Discover Your Perfect Dock Square Vacation Homes

Best Vacation Homes in Dock Square

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10.0 (16 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • TV
|
10.0 (1 Review)
House
  • Wheelchair Accessible
  • Balcony/Terrace
  • Accessibility
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9.6 (129 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Balcony/Terrace
|
9.6 (102 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Pool

Why Choose Rent By Owner for your Dock Square 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.

Best Times to Visit Dock Square

When should you plan your Vacation Rentals stay?

Choosing the right time to visit ensures you can enjoy the area's charming ambiance and find the perfect vacation rentals for a memorable getaway in this scenic coastal region.

Peak Season Highlights

summer
Summer (June to August)

During the summer months, this popular destination experiences its peak season with vibrant outdoor activities and lively coastal gatherings.

Average Temperature Daytime: 75°F to 85°F - Nighttime: 60°F to 65°F
autumn
Fall (September to October)

The early fall offers stunning foliage views and pleasant weather, attracting visitors seeking scenic beauty and outdoor exploration.

Average Temperature Daytime: 65°F to 70°F - Nighttime: 50°F to 55°F

Off-Season Highlights

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Late Fall to Early Winter (November to December)

As the region transitions into winter, quieter streets and fewer tourists create a peaceful atmosphere ideal for cozy getaways.

Average Temperature Daytime: 45°F to 55°F - Nighttime: 35°F to 40°F
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Early Spring (March to April)

Before the busy summer season kicks in, early spring offers a tranquil setting with fewer visitors and budding scenery.

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

Weekly Weather Forecast for Dock Square

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 lounging spaces with comfortable seating to relax while taking in the fresh ocean air.
  • Benefit from private patios or decks perfect for outdoor dining and morning coffee sessions.
  • Make use of scenic gardens or landscaped yards that showcase the natural beauty of this coastal region.
  • Take advantage of outdoor grilling areas to prepare delicious meals during your stay here.
  • Utilize convenient outdoor showers, ideal for rinsing off after a day at the nearby beaches.
  • Experience the tranquility of private verandas or porches with views of the surrounding scenery.
  • Access to nearby walking trails or outdoor recreational spaces that showcase the area's coastal charm.
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Family Activities

  • Kenbunkenport Whale Watching Tours: Embark on an exciting whale watching adventure that gives your family a chance to see majestic marine life right off the coast of this charming seaside town.
  • Kennebunkport Art Galleries: Explore local art at the galleries scattered around the area, offering engaging exhibits that inspire creativity for visitors of all ages.
  • Dock Square Shops and Boutiques: Stroll through the vibrant shops and boutiques in the square, where you can find unique souvenirs and handcrafted goods to remember your trip.
  • Walk along the Kennebunkport Seaside Path: Enjoy scenic views and fresh ocean air as you walk along the picturesque seaside path, perfect for family outings and appreciating the region’s natural beauty.
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Adult Activities

  • Boat Tours and Sightseeing Cruises: Embark on a scenic boat tour to enjoy the stunning coastline and marine wildlife in this charming region.
  • Shopping and Boutique Browsing: Explore the unique local shops and boutiques in the area, perfect for finding memorable souvenirs and handcrafted goods.
  • Fine Dining Experiences: Savor fresh seafood and regional cuisine at renowned restaurants that showcase the culinary delights of here.
  • Art Galleries and Cultural Attractions: Visit local art galleries and cultural sites to appreciate the creative spirit and heritage of this destination.

Dock Square Travel Tips

How Can You Make the Most of Your Stay?

  • Explore Local Dining and Shopping: Take advantage of the charming shops and eateries in the area to immerse yourself in the local culture and support small businesses during your stay.
  • Plan Day Trips to Nearby Attractions: Use this destination as a base to discover scenic spots and cultural sites nearby, enriching your visit with memorable excursions.
  • Book Your Stay in Advance: Secure your preferred vacation rentals early to ensure a comfortable and convenient experience here, especially during peak seasons.
  • Take Advantage of Waterfront Views: Choose accommodations that offer water vistas or are close to the harbor to maximize your relaxing and picturesque moments throughout your trip.

Transportation Options

  • Car Rentals: Renting a car here offers the flexibility to explore the wider region at your own pace, with multiple rental agencies conveniently located nearby.
  • Taxis and Ride-Sharing Services: Taxis and popular ride-sharing options provide quick and reliable transportation within the area and to neighboring attractions.
  • Public Transportation: Local buses connect you to key spots in Kennebunkport, making it easy to get around without a personal vehicle.
  • Bicycle Rentals: Cycling is a scenic way to enjoy this destination’s charming streets and nearby coastal paths, with bike rentals available close to the heart of the region.

Local Customs Options

  • Clam Shucking:** Locals here cherish the tradition of clam shucking, a common activity that reflects the area's rich maritime heritage.
  • Seafood Etiquette:** When dining in this region, expect a casual yet respectful approach to seafood sharing, emphasizing freshness and local sourcing.
  • Festival Celebrations:** Participating in seasonal festivals offers a glimpse into the community's customs, celebrating the region’s coastal culture.
  • Harbor Practices:** Respect for boat docking procedures and maritime safety is central to daily life along the waterfront here in the area.

Frequently Asked Questions About Dock Square?

2. How many Rentbyowner vacation rentals are available in Dock Square?

Currently, the total number of properties listed by Rent By Owner in 2025 is over 604 in the Dock Square 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 Dock Square. 

3. What is the cancellation policy for booking a vacation rental in Dock Square, Kennebunkport?

Cancellation policies vary depending on the property listing. It is recommended to review the specific terms outlined in the rental agreement or contact the property owner directly to understand the cancellation details before completing your booking.

4. Are there any requirements or restrictions when booking a vacation rental here?

Yes, each property may have its own set of requirements or restrictions, such as minimum stay durations, age limits, or pet policies. Please read the listing details carefully or reach out to the host for clarification before confirming your reservation.

5. How do I know if my preferred dates are available for a vacation rental?

Availability is shown directly on each listing. You can select your desired dates to see if the property is available or contact the property owner for more precise information, especially during peak travel seasons.

6. Is there a deposit required to secure my booking in this destination?

Most properties require a security deposit or upfront payment at the time of booking. Check the specific listing details or contact the host to understand the deposit amount and payment process.

7. What amenities can I expect from vacation rentals in this area?

Amenities vary by property but typically include essentials such as Wi-Fi, kitchen facilities, and comfortable furnishings. For a detailed list of amenities, review the individual property listing or communicate directly with the owner.

Best Vacation Homes in Dock Square

|
9.7 (281 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Pet Friendly
|
9.7 (9 Reviews)
Apartment
  • Security/Safety
  • Sports/Activities
  • Fireplace/Heating