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Cuttyhunk Luxury Rentals

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Why Choose Rent By Owner for your Cuttyhunk 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 Cuttyhunk

When should you plan your Vacation Rentals stay?

Choosing the best time to visit here can enhance your experience, as the region offers distinct advantages during each season, making it essential to consider weather patterns and local events when planning your stay in this charming destination.

Peak Season Highlights

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Summer (June to August)

This destination experiences its peak during the warm summer months, making it ideal for enjoying the region's scenic outdoor activities and relaxing by the water.

Average Temperature Daytime: 75-85°F - Nighttime: 60-70°F
autumn
Early Fall (September to October)

The early fall offers pleasant weather and fewer crowds, providing a peaceful setting for exploring the area’s natural beauty and local charm.

Average Temperature Daytime: 65-75°F - Nighttime: 55-60°F

Off-Season Highlights

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Late Fall to Early Winter (November to December)

During these months, the quiet ambiance invites you to enjoy a more secluded experience while experiencing cooler temperatures and off-season tranquility.

Average Temperature Daytime: 50-60°F - Nighttime: 40-50°F
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Winter (January to February)

Visit during winter to embrace the peacefulness of this smaller destination, with fewer visitors and a serene atmosphere perfect for cozy getaways.

Average Temperature Daytime: 30-45°F - Nighttime: 25-35°F

Weekly Weather Forecast for Cuttyhunk

How to Book Your Cuttyhunk 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 Cuttyhunk

More Top-Rated Vacation Rentals in Cuttyhunk 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

  • Enjoy a private outdoor space with a garden or patio to relax and unwind after your day exploring the region.
  • Take advantage of outdoor dining areas, perfect for savoring fresh local seafood or a morning coffee.
  • Make use of outdoor grilling equipment to prepare delicious meals amidst scenic surroundings.
  • Benefit from access to nearby beaches or waterfronts for swimming, sunbathing, or water sports.
  • Utilize outdoor recreational facilities such as a fire pit or lounge area for evening gatherings.
  • Explore well-maintained yards or landscaped gardens that provide peaceful spots for reading or picnicking.
  • Look for properties with outdoor showers to rinse off after a day at the sandy shoreline nearby.

Top Attractions Around Cuttyhunk

What attractions are nearby?

In this charming destination, you can enjoy a variety of outdoor activities such as boating, fishing, and exploring scenic trails just moments from your vacation rental.

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Family Activities

  • Clamming and Beachcombing: You can enjoy exploring the pristine shores to find unique shells and clams, making it a fun and engaging activity for the whole family.
  • Hiking along scenic trails: The area offers family-friendly hiking paths that wind through picturesque landscapes, perfect for discovering local flora and fauna.
  • Fishing excursions: Embark on a fishing trip in the calm waters surrounding this destination, where kids can learn about local marine life while trying their luck at catching fish.
  • Wildlife watching opportunities: Spot various seabirds and other wildlife native to the region, providing educational and memorable experiences for children of all ages.
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Adult Activities

  • Boating Adventures: Embark on a scenic boat tour around the region, offering a unique perspective of the area's natural beauty and maritime history.
  • Fishing Excursions: Enjoy a relaxing day of fishing in the waters surrounding here, which are renowned for their abundant marine life.
  • Hiking Trails: Explore the scenic trails that wind through the island’s landscape, providing breathtaking views and a peaceful escape into nature.
  • Sailing Experiences: Take part in sailing excursions that allow you to harness the wind and discover the coastal charm of this destination.

Other Places to Stay in Cuttyhunk, MA

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Barges Beach Vacation Rentals
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Cuttyhunk Travel Tips

How Can You Make the Most of Your Stay?

  • Plan Ahead for the Season: Book your preferred vacation rentals early to secure the best options during peak seasons in this charming destination.
  • Explore Local Water Activities: Take advantage of the region’s serene waters by kayaking or boating, making your stay here truly memorable.
  • Discover Quiet Beaches: Visit the area’s lesser-known beaches to enjoy peaceful moments and scenic views away from crowds.
  • Engage with the Community: Participate in local events or visit nearby eateries to immerse yourself in the authentic charm of this inviting destination.

Transportation Options

  • Ferry Service: The primary way to reach the area is by ferry, offering scenic and reliable transport from the mainland directly to your vacation rental destination.
  • Private Boat Charters: For a personalized experience, private boat charters provide flexible transportation options around this destination’s beautiful waters.
  • Rental Bicycles and Kayaks: Exploring locally on bicycle or kayak rentals allows you to enjoy the region's natural beauty at your own pace.
  • Walking and Small Vehicle Access: Once here, walking is convenient for short distances, and small vehicle access helps you navigate between different parts of this destination comfortably.

Local Customs Options

  • Sea Shanty Traditions: Engaging in or listening to traditional sea shanties is a cherished custom, reflecting the area's maritime heritage and welcoming visitors to partake in local musical gatherings.
  • Clam Digging Etiquette: Respect for the environment and adherence to community guidelines are key when participating in clam digging, a popular local activity that connects you with the region’s maritime culture.
  • Community Seafood Festivals: Attending seasonal seafood festivals offers an authentic taste of local flavors and a chance to connect with residents celebrating their coastal traditions.
  • Maritime Conservation Practices: Supporting and practicing sustainable fishing and boating habits demonstrates respect for the area's natural resources and preserves its marine beauty for future visitors.

Cuttyhunk Vacation Rental Frequently Asked Questions

1. What are the top vacation rentals in Cuttyhunk?

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

2. How many vacation rentals have private pools in Cuttyhunk?

There are 1 vacation rentals with private pools near Cuttyhunk. Top-rated RBO homes that have access to a swimming pool include:

3. Which vacation homes in Cuttyhunk are best for families?

If you are looking for a family-friendly vacation home in Cuttyhunk, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Cuttyhunk:

4. How many Rentbyowner vacation rentals are available in Cuttyhunk?

Currently, the total number of properties listed by Rent By Owner in 2026 is over 263 in the Cuttyhunk 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 Cuttyhunk. 

5. What is the cancellation policy for vacation rentals in this area?

Cancellation policies vary depending on the property owner and the specific listing. To ensure you understand the terms, please review the cancellation details provided in the listing or contact the owner directly before booking.

6. Are there any specific check-in and check-out times I should be aware of?

Check-in and check-out times are determined by each property owner. Details are typically included in the listing information, so it’s recommended to review these or reach out to the host for clarification.

7. How do I find verified vacation rentals in this region that meet my needs?

You can filter search results by amenities, price range, and guest capacity to find verified vacation rentals that suit your preferences. Always read reviews and confirm details with the host to ensure a smooth stay.

8. Is there parking available at the vacation rentals here?

Parking options depend on the specific rental property. Some listings specify parking availability, while others may require street parking or nearby facilities. Check the listing details or contact the owner for parking information.

9. What should I know about local regulations and restrictions when booking a vacation rental here?

Local regulations regarding short-term rentals may apply, including registration or permit requirements. It’s advisable to review the listing details carefully or contact the property owner to ensure compliance with regional rules during your stay.