Best Vacation Homes in Ocean Pines
New
House
4 Bedrooms
2 Baths
10 Guests
Fireplace/Heating
Ocean View
Balcony/Terrace
View
US $1,896/Night
7 Nights - US $13,273
House
10.0(5 Reviews)
2 Bedrooms
1 Bath
3 Guests
699.65 ft²
Oceanfront
Spa- Fireplace/Heating
Pool
US $349/Night
7 Nights - US $2,443
House
9.8(8 Reviews)
1 Bedroom
1 Bath
Pet Friendly
Kitchen
Internet
Child Friendly
US $300/Night
7 Nights - US $2,100
New
House
5 Bedrooms
4 Baths
10 Guests
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
US $944/Night
7 Nights - US $6,606
House
10.0(3 Reviews)
4 Bedrooms
4 Baths
10 Guests
2195.84 ft²
Hot Tub- Fireplace/Heating
- Pool
- Pet Friendly
US $786/Night
7 Nights - US $5,500
House
3 Bedrooms
2 Baths
6 Guests
1369 ft²
- Fireplace/Heating
- Pool
- Kitchen
Parking
US $397/Night
7 Nights - US $2,779
House
10.0(44 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Pool
- Kitchen
- Parking
US $161/Night
7 Nights - US $1,129
House
10.0(6 Reviews)
2 Bedrooms
1 Bath
6 Guests
1150 ft²
- Fireplace/Heating
- Pool
- Ocean View
- Balcony/Terrace
US $298/Night
7 Nights - US $2,085
Ocean Pines Luxury Rentals
House
8 Bedrooms
7 Baths
22 Guests
Air Conditioner- Child Friendly
Laundry
Bedding/Linens
US $1,607/Night
7 Nights - US $11,252
House
10.0(33 Reviews)
6 Bedrooms
6 Baths
14 Guests
6000 ft²
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
US $1,483/Night
7 Nights - US $10,380
House
6 Bedrooms
5 Baths
17 Guests
- Air Conditioner
- Internet
- Child Friendly
- Laundry
US $1,288/Night
7 Nights - US $9,016
House
10.0(6 Reviews)
6 Bedrooms
4 Baths
13 Guests
1943 ft²
- Hot Tub
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $1,259/Night
7 Nights - US $8,810
House
10.0(20 Reviews)
5 Bedrooms
2 Baths
13 Guests
3660 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
US $989/Night
7 Nights - US $6,925
House
5 Bedrooms
3 Baths
13 Guests
3200 ft²
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
US $965/Night
7 Nights - US $6,753
House
3 Bedrooms
2 Baths
8 Guests
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
US $848/Night
7 Nights - US $5,934
New
House
10.0(1 Review)
4 Bedrooms
4 Baths
10 Guests
4233 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
US $792/Night
7 Nights - US $5,544
Ocean Pines Pet Friendly Vacation Rentals
House
9.8(152 Reviews)
2 Bedrooms
1 Bath
6 Guests
1000 ft²
Private Pool- Oceanfront
- Hot Tub
- Fireplace/Heating
US $372/Night
7 Nights - US $2,604
House
10.0(1 Review)
3 Bedrooms
2 Baths
7 Guests
1485.42 ft²
- Spa
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $323/Night
7 Nights - US $2,261
House
9.8(71 Reviews)
2 Bedrooms
1 Bath
3 Guests
700 ft²
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Pet Friendly
US $337/Night
7 Nights - US $2,360
House
10.0(1 Review)
3 Bedrooms
2 Baths
8 Guests
1517.71 ft²
- Fireplace/Heating
- Pool
- Pet Friendly
- Air Conditioner
US $440/Night
7 Nights - US $3,080
Cottage
9.6(17 Reviews)
2 Bedrooms
1 Bath
2 Guests
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
US $156/Night
7 Nights - US $1,092
House
9.6(5 Reviews)
2 Bedrooms
1 Bath
6 Guests
1152 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
US $348/Night
7 Nights - US $2,437
House
8.0(8 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $304/Night
7 Nights - US $2,125
House
10.0(109 Reviews)
3 Bedrooms
2 Baths
8 Guests
2000 ft²
- Fireplace/Heating
- Pool
- Ocean View
- Balcony/Terrace
US $435/Night
7 Nights - US $3,046
Ocean Pines Large Vacation Homes
