Chatham vacation rentals

We found 3,441 vacation rentals — enter your dates for availability

Select from 296 homes, 30 cottages, and other vacation rentals in Chatham to find one that's perfect for your trip. Vacation homes offer the amenities you expect for your family, friends, or furry companion, such as parking and a pool. At the end of the day, you're sure to find a rental that has what everyone needs, including a place that's non-smoking or offers accessibility.

Vacation rentals with weekly discounts - Chatham

Showing deals for:Oct 17 - Oct 24

Image gallery for Stunning Waterfront Compound with Private Beach, Private Dock, Sunset View

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10 out of 10 rating
Exceptional
(16 reviews)

Stunning Waterfront Compound with Private Beach, Private Dock, Sunset View

South Chatham, MA

9% off
Price is $904
$6,327 for 7 nights
Fees included upfront
Stunning Waterfront Compound with Private Beach, Private Dock, Sunset View

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Find out more about Chatham

Why visit Chatham

  1. Stunning Beaches: Chatham boasts beautiful sandy beaches perfect for sunbathing, swimming, and beachcombing.
  2. Historic Lighthouses: Explore charming lighthouses that offer a glimpse into the region's maritime history.
  3. Cultural Experiences: Enjoy local museums and art galleries that showcase the vibrant culture of Cape Cod.
  4. Outdoor Activities: Take advantage of nature trails, kayaking, and biking for an adventurous getaway.
  5. Welcoming Atmosphere: Experience the friendly locals and charming ambiance that make Chatham a memorable destination.

Popular types of accommodation in Chatham

Discover the charm of Chatham with our diverse vacation rentals. Whether you’re looking for a cozy cottage, a spacious apartment, or a private vacation home, we have options that cater to every need. Enjoy beach rentals and waterfront homes that offer stunning views, or unwind on a deck amidst the beauty of Chatham. With spacious bedrooms and family-friendly amenities, your perfect getaway awaits!

  • Houses: The top choice for vacationers in Chatham, these homes offer a spacious and comfortable setting, perfect for families or groups.
  • Cottages: These charming, often coastal retreats provide a cozy atmosphere, ideal for a relaxing getaway.
  • Apartments: A convenient option for travelers looking for a home-like experience with essential amenities.
  • Condos: Offering a blend of luxury and convenience, condos are popular for those seeking modern facilities.
  • Villas: These upscale accommodations provide a lavish experience for those wanting an indulgent stay.**

Top attractions in Chatham

Chatham, Massachusetts, is a perfect destination for beach and outdoor enthusiasts. Explore its stunning beaches, historic lighthouses, and intriguing museums. Ideal for those seeking cultural experiences and relaxation, visitors can enjoy nature trails and book outdoor activities. Whether you're planning a Cape Cod vacation or simply looking to unwind, Chatham offers a delightful blend of scenery and adventure for everyone.

  1. Harwich Port: A charming seaside neighborhood with a vibrant town atmosphere, Harwich Port offers delightful shops, restaurants, and scenic views. Enjoy leisurely strolls along the waterfront and experience the local culture.
  2. Chatham Lighthouse: This historic lighthouse is a symbol of Chatham's maritime heritage. With stunning architecture and breathtaking views of the Atlantic, it's a perfect spot for photography and appreciating the area's rich history.
  3. Chatham Lighthouse Beach: Located just a mile from Chatham, this picturesque beach features soft sands and gentle waves, ideal for sunbathing, swimming, and beachcombing while enjoying the serene coastal scenery.

Things to do recommended for couples

Embark on a romantic getaway in Chatham! Enjoy a concert at the Cape Cod Melody Tent, pamper yourselves at Sol Spa for ultimate relaxation, and challenge each other at Cape Escape Adventure Golf for some lighthearted fun. Create unforgettable memories together in this charming seaside town!

Things to do recommended for families

Your family will love the excitement at Veterans Field, where sports vibes abound. For more adventure, head to Cape Cod Inflatable Park, just 14 miles away, or enjoy fun at Cape Cod Baseball & Bumper Boats, located 7 miles from Chatham. Great memories await!

Things to do recommended for groups

Start your adventure at the bustling Chatham Fish Pier, then hit the greens at Ocean Edge Golf Club, just 7 miles away. For a scenic experience, explore the Cape Cod Rail Trail, located 10 miles from Chatham, perfect for outdoor enthusiasts and adventure seekers.

