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Caine Woods holiday lettings

We found 840 holiday rentals — enter your dates for availability

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August 2025

September 2025

Find the perfect place for you stay in Caine Woods by choosing from 108 houses, 86 flats and other holiday rentals. Whether you're staying in a holiday rental with family, friends or just your furry companion, you'll find the amenities that you need and want, including parking and a TV. You're sure to find a property to rent to meet everyone's needs, including places that are non-smoking or accessible.

Holiday rentals with weekly discounts - Caine Woods

Showing deals for:7 Nov - 14 Nov

The bay is just a short kayak or paddle board ride up the canal.

Exceptional

(13 reviews)

Miss Fenwick’s Castle by the Bay, a Fenwick Bayfront Oasis

Selbyville, DE

8% off

£631 per night

includes taxes & fees

Exceptional

(18 reviews)

Ideal for a family getaway, newly furnished home in Montego Bay waiting for you!

Ocean City, MD

7% off

£271 per night

includes taxes & fees

Exceptional

(10 reviews)

MADISON BAY BEACH GETAWAY-PRIVATE POOL-HOT TUB- FIRE PIT- WEEKLY STAY DISCOUNT

Ocean City, MD

8% off

£776 per night

includes taxes & fees

Exceptional

(6 reviews)

Large oceanblock beach home - Short walk to beach, shops & great restaurants!

Fenwick Island, DE

8% off

£432 per night

includes taxes & fees

Exceptional

(32 reviews)

Large Fenwick Island 6-Bedroom Home just steps from Delaware/Maryland Beaches

Fenwick Island, DE

8% off

£712 per night

includes taxes & fees

Exceptional

(10 reviews)

- NEW - 141st Street 3BR-3BA Cottage - Ocean Block Oasis for Family Gatherings!

Ocean City, MD

7% off

£408 per night

includes taxes & fees

Wonderful

(51 reviews)

Outstanding large Beach House on the Ocean Side with a private heated Pool!

Fenwick Island, DE

8% off

£644 per night

includes taxes & fees

Exceptional

(51 reviews)

The Blue House! Walk to the Beach! FirePit-Bikes-PingPong- Fully Fenced Yard!

Ocean City, MD

13% off

£201 per night

includes taxes & fees

Exceptional

(16 reviews)

Private 3 Bed 2 Bath Beach House. Remodeled, short walk to beach, wifi & laundry

Ocean City, MD

8% off

£384 per night

includes taxes & fees

Very large family room to seat plenty comfortably.

Exceptional

(49 reviews)

Book now for 2025! Perfect for large family. Ocean block. Steps to Beach & Pool!

Ocean City, MD

8% off

£283 per night

includes taxes & fees

Your oasis on the canal with a walk to the beach in Fenwick Island

Exceptional

(23 reviews)

Canal Front Views, Boat Dock, Kayaks, 10" Walk to the Beach, Free Activities inc. Golf at Bear Trap.

Fenwick Island, DE

23% off

£333 per night

includes taxes & fees

Exceptional

(15 reviews)

Fully Renovated, Great Beach View-Indoor Pool -Game Room-90 Steps to the Beach!

Ocean City, MD

8% off

£274 per night

includes taxes & fees

Find spaces that suit your style

House

Condo/Apartment

Find the best place to stay - Caine Woods

Spacious 2 Bedroom Condo with Hot Tub!

Sleeps 6 · 2 bedrooms · 2 bathrooms

New Luxe Home Steps to Ocean, Baby-Friendly, Garage, 2600 sq.ft - Sleeps 12

Sleeps 12 · 3 bedrooms · 3+ bathrooms

Experience your vacation in this spacious one bedroom condo with an ocean view.