House
10.0(65 Reviews)
5 Bedrooms
3 Baths
10 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $560/Night
7 Nights - US $3,920
House
10.0(1 Review)
6 Bedrooms
4 Baths
13 Guests
1948.27 ft²
- Hot Tub
- Fireplace/Heating
- Pool
- Pet Friendly
US $417/Night
7 Nights - US $2,917
House
10.0(51 Reviews)
5 Bedrooms
2 Baths
10 Guests
2643 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
US $627/Night
7 Nights - US $4,390
House
10.0(1 Review)
3 Bedrooms
2 Baths
10 Guests
1582.29 ft²
- Parking
- Internet
- Child Friendly
Wheelchair Accessible
US $265/Night
7 Nights - US $1,855
House
10.0(27 Reviews)
4 Bedrooms
2 Baths
10 Guests
1800 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $466/Night
7 Nights - US $3,261
House
10.0(20 Reviews)
4 Bedrooms
3 Baths
11 Guests
2400 ft²
- Fireplace/Heating
- Balcony/Terrace
- View
- Kitchen
US $392/Night
7 Nights - US $2,744
House
10.0(18 Reviews)
4 Bedrooms
4 Baths
10 Guests
2193 ft²
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Pool
US $721/Night
7 Nights - US $5,046
House
10.0(15 Reviews)
6 Bedrooms
3 Baths
14 Guests
- Hot Tub
- Fireplace/Heating
- Pool
- Ocean View
US $562/Night
7 Nights - US $3,934
Why Choose Rent By Owner for your Ocean Pines Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Popular Areas for Ocean Pines Vacation Rentals
Where are the best neighborhoods to stay in Ocean Pines?
When planning your stay in Ocean Pines, exploring the different neighborhoods can help you find the perfect setting for your vacation. Located near Berlin, Maryland, this area offers a variety of communities that cater to different preferences, from quiet, family-friendly streets to lively waterfront areas. Whether you're seeking a peaceful retreat or a vibrant spot close to local amenities, staying in Ocean Pines allows you to enjoy the relaxed coastal atmosphere while remaining conveniently connected to nearby attractions. By choosing the right neighborhood, you can enhance your experience and make the most of your visit to Maryland’s charming shore."}
Glen Riddle
Located within the scenic region near Ocean Pines, this neighborhood offers a tranquil setting ideal for relaxing getaway experiences. You’ll find it convenient to access the relaxing beaches and outdoor activities that make this area a desirable destination for vacationers.
View 626+ Rentals in Glen RiddleBest Times to Visit Ocean Pines
When should you plan your Vacation Rentals stay?
Choosing the right time to visit here can enhance your experience, as the peak seasons and quieter months each offer unique advantages for enjoying the best of Ocean Pines and the surrounding region.
Peak Season Highlights
Summer (June to August)
During the summer months, you'll experience warm weather ideal for enjoying the outdoor amenities and scenic views that this region offers.
Average Temperature Daytime: 85°F - Nighttime: 70°F
Fall (September to November)
The fall season brings mild temperatures and colorful foliage, making it a perfect time to explore the natural beauty of the area.
Average Temperature Daytime: 75°F - Nighttime: 55°F
Off-Season Highlights
Winter (December to February)
In winter, you can enjoy fewer crowds and more relaxing stays while experiencing cooler temperatures in this destination.
Average Temperature Daytime: 45°F - Nighttime: 30°F
Spring (March to May)
Spring offers a pleasant atmosphere with blooming scenery and less busy periods, perfect for a peaceful retreat here.
