Discover Your Perfect Ragged Island Vacation Homes

Best Vacation Homes in Ragged Island

Why Choose Rent By Owner for your Ragged Island Vacation Rental Homes?

What makes our Vacation Rentals special?

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Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
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Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
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Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.

Popular Areas for Ragged Island Vacation Rentals

Where are the best neighborhoods to stay in Ragged Island?

When choosing where to stay on Bailey Island in Ragged Island, Maine, you'll find that the neighborhoods offer a perfect blend of tranquility and scenic beauty. This coastal area is ideal for those seeking a peaceful retreat surrounded by stunning ocean views and charming seaside landscapes. Whether you prefer staying close to the waterfront or in quieter inland communities, each neighborhood provides easy access to the natural splendor of Maine’s coast. Booking one of the reliable vacation rentals in this region ensures a comfortable and convenient base to explore all that Bailey Island has to offer.

West Point

Nestled along the scenic coast, this area offers a tranquil setting for those seeking a peaceful retreat in Maine. You can enjoy serene water views and easy access to local amenities that enhance your stay.

View 61+ Rentals in West Point

Small Point

Known for its charming waterfront ambiance, this neighborhood provides an ideal backdrop for relaxation and exploration. Here, you’ll find a quiet atmosphere perfect for unwinding amidst Maine’s natural beauty.

View 97+ Rentals in Small Point

Bustins Island

Accessible by boat, this island community is perfect for visitors looking to escape the hustle and enjoy pristine shoreline and outdoor activities. It’s a secluded spot that embodies the charm of coastal Maine.

View 41+ Rentals in Bustins Island

Cliff Island

Offering breathtaking ocean vistas, this neighborhood caters to travelers who appreciate scenic landscapes and a close connection with nature. It’s an inviting destination for a peaceful getaway in the region.

View 225+ Rentals in Cliff Island

Sabino

Situated near historic towns, this lively neighborhood combines maritime heritage with modern comforts. It serves as a wonderful base for exploring the cultural and natural attractions nearby here.

View 69+ Rentals in Sabino

Best Times to Visit Ragged Island

When should you plan your Vacation Rentals stay?

Choosing the right time to visit here can enhance your experience, as the region offers unique seasonal charm that caters to different preferences for outdoor activities and scenic beauty.

Peak Season Highlights

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June to August

During the summer months, this destination experiences its peak season with warm weather ideal for outdoor activities and enjoying the scenic coastline.

Average Temperature Daytime: 75°F to 80°F - Nighttime: 55°F to 60°F
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September to October

Early fall marks another popular time to visit, offering pleasant temperatures and vibrant natural scenery that enhances your stay at prime vacation rentals here.

Average Temperature Daytime: 65°F to 70°F - Nighttime: 45°F to 50°F

Off-Season Highlights

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November to February

The cooler winter months see fewer visitors, making it a quiet time to enjoy serene surroundings at your chosen vacation rental while experiencing the region's tranquility.

Average Temperature Daytime: 35°F to 45°F - Nighttime: 20°F to 30°F
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March to May

Early spring offers a subtle transition with moderate temperatures, perfect for those seeking a peaceful escape before the busy summer season begins.

Average Temperature Daytime: 45°F to 55°F - Nighttime: 30°F to 40°F

Weekly Weather Forecast for Ragged Island

How to Book Your Ragged Island 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 Ragged Island

More Top-Rated Vacation Rentals in Ragged Island Area

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

  • Access to private or shared outdoor decks with scenic views of the region's coastline
  • Well-maintained gardens or landscaped yards ideal for relaxing or outdoor dining
  • Beach equipment such as kayaks, paddleboards, or beach chairs for exploring nearby shorelines
  • Outdoor barbecue grills perfect for hosting cookouts in this coastal destination
  • Patios or verandas equipped with outdoor furniture for enjoying the fresh sea air
  • Fire pits or outdoor fireplaces to gather around during cooler evenings
  • Spacious lawns or open areas suitable for outdoor activities and family fun

Top Attractions Around Ragged Island

What attractions are nearby?

Here, you can enjoy a variety of outdoor activities such as exploring scenic coastal walks, kayaking along the pristine waters, or simply relaxing on picturesque beaches just minutes from your vacation rental in Ragged Island, Bailey Island, Maine.

