Best Vacation Homes in Chatham
Apartment
9.8(6 Reviews)
1 Bedroom
1 Bath
4 Guests
900 ft²
Fireplace/Heating
Kitchen
Parking
Air Conditioner
US $293/Night
7 Nights - US $2,052
House
9.3(4 Reviews)
3 Bedrooms
2 Baths
6 Guests
1905.21 ft²
- Fireplace/Heating
Balcony/Terrace- Parking
Internet
US $430/Night
7 Nights - US $3,012
US $207/Night
7 Nights - US $1,448
Apartment
9.6(5 Reviews)
2 Bedrooms
1 Bath
4 Guests
1000 ft²
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $517/Night
7 Nights - US $3,620
Apartment
9.2(9 Reviews)
2 Bedrooms
2 Baths
8 Guests
780.38 ft²
- Fireplace/Heating
Breakfast
Pet Friendly- Parking
US $137/Night
7 Nights - US $959
Apartment
9.6(5 Reviews)
1 Bedroom
1 Bath
3 Guests
1000 ft²
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $300/Night
7 Nights - US $2,097
Apartment
9.6(5 Reviews)
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $101/Night
7 Nights - US $704
Apartment
8.8(15 Reviews)
2 Bedrooms
1 Bath
7 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
US $399/Night
7 Nights - US $2,793
Chatham Luxury Rentals
House
5 Bedrooms
3 Baths
10 Guests
Private Pool
Hot Tub- Fireplace/Heating
Pool
US $7,246/Night
7 Nights - US $50,724
House
6 Bedrooms
7 Baths
12 Guests
- Hot Tub
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
US $6,969/Night
7 Nights - US $48,780
House
9 Bedrooms
10 Baths
18 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
US $2,800/Night
7 Nights - US $19,601
New
House
4 Bedrooms
4 Baths
7 Guests
- Fireplace/Heating
- Air Conditioner
Child Friendly
Laundry
US $2,791/Night
7 Nights - US $19,534
New
House
4 Bedrooms
3 Baths
8 Guests
- Fireplace/Heating
- Air Conditioner
- Internet
- Child Friendly
US $2,482/Night
7 Nights - US $17,376
House
5 Bedrooms
5 Baths
12 Guests
5000 ft²
- Fireplace/Heating
Ocean View- Balcony/Terrace
View
US $2,035/Night
7 Nights - US $14,242
House
3 Bedrooms
2 Baths
6 Guests
2000 ft²
- Fireplace/Heating
- Kitchen
- Air Conditioner
- Internet
US $2,011/Night
7 Nights - US $14,074
Hotel
4 Baths
- Fireplace/Heating
- Pool
- Breakfast
- Kitchen
US $1,396/Night
7 Nights - US $9,773
Chatham Pet Friendly Vacation Rentals
House
10.0(1 Review)
3 Bedrooms
1 Bath
6 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
US $447/Night
7 Nights - US $3,126
Hotel
9.0(126 Reviews)
10 Baths
419.79 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $439/Night
7 Nights - US $3,074
House
5 Bedrooms
2 Baths
10 Guests
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $651/Night
7 Nights - US $4,558
House
7.0(2 Reviews)
5 Bedrooms
2 Baths
11 Guests
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $1,162/Night
7 Nights - US $8,137
Hotel
8.8(229 Reviews)
1 Bath
400.42 ft²
- Fireplace/Heating
- Pet Friendly
- Parking
- Air Conditioner
US $378/Night
7 Nights - US $2,646
Apartment
10.0(2 Reviews)
1 Bedroom
1 Bath
4 Guests
750 ft²
Oceanfront- Fireplace/Heating
- Ocean View
- View
US $252/Night
7 Nights - US $1,767
House
8.6(7 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
US $213/Night
7 Nights - US $1,494
House
8.8(6 Reviews)
3 Bedrooms
2 Baths
6 Guests
2148 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $511/Night
7 Nights - US $3,579
Chatham Large Vacation Homes
House
5 Bedrooms
4 Baths
12 Guests
4000 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $509/Night
7 Nights - US $3,562
House
1 Bedroom
5 Baths
12 Guests
5005.22 ft²
- Fireplace/Heating
- Pool
- Balcony/Terrace
- View
US $1,058/Night
7 Nights - US $7,405
US $5,664/Night
7 Nights - US $39,647
House
8 Bedrooms
5 Baths
16 Guests
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
US $3,371/Night
7 Nights - US $23,597
House
4.0(1 Review)
8 Bedrooms
3 Baths
17 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $916/Night
7 Nights - US $6,413
House
3.4(3 Reviews)
8 Bedrooms
3 Baths
20 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $801/Night
7 Nights - US $5,609
House
1.0(1 Review)
4 Bedrooms
2 Baths
18 Guests
- Pet Friendly
- Kitchen
- Air Conditioner
- Child Friendly
US $273/Night
7 Nights - US $1,911
House
4 Bedrooms
2 Baths
10 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
US $553/Night
7 Nights - US $3,874
Why Choose Rent By Owner for your Chatham Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
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 here can enhance your experience, as seasonal and regional factors in this destination influence the perfect period for booking your vacation rentals in the area.
