Five Islands Accommodations

House
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like-icon10.0
Exceptional
(3 Reviews)
2 Bedrooms 1 Bath 4 Guests 1000 ft²
  • Oceanfront
    Oceanfront
  • Fireplace/Heating
    Fireplace/Heating
More amenities
US $322/Night 7 Nights - US $2,256
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House
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like-icon9.5
Exceptional
(2 Reviews)
4 Bedrooms 2 Baths 8 Guests 2098.96 ft²
  • Oceanfront
    Oceanfront
  • Skiing
    Skiing
More amenities
US $549/Night 7 Nights - US $3,843
House
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like-icon10.0
Exceptional
(2 Reviews)
1 Bedroom 1 Bath 2 Guests 461 ft²
  • Oceanfront
    Oceanfront
  • Spa
    Spa
More amenities
US $366/Night 7 Nights - US $2,560
New
Cabin
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like-icon10.0
Exceptional
(1 Review)
2 Bedrooms 1 Bath 6 Guests 800 ft²
  • Oceanfront
    Oceanfront
  • Fireplace/Heating
    Fireplace/Heating
More amenities
US $568/Night 7 Nights - US $3,978
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House
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like-icon8.0
Excellent
(1 Review)
3 Bedrooms 1 Bath 6 Guests 1905.21 ft²
  • Skiing
    Skiing
  • Fireplace/Heating
    Fireplace/Heating
More amenities
US $561/Night 7 Nights - US $3,928
Cabin
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like-icon9.8
Exceptional
(48 Reviews)
2 Bedrooms 2 Baths 6 Guests 1152 ft²
  • Oceanfront
    Oceanfront
  • Fireplace/Heating
    Fireplace/Heating
More amenities
US $534/Night 7 Nights - US $3,738
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House
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like-icon7.3
Very Good
(4 Reviews)
2 Bedrooms 1 Bath 6 Guests 1786.81 ft²
  • Oceanfront
    Oceanfront
  • Skiing
    Skiing
More amenities
US $308/Night 7 Nights - US $2,154
House
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like-icon9.6
Exceptional
(108 Reviews)
1 Bedroom 1 Bath 2 Guests 733 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
US $323/Night 7 Nights - US $2,258
House
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like-icon7.0
Very Good
(1 Review)
2 Bedrooms 2 Baths 8 Guests 3584.38 ft²
  • Oceanfront
    Oceanfront
  • Fireplace/Heating
    Fireplace/Heating
More amenities
US $569/Night 7 Nights - US $3,983
House
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like-icon9.6
Exceptional
(19 Reviews)
2 Bedrooms 2 Baths 8 Guests 3587 ft²
  • Oceanfront
    Oceanfront
  • Fireplace/Heating
    Fireplace/Heating
More amenities
US $690/Night 7 Nights - US $4,833
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House
Map-icon
2 Bedrooms 2 Baths 6 Guests 1754.52 ft²
  • Oceanfront
    Oceanfront
  • Skiing
    Skiing
More amenities
US $667/Night 7 Nights - US $4,672
Apartment
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1 Bedroom 1 Bath 2 Guests 8611 ft²
  • Kitchen
    Kitchen
  • Air Conditioner
    Air Conditioner
More amenities
US $138/Night 7 Nights - US $964

Discover & compare premier experiences around Boothbay Harbor

We understand the importance of quality and reliability in your travel experiences. That's why we've curated options from the most reputable tour and activity providers globally, ensuring you have access to top-tier adventures.

Why Choose Rent By Owner for your Five Islands Accommodations?

What makes our Accommodations 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.

Best Times to Visit Five Islands

When should you plan your Accommodations stay?

Finding the perfect time to visit here can significantly enhance your experience, as seasonal variations in this region influence everything from weather to local activities, ensuring you choose the right period to enjoy the natural beauty and peaceful ambiance of Five Islands when booking your ideal accommodations.

Peak Season Highlights

summer
Summer (June to August)

During the warm summer months, this destination experiences its peak season, attracting visitors seeking outdoor activities and scenic views. Booking your accommodations early ensures you secure the best options here during this lively period.

Average Temperature Daytime: 75°F to 85°F - Nighttime: 55°F to 65°F
autumn
Early Fall (September to October)

The region reaches another peak as leaves change color, making it a popular time for visitors wanting to enjoy the vibrant landscape. Reserve your accommodations in advance to enjoy the best stay during this colorful season.

Average Temperature Daytime: 65°F to 70°F - Nighttime: 45°F to 55°F

Off-Season Highlights

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Late Fall to Early Winter (November to December)

As temperatures drop and the area prepares for winter, this is a quieter time to visit. Traveling during these months offers more tranquility and better deals on accommodations here.

Average Temperature Daytime: 40°F to 50°F - Nighttime: 30°F to 40°F
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Winter (January to February)

In the cold winter months, fewer visitors come, making it an ideal period for peaceful getaways. Look for cozy accommodations that provide comfort during the chilly season here.