Average Temperature Daytime: 65°F - Nighttime: 45°F
Weekly Weather Forecast for Ocean Pines
How to Book Your Ocean Pines Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Ocean Pines
Common Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy a private outdoor swimming pool to relax and unwind during your stay.
- Take advantage of spacious patios or decks ideal for outdoor dining and entertaining.
- Benefit from access to well-maintained gardens or landscaped yards for leisurely strolls.
- Make the most of designated barbecue areas to host cookouts with friends and family.
- Discover outdoor fire pits perfect for cozy evenings under the stars.
- Utilize nearby boat docks or launch points if you plan to explore local waterways.
- Experience the convenience of parking spaces suitable for outdoor activities and excursions.
Top Attractions Around Ocean Pines
What attractions are nearby?
While staying here, you'll enjoy nearby activities such as fishing, boating, and golfing, allowing you to make the most of your visit to this charming region.
Family Activities
- Ocean Pines Community Center Activities: Engage your family in recreational classes and events that highlight the area’s vibrant community spirit.
- Berlin Museum of History: Discover local heritage and enjoy interactive exhibits designed to entertain and educate children of all ages.
- Assateague Island National Seashore: Experience the natural beauty of this coastal area with opportunities for beachcombing, wildlife viewing, and picnicking.
- Pines Point Golf Course: Spend quality time together on a scenic course that offers family-friendly golfing experiences amidst the region’s picturesque surroundings.
Adult Activities
- Golfing at River Run Golf Club: Enjoy a round of golf on the scenic courses nestled within the region, perfect for relaxing and practicing your swing.
- Windsurfing and kayaking in the nearby waterways: Explore the tranquil waters around here by renting equipment suitable for both windsurfing and kayaking adventure enthusiasts.
- Taste local flavors at Chesapeake Bay wineries: Indulge in wine tasting sessions at the area's renowned wineries, offering a taste of Maryland’s finest vineyards.
- Explore nature trails at Pocomoke State Forest: Discover the region's natural beauty through hiking, birdwatching, or simply enjoying a peaceful walk in this expansive forest area.
Other Places to Stay in Ocean Pines, MD
Ocean Pines Golf and Country Club
Pine Shore Golf North
River Run Golf Club
Ocean Pines Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local Events and Festivals: Keep an eye on community happenings in Ocean Pines to immerse yourself in the area's unique culture and seasonal festivities.
- Utilize Water Access Points: Take advantage of nearby boat launches and beaches to enjoy the region's renowned waterfront activities and scenic views.
- Plan Outdoor Adventures: Discover the area's parks and nature trails for outdoor excursions that highlight the natural beauty of this destination.
- Visit Local Dining Spots: Savor regional flavors at eateries close to your rental, enhancing your experience of the local cuisine in the region.
Transportation Options
- Ocean Pines Transit: This local bus service offers convenient transportation options within the area, making it easy to explore the region without a personal vehicle.
- Berlin Regional Airport: Located nearby, this airport provides domestic flights and rental car services to help you reach the destination comfortably.
- Rental Car Services: Major providers at the regional airports give you flexibility and independence to visit attractions around this Maryland seaside community.
- Taxi and Ride-Sharing Services: Available throughout the destination, these options offer quick and reliable transport for exploring the region or heading to the beaches.
Local Customs Options
- Welcome Celebrations: You will notice that community events and local festivals are an important part of life here, reflecting the area's friendly and welcoming spirit.
- Southern Hospitality: Expect a warm greeting and courteous interactions, as locals take pride in their gracious hospitality towards visitors.
- Seafood Traditions: The region's love for fresh seafood, especially Maryland blue crabs, is evident in local dining customs and gatherings along the coast.
- Respect for Nature: Preserving the natural beauty of the area is vital, with residents often engaging in environmentally conscious practices during outdoor activities.