Peak Season Highlights
Late Spring to Early Summer (May to June)
Experience the region's pleasant weather during this peak season, making it ideal for outdoor activities and exploring local attractions.
Average Temperature Daytime: 70°F to 80°F - Nighttime: 50°F to 60°F
Early Fall (September to October)
Enjoy the vibrant fall foliage and mild temperatures that attract visitors seeking a scenic and comfortable stay here in the area.
Average Temperature Daytime: 65°F to 75°F - Nighttime: 45°F to 55°F
Off-Season Highlights
Winter (December to February)
During winter months, the area's quiet charm offers a peaceful retreat away from the crowds, with cooler temperatures perfect for cozy getaways.
Average Temperature Daytime: 35°F to 45°F - Nighttime: 20°F to 30°F
Late Autumn (November)
As the region transitions into colder weather, you’ll find fewer tourists and more affordable rates for your stay here in the destination.
Average Temperature Daytime: 50°F to 60°F - Nighttime: 30°F to 40°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
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 dining area perfect for summer meals in the region's pleasant climate.
- Relax by your own outdoor swimming pool, ideal for cooling off during warm days here.
- Take advantage of a spacious backyard with lush landscaping, great for outdoor activities.
- Use the available outdoor fire pit for cozy evenings and social gatherings in this destination.
- Make the most of a well-equipped patio with lounge furniture to unwind after exploring the area.
- Benefit from direct access to landscaped gardens that enhance your outdoor experience.
- Utilize a dedicated outdoor recreational area, such as a tennis court or basketball hoop, nearby or on-site.
Top Attractions Around Chatham
What attractions are nearby?
Here in the region, you can enjoy a variety of outdoor activities and local attractions that make your stay memorable, all conveniently accessible from your chosen vacation rentals.
Family Activities
- Chatham Railroad Station Museum: Explore local history and enjoy a family-friendly walk through the charming Chatham station, which offers engaging exhibits about the area's railway heritage.
- Nanina's Woods Park: Spend quality time outdoors in this scenic park featuring walking trails, playgrounds, and open spaces perfect for picnics and family activities in the area.
- Spring Lake Pool & Recreation: Relax and have fun at the local recreation center with swimming facilities, sports courts, and family-friendly events during warmer months.
- Downtown Chatham Shopping and Dining: Discover local shops and eateries where families can stroll together and enjoy the neighborhood’s inviting atmosphere within the region.
Adult Activities
- Golf at Chatham Golf Course: Enjoy a leisurely round of golf on this scenic course nestled in the heart of the region, perfect for a relaxing day outdoors.
- Explore the South Mountain Reservation: Discover nature trails, picnic areas, and scenic views within this expansive natural preserve nearby, ideal for outdoor enthusiasts seeking tranquility.
- Visit local art galleries: Immerse yourself in the area’s vibrant arts scene by exploring charming galleries that showcase regional talents and creative works.
- Dine at fine restaurants: Savor exquisite cuisine at acclaimed eateries within town, offering a variety of flavors to enhance your stay in this destination.
Chatham Travel Tips
How Can You Make the Most of Your Stay?
- Plan Ahead with Local Insights: Research seasonal events and local customs to immerse yourself in the area's culture and make your stay in Chatham truly memorable.
- Choose a Convenient Location: Select vacation rentals that are close to key attractions and transportation options to maximize your time exploring this destination.
- Take Advantage of Outdoor Activities: Enjoy the region’s natural beauty by scheduling outdoor pursuits such as hiking or walking tours near your accommodation.