What do I need to keep in mind when booking a vacation in Chatham

If you're planning a trip with a group, family, pets, or seeking extended stays, be sure to filter your options according to your key priorities. Here are some helpful Vrbo booking tips to assist you.

  • Traveling to Chatham with a group: Think about how many bedrooms you'll require, along with features like a complete kitchen or outdoor areas for group get-togethers. Luckily, you can easily narrow down your options on Vrbo to find exactly what you need and more.
  • Traveling to Chatham with young kids: Traveling with little ones can present its challenges. It's important to prioritize their comfort and safety, along with suitable amenities like a private pool. Additionally, think about how close you are to family-friendly attractions to make your trip more enjoyable.
  • Taking your pets with you to Chatham: For many families, a vacation wouldn't be the same without their furry companions. If you relate to this, explore Vrbo listings that welcome pets. Many of these pet-friendly properties come equipped with feeding bowls and beds, ensuring that your entire family feels comfortable and at home.
  • Planning for a long term stay visiting Chatham: If you're in search of vacation rentals that offer discounts for stays of a month or more, you've come to the right spot. By using the appropriate filters, you can effortlessly discover and save on monthly rental options. Don't forget to include features like a parking space, a well-equipped kitchen, or a private pool in your search criteria.

Where to stay in Chatham

Chatham, Massachusetts, is a delightful vacation spot that offers stunning beaches, breathtaking scenery, and a trendy art scene. Just a short distance from downtown Chatham, visitors can explore charming Cape Cod and enjoy family-friendly excursions. Whether you're seeking a romantic getaway or a relaxing retreat, Chatham's welcoming atmosphere and friendly locals make it a memorable destination for everyone.

  • Nantucket: Nantucket is a charming island city located 28 miles from Chatham, renowned for its stunning beaches and picturesque scenery. This destination offers a quintessential New England experience with its historic cobblestone streets and beautiful lighthouses. Visitors can enjoy outdoor activities such as golfing at scenic courses or relaxing on breathtaking beaches. Popular spots include the family-friendly beaches and the captivating Cape Cod National Seashore. With its rich maritime history, Nantucket is perfect for those seeking a blend of relaxation and exploration.
  • Eastham: Situated 10 miles from Chatham, Eastham is a delightful town that emphasizes natural beauty and outdoor adventure. Known for its scenic landscapes and pristine beaches, Eastham is an ideal spot for nature lovers. Visitors can hit the hiking trails or enjoy a round of golf at one of the local courses. The area is also famous for its family-friendly beaches and proximity to the stunning Cape Cod National Seashore, making it a perfect destination for a day of exploration and relaxation by the water.
  • North Chatham: Just 1 mile away from Chatham, North Chatham offers a serene atmosphere with easy access to beautiful beaches and scenic outdoor spaces. This quaint locale is perfect for families, featuring playgrounds and theaters for entertainment. Outdoor enthusiasts can take advantage of the local golf courses and enjoy the area's stunning coastline. With its welcoming community vibe and proximity to the beach, North Chatham is an excellent spot for those looking to unwind while enjoying the natural beauty of Cape Cod.

Best time to go to Chatham

If you're planning a trip to Chatham, it's a good idea to check both the weather and property rates. The warmest month is August. Peak season runs from June to August, while off-peak times, like October to December tend to have fewer bookings and better deals.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January35.6°F (2.0°C)Light RainMostly CloudyAverageModerately Low
February35.4°F (1.9°C)Light RainMostly CloudyAverageModerately Low
March38.5°F (3.6°C)Light RainMostly CloudyAverageModerately Low
April45.3°F (7.4°C)Light RainMostly SunnyAverageAverage
May53.1°F (11.7°C)Light RainMostly SunnyAverageAverage
June61.7°F (16.5°C)Light RainMostly SunnyModerately HighModerately High
July69.6°F (20.9°C)Light RainMostly SunnyModerately HighModerately High
August70.3°F (21.3°C)Light RainMostly SunnyModerately HighModerately High
September65.7°F (18.7°C)Light RainMostly SunnyAverageAverage
October57.9°F (14.4°C)Light RainMostly SunnyModerately LowAverage
November48.6°F (9.2°C)Light RainMostly SunnyModerately LowAverage
December41.5°F (5.3°C)Light RainMostly CloudyModerately LowAverage

Booking with Vrbo is simple

Are you hoping to save on your upcoming trip? Being flexible with your travel dates can make a big difference, as prices often fluctuate. Additionally, consider booking a longer stay to unlock even more savings. To discover a Vrbo property that meets your budget, feel free to use our filters to sort by price, location, and type of vacation rental. We're here to help you find the perfect place for your getaway!

