Discover Your Perfect Old Chatham Vacation Homes

Old Chatham Luxury Rentals

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Old Chatham Pet Friendly Vacation Rentals

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Why Choose Rent By Owner for your Old 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 Old Chatham

When should you plan your Vacation Rentals stay?

Choosing the right time to vacation in Old Chatham ensures you can fully enjoy the area's natural beauty and tranquil atmosphere, making it an ideal destination for your next getaway.

Peak Season Highlights

summer
Late Spring to Early Summer (May to June)

This is the most popular time to visit, as the area blossoms with vibrant scenery and pleasant weather that is ideal for outdoor activities.

Average Temperature Daytime: 70-80°F - Nighttime: 50-60°F
autumn
Early Fall (September to October)

During this period, the region offers stunning fall foliage and comfortable temperatures, making it perfect for exploring local attractions and enjoying seasonal events.

Average Temperature Daytime: 65-75°F - Nighttime: 45-55°F

Off-Season Highlights

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Winter (December to February)

The winter months see fewer visitors, providing a peaceful atmosphere for those seeking tranquility and cozy accommodation options amidst scenic winter landscapes.

Average Temperature Daytime: 30-40°F - Nighttime: 15-25°F
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Late Fall (November)

As the leaves have fallen and before the winter chill sets in, this is a quieter time to experience the region’s natural beauty at a slower pace.

Average Temperature Daytime: 45-55°F - Nighttime: 35-45°F

Weekly Weather Forecast for Old Chatham

How to Book Your Old 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 Old Chatham

More Top-Rated Vacation Rentals in Old 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 a private outdoor patio or deck, perfect for relaxing and dining in the fresh air.
  • Take advantage of spacious yards or gardens to unwind or engage in outdoor activities.
  • Make use of built-in barbecue grills for outdoor cooking and family cookouts.
  • Relax by a private or community swimming pool available at some properties.
  • Explore nearby walking trails or hiking paths to experience the natural beauty of the area.
  • Utilize outdoor fire pits for cozy evenings under the stars.
  • Benefit from ample parking spaces or designated outdoor parking for your convenience.

Top Attractions Around Old Chatham

What attractions are nearby?

Nearby, you can enjoy a range of outdoor activities such as hiking, biking, and exploring scenic trails that showcase the natural beauty of this region.

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Family Activities

  • Old Chatham Historical Museum: Explore the region’s rich history through engaging exhibits that both educate and entertain young visitors.
  • Local Nature Trails: Enjoy family-friendly walks along scenic trails where you can observe wildlife and connect with nature in the area.
  • Farmers' Markets: Visit local markets to experience fresh, regional produce and handmade crafts that showcase the best of this destination’s community spirit.
  • Outdoor Recreation at Nearby Parks: Spend quality time outdoors at parks near here, offering activities like picnicking, playgrounds, and leisurely strolls suited for all ages.
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Adult Activities

  • Golfing at Chatham Hills Golf Course: Enjoy a relaxing day on the greens at this popular golf course known for its scenic views and well-maintained fairways, perfect for a leisurely round near your vacation rental.
  • Exploring local art galleries: Discover the region’s vibrant arts scene by visiting charming galleries that showcase local artists’ work, offering a cultural experience just minutes from your stay.
  • Wine tasting at nearby vineyards: Savor the flavors of regional wines through guided tastings at nearby vineyards, making for an excellent outing within easy reach of your accommodation.
  • Hiking and nature walks in the surrounding area: Take advantage of scenic trails and nature walks that highlight the natural beauty of this destination, providing a peaceful retreat close to your vacation rental.

Other Places to Stay in Old Chatham, NY

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Old Chatham Travel Tips

How Can You Make the Most of Your Stay?

  • Explore Local Nature Trails: Take advantage of the area’s scenic outdoor trails to enjoy peaceful walks or hikes right from your vacation rental, immersing yourself in the natural beauty surrounding here.
  • Visit Seasonal Events: Check the local calendar for seasonal festivals and markets that showcase the region’s culture, helping you experience authentic local traditions during your stay.
  • Discover Nearby Farm-to-Table Dining: Savor fresh, locally sourced meals at nearby eateries or farms, offering a true taste of what the region has to offer cuisine-wise.
  • Plan Your Activities Ahead: Coordinate outdoor adventures, cultural visits, or relaxation time based on seasonal weather and local offerings to maximize your time here.

Transportation Options

  • Old Chatham Transportation Services: Local transportation options include reliable shuttle and taxi services that connect you to nearby attractions and the region’s amenities.
  • Private Car Rentals: Renting a car provides the flexibility to explore this destination at your own pace, with several local providers available for convenient pickup and drop-off.
  • Bus Services: Regional bus lines serve the area, offering an affordable way to travel between Old Chatham and surrounding towns or cities.
  • Bicycle Rentals: For eco-friendly travel and scenic exploration, bicycle rentals are popular among visitors seeking an active way to enjoy this part of New York state.

Local Customs Options

  • Respect for Local Heritage: You will find that preserving the area's historical traditions is a cherished practice among residents here, reflecting a deep respect for this destination’s rich past.
  • Community Gatherings: Participating in local events and festivals offers a wonderful way to connect with neighbors and experience authentic cultural customs in the region.
  • Farmers' Market Etiquette: When visiting the area’s farmers’ markets, it’s customary to support local artisans and produce, embracing sustainable shopping practices.
  • Environmental Consciousness: The community values eco-friendly habits, encouraging visitors to be mindful of their environmental impact during their stay at this destination.

Frequently Asked Questions About Old Chatham?

1. What are the top vacation rentals in Old Chatham?

There are a lot of options in Old Chatham. If you plan on staying in the Old 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 Old Chatham:

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

There are 2 vacation rentals with private pools near Old Chatham. Top-rated RBO homes that have access to a swimming pool include:

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

If you are looking for a family-friendly vacation home in Old 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 Old Chatham:

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

Currently, the total number of properties listed by Rent By Owner in 2025 is over 94 in the Old 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 Old Chatham. 

5. What is the cancellation policy for vacation rentals in Old Chatham, New York?

The cancellation policy varies depending on the property listing. You should review the specific terms outlined by the host before confirming your booking to understand any applicable fees or restrictions.

6. How do I find pet-friendly vacation rentals in Old Chatham?

To locate pet-friendly options, use the search filters available when browsing properties in the area. It's important to read the listing details carefully, as some hosts may have specific rules regarding pets.

7. Are there any minimum stay requirements for booking here?

Minimum stay requirements can differ between properties. Check the individual listing information or contact the owner directly for details related to your desired dates.

8. What amenities are typically included in vacation rentals in Old Chatham?

Most listings detail the amenities offered, which often include Wi-Fi, kitchen facilities, parking, and outdoor spaces. Always verify these features on the property page to ensure they meet your needs.

9. How can I ensure my booking is secure when reserving a vacation rental?

Reservations are handled through trusted systems that protect your personal and payment information. For added peace of mind, review the host's reviews and ratings before completing your booking.