Photo by Julia

Caine Woods holiday rentals

We found 861 holiday rentals — enter your dates for availability
Find the perfect place for you stay in Caine Woods by choosing from 59 houses, 46 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:25 Dec - 1 Jan

Main Suite Dining Area
Main Suite Kitchen Area
Stairs down from 1st Level Suites to Entrance of House
Seashell Suite Pano of Main Living Area
Exceptional
(77 reviews)

Beautiful Oceanside House in Fenwick Island DE with 12 Person Hot Tub

Fenwick Island

8% off
AU$27,918
for 7 nights, 1 home
AU$3,988 per night
includes taxes & fees
Beautiful Oceanside House in Fenwick Island DE with 12 Person Hot Tub
Poolside fire pit
Patio, grill, saltwater pool
Exterior front view
Hot tub
Exceptional
(18 reviews)

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

Ocean City

8% off
AU$13,453
for 7 nights, 1 home
AU$1,922 per night
includes taxes & fees
MADISON BAY BEACH GETAWAY-PRIVATE POOL-HOT TUB- FIRE PIT- WEEKLY STAY DISCOUNT
Exterior
Outdoor dining
Dining
Private kitchen
Exceptional
(34 reviews)

4 Shelter Beach Semi-Oceanfront Townhome with Incredible Views

Fenwick Island

6% off
AU$6,932
for 7 nights, 1 home
AU$990 per night
includes taxes & fees
4 Shelter Beach Semi-Oceanfront Townhome with Incredible Views
Living room with Lighthouse Cove views- 3rd level
Chef kitchen & dining room- 3rd level
Primary Bedroom- 2nd level
Views from the 4th level rooftop deck
Exceptional
(14 reviews)

GORGEOUS NEW Fenwick Island Duplex with views of LIGHTHOUSE COVE

Fenwick Island

8% off
AU$5,523
for 7 nights, 1 home
AU$789 per night
includes taxes & fees
GORGEOUS NEW Fenwick Island Duplex with views of LIGHTHOUSE COVE
Eat at the breakfast bar or dining table - or both!
Private kitchen
Room
Slider goes out to balcony.
Exceptional
(53 reviews)

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

Ocean City

8% off
AU$4,291
for 7 nights, 1 apartment
AU$613 per night
includes taxes & fees
Book now for 2025! Perfect for large family. Ocean block. Steps to Beach & Pool!
Interior
kitchen
living room
front
Exceptional
(72 reviews)

3 Bedroom, 2 Bath, Ocean Block Condo in North OC, Sleeps 6

Ocean City

8% off
AU$4,460
for 7 nights, 1 apartment
AU$637 per night
includes taxes & fees
3 Bedroom, 2 Bath, Ocean Block Condo in North OC, Sleeps 6
Room
Private kitchen
Interior
Dining
Exceptional
(11 reviews)

Wave Watcher's Condo - Steps to the beach!

Ocean City

5% off
AU$2,688
for 7 nights, 1 home
AU$384 per night
includes taxes & fees
Wave Watcher's Condo - Steps to the beach!
Welcome to Castaways Beach House!
Dining room with sliding doors to deck
The view from the deck in early spring.
Living area
Exceptional
(39 reviews)

Coastal chic waterfront townhouse w/bayside sunsets.

Ocean City

8% off
AU$2,998
for 7 nights, 1 home
AU$428 per night
includes taxes & fees
Coastal chic waterfront townhouse w/bayside sunsets.
Terrace/patio
Exterior
Huge 24x17 Deck
Outdoor dining
Exceptional
(17 reviews)

Direct Oceanfront at 129th St--2 BR--2 BA--Huge Deck--Recently Renovated

Ocean City

8% off
AU$4,013
for 7 nights, 1 apartment
AU$573 per night
includes taxes & fees
Direct Oceanfront at 129th St--2 BR--2 BA--Huge Deck--Recently Renovated
Dining table for 6-8 with additional counter seating
View towards living room and dining area
Covered porch with additional dining area for 6 and rocking chairs
Open concept and updated kitchen with granite counters and island seating.
Exceptional
(11 reviews)

⛱️⛱️ Ocean City Bayside 🦀

Ocean City

8% off
AU$3,609
for 7 nights, 1 home
AU$516 per night
includes taxes & fees
⛱️⛱️ Ocean City Bayside 🦀
Living area
Interior
Dining
Living area
Exceptional
(55 reviews)

10 minute walk to the beach! Family- size condo

Ocean City

8% off
AU$2,140
for 7 nights, 1 apartment
AU$306 per night
includes taxes & fees
10 minute walk to the beach! Family- size condo
Large open concept kitchen that looks over living room.
Beach
Pull out couch with Queen bed
Property grounds
Exceptional
(25 reviews)

Relax Here in this quiet Beach house!