Save more with One Key

When you reserve an eligible Vrbo for your group getaway, you'll receive OneKeyCash™ on the full booking amount. Being the organizer truly has its perks! Become a member of our OneKey rewards program to unlock special savings and earn OneKeyCash™ on qualifying stays. Sign up now and begin accumulating rewards.

Vrbo Trips: Effortless planning

Vrbo's Trip Board offers a user-friendly platform where you can easily plan new trips, continue from where you previously paused, or manage your travel arrangements. You'll see your saved or booked properties organized into categories: Potential, Upcoming, and Current Trips. To begin utilizing Trip Boards, simply visit: https://www.vrbo.com/trips.

**Based on Vrbo properties booked during 2023 and 2024.

Find beachfront fun with a Chatham house rental

Enjoying the most coastline of any town in the area, Chatham features Cape Cod house rentals with plenty of space and very short walks to the water. Gorgeous sunsets make this lovely town glow by evening. Visit the picturesque Chatham Lighthouse or some of the many historic homes and buildings to learn the area’s history. If you visit in July, don’t miss the Cape Cod Hydrangea Festival, which features tours of meticulously maintained private backyard gardens and benefits local nonprofits.

 

Tourist attractions near Chatham vacation rentals

Chatham offers many points of interest for history lovers and is a great place to explore Cape Cod’s maritime past. Originally a fishing village, the town still boasts its famous lighthouse, with many of the buildings dating back to the 18th century. Visit Chatham’s popular railroad museum, which dates back to 1887 and houses hundreds of exhibits, including both models and full-size engines that the whole family will enjoy. Experience the area’s colonial past at Caleb Nickerson Homestead, or see how life in the area used to be at Chatham’s Old Grist Mill, built in 1797.

Things to do near Chatham vacation homes

No visit to Chatham is complete without a day at one of the area’s pristine, white sandy beaches. You may even catch a glimpse of the local seals at the famous Chatham Lighthouse Beach, or handsome Harding Beach. The area is well-suited to sea lovers, with many exciting ways to enjoy the waves. Chatham vacation rentals mean you're in a prime position to get involved in the local sport-fishing scene, hire a boat for the day, or take a windsurfing lesson. Alternatively, sign up for a seal tour and get a close-up view of these fascinating creatures.

Local weather for your trip to Chatham vacation homes

You can't beat Chatham for a warm, sunny beach holiday complemented by Cape Cod’s cool, Atlantic breeze. The town is at its most lively in the summer months when the weather is reliably warm, with comfortable average highs of around 70 F between June and September. The weather makes the area perfect for outdoor activities such as hiking, biking, or golfing, with wonderful views of the Atlantic Ocean from the Seaside Links. Many Chatham vacation rentals are located within walking distance of the area’s white, sandy beaches.

Keep an eye out for nature in charming, coastal Chatham

With a Chatham vacation rental, you'll be a hop, skip, and a jump from some of the northeast's most compelling natural splendor. Thanks to its position on the Atlantic, the area has plenty of broad, sandy beaches and rocky coastline, most of which offers scenic views of the calm Nantucket Sound. If you enjoy birdwatching then don't forget to pack your binoculars. A complex ecosystem of marshland and sandy dunes, the 7,600-acre Monomoy National Wildlife Refuge is a popular destination where you can see intertidal life and numerous species of migratory birds.

How to get to and around Chatham

The nearest airport is in Hyannis, MA (HYA-Barnstable Municipal), located 16.8 mi (27 km) from the city center. If you can't find a flight that works for your travel itinerary, you could also fly into Nantucket, MA (ACK-Nantucket Memorial), which is 29.9 mi (48.1 km) away.