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Family Activities

  • Exploring Bailey Island's Scenic Trails: Embark on family-friendly walks along the island’s picturesque trails, offering stunning views of the coastline and opportunities for wildlife spotting.
  • Visiting the Maine Maritime Museum: Discover the region’s maritime history through engaging exhibits that entertain and educate children and adults alike.
  • Enjoying a Day at Orr’s Island Harbor: Spend relaxing hours by the harbor, watching boats come and go while picnicking with loved ones against a charming coastal backdrop.
  • Participating in Local Family Events: Take advantage of seasonal festivals and community gatherings that bring families together and showcase the area's welcoming spirit.
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Adult Activities

  • Sea Kayaking Adventures: Explore the scenic coastline and hidden coves by kayak, offering a peaceful way to experience the natural beauty of this coastal destination.
  • Fishing Excursions: Spend a day on the water trying your hand at local fishing spots renowned for their abundance of Maine's iconic species.
  • Harbor Cruises: Enjoy a leisurely boat tour around the region’s waters, taking in stunning vistas and learning about the area's maritime history.
  • Wildlife Watching: Observe seabirds and marine life such as seals and whales, which frequently frequent these waters, providing an unforgettable nature experience.

Ragged Island Travel Tips

How Can You Make the Most of Your Stay?

  • Plan Outdoor Activities Early: Take advantage of the region’s scenic coastal landscapes by scheduling outdoor adventures during the morning hours to enjoy calmer weather and stunning views.
  • Explore Local Seafood Cuisine: Savor the fresh flavors of the area's renowned seafood offerings by visiting nearby eateries or preparing meals in your rental that highlight local catches.
  • Respect Natural Surroundings: Preserve the area's natural beauty by staying on designated paths and practicing Leave No Trace principles during your stay.
  • Utilize Local Resources: Make the most of the region’s visitor centers and community guides to discover hidden gems and insider tips for an authentic experience here.

Transportation Options

  • Private Car Services: You can opt for local private car services to explore the region at your own pace and comfort.
  • Public Transit: Buses provide an affordable and eco-friendly transportation option connecting you to nearby towns and attractions in this coastal area.
  • Ferries: Ferries are available for scenic crossings and quick access to neighboring islands, offering a unique way to experience the region's maritime charm.
  • Bicycle Rentals: Renting a bicycle is a great way to enjoy the area's scenic views while maintaining flexibility during your stay here.

Local Customs Options

  • Maritime Greetings: Locals here typically exchange warm welcomes and friendly nods, reflecting the region’s strong maritime heritage.
  • Seafood Tradition: Enjoying freshly caught shellfish, especially lobster and clams, is a cherished custom that highlights this destination’s coastal culture.
  • Respect for Nature: There’s a deep reverence for the natural environment, with residents often engaging in conservation efforts to preserve the scenic beauty of the area.
  • Community Events: Participating in local gatherings and festivals centered around fishing and boat parades allows visitors to experience authentic regional customs.

Frequently Asked Questions About Ragged Island?

1. What are the top vacation rentals in Ragged Island?

There are a lot of options in Ragged Island. If you plan on staying in the Ragged Island area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Ragged Island:

2. How many Rentbyowner vacation rentals are available in Ragged Island?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 95 in the Ragged Island 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 Ragged Island. 

3. What is the cancellation policy for vacation rentals here in Bailey Island, Maine?

Cancellation policies vary by property. You should review the specific rental listing for details on refund eligibility and deadlines, or contact the property owner directly for clarification.

4. Are there any additional fees I should be aware of when booking a rental in this region?

Additional fees such as cleaning charges, service fees, or local taxes are typically included in the listing description. Confirm these details with the owner before completing your reservation to ensure transparency.

5. How can I find out about check-in and check-out times for my rental?

Check-in and check-out times are specified in each listing. If not clearly stated, it’s best to contact the property owner directly to confirm your arrival and departure schedule.

6. Is there parking available at properties in this destination?

Many rentals offer parking options, but availability varies. Refer to the property details or contact the owner to verify if parking is included and inquire about any associated costs.

7. What amenities are typically included in vacation rentals here, and how do I request them?

Amenities such as Wi-Fi, kitchens, or outdoor spaces are listed for each property. For specific requests or questions about available amenities, reach out directly to the property owner before booking.

Best Vacation Homes in Ragged Island