Best Vacation Homes in Chatham
House
10.0(119 Reviews)
2 Bedrooms
1 Bath
5 Guests
1230 ft²
Oceanfront
Fireplace/Heating
Ocean View
Balcony/Terrace
US $559/Night
7 Nights - US $3,916
House
10.0(6 Reviews)
4 Bedrooms
2 Baths
10 Guests
1905.21 ft²
- Fireplace/Heating
View
Parking
Air Conditioner
US $908/Night
7 Nights - US $6,356
Bed & Breakfast
9.8(217 Reviews)
1 Bedroom
1 Bath
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $502/Night
7 Nights - US $3,517
Apartment
10.0(112 Reviews)
1 Bedroom
1 Bath
2 Guests
Hot Tub- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $252/Night
7 Nights - US $1,763
House
10.0(3 Reviews)
3 Bedrooms
2 Baths
8 Guests
1194.79 ft²
- Fireplace/Heating
- View
Pet Friendly- Parking
US $645/Night
7 Nights - US $4,513
House
10.0(102 Reviews)
2 Bedrooms
2 Baths
3 Guests
1700 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $606/Night
7 Nights - US $4,241
Condo
10.0(95 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
Kitchen
US $519/Night
7 Nights - US $3,634
Cottage
10.0(90 Reviews)
1 Bedroom
1 Bath
2 Guests
1000 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $551/Night
7 Nights - US $3,856
Chatham Luxury Rentals
Bed & Breakfast
9.5(93 Reviews)
11 Bedrooms
9 Baths
18 Guests
297.8 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $5,351/Night
7 Nights - US $37,457
House
10.0(8 Reviews)
5 Bedrooms
8 Baths
12 Guests
7000 ft²
Private Pool- Oceanfront
- Hot Tub
- Fireplace/Heating
US $4,529/Night
7 Nights - US $31,703
House
7 Bedrooms
7 Baths
16 Guests
- Private Pool
Pool- Kitchen
- Parking
US $4,074/Night
7 Nights - US $28,515
House
6 Bedrooms
4 Baths
12 Guests
- Private Pool
- Oceanfront
- Pool
- Ocean View
US $3,668/Night
7 Nights - US $25,677
House
5 Bedrooms
9 Baths
10 Guests
- Kitchen
- Parking
- Air Conditioner
Internet
US $3,541/Night
7 Nights - US $24,787
House
4 Bedrooms
3 Baths
8 Guests
3335 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
US $3,417/Night
7 Nights - US $23,921
House
10.0(7 Reviews)
4 Bedrooms
4 Baths
8 Guests
- Private Pool
- Oceanfront
- Hot Tub
- Pool
US $3,299/Night
7 Nights - US $23,094
House
10.0(46 Reviews)
8 Bedrooms
5 Baths
18 Guests
6000 ft²
- Private Pool
- Oceanfront
- Fireplace/Heating
- Pool
US $3,162/Night
7 Nights - US $22,132
Chatham Pet Friendly Vacation Rentals
Condo
10.0(33 Reviews)
2 Bedrooms
2 Baths
5 Guests
1400 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $563/Night
7 Nights - US $3,939
House
10.0(2 Reviews)
4 Bedrooms
3 Baths
8 Guests
1819.1 ft²
- Fireplace/Heating
- Balcony/Terrace
- View
- Pet Friendly
US $999/Night
7 Nights - US $6,993
House
10.0(8 Reviews)
5 Bedrooms
3 Baths
10 Guests
2100 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $1,105/Night
7 Nights - US $7,734
Cottage
10.0(28 Reviews)
2 Bedrooms
1 Bath
4 Guests
540 ft²
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $330/Night
7 Nights - US $2,313
House
10.0(2 Reviews)
4 Bedrooms
2 Baths
10 Guests
2798.62 ft²
- Fireplace/Heating
- View
- Pet Friendly
- Parking
US $739/Night
7 Nights - US $5,173
Cottage
10.0(19 Reviews)
1 Bedroom
1 Bath
4 Guests
864 ft²
- Oceanfront
- Ocean View
- View
- Pet Friendly
US $437/Night
7 Nights - US $3,057
Cottage
10.0(6 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
- View
US $466/Night
7 Nights - US $3,265
House
10.0(2 Reviews)
2 Bedrooms
1 Bath
6 Guests
872 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $567/Night
7 Nights - US $3,966
Chatham Large Vacation Homes
House
10.0(132 Reviews)
5 Bedrooms
3 Baths
10 Guests
2400 ft²
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Ocean View
US $1,116/Night
7 Nights - US $7,811
House
10.0(1 Review)
7 Bedrooms
5 Baths
16 Guests
4004.17 ft²
- Hot Tub
- Fireplace/Heating