Family attractions near Chatham vacation rentals

Chatham has plenty of family-friendly attractions for kids of all ages. Vacation homes are close to places like the Cape Cod National Seashore, a shoreline with miles of dunes, sandy beaches, salt marshes, and hiking trails, and the Chatham Lighthouse, a historic lighthouse with a keeper’s cottage and spectacular views. You may also like Monomoy National Wildlife Refuge, a protected habitat for migratory birds and salt and freshwater marshes.

Romantic vacation homes in Chatham

Couples looking for romance can enjoy an array of attractions in Chatham. Vacation rentals can be found near places like Atwood Museum, a restored historic home with galleries exploring the history and culture in the region, and Kate Gould Park, a vibrant park with recreation areas and festivals. You'll also like Linnell Landing Beach, a bayside beach with scenic sunsets and calm waters for swimming and kayaking.

Frequently asked questions

What is the best area to stay in Chatham when booking a vacation rental?
When booking a vacation rental in Chatham, Massachusetts, one of the best areas to consider is the Downtown district. This vibrant neighborhood offers a charming atmosphere filled with boutique shops, delightful restaurants, and easy access to the waterfront. Staying in Downtown Chatham puts you within walking distance of the iconic Chatham Lighthouse and the picturesque Chatham Fish Pier, where you can enjoy fresh seafood and watch the local fishing boats come in. The concentration of rental properties in this area is quite high, providing plenty of options for visitors looking for everything from cozy cottages to more luxurious accommodations.

Another excellent option is the area around Stage Harbor. This scenic neighborhood boasts stunning waterfront views and proximity to the Stage Harbor Lighthouse. Visitors staying here can enjoy the tranquility of the beach and take advantage of the nearby walking trails. The properties in this area tend to be more spacious, often featuring beautiful outdoor spaces great for family gatherings or relaxing after a day of exploring.

Lastly, the Chatham Bars Inn area offers a more upscale experience with its beautiful beachfront properties and luxurious amenities. This area is great for those looking for a resort-style vacation while still being close to attractions like the Monomoy National Wildlife Refuge, where you can explore nature trails and spot local wildlife. The variety of vacation rentals here caters to different preferences, making it easy to find a great spot for your getaway.
How much does it cost to rent a vacation home in Chatham?
Prices for vacation rentals in Chatham vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options---whether you're traveling solo, as a couple, with family, or in a group. Vrbo offers something for every taste and budget, from affordable rentals in Chatham to more spacious homes. To get the best value, book early and take advantage of Vrbo's free rewards program.
Are there any discounts for Chatham vacation house rentals?
You can find great discounts on house rentals in Chatham on Vrbo, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for Last minute bookings, and Early bird bookings too. The best part is, there's no need for a discount code---just enter your travel dates and apply the discount filters to view the top rates.
Where are the best areas for renting a beach house in Chatham?
For renting a beach house in Chatham, Massachusetts, consider the picturesque neighborhoods along the Cape Cod coastline, particularly those near Chatham Lighthouse Beach and Nauset Beach. The areas surrounding these beaches are known for their charming, shingle-style homes that often come equipped with modern amenities such as spacious decks, outdoor grills, and beach access. Many properties in this region also feature private yards, great for families and gatherings, along with fully stocked kitchens ideal for preparing fresh seafood from local markets.

In addition, the area around Stage Harbor provides a more tranquil setting, with waterfront homes that offer stunning views of the harbor and direct access to the water. Here, you can find rentals that include features like kayaks, paddleboards, and outdoor showers, enhancing the beach experience. This neighborhood is also conveniently located near the scenic Lighthouse Beach, where visitors can enjoy walking along the shore or taking in breathtaking sunsets.

Chatham's historic district is another excellent option for those interested in a beach house rental. Properties here often have a blend of classic New England charm and contemporary comforts, including air conditioning, Wi-Fi, and cozy living areas. Being close to local boutiques, cafes, and restaurants provides an added layer of convenience for travelers looking to explore the culinary delights of Cape Cod. Find your rental near the beach in Chatham.
What is the most popular type of vacation rental accomodation in Chatham?
In Chatham, vacation houses are the most popular type of accommodation, with about 258 available throughout the area. These houses are often located near the charming downtown area and the beautiful beaches, providing easy access to local shops, restaurants, and outdoor activities such as whale watching and kayaking. Most of these vacation houses come equipped with fully stocked kitchens, spacious living areas, and outdoor decks or patios, great for enjoying the coastal breeze.

