Best Vacation Homes in Pebble Beach
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Security/Safety
- Bedding/Linens
Why Choose Rent By Owner for your Pebble Beach Vacation Rental Homes?
What makes our Vacation Rentals special?
Popular Areas for Pebble Beach Vacation Rentals
Where are the best neighborhoods to stay in Pebble Beach?
When planning your stay in Pebble Beach, Rockport, Massachusetts, you’ll find a variety of neighborhoods that offer unique coastal charm and scenic beauty. Whether you prefer the quiet serenity of seaside locales or vibrant community areas close to local attractions, this region provides an ideal setting for your vacation. Exploring the different neighborhoods allows you to choose the perfect spot that matches your preferred pace and style, ensuring a memorable and comfortable experience. With dependable and accessible vacation rentals available, you can enjoy the authentic atmosphere of Rockport while staying conveniently close to its stunning shoreline and charming streets.
Annisquam
Nestled within the scenic Gloucester area, Annisquam offers charming surroundings and a peaceful coastal atmosphere that enhances your stay in this part of Massachusetts. It's an ideal spot to find vacation rentals that provide both comfort and convenience while exploring the region.
View 310+ Rentals in AnnisquamGreat Neck
Located near Ipswich, Great Neck is known for its tranquil waterfront views and inviting community ambiance. Here, you can choose from a variety of vacation rentals that make it easy to experience the natural beauty and serene environment of this beloved Massachusetts destination.
View 36+ Rentals in Great NeckBest Times to Visit Pebble Beach
When should you plan your Vacation Rentals stay?
Timing your visit to this charming coastal area can enhance your experience, so consider the local seasons and weather patterns to find the ideal time for your stay in Pebble Beach, Rockport, Massachusetts, USA.
Peak Season Highlights
June to September
During the summer months, you can experience warm weather and longer days, ideal for exploring the scenic coastline and enjoying outdoor activities in this destination.
Late April to May
Spring brings mild temperatures and blooming landscapes, making it a popular time for visitors seeking pleasant weather and fewer crowds at your chosen area.
Off-Season Highlights
October to March
During the fall and winter months, cooler weather and quieter surroundings make it an excellent choice for those looking to enjoy the region’s tranquility and beautiful seasonal scenery.
Late November to December
The holiday season offers a peaceful atmosphere with fewer visitors, perfect for savoring the area's serene environment and picturesque views during this quiet period.
Weekly Weather Forecast for Pebble Beach
How to Book Your Pebble Beach Vacation Rental Home
What's our booking process?
Booking Steps
Search Properties
Select a Rental
Book Online
Explore and book the perfect rental in Pebble Beach
Common Vacation Rentals Amenities
What amenities can you expect?
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 outdoor seating areas with scenic views of the surrounding coastline
- Take advantage of private gardens or landscaped yards to relax and unwind
- Experience easy access to nearby beaches for swimming, sunbathing, or beachcombing
- Make use of outdoor grilling facilities for memorable cookouts amid fresh sea air
- Relax on spacious patios or decks perfect for outdoor dining and entertaining
- Utilize covered porches or shaded verandas to stay comfortable during warm days
- Benefit from dedicated parking spaces within close proximity to outdoor amenities
Top Attractions Around Pebble Beach
What attractions are nearby?
Nearby, you can enjoy a variety of outdoor activities such as scenic coastal walks, boating, and exploring charming local shops, making it easy to immerse yourself in the beauty and charm of this seaside destination.
Family Activities
- Bearskin Neck walking tour: Explore the charming historic harbor area with its quaint shops and galleries, ideal for family outings in this scenic seaside destination.
- Rockport Maritime Museum visit: Discover local maritime history through engaging exhibits that provide an educational and fun experience for children and adults alike.
- Cape Ann Coastal Trail: Enjoy a family hike along this picturesque trail that offers stunning views of the Atlantic Ocean and the region’s natural beauty.
- Fishermen’s Memorial Statue: Pay a visit to this iconic monument that highlights the area's rich fishing heritage, perfect for a memorable family photo opportunity.
Adult Activities
- Golfing at Pebble Beach Golf Links: Enjoy a round of world-renowned golf on the scenic course that offers stunning ocean views and challenging play for enthusiasts visiting this part of Massachusetts.