Ocean City

8% off
AU$3,288
for 7 nights, 1 home
AU$470 per night
includes taxes & fees
Relax Here in this quiet Beach house!
Room
View from the Kitchen and living room. Back Deck
Private kitchen
Living area
Exceptional
(31 reviews)

SERENE WATER VIEWS-Relaxing family beach house

Ocean City

8% off
AU$5,265
for 7 nights, 1 home
AU$752 per night
includes taxes & fees
SERENE WATER VIEWS-Relaxing family beach house
DINING ROOM
LIVING ROOM
Private kitchen
Room
Exceptional
(13 reviews)

Best Oceanfront - North Ocean - 134th Street

Ocean City

8% off
AU$4,293
for 7 nights, 1 apartment
AU$613 per night
includes taxes & fees
Best Oceanfront - North Ocean - 134th Street
Room
You'll want to hang out on this deck all day long - catch a view of the ocean, people-watch and sip some cocktails.
142 steps to the beach from this 3-bed / 2-bath with recent upgrades!
You'll be on the beach in half a block!
Exceptional
(17 reviews)

Easy Access to Sand, Sun + Surf

Ocean City

7% off
AU$3,420
for 7 nights, 1 apartment
AU$489 per night
includes taxes & fees
Easy Access to Sand, Sun + Surf
Living area
Property grounds
Private kitchen
Dining
Exceptional
(9 reviews)

Cozy Beachside Condo a short walk to the sand

Ocean City

6% off
AU$3,857
for 7 nights, 1 apartment
AU$551 per night
includes taxes & fees
Cozy Beachside Condo a short walk to the sand
Kitchen
Balcony View
Living room ocean view window
Building Hallway
Excellent
(103 reviews)

Spacious Ocean View Condo

Ocean City

5% off
AU$1,427
for 7 nights, 1 apartment
AU$204 per night
includes taxes & fees
Spacious Ocean View Condo
Living area
Living area
Living area
Pool
Exceptional
(30 reviews)

OC BEACH BLISS! OCEANVIEW BEAUTY STEPS TO BEACH! INDOOR POOL & ELEVATOR

Ocean City

11% off
AU$2,014
for 7 nights, 1 apartment
AU$288 per night
includes taxes & fees
OC BEACH BLISS! OCEANVIEW BEAUTY STEPS TO BEACH! INDOOR POOL & ELEVATOR
Dining
Living area
Private kitchen
Interior
Exceptional
(12 reviews)

Brand New 3-bedroom, 3 1/2 bathroom townhome walking distance to the beach.

Ocean City

12% off
AU$9,340
for 7 nights, 1 home
AU$1,334 per night
includes taxes & fees
Brand New 3-bedroom, 3 1/2 bathroom townhome walking distance to the beach.
  • Peace of mind

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  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

