Discover Your Perfect Chatham Vacation Homes

Chatham Luxury Rentals

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9.5 (93 Reviews)
Bed & Breakfast
Old Harbor Inn
  • Air Conditioner
  • Parking
  • View
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Chatham Pet Friendly Vacation Rentals

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Chatham Large Vacation Homes

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Why Choose Rent By Owner for your Chatham 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 Chatham

When should you plan your Vacation Rentals stay?

Choosing the ideal time to visit ensures you can fully enjoy the tranquility and natural beauty of this destination, making your stay in the area truly memorable and tailored to your preferences.

Peak Season Highlights

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Summer (June to August)

During the peak summer months, you will experience warm days ideal for enjoying the coastal scenery and outdoor activities that make this destination popular.

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

The early fall offers mild weather and vibrant foliage, making it a perfect time for exploring local sights and relaxing in comfortable vacation rentals here.

Average Temperature Daytime: 65-75°F - Nighttime: 50-55°F

Off-Season Highlights

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Late Fall to Early Winter (November to December)

As the region transitions into winter, fewer visitors arrive, providing a quieter experience while still enjoying some of the area's scenic beauty.

Average Temperature Daytime: 50-55°F - Nighttime: 40-45°F
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Winter (January to February)

The cold winter season sees lower temperatures and fewer travelers, making it an ideal period for those seeking tranquility and cozy stays in the area’s rental properties.

Average Temperature Daytime: 40-45°F - Nighttime: 30-35°F

Weekly Weather Forecast for Chatham

How to Book Your Chatham 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 Chatham

More Top-Rated Vacation Rentals in Chatham 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 your outdoor living space with a private patio or deck perfect for relaxing or dining al fresco.
  • Take advantage of beautifully maintained landscaped gardens that add charm and serenity to your stay.
  • Benefit from access to a lush, grassy yard ideal for outdoor games or simply unwinding in the fresh air.
  • Make use of a charming porch or veranda, offering a peaceful spot to enjoy morning coffee or evening sunsets.
  • Relax by a private swimming pool, perfect for cooling off during warm summer days in this coastal region.
  • Utilize outdoor grilling facilities to prepare delicious meals while enjoying the scenic surroundings.
  • Take advantage of nearby beaches or waterfront access, providing opportunities for swimming, kayaking, or sunbathing.

Top Attractions Around Chatham

What attractions are nearby?

Within this charming region, you can enjoy a variety of outdoor activities and scenic explorations nearby your vacation rentals, ensuring a memorable stay in the area.

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Family Activities

  • Chatham Lighthouse Beach: Enjoy a family day by the shore at this iconic lighthouse beach, perfect for swimming, picnicking, and building sandcastles along the scenic coast.
  • The Chatham Marconi Maritime Center: Explore interactive exhibits and maritime history that captivate children and adults alike, offering an educational experience right here in the region.
  • Monomoy National Wildlife Refuge: Discover diverse wildlife through family-friendly hiking trails and birdwatching opportunities at this protected natural area nearby.
  • Chatham Fish Pier: Observe local fishermen at work and learn about the region’s fishing industry, making it an engaging activity for the whole family to enjoy.
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Adult Activities

  • Whale Watching Tours: Embark on an exciting whale watching adventure that offers a close-up view of marine life in the waters surrounding the region.
  • Fishing Charters: Spend a day deep-sea fishing with local guides, perfect for those seeking both relaxation and a bit of a challenge in this coastal area.
  • Beach Exploration: Relax or engage in water activities along the pristine beaches, enjoying the scenic beauty and tranquil atmosphere of the region.
  • Historic Lighthouse Tours: Discover the area's maritime history by visiting iconic lighthouses, where you can learn about local navigation and enjoy stunning coastal views.