Ocean Pines Vacation Rental Frequently Asked Questions
1. What are the top vacation rentals in Ocean Pines?
There are a lot of options in Ocean Pines. If you plan on staying in the Ocean Pines area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Ocean Pines:
- Newly Renovated Home With Impressive Views Of The 7Th Green!
- Million Dollar View! Waterfront oasis with Ocean City skyline view!
- FAIRWAY TO HEAVEN: GOLF course views and BEACH parking pass
- CANAL FRONT - GREAT VIEWS - 5 BDRM, 3&1/2 BATHS, 2 KINGS, GOLF, RELAX.
- Scenic Water front secluded house with pier and view of the bay overlooking OC
- Near it all OC beaches,Assateague island.Family-friendly white horse park
- Salty Air Serenity @ 728 Ocean Parkway in Ocean Pines, Maryland
- Ocean Pines Retreat with Beach Club
- Spacious waterfront/3 Levels/6 BR/5.5Ba/Elevator/4 Decks/Views! 5 stars
- Rhapsody in Blue Beach Cottage in Ocean Pines OC MD w/Beach Club Parking Pass
2. How many vacation rentals have private pools in Ocean Pines?
There are 24 vacation rentals with private pools near Ocean Pines. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in Ocean Pines are best for families?
If you are looking for a family-friendly vacation home in Ocean Pines, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Ocean Pines:
4. How many Rentbyowner vacation rentals are available in Ocean Pines?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 509 in the Ocean Pines area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Ocean Pines.
5. What is the cancellation policy for vacation rentals in Ocean Pines, Maryland?
Cancellation policies vary depending on the listing owner. It is important to review the specific terms outlined in each rental's listing or contact the owner directly for detailed information regarding cancellations and potential fees.
6. How do I know if a vacation home in Berlin has the amenities I need?
Each property listing provides a comprehensive list of amenities, allowing you to verify if it meets your requirements. For personalized assistance, reaching out to the property owner can help clarify any additional questions about the amenities offered.
7. Are there any booking restrictions or minimum stay requirements for properties here?
Many rentals in this region have specific booking policies, including minimum stay requirements. These details are typically specified within the individual listing, so reviewing those before booking or contacting the owner for clarification is recommended.
8. What should I consider when choosing a vacation rental in the area?
When selecting a property, consider factors such as location, available amenities, guest capacity, and reviews from previous visitors. Reading the listing carefully and communicating with the owner ensures your stay aligns with your expectations.
9. How can I ensure a smooth check-in process at my chosen rental in Ocean Pines?
Check the listing details for specific check-in instructions provided by the host. If you have any uncertainties or special requests, reaching out to the owner beforehand can facilitate a seamless arrival experience.
Ocean Pines Top Rated Vacation Rentals
House
10.0(99 Reviews)
3 Bedrooms
2 Baths
9 Guests
2400 ft²
- Fireplace/Heating
- Pool
- Ocean View
- Balcony/Terrace
US $504/Night
7 Nights - US $3,528
Condo
10.0(67 Reviews)
3 Bedrooms
2 Baths
7 Guests
1418 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
US $392/Night
7 Nights - US $2,741
House
10.0(43 Reviews)
3 Bedrooms
2 Baths
8 Guests
2200 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
US $480/Night
7 Nights - US $3,357
House
10.0(41 Reviews)
3 Bedrooms
2 Baths
6 Guests
1800 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
US $498/Night
7 Nights - US $3,489
House
10.0(31 Reviews)
4 Bedrooms
2 Baths
6 Guests
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
US $330/Night
7 Nights - US $2,313
House
10.0(26 Reviews)
3 Bedrooms
2 Baths
8 Guests
1700 ft²
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Pet Friendly
US $364/Night
7 Nights - US $2,548
House
10.0(25 Reviews)
3 Bedrooms
2 Baths
7 Guests
1380 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
US $646/Night
7 Nights - US $4,521
House
10.0(25 Reviews)
4 Bedrooms
2 Baths
8 Guests
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
US $319/Night
7 Nights - US $2,234