- Pool
- Pet Friendly
US $2,371/Night
7 Nights - US $16,597
House
10.0(117 Reviews)
5 Bedrooms
5 Baths
14 Guests
4500 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $1,127/Night
7 Nights - US $7,891
House
10.0(1 Review)
5 Bedrooms
4 Baths
10 Guests
2023.62 ft²
- Fireplace/Heating
- Pool
- View
- Parking
US $1,005/Night
7 Nights - US $7,037
House
10.0(117 Reviews)
4 Bedrooms
2 Baths
10 Guests
1764 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $691/Night
7 Nights - US $4,836
House
10.0(102 Reviews)
5 Bedrooms
4 Baths
10 Guests
3500 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $781/Night
7 Nights - US $5,464
House
10.0(64 Reviews)
7 Bedrooms
4 Baths
14 Guests
2664 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $1,717/Night
7 Nights - US $12,017
House
10.0(57 Reviews)
5 Bedrooms
4 Baths
12 Guests
4800 ft²
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Ocean View
US $1,164/Night
7 Nights - US $8,148
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 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
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
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
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
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
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.
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.
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
Cockle Cove Beach
Hardings Beach
Chatham Drama Guild
Monomoy Theatre
Hardings Lighthouse
Veterans Field
Chatham Railroad Museum
Atwood House Museum
Gallery Antonia
Fox Hill
West 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.
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:
- Waterfront Chatham Village, Short Walk to Town & Lighthouse Beach
- Chatham walk to Cape Cod beach
- Quaint & Cozy Downtown Chatham Home, Walk to Town and Beaches
- Water View-Walk town/beach, pets considered, Linen Option
- Pool Table, Bar, Ping Pong, Sun Rm, Deck,4 BR, Private
- Cape Cod Chatham Water View Retreat
- Near Harding's Beach, 4 min walk to Oyster River. 3BR, 2Bath, enclosed deck area
- 5 Bdrm Spectacular Walk To Hardings Beach Ocean View Home
- Walk to Chatham Main St., boutiques, restaurants, galleries, and nightlife!
- See the World Cup AND Enjoy a Chatham Vacation June 2026
2. How many vacation rentals have private pools in Chatham?
There are 37 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 695 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
House
10.0(54 Reviews)
4 Bedrooms
5 Baths
10 Guests
3500 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
US $2,361/Night
7 Nights - US $16,524
House
10.0(43 Reviews)
5 Bedrooms
3 Baths
12 Guests
5000 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
US $1,923/Night
7 Nights - US $13,459
House
10.0(42 Reviews)
9 Bedrooms
10 Baths
21 Guests
5300 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
US $2,957/Night
7 Nights - US $20,696
House
10.0(26 Reviews)
4 Bedrooms
5 Baths
14 Guests
2500 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
US $1,412/Night
7 Nights - US $9,883
House
10.0(14 Reviews)
4 Bedrooms
4 Baths
10 Guests
2500 ft²
- Fireplace/Heating
- Pool
- Ocean View
- Balcony/Terrace
US $1,297/Night
7 Nights - US $9,082
House
10.0(13 Reviews)
8 Bedrooms
9 Baths
16 Guests
4290 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
US $2,207/Night
7 Nights - US $15,450
House
10.0(12 Reviews)
4 Bedrooms
4 Baths
10 Guests
38750 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
US $2,024/Night
7 Nights - US $14,166
House
10.0(12 Reviews)
2 Bedrooms
2 Baths
8 Guests
2000 ft²
- Oceanfront
- Fireplace/Heating
- Pool
- Ocean View
US $1,083/Night
7 Nights - US $7,580
