Photo by Julia

Caine Woods vacation rentals

We found 800 vacation rentals — enter your dates for availability

Find the perfect place for your stay in Caine Woods by choosing from 54 houses, 33 condos, and other vacation rentals. Whether you're staying in a vacation rental 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 a hot tub and a washer and dryer. You'll be able to choose a rental for everyone's needs, including places that are non-smoking or accessible.

Vacation rentals with weekly discounts - Caine Woods

Showing deals for:Apr 3 - Apr 10

Image gallery for ⛱️⛱️ Ocean City Bayside 🦀

Community park to left of house. Fully fenced back yard.
10 out of 10, Exceptional, (6 reviews)
Exceptional
(6 reviews)

⛱️⛱️ Ocean City Bayside 🦀

Ocean City

9% off
Price is $403
$2,819 for 7 nights
All fees included
⛱️⛱️ Ocean City Bayside 🦀

Find spaces that suit your style

  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, yards and more

  • More for less

    More space, more privacy, more amenities — more value

  • A place for everyone

    We stand for diversity, inclusion and families everywhere.
    Learn more

Find out more about Caine Woods

Why visit Caine Woods

  • Beautiful Beaches: Caine Woods offers stunning beaches perfect for relaxation and outdoor activities.
  • Family-Friendly Attractions: Enjoy nearby amusement parks and local activities that cater to all ages.
  • Scenic Neighborhood: The area features charming oak trees and picturesque scenery, ideal for walks and romantic getaways.
  • Welcoming Community: Experience the warmth of friendly locals, enhancing your vacation with a sense of community.
  • Variety of Accommodations: Choose from private homes, cozy condos, and stylish apartments for a comfortable stay.

Popular types of accommodation around Caine Woods

If you’re looking for the perfect getaway in Caine Woods, you’re in the right place. Our most popular vacation rental options include houses, cozy condos, and stylish apartments. Whether you’re searching for Caine Woods homes, listings, or a vacation home by the bay, we have a variety of bayside condos and more to suit your needs. Enjoy your stay with comfort and convenience in mind.

  • Houses: The top choice for travelers in Caine Woods, offering spacious and comfortable accommodations perfect for families or groups.
  • Condos: A popular option, these stylish rentals often feature modern amenities and are located near the beach.
  • Apartments: Ideal for solo travelers or couples, providing a cozy and convenient home base for your adventures.
  • Cottages: These charming retreats offer a quaint and cozy atmosphere, perfect for a relaxing getaway.
  • Villas: Luxurious and spacious, villas provide an upscale experience for those seeking a bit more comfort.**

Top attractions near Caine Woods

Caine Woods in Ocean City, Maryland, is perfect for outdoor enthusiasts and those seeking a romantic getaway. With its stunning beaches, lively amusement parks, and scenic esplanades, visitors can enjoy a variety of attractions that cater to families and culture lovers alike. Whether you're exploring the coast or enjoying local activities, Caine Woods offers a memorable vacation experience for everyone.

  • Maryland Beach: A beautiful, sandy beach located just 0.4 miles from Caine Woods, perfect for sunbathing, swimming, and enjoying the refreshing ocean breeze.
  • Jolly Roger Amusement Park: Located 6 miles away, this family-friendly amusement park offers thrilling rides, games, and outdoor adventures, making it a great spot for fun and excitement.
  • Roland E. Powell Convention Center: Situated 5 miles from Caine Woods, this venue hosts various events and conferences, providing a professional atmosphere for business gatherings.

Things to do recommended for couples

For a memorable couple's getaway in Caine Woods, indulge in a round of mini-golf at Lost Treasure Golf, only 0.3 miles away. Try thrilling water sports at Shark's Cove Marina, just 0.6 miles away, or savor romance at Costa Ventosa Vineyard and Winery, located 11 miles away.

Things to do recommended for families

Your family will have a blast at Thunder Lagoon Waterpark, just 0.5 miles from Caine Woods, enjoying thrilling water slides. Don’t miss Northside Park, a serene recreational spot 1 mile away, or the fun-filled Carousel Ice Skating Rink, located 2 miles from your stay.

Things to do recommended for groups

Experience the lively atmosphere at Seacrets Distilling Company, just 5 miles from Caine Woods, for a unique tasting. Enjoy a round of golf at Bayside Resort Golf Club, 3 miles away, or shop and unwind at the Montego Bay Shopping Center, only 0.9 miles from your stay.

*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 around Caine Woods

When planning your trip, whether you're traveling with friends, family, pets, or seeking extended stays, it's important to prioritize your filters accordingly. Here are some helpful booking tips for Vrbo.