Average Temperature Daytime: 30°F to 40°F - Nighttime: 20°F to 30°F

Weekly Weather Forecast for Five Islands

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.

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 access to private or shared outdoor decks and patios with scenic views of the surrounding area.
  • Relish in well-maintained gardens or lawn spaces for outdoor relaxation and gatherings.
  • Benefit from convenient outdoor parking options close to your rental property.
  • Take advantage of outdoor dining areas, perfect for enjoying meals amidst nature.
  • Explore nearby walking trails or pathways that offer scenic routes along the coast or through local landscapes.
  • Make use of outdoor grilling stations or barbecue facilities to enhance your dining experience.
  • Access to waterfront amenities such as docks, piers, or direct beach proximity for water activities.
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Family Activities

  • Visit Five Islands Lobster Co-op Experience a fun and educational tour where your family can learn about Maine's famous lobster fishing industry right here in the area.
  • Explore Reid State Park Enjoy a day at this scenic park with its sandy beaches, saltwater ponds, and walking trails perfect for outdoor family activities.
  • Go Kayaking in Georgetown Paddle along the tranquil waters of this coastal town to discover breathtaking views and marine wildlife suitable for all ages.
  • Discover local Maritime Museums Spend time exploring maritime history that provides engaging insights into this region’s rich seafaring heritage for the whole family.
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Adult Activities

  • Boating and Sailing: Experience the region’s scenic waters by renting a boat or joining a sailing tour to enjoy the breathtaking coastline views.
  • Fishing Adventures: Engage in freshwater or saltwater fishing along the coast, offering a relaxing way to connect with nature here.
  • Bird Watching: Explore local bird habitats and observe diverse species in their natural environment, perfect for outdoor enthusiasts.
  • Historic Tours: Discover the area's rich maritime history through guided tours that provide insight into its cultural heritage.

Five Islands Travel Tips

How Can You Make the Most of Your Stay?

  • Plan outdoor activities early: Take advantage of the region’s scenic coastline by scheduling boat trips, kayaking, or fishing in the morning when the weather is typically calm and more predictable.
  • Explore local dining options: Savor fresh seafood and regional specialties at nearby eateries to fully experience the authentic flavors of this destination.
  • Reserve accommodations in advance: Secure your preferred property through RentByOwner.com early, especially during peak seasons, to ensure the best availability and rates.
  • Discover hidden viewpoints: Seek out quiet spots along the coast for stunning sunset views and memorable photography opportunities during your stay here.

Transportation Options

  • Car Rentals: You can easily rent a vehicle to explore the charming surroundings and enjoy flexibility when visiting nearby attractions in this coastal area.
  • Regional Airport: The closest regional airport offers convenient flights for travelers arriving from distant locations seeking comfortable transit options.
  • Public Transit Services: Local bus services provide an affordable and reliable way to get around within the region, making it simple to access various points of interest.
  • Taxis and Rideshare: Taxis and rideshare options are readily available to provide you with quick and hassle-free transportation throughout this peaceful destination.

Local Customs Options

  • Maritime Greetings Locals here often exchange warm, maritime-inspired greetings that reflect the area's deep connection to the sea and nautical heritage.
  • Seafood Traditions Enjoy the custom of sharing freshly caught seafood, which is a central part of community gatherings and local celebrations in this coastal region.
  • Respect for Nature Visitors should observe the local customs of preserving the natural beauty and respecting wildlife, which are highly valued by residents.
  • Community Festivals Participating in the regional festivals often involves honoring longstanding traditions that celebrate the area's maritime history and cultural identity.

Frequently Asked Questions about Five Islands Accommodations

2. How many Accommodations are available in Five Islands?

Currently, the total number of properties listed by RBO in 2026 is over 90 in the Five Islands area, and still counting. By aggregating listings from multiple websites, RBO offers an immense amount of choice of the best Accommodations in Five Islands. 

3. What is the cancellation policy for accommodations in this area?

Cancellation policies vary by property, so it's best to review the specific listing details or contact the owner directly to understand the terms and any applicable fees.

4. Are there any amenities or services included with my stay?

Amenities differ depending on the accommodation type; please check the property description for details on what is offered, or reach out to the owner for clarification.

5. How do I confirm my booking and what should I expect during the reservation process?

Booking confirmation is typically received via email once your reservation is complete. For additional guidance, consult the listing details or contact the property owner directly.

6. Is there a minimum stay requirement for bookings in this destination?

Minimum stay requirements vary among properties. Review each listing for specific policies or contact the owner if you have questions about length of stay.

7. What should I do if I need to modify or cancel my reservation?

Modifications or cancellations are subject to the individual property's policies. Check the specific listing for instructions or reach out to the owner to discuss your options.

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4 Bedrooms 2 Baths 8 Guests 1850 ft²
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  • Fireplace/Heating
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  • Ocean View
    Ocean View
More amenities
US $3,906/Night 7 Nights - US $27,341