1. USA
  2. Maine
  3. Ashland
  4. Island Pond
  5. Rentals by Owner

Island Pond Rentals by Owner

10.0 (57 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Security/Safety
|
10.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Why Choose Rent By Owner for your Island Pond vacation rental?

What makes our Rentals by Owner 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 Island Pond

When should you plan your Rentals by Owner stay?

Choosing the right time to visit can enhance your experience here, as seasonal weather patterns and local events often influence the best periods for a memorable vacation in this destination.

Peak Season Highlights

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Summer (June to August)

During the summer months, this destination experiences its peak season, attracting visitors seeking warm weather and outdoor activities.

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

Autumn brings colorful foliage and cooler temperatures, making it a popular time for travelers looking to enjoy scenic views and outdoor adventures.

Average Temperature Daytime: 60-70°F - Nighttime: 40-50°F

Off-Season Highlights

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Late Fall to Early Winter (December to February)

During late fall and winter, fewer visitors come here, providing a quieter experience and an opportunity to enjoy the region’s peaceful winter landscape.

Average Temperature Daytime: 30-40°F - Nighttime: 15-25°F
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Early Spring (March to May)

This period sees a slowdown in tourism as the area begins to thaw, offering a tranquil setting for those seeking a serene escape before summer arrives.

Average Temperature Daytime: 40-55°F - Nighttime: 25-35°F

Weekly Weather Forecast for Island Pond

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 outdoor dining areas perfect for meals with scenic views of the surrounding nature.
  • Relax on spacious patios or decks that offer a peaceful setting to unwind after your adventures.
  • Take advantage of private yards or gardens, providing a great space for outdoor activities or relaxing in the fresh air.
  • Benefit from access to nearby lakes or rivers with opportunities for fishing, kayaking, or swimming.
  • Make use of outdoor fire pits or grills, ideal for evening gatherings and barbecues under the stars.
  • Use outdoor recreational facilities such as basketball hoops, swing sets, or play areas for family fun.
  • Explore scenic walking or hiking trails directly accessible from your rental property, allowing you to immerse yourself in the natural beauty of the area.
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Family Activities

  • Island Pond Scenic Trail: Enjoy a family-friendly hike along this picturesque trail that offers stunning views and easy access to the region's natural beauty.
  • Local Fishing Opportunities: Experience quality fishing in the area, where you can spend relaxing hours casting in serene waters perfect for all ages and skill levels.
  • Boating and Canoeing: Rent a boat or canoe to explore the peaceful waters nearby, providing a fun and engaging activity for the entire family.
  • Nature Observation and Wildlife Viewing: Venture into the surrounding forests and wetlands, ideal for spotting local wildlife and teaching young explorers about nature here.
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Adult Activities

  • Hiking and Nature Walks: Explore scenic trails in the area that offer serene views and a chance to connect with the natural beauty surrounding the region.
  • Fishing Adventures: Spend a relaxing day at local lakes and rivers, renowned for their excellent fishing opportunities suited for all skill levels.
  • Wildlife Viewing: Observe diverse wildlife in their natural habitat, making the area a perfect destination for nature enthusiasts seeking tranquility and outdoor activities.
  • Boating and Canoeing: Enjoy peaceful water excursions on nearby lakes, providing an ideal setting for boating or canoeing amidst the area's picturesque landscape.

Island Pond Travel Tips

How Can You Make the Most of Your Stay?

  • Explore Local Outdoor Activities: Take advantage of the area's natural beauty by enjoying outdoor pursuits such as hiking or fishing, which showcase the region's scenic landscapes and make your stay memorable.
  • Connect with Your Rental Host: Engage with your owner rental to gain insider tips about the best spots and hidden gems in this destination for an authentic experience.
  • Plan Ahead for Peak Seasons: Book your accommodations early during busy periods to ensure availability and secure the best rental options in the region.
  • Utilize Nearby Amenities: Make use of the local amenities available through your rental to enhance comfort and convenience during your visit here.

Transportation Options

  • Island Pond, Ashland's Car Rentals: Explore the area at your own pace with local car rental services that provide convenient access to this scenic region.
  • Public Transit in the Region: Buses and regional transit options connect you to nearby towns and essential amenities within this destination.
  • Taxi and Rideshare Services: Reliable taxi and rideshare providers offer quick and easy transportation throughout here and its surrounding communities.
  • Private Shuttle Services: For a more personalized experience, private shuttles operate within the area, ensuring smooth transfers to key locations.

Local Customs Options

  • Respect for Nature: Locals place a high value on preserving the pristine environment, encouraging visitors to engage in eco-friendly practices during their stay.
  • Community Gatherings: Participating in local events and festivals is an appreciated way to connect with residents and experience the region's authentic cultural heritage.
  • Traditional Crafts: Supporting handmade crafts and local artisans allows visitors to experience the region’s rich artisanal traditions firsthand.
  • Lodging Etiquette: Respecting property owners' guidelines ensures a harmonious stay, especially when renting directly from locals in this charming area.

Frequently Asked Questions About Island Pond Rentals by Owner

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

Currently, the total number of properties listed by Rent By Owner in 2025 is over 309 in the Island Pond 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 Island Pond. 

3. What is the cancellation policy for a rental by owner in the area?

The cancellation policy varies depending on the specific listing. You should review the cancellation terms listed on the property’s page or contact the owner directly for detailed information.

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

Additional fees, such as cleaning or service charges, are specified in each listing. It's best to read the full details on the rental page or confirm with the owner before finalizing your reservation.

5. How do I confirm my reservation and what is required upon check-in?

Reservation confirmation details are provided once you book. Check-in procedures, including key access and any requirements, are typically outlined in the listing description or communicated directly by the owner.

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

Minimum stay requirements vary by property. You can find this information on the listing page or by contacting the owner directly to ensure your travel plans align.

7. Can I get assistance if I encounter issues during my stay?

Support is available through the Rent By Owner platform, and you should also reach out to the property owner for immediate assistance during your stay to resolve any concerns quickly.

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