Frequently asked questions

What is the most popular type of holiday rental in Caine Woods?
In Caine Woods, condos are the most popular choice for holiday rentals, with about 116 available throughout the area. These condos are typically located in close proximity to the beach and offer modern amenities such as fully equipped kitchens, spacious living areas, and often private balconies or patios for enjoying the coastal views.For those seeking more space, there are around 56 holiday houses available, which cater well to families or larger groups. These properties generally include multiple bedrooms, outdoor areas for barbecues, and sometimes private gardens, providing a comfortable setting for relaxation after a day of exploring nearby attractions.
Are there any beach house rentals in Caine Woods?
In Caine Woods, there are about 39 beach house rentals available, making it a popular choice for travellers seeking a coastal getaway. These rentals typically feature spacious living areas, fully equipped kitchens, and outdoor decks or patios where guests can enjoy the pleasant Maryland climate. Many of the properties are situated close to the beach, allowing easy access to the sandy shores and local attractions. Families and groups will appreciate the availability of multiple bedrooms and bathrooms, as well as amenities like BBQ grills and swimming pools in some properties.
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, along with onsite parking for convenience. Many properties also feature a coffee and tea maker for those early mornings or relaxing afternoons. Additionally, balconies and decks or patios are common, providing lovely outdoor spaces where visitors can enjoy the pleasant surroundings.
Can I find family house rentals in Caine Woods?
In Caine Woods, Maryland, there are numerous family-friendly house rentals available, with around 33 options to choose from. This neighbourhood is known for its tranquil atmosphere and proximity to the beautiful beaches of Ocean City. Many of these homes feature spacious living areas, fully equipped kitchens for preparing family meals, and outdoor decks or patios superb for barbecues or enjoying the fresh air.Visitors can also expect amenities such as Wi-Fi, air conditioning, and laundry facilities, which add to the convenience of family stays. The area is within easy reach of local attractions, including the vibrant boardwalk, water sports, and parks where children can play.
Can I rent a holiday home with a pool or hot tub in Caine Woods?
In Caine Woods, Maryland, there are several holiday homes available for rent that feature both pools and hot tubs, with around 14 options specifically offering pool amenities and several others with hot tubs. This coastal area is known for its proximity to the beach and vibrant local attractions, making it a popular choice for travellers.Rentals typically come equipped with a range of amenities, including private pools, hot tubs, spacious outdoor areas for relaxation, and fully equipped kitchens ideal for family gatherings or entertaining. Many properties also provide conveniences such as Wi-Fi, air conditioning, and outdoor grills, enhancing the comfort and enjoyment of your stay.
Can I book pet-friendly holiday rentals in Caine Woods?
In Caine Woods, Maryland, there are several pet-friendly holiday rentals available, making it a great destination for travellers looking to bring their furry friends along. With around twelve options to choose from, visitors can find accommodations that often feature spacious layouts, fully equipped kitchens, and outdoor spaces such as patios or decks, great for relaxing after a day of exploration.The neighbourhood is close to the beaches, providing opportunities for pet-friendly activities along the shoreline. Additionally, nearby areas like Ocean City boast parks and boardwalks where pets are welcome, allowing guests to enjoy scenic walks and fresh air. Many rentals in Caine Woods also come equipped with conveniences like laundry facilities, Wi-Fi, and off-street parking, ensuring a comfortable stay for both pets and their owners.
When is the best time to visit Caine Woods for a holiday rental?
The best time to visit Caine Woods for a holiday rental is during the peak season from June to August, with July being the most popular month. This vibrant period attracts families and beachgoers eager to enjoy the sun-soaked shores of the Atlantic. With warm temperatures averaging around 25 to 30 degrees Celsius, you can indulge in a variety of outdoor activities, from swimming and sunbathing to kayaking and paddleboarding.During the summer months, you'll find plenty of opportunities for family fun, including local festivals, farmers' markets, and the lively option of nearby boardwalks. The convenience of having a holiday rental means you can easily access the beach and local attractions, allowing you to create cherished memories with loved ones.If you're looking for a more budget-friendly option, consider visiting in November. This quieter month offers a serene escape, with fewer crowds and beautiful autumn scenery. While the temperatures are cooler, averaging around 10 to 15 degrees Celsius, you can still enjoy leisurely strolls along the beach and peaceful moments in nature.Ultimately, the ideal time to book your stay in Caine Woods depends on whether you seek the lively summer experience or the tranquil charm of the off-season.
Are there any remote work holiday rentals in Caine Woods?
In Caine Woods, Maryland, there is a substantial selection of remote work holiday rentals available, with around 172 options to choose from. This area is well-suited for those looking to combine work and leisure, as many properties come equipped with essential amenities for remote work. Travellers can expect features such as dedicated desk spaces, comfortable desk chairs, and reliable Wi-Fi, ensuring a productive environment away from home.The neighbourhood is in close proximity to beautiful beaches, local parks, and various recreational activities, making it an ideal place to unwind after a day of work. Many rentals also have communal areas and outdoor spaces, providing opportunities for relaxation and socialising. To help narrow your search, insert your dates and apply the "WiFi" filter on Stayz.
What are the top attractions in Caine Woods, Maryland, United States of America?
Caine Woods, Maryland, offers a variety of attractions primarily centred around its beautiful coastal environment. The nearby Ocean City is a major draw, with its famous boardwalk lined with shops, restaurants, and amusement parks, providing entertainment for all ages. Visitors can enjoy activities such as fishing, boating, and water sports in the surrounding area, particularly in the Assawoman Bay.Nature enthusiasts may wish to explore the nearby Fenwick Island State Park, which features pristine beaches and trails for walking and biking. Additionally, the Caine Woods community itself boasts scenic parks and recreational areas, great for leisurely strolls or family picnics.
Are all fees included in the Caine Woods 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 Caine Woods holiday homes with parking?
Stayz offers a wide selection of holiday homes 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 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 Caine Woods holiday homes?
You can find great discounts on holiday homes in Caine Woods 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 Caine Woods holiday home booking on Stayz?
To find Caine Woods 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 Caine Woods?
A long-stay holiday home 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 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 Caine Woods holiday home?
Book your Caine Woods 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 Caine Woods?
Prices for holiday homes 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 travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Caine Woods 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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