Sleeps 4 · 1 bedroom · 1 bathroom

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More quality time
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All the privacy of home
Enjoy full kitchens, pools, gardens and more
More for less
More space, more privacy, more amenities — more value

Find out more about Caine Woods

Why visit Caine Woods

Stunning beaches: Enjoy breathtaking beach views and the opportunity for sunbathing, swimming, and various water sports.
Outdoor adventures: Caine Woods is perfect for outdoor enthusiasts, offering ample opportunities for hiking and exploring nature.
Family-friendly attractions: Discover nearby amusement parks and hidden gems ideal for a fun-filled family holiday.
Romantic getaways: Experience a charming atmosphere perfect for couples seeking a romantic escape.
Diverse accommodation: Choose from a variety of vacation rentals, from cosy retreats to spacious family homes.

Popular types of accommodation around Caine Woods

Find your perfect getaway in Caine Woods with our selection of houses, condos, and apartments. Whether you're seeking a cosy retreat or a spacious family abode, our listings cater to every need. Explore our Caine Woods homes and MLS listings to discover the ideal vacation home for your stay. Enjoy transparency, savings, and reassurance as you embark on your holiday in this charming destination.

Houses: The most sought-after option for visitors to Caine Woods, offering a home-like atmosphere perfect for families or groups.
Condos: A popular choice, these self-contained units provide convenience and comfort for couples and small families.
Apartments: Ideal for those seeking a central location, apartments offer flexibility and a homely feel during your stay.
Cottages: These quaint retreats are perfect for a peaceful getaway, nestled in scenic surroundings.
Villas: Offering luxury and space, villas are a great choice for those looking to indulge during their holiday.**

Top attractions near Caine Woods

Caine Woods in Ocean City, Maryland, offers an ideal setting for outdoor, beach, and romantic holidays. Visitors can enjoy a variety of attractions, including beautiful beaches, amusement parks, and event venues that cater to those seeking cultural and beach experiences. For a comfortable stay, consider exploring Caine Woods vacation rentals or oceanfront options to fully immerse yourself in the local charm.

Maryland Beach: A charming stretch of sand located 249m from Caine Woods, Maryland Beach offers a quintessential beach experience with vibrant seaside vibes, perfect for sunbathing, swimming, and leisurely strolls along the shore.
Roland E. Powell Convention Center: Located 3.1km away, this versatile venue hosts a variety of business events and conferences, providing a professional atmosphere with modern facilities, ideal for networking and exhibitions.
Jolly Roger Amusement Park: Situated 3.7km from Caine Woods, this family-friendly park is packed with outdoor adventures, thrilling rides, and attractions that guarantee a fun-filled day for visitors of all ages.

Things to do recommended for couples

For a romantic getaway in Caine Woods, enjoy a round of mini-golf at Golf Down Under, only 249m away. For adventure, try water sports at Shark's Cove Marina, 373m away. Don’t miss a visit to Costa Ventosa Vineyard and Winery, a charming 6.8km from your stay.

Things to do recommended for families

Your family will have a splendid time at Northside Park, offering relaxation vibes just 1.6km away. Enjoy thrilling adventures at Thunder Lagoon Waterpark, only half 1.6km away, and glide across the ice at Carousel Ice Skating Rink, located two miles from Caine Woods.

Things to do recommended for groups

Groups visiting Caine Woods can indulge in crafted spirits at Seacrets Distilling Company, play a round of golf at Bayside Resort Golf Club, or enjoy shopping and entertainment at Montego Bay Shopping Center, all within a short distance from your accommodation.

What do I need to keep in mind when booking a vacation around Caine Woods

When planning your journey, whether you're travelling with a group, a family, pets, or seeking extended stays, be sure to refine your search according to your key preferences. Here are some helpful Vrbo booking suggestions for you.