  • Traveling to Caine Woods with a group: Think about how many bedrooms you'll require, along with features like a complete kitchen or outdoor areas for group get-togethers. Luckily, you can easily filter these options and more on Vrbo.
  • Traveling to Caine Woods with young kids: Traveling with young kids can present its own set of challenges. 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 attractions that are family-friendly.
  • Taking your pets with you to Caine Woods: For many families, a vacation just isn’t the same without their beloved pets by their side. If you can relate, explore Vrbo listings that welcome furry companions. Most pet-friendly properties come equipped with feeding bowls and cozy beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Caine Woods: If you're in search of vacation rentals with special offers for stays of a month or more, you've come to the perfect spot. By using the appropriate filter, you can 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 near Caine Woods

Caine Woods in Ocean City, Maryland, offers a delightful blend of family-friendly charm and serene beach vibes. This walkable neighborhood is adorned with oak trees and beautiful scenery, making it perfect for outdoor adventures or a romantic getaway. Explore the nearby attractions to experience the luxury and warmth of friendly locals, all while enjoying the relaxing atmosphere that Caine Woods provides. It's an ideal destination for those seeking both tranquility and community spirit.

  • Ocean City: Ocean City is a vibrant coastal city that offers a perfect blend of outdoor adventure and family-friendly fun. Nestled along the Atlantic Ocean, it features a famous boardwalk filled with shops, restaurants, and amusement parks. Visitors can enjoy sunbathing on the beautiful beaches, take part in water sports, or explore the local attractions like the Esplanade and the water park. With its lively atmosphere and endless activities, Ocean City is ideal for romantic getaways, family vacations, and outdoor enthusiasts alike.
  • North Ocean City: Located just 0.6 miles from Caine Woods, North Ocean City is a charming neighborhood known for its serene beaches and recreational parks. This area is perfect for travelers seeking a more laid-back beach experience, with easy access to family beaches and local shops. Enjoy a romantic stroll along the boardwalk, indulge in fresh seafood at nearby restaurants, or spend the day at the local recreation park. North Ocean City combines the best of beach relaxation with convenient amenities, making it a must-visit destination.
  • Fenwick Island: Fenwick Island is a picturesque coastal city located 1 mile from Caine Woods, known for its stunning natural beauty and tranquil beaches. This charming island offers a perfect setting for outdoor activities such as golfing and water sports, with beautiful boardwalks and scenic views. Visitors can explore the pristine family beaches, enjoy fresh seafood dining, or take leisurely walks along the esplanade. Fenwick Island is an ideal spot for those seeking a romantic escape or a relaxing beach vacation.

Best time to go to Caine Woods

If you're planning a trip to Caine Woods, 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
January38.8°F (3.8°C)Light RainMostly SunnyLowSlightly Low
February40.5°F (4.7°C)Light RainMostly SunnyLowSlightly Low
March45.3°F (7.4°C)Light RainMostly SunnyAverageSlightly Low
April54.3°F (12.4°C)Light RainMostly SunnyAverageAverage
May63.0°F (17.2°C)Light RainMostly SunnyAverageAverage
June72.0°F (22.2°C)Light RainMostly SunnyHighSlightly High
July77.7°F (25.4°C)Light RainMostly SunnyHighSlightly High
August76.6°F (24.8°C)Light RainMostly SunnyHighSlightly High
September72.0°F (22.2°C)Light RainMostly SunnyAverageAverage
October63.0°F (17.2°C)Light RainMostly SunnyAverageAverage
November52.0°F (11.1°C)Light RainMostly SunnyAverageAverage
December45.0°F (7.2°C)Light RainMostly SunnyLowAverage

Booking with Vrbo is simple

Are you aiming to get the best deal on your upcoming trip? Being flexible with your travel dates can make a big difference, as prices often fluctuate. Additionally, you can enjoy substantial savings by opting for a longer stay. To discover a Vrbo property that suits your budget, simply use our filters to sort by price, location, and type of vacation rental. We're here to help you find the perfect getaway.

Save more with One Key

When you reserve an eligible Vrbo for your group getaway, you'll earn OneKeyCash on the full booking amount. Being the organizer certainly has its rewards. Enroll in our OneKey rewards program to unlock exclusive savings for members and accumulate OneKeyCash on qualifying stays. Sign up today and begin earning.

Vrbo Trips: Planning made easy

Vrbo’s Trip Board provides a dedicated area for you to plan new trips, refine your existing plans, or manage your bookings effectively. Your saved or booked properties are conveniently categorized into Potential, Upcoming, or Current Trips. To discover the Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

What is the most popular type of vacation rental in Caine Woods?
In Caine Woods, condos are the most popular vacation rental option, with around 38 available throughout the area. These condos typically feature modern amenities such as fully equipped kitchens, spacious living areas, and often access to communal facilities like pools or fitness centers. Many are situated within close proximity to the beach, providing easy access to outdoor activities and water sports.