Other Places to Stay in Chatham, MA

Ridgevale Beach
Ridgevale Beach Vacation Rentals
Cockle Cove Beach
Cockle Cove Beach Vacation Rentals
Hardings Beach
Hardings Beach Vacation Rentals
Chatham Drama Guild
Chatham Drama Guild Vacation Rentals
Monomoy Theatre
Monomoy Theatre Vacation Rentals
Hardings Lighthouse
Hardings Lighthouse Vacation Rentals
Veterans Field
Veterans Field Vacation Rentals
Chatham Railroad Museum
Chatham Railroad Museum Vacation Rentals
Atwood House Museum
Atwood House Museum Vacation Rentals
Gallery Antonia
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Fox Hill
Fox Hill Vacation Rentals
West Chatham
West Chatham Vacation Rentals
More Places to Stay Near Chatham

Chatham Travel Tips

How Can You Make the Most of Your Stay?

  • Plan Your Visit During Off-Peak Seasons: Visiting during less busy times allows you to enjoy the area's natural beauty and local attractions with fewer crowds while potentially benefiting from better rates on vacation rentals.
  • Explore Local Beaches and Nature Trails: Take advantage of the region’s scenic coastal areas and hiking paths to experience the area's stunning landscapes and outdoor activities firsthand.
  • Book Early for Popular Properties: Securing your preferred vacation rentals well in advance ensures you have the best selection and can enjoy a more relaxed stay at this sought-after destination.
  • Support Local Businesses and Eateries: Enhance your visit by dining at local restaurants and shopping at neighborhood markets, immersing yourself in the authentic charm of the area.

Transportation Options

  • Car Rentals: Local car rental agencies provide convenient transportation options for exploring the scenic areas and attractions here.
  • Public Transit: The regional bus services offer affordable and reliable travel throughout the region, making it easy to get around without a vehicle.
  • Taxi and Rideshare Services: Taxis and popular rideshare companies are readily available for quick trips within the area or to nearby destinations.
  • Bicycle Rentals: Biking is a charming way to experience the region’s coastal beauty, with several rental shops offering bikes suited for all levels.

Local Customs Options

  • Clam Shucking Tradition: Locals take pride in the region's clam shucking customs, which are a staple of seaside dining experiences here.
  • Boat Parade Celebrations: The area hosts annual boat parades where community members showcase their vessels, reflecting its maritime heritage.
  • Fishing Etiquette: Respectful fishing practices are observed by residents, emphasizing sustainability and local conservation efforts.
  • Seasonal Festivals: This destination features seasonal festivals that celebrate its coastal culture, providing authentic local experiences for visitors.

Frequently Asked Questions About Chatham?

1. What are the top vacation rentals in Chatham?

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

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

There are 38 vacation rentals with private pools near Chatham. Top-rated RBO homes that have access to a swimming pool include:

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

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

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

Currently, the total number of properties listed by Rent By Owner in 2026 is over 655 in the Chatham 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 Chatham. 

5. What is the cancellation policy for vacation rentals in Chatham, Massachusetts?

The cancellation policy varies by property listing. For specific details regarding your booking, please review the cancellation terms on the listing or contact the property owner directly.

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

Additional fees such as cleaning charges, service fees, or taxes are typically outlined in the listing details. It’s advisable to read the full description or ask the host for clarification before confirming your reservation.

7. How do I secure my reservation and what payment options are accepted for properties here?

Reservations are secured through the online booking process, which accepts various secure payment methods. Specific payment options are detailed during the checkout, and you can also contact the owner if you need assistance.

8. What amenities are generally available in vacation rentals in this destination?

Amenities vary by property but often include essentials like Wi-Fi, parking, kitchen facilities, and outdoor spaces. To find accommodations with your preferred amenities, review the listing details carefully or reach out to the property owner.

9. Is there a minimum stay requirement for booking vacation rentals in this area?

Many listings specify a minimum stay requirement, which can range from one night to several nights depending on the property and season. Confirm the minimum stay by reviewing the individual listing or contacting the host directly.

Chatham Top Rated Vacation Rentals

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