy reach, offering amusement parks, boardwalks, and various entertainment options.
Can I change or cancel my Bayside home rental booking on Vrbo?
To find Bayside 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 Bayside 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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