- Communicate with Hosts Effectively: Reach out to your rental hosts beforehand to clarify amenities and ask for personalized recommendations to enhance your experience here.
Transportation Options
- Chatham Train Station: This station offers convenient NJ Transit train service, making it easy to explore the region without a car.
- Local Bus Services: Multiple bus routes connect here to neighboring towns and cities, providing flexible transportation options within the area.
- Car Rentals: Several rental agencies are available nearby, allowing you to explore this destination and its surroundings at your own pace.
- taxis and Rideshare Services: Reliable taxis and popular ride-sharing apps offer quick and accessible transportation throughout the region.
Local Customs Options
- Greeting Etiquette: You will notice a friendly and respectful approach to greeting neighbors and visitors, which reflects the welcoming spirit of this region.
- Dining Customs: Sharing meals with local family and friends is a common tradition here, emphasizing community and hospitality in this area.
- Festive Celebrations: Participating in seasonal festivals and local events is a cherished way to immerse yourself in the area's cultural heritage.
- Respect for Nature: Maintaining cleanliness and respecting outdoor spaces are important customs that highlight the region's appreciation for its natural surroundings.
Chatham Vacation Rental Frequently Asked Questions
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:
- 1bd 1ba Private Apartment Sleeps 4
- Beautiful Large Home in the Heart of Morristown- FIFA host and more!
- Charming 1-BR 1st Flr apt in Scotch Plains - Full Kitchen on a quiet cul-de-sac
- C&J Signature Stays Downtown Apartment
- Turkey Hill Inn
- C&J Signature Stays Historic renovated apartment
- C &J Signature Stays 1864 Downtown Morristown Apartment
- Gorgeous 1br in nature setting, 5 min to NYC train
- Madison Home w/Patio: Walk to Main Street!
- Private 1BR Apt, WiFi, Reliable, Near NYC
2. How many vacation rentals have private pools in Chatham?
There are 1 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 193 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 a vacation rental in this area?
Cancellation policies vary by listing, so it’s important to review the specific terms provided on each property’s page. You can find detailed information about cancellations and whether there are any applicable fees by reading the individual rental agreement or contacting the owner directly.
6. How do I ensure the vacation rental I choose is available for my travel dates?
Availability is shown in real-time on the listing, but it's recommended to confirm your dates directly with the property owner or manager through the booking platform to secure your reservation before making travel arrangements.
7. Are pets allowed in vacation rentals around here?
Pet policies differ among properties, with some welcoming animals and others not. Be sure to check the specific listing details or contact the owner to verify if pets are permitted during your stay.
8. What amenities can I expect in a typical rental in this destination?
Amenities can include features like Wi-Fi, parking, kitchens, and outdoor spaces. To see what’s available, review the amenities list on each listing or reach out to the owner for more detailed information.
9. How do I get support if I encounter issues during my stay or booking process?
Support is available through the booking platform’s customer service team, who can assist with inquiries related to reservations, payments, or any problems that arise during your stay. Contact details are provided on the website for immediate assistance.
Chatham Top Rated Vacation Rentals
Hotel
8.6(312 Reviews)
1 Bath
386.16 ft²
- Private Pool
- Pool
- Pet Friendly
- Parking
US $158/Night
7 Nights - US $1,109
Hotel
8.6(273 Reviews)
1 Bath
503.75 ft²
- Private Pool
- Pool
- Balcony/Terrace
- Parking
US $189/Night
7 Nights - US $1,323
Hotel
8.5(293 Reviews)
10 Baths
481.98 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
US $217/Night
7 Nights - US $1,517
Hotel
8.4(102 Reviews)
8 Baths
331.73 ft²
- Private Pool
- Pool
- Balcony/Terrace
- Breakfast
US $109/Night
7 Nights - US $763
Hotel
8.3(189 Reviews)
1 Bath
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $345/Night
7 Nights - US $2,417
Hotel
8.0(214 Reviews)
1 Bath
399.8 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
US $199/Night
7 Nights - US $1,391
Hotel
7.7(62 Reviews)
7 Baths
353.86 ft²
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Breakfast
US $247/Night
7 Nights - US $1,732
Hotel
4 Baths
- Fireplace/Heating
- Pool
- Breakfast
- Kitchen
US $1,136/Night
7 Nights - US $7,952