Traveling to Caine Woods with a group: Think about how many bedrooms you'll require, as well as features like a fully-equipped kitchen or outdoor areas for group gatherings. Thankfully, you can easily refine your search for all these options and more on Vrbo.
Traveling to Caine Woods with young kids: Journeying with young children can present its own set of challenges. It’s important to prioritise their comfort and safety, alongside suitable amenities like a private swimming pool. Additionally, it’s wise to think about how close you are to attractions that cater to families.
Taking your pets with you to Caine Woods: For many, a family holiday isn’t truly complete without their furry companion by their side. If this resonates with you, take a look at Vrbo accommodations that welcome pets. Most pet-friendly properties offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
Planning for a long term stay visiting Caine Woods: If you're in search of holiday rentals with great 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 accommodations. 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

Your holiday in Caine Woods, Ocean City, Maryland, promises a delightful blend of relaxation and adventure. This charming neighbourhood is perfect for outdoor enthusiasts and offers stunning beach vistas. Just west of Caine Woods, you'll discover family-friendly attractions and hidden gems that capture the essence of coastal living. With its welcoming atmosphere and luxurious surroundings, Caine Woods is an ideal spot for a romantic getaway or a memorable family vacation.

North Ocean City: Situated a mere 373m from Caine Woods, North Ocean City is a delightful neighbourhood known for its vibrant outdoor and romantic beach experiences. Visitors flock here to enjoy the expansive boardwalk, which offers a variety of shops and eateries, as well as a recreational park perfect for family outings. The local beach, ideal for sunbathing and swimming, is complemented by an inviting esplanade, making it a perfect spot for leisurely strolls and sunset views.
Bethany Beach: Located 3.7km from Caine Woods, Bethany Beach is a charming coastal city that beckons those seeking a quintessential beach experience. With its picturesque boardwalk and inviting shopping area, it’s an ideal destination for both relaxation and exploration. Golf enthusiasts will appreciate the nearby golf courses, while families can enjoy the family-friendly beach and esplanade. This city encapsulates the perfect blend of outdoor adventure and romantic seaside ambiance, making it a must-visit.
Fenwick Island: Just 621m from Caine Woods, Fenwick Island is a stunning destination characterised by its beautiful beaches and outdoor activities. A favourite among visitors, this island city offers access to a scenic boardwalk and excellent golf courses. The local beaches are perfect for family fun and sun-soaked relaxation. Fenwick Island’s esplanade provides a scenic backdrop for leisurely walks, ensuring a romantic and enjoyable experience for all who visit.

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.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	38.8°F (3.8°C)	Light Rain	Mostly Sunny	Low	Slightly Low
February	40.5°F (4.7°C)	Light Rain	Mostly Sunny	Low	Slightly Low
March	45.3°F (7.4°C)	Light Rain	Mostly Sunny	Average	Slightly Low
April	54.3°F (12.4°C)	Light Rain	Mostly Sunny	Average	Average
May	63.0°F (17.2°C)	Light Rain	Mostly Sunny	Average	Average
June	72.0°F (22.2°C)	Light Rain	Mostly Sunny	High	Slightly High
July	77.7°F (25.4°C)	Light Rain	Mostly Sunny	High	Slightly High
August	76.6°F (24.8°C)	Light Rain	Mostly Sunny	High	Slightly High
September	72.0°F (22.2°C)	Light Rain	Mostly Sunny	Average	Average
October	63.0°F (17.2°C)	Light Rain	Mostly Sunny	Average	Average
November	52.0°F (11.1°C)	Light Rain	Mostly Sunny	Average	Average
December	45.0°F (7.2°C)	Light Rain	Mostly Sunny	Low	Average

Booking with Vrbo is simple

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

Vrbo Trips: Effortless planning

Vrbo's cutting-edge Trip Board offers you a dedicated space to plan new adventures, pick up from where you last stopped, or review and arrange your travel plans. You can easily locate the properties you've saved and booked in the sections for Potential, Upcoming, or Current Trips. To explore the Trip Boards, simply visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

Frequently asked questions

What is the most popular type of holiday rental in Caine Woods?

In Caine Woods, condos are the most popular type of holiday rental, with approximately 38 available in the area. These condos typically come equipped with modern amenities, including fully equipped kitchens, spacious living areas, and access to communal facilities such as pools or fitness centres. Many are situated close to the beach, providing easy access for sunbathing or water activities.

Are there any beach house rentals in Caine Woods?