In addition to condos, there are about 17 vacation houses available, which are ideal for families or larger groups. These houses generally offer multiple bedrooms, private outdoor spaces, and facilities for grilling, making them great for gatherings after a day of exploring the local attractions.
Are there any beach house rentals in Caine Woods?
In Caine Woods, Maryland, there are about 46 beach house rentals available, primarily located in family-friendly neighborhoods close to the beach and local amenities. These rentals typically offer spacious living areas, multiple bedrooms, fully equipped kitchens, and outdoor decks or patios for enjoying the coastal air. Many properties also feature amenities such as private pools, BBQ grills, and easy access to nearby recreational activities, making them ideal for families and groups looking to relax by the sea. Find your rental near the beach in Caine Woods.
How much does it cost to rent a vacation home in Caine Woods?
Prices for vacation rentals in Caine Woods 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 Caine Woods 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 Caine Woods vacation house rentals?
You can find great discounts on house rentals in Caine Woods 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 are popular rental amenities in Caine Woods?
In Caine Woods, popular rental amenities include fully equipped kitchens, which allow guests to prepare their own meals and enjoy dining in comfort. Many properties also feature coffee and tea makers for a cozy start to the day. Onsite parking is a convenient option for travelers with vehicles.
Are there any family house rentals in Caine Woods?
In Caine Woods, Maryland, there are numerous family-friendly house rentals available, with about 38 options to choose from. This area is known for its close proximity to the beach and family-friendly activities. Many of these homes come equipped with spacious living areas, full kitchens for preparing meals, and outdoor decks or patios, great for enjoying warm evenings.

Visitors can expect amenities such as Wi-Fi, air conditioning, and sometimes even private pools or game rooms, suiting both relaxation and entertainment needs. The nearby beaches provide opportunities for swimming, sunbathing, and water sports, while local parks offer playgrounds and picnic areas for outdoor fun.
Can I rent a vacation home with a pool or hot tub in Caine Woods?
In Caine Woods, Maryland, travelers can find a variety of vacation homes available for rent that feature pools, with approximately 18 options to choose from. This charming area offers a peaceful retreat, ideal for families and groups looking to enjoy the outdoors. Many of these properties come equipped with amenities such as private pools, outdoor patios, and spacious living areas, great for relaxation and entertainment after a day at the beach or exploring the local area. Additionally, there are several rentals that include hot tubs, providing a luxurious way to unwind.
Are there any Caine Woods vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Caine Woods 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.
Are there pet-friendly vacation rentals in Caine Woods?
In Caine Woods, Maryland, travelers can find a selection of pet-friendly vacation rentals available, with about 14 options to choose from. This charming area is known for its proximity to the beach and various outdoor activities, making it an ideal spot for those traveling with pets. Many of the vacation rentals in this area feature amenities such as fully equipped kitchens, spacious living areas, and private outdoor spaces where pets can enjoy the fresh air.

The nearby Assateague Island National Seashore is a great destination for pet owners, offering scenic trails and the chance to see the famous wild ponies. Additionally, the surrounding neighborhoods provide access to local parks and pet-friendly beaches, enhancing the overall experience for visitors with furry companions.
Can I find long-stay vacation rentals in Caine Woods?
A long-stay vacation rental in Caine Woods 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.
When is the best time to visit Caine Woods for a vacation rental?
The best time to visit Caine Woods for a vacation rental is during the vibrant summer months, specifically from June to August. This peak season attracts families and adventure enthusiasts alike, as the warm weather creates ideal conditions for outdoor activities such as beach outings, water sports, and leisurely strolls along the scenic coastline.

July stands out as the most popular month, bringing a lively atmosphere with both tourists and locals enjoying the myriad of events and attractions. With temperatures typically ranging from the mid-70s to mid-80s Fahrenheit, visitors can relish in comfortable conditions great for sunbathing or taking part in community festivities.

For those looking to maximize their budget, consider planning your trip in November. This month offers a quieter experience, allowing for peaceful walks on the beach and the opportunity to explore the natural beauty of the area without the summer crowds. The milder temperatures in November can still be pleasant, making it an enjoyable time for sightseeing and relaxation.

Ultimately, whether you prefer the bustling energy of the summer months or the tranquil charm of the shoulder season, Caine Woods has something special to offer.
Are there any remote work vacation rentals in Caine Woods?
In Caine Woods, Maryland, there are numerous remote work vacation rentals available, with around 53 options to choose from. This area is known for its proximity to both the beach and the scenic beauty of the surrounding natural landscape, making it an ideal spot for blending work and leisure. Many of these rentals come equipped with essential amenities for remote work, such as high-speed Wi-Fi, dedicated desk spaces, ergonomic desk chairs, and even computer monitors in some properties.

Travelers can expect comfortable living areas that provide a conducive environment for productivity, along with the convenience of fully equipped kitchens for meal preparation. The neighborhood offers a relaxed atmosphere, with easy access to the beach, local shops, and dining options, allowing for enjoyable breaks in between work hours. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
How early should I book a Caine Woods vacation rental?
Book your Caine Woods 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 Caine Woods?
In Caine Woods, Maryland, visitors can enjoy a variety of attractions that highlight the area's natural beauty and recreational opportunities. The nearby beach offers access to the Atlantic Ocean, great for swimming, sunbathing, and water sports. The neighborhood is also close to the scenic Assawoman Bay, where travelers can explore kayaking and paddleboarding options.

For those looking to experience local dining and shopping, the bustling area of Ocean City is just a short drive away, featuring a vibrant boardwalk filled with shops, restaurants, and amusement rides.
Can I change or cancel my Caine Woods home rental booking on Vrbo?
To find Caine Woods 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 Caine Woods 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.

More Vacation Ideas