- Exploring Rockport’s Art Galleries: Discover the vibrant local art scene by browsing through galleries featuring works inspired by the breathtaking coastal surroundings.
- Seaside Dining Experiences: Savor fresh seafood and local flavors at waterfront restaurants where you can indulge in exquisite meals with picturesque views.
- Harbor Cruises and Whale Watching: Embark on a boat tour from the area to get up close to marine life and enjoy spectacular vistas of the Atlantic along this coast.
Pebble Beach Travel Tips
How Can You Make the Most of Your Stay?
- Explore the Local Beaches: Take advantage of the pristine shoreline to enjoy relaxing walks, scenic picnics, or engaging in water activities that highlight this coastal area’s natural beauty.
- Visit Local Art Galleries and Shops: Stroll through charming galleries and boutiques to discover unique crafts and souvenirs that reflect the region's artistic spirit.
- Discover Scenic Outdoor Activities: Embrace outdoor adventures such as hiking, birdwatching, or kayaking to immerse yourself in the area's diverse landscape.
- Plan Your Dining Experiences: Savor fresh seafood and local cuisine at popular eateries to experience authentic flavors distinctive to this destination.
Transportation Options
- Driving: You can explore the region at your own pace by renting a car, offering flexibility to visit local attractions and scenic spots around Pebble Beach.
- Public Transportation: Local bus services provide convenient access to nearby towns and key points of interest in this coastal area.
- Taxis and Rideshare Services: Taxis and ridesharing options like Uber or Lyft are readily available for quick and hassle-free transportation within and around Rockport.
- Bike Rentals: Biking is an eco-friendly way to enjoy the area’s scenic views, with several bike rental shops catering to visitors seeking outdoor adventures.
Local Customs Options
- Respect for Maritime Traditions: You’ll find that honoring the region’s fishing heritage is a cherished custom, often reflected in local festivals and community events here.
- Greeting with Warmth: It’s customary to exchange friendly greetings and demonstrate genuine hospitality when interacting with residents around this coastal destination.
- Local Seafood Etiquette: When enjoying fresh seafood, it’s polite to appreciate the culinary traditions and engage with locals about their favorite dishes and preparation methods.
- Preservation of Natural Beauty: Visitors are encouraged to participate in or respect initiatives focused on conserving the scenic landscapes and coastal environment that define this area’s charm.
Frequently Asked Questions About Pebble Beach?
1. What are the top vacation rentals in Pebble Beach?
There are a lot of options in Pebble Beach. If you plan on staying in the Pebble Beach area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Pebble Beach:
- Good Harbor Beach House - walk to beach, close to restaurants and shopping!
- 'We can't wait to return to Four Winds'
- WaterViews Overlooking Gloucester Inner Harbor/Sunroom/Deck/Walk to Town/AC
- Gladview Rockport Apt #gladview#thacher
- Romantic Summerwind Cottage, Scenic Harbor View w/Large Deck
- Come home to Rockport!
- "Absolutely lovely. The cottage, the beach, the town, the owners."
- Walk to Good Harbor Beach. 3BR home, NEW Kitchen
- Enchanting Harbor Views - Historic Bradley Wharf Bearskin Neck
- Luxury Home in the Heart of Rockport
2. How many Rentbyowner vacation rentals are available in Pebble Beach?
Currently, the total number of properties listed by Rent By Owner in 2025 is over 367 in the Pebble Beach 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 Pebble Beach.
3. What is the cancellation policy for booking a vacation rental in this area?
4. How do I secure my reservation at a vacation rental in this destination?
5. Are there any additional fees I should be aware of when booking a vacation rental here?
6. What amenities can I expect in a vacation rental in this region?
7. Is there a minimum stay requirement for booking here?
Best Vacation Homes in Pebble Beach
- Air Conditioner
- TV
- View
- Air Conditioner
- Parking
- TV
- Air Conditioner
- Parking
- Pet Friendly
- Air Conditioner
- Parking
- TV
- Parking
- Security/Safety
- Bedding/Linens
- Air Conditioner
- Parking
- TV
- Air Conditioner
- Parking
- TV
- Air Conditioner
- Parking
- TV