In Caine Woods, Maryland, there are approximately 39 beach house rentals available, predominantly situated in serene coastal neighbourhoods. These beach houses offer a variety of amenities that cater to holidaymakers looking for a relaxing getaway. Most properties typically feature multiple bedrooms, spacious living areas, and fully equipped kitchens, making them ideal for families or groups. Many also include outdoor spaces such as decks or patios, which are superb for enjoying the pleasant weather and stunning views of the nearby coastline.

How much does it cost to rent a holiday home in Caine Woods?

Prices for holiday 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 holiday 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, allowing guests to prepare their own meals, and coffee and tea makers for a comforting start to the day. Most properties also offer onsite parking, which is convenient for those travelling with their own vehicles. Many rentals feature patios or balconies, providing outdoor spaces for relaxation and enjoying the pleasant surroundings.

Are there any family house rentals in Caine Woods?

In Caine Woods, Maryland, there are several family-friendly house rentals available, with around 38 options to choose from. This area is known for its proximity to the beautiful beaches of Ocean City, making it an ideal spot for families seeking a seaside getaway. Many of the properties feature spacious living areas, fully equipped kitchens for preparing meals, and outdoor spaces superb for children to play or for families to gather.

Can I rent a holiday home with a pool or hot tub in Caine Woods?

In Caine Woods, Maryland, there are plenty of holiday homes available for rent that feature both pools and hot tubs, with around 19 options to choose from. This area, known for its proximity to the coastline and recreational activities, offers a variety of properties that cater to families and groups. Many rentals come equipped with private pools, outdoor spaces for entertaining, and hot tubs, providing a superb setting for relaxation after a day at the beach or exploring the local area.

Are there any Caine Woods holiday rentals with parking?

Vrbo offers a wide selection of holiday rentals in Caine Woods 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.

Are there pet-friendly holiday rentals in Caine Woods?

In Caine Woods, Maryland, travellers can find a selection of pet-friendly holiday rentals, with around 13 options available to choose from. Many of these properties come with convenient amenities such as fully equipped kitchens, spacious living areas, and private outdoor spaces, making them ideal for families or groups travelling with pets.

Can I find long-stay holiday rentals in Caine Woods?

A long-stay holiday rental in Caine Woods 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.

When is the best time to visit Caine Woods for a holiday rental?

July is the most popular month to visit Caine Woods, with a vibrant atmosphere that many holidaymakers cherish. The peak season runs from June to August, offering warm weather ideal for outdoor activities such as beach outings, hiking, and exploring the scenic coastal area of Maryland. During this time, visitors can enjoy the beauty of the nearby Assateague Island National Seashore, famous for its wild horses and pristine beaches.

Temperatures in July typically hover in the mid-20s Celsius, providing the great backdrop for a range of activities, from sunbathing to water sports. Families and groups flock to Caine Woods to relish the convenience of nearby amenities, including restaurants, shops, and various entertainment options.

For those seeking a more budget-friendly experience, consider visiting in November. While this month may be quieter, it offers a unique charm with fewer crowds and the chance to enjoy the serene beauty of the area during the fall. The mild temperatures in late autumn are still pleasant for scenic walks and enjoying the local parks.

Are there any remote work holiday rentals in Caine Woods?

In Caine Woods, Maryland, there are numerous options for remote work holiday rentals, with around 53 properties available to suit your needs. Many of these rentals are well-equipped for those looking to balance work and leisure, featuring amenities such as high-speed Wi-Fi, dedicated desk spaces, and comfortable chairs. Some properties even include additional features like computer monitors and laptop workspaces, ensuring you have everything necessary for productivity during your stay. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.

How early should I book a Caine Woods holiday rental?

Book your Caine Woods 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.

Can I change or cancel my Caine Woods home rental booking on Vrbo?

To find Caine Woods 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 flat or a countryside retreat, you can turn your space into a standout destination—become a host and let Vrbo handle the heavy lifting to help you thrive.

Are all fees included in the Caine Woods 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.