Cottages also have a presence in Chatham, with around 25 options that offer a cozy, rustic charm. These typically feature intimate layouts, kitchen facilities, and proximity to picturesque landscapes, making them ideal for couples or smaller families. Additionally, there are around 17 condos and 10 apartments available, suiting travelers looking for a more compact living space with modern amenities.
Are there any family house rentals in Chatham?
In Chatham, Massachusetts, families will find a wealth of vacation rentals, with around 212 options available throughout the area. This charming seaside town offers a variety of family-friendly homes, particularly in neighborhoods like Chatham Village and Hardings Beach. Properties in Chatham Village often feature spacious living areas, fully equipped kitchens for preparing family meals, and delightful outdoor spaces superb for gatherings or playtime.

Additionally, many rentals boast amenities such as private decks, outdoor grills, and laundry facilities, enhancing the convenience for families. The proximity to beautiful beaches, such as Lighthouse Beach and Hardings Beach, allows for easy access to sun and sand, making it a top choice for families looking to enjoy the coastal environment.

Moreover, visitors can explore local attractions like the Chatham Lighthouse and the Monomoy National Wildlife Refuge, providing opportunities for outdoor activities and nature walks. See all family-friendly rentals in Chatham.
Can I rent a vacation home with a pool or hot tub in Chatham?
In Chatham, there are many vacation homes available for rent that feature pools and hot tubs, with around 32 options to choose from. This picturesque town on Cape Cod is known for its stunning beaches and charming New England atmosphere, making it a desirable destination for travelers. Many of these properties come equipped with private pools, hot tubs, spacious outdoor decks, and fully furnished kitchens, superb for enjoying summer days and relaxing evenings.

Travelers can also expect a variety of amenities, including outdoor dining areas, barbecue grills, and, in some cases, easy access to nearby beaches and scenic walking trails. Find your rental in Chatham with a pool or a hot tub.
Can I find long-stay vacation rentals in Chatham?
A long-stay vacation rental in Chatham is the best way to experience local living. Plus, you can make the most of long-stay discounts. For month-long stays, save an average of 19%, and for week-long bookings you can save an average of 10%.* Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
Are there pet-friendly house rentals in Chatham?
In Chatham, there are numerous pet-friendly house rentals available, providing a welcoming environment for travelers with furry companions. Many of these rentals feature amenities such as spacious backyards, outdoor patios, and fully equipped kitchens, making them ideal for families or groups. The properties often include comfortable living spaces, multiple bedrooms, and sometimes even access to laundry facilities for added convenience.

Chatham is known for its picturesque coastal scenery and charming downtown area, which is just a short drive from many vacation homes. The nearby Chatham Lighthouse Beach offers a lovely spot for walks by the ocean, and the surrounding parks and nature trails provide excellent opportunities for outdoor activities with pets. Additionally, the town's dog-friendly beaches and local pet-friendly cafes enhance the experience for those traveling with pets, ensuring both enjoyment and relaxation during your stay. See all pet-friendly rentals in Chatham.
Are there any remote work vacation rentals in Chatham?
In Chatham, Massachusetts, there are numerous vacation rentals suitable for remote work, with about 293 options available. Travelers can expect properties equipped with essential amenities for a productive work environment, including dedicated office spaces with desks, comfortable chairs, and high-speed Wi-Fi. Many rentals also offer additional features like computer monitors and safes for secure storage of personal items.

The charming town of Chatham is known for its picturesque beaches, scenic coastal views, and vibrant local culture, making it an ideal spot for balancing work and leisure. Properties often come with outdoor spaces where you can relax after a day of work, and some may include kitchens for preparing meals. The proximity to local attractions such as the Chatham Lighthouse and the Cape Cod National Seashore adds to the appeal of working remotely in this beautiful location. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Chatham vacation rentals with parking?
Vrbo offers a wide selection of vacation rentals in Chatham with parking available---perfect for families or travelers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details on Vrbo and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
What are popular rental amenities in Chatham?
In Chatham, popular rental amenities include WiFi, which ensures travelers stay connected during their stay. Most vacation rentals feature fully equipped kitchens, allowing guests to prepare their own meals with ease. Many properties also come with patios or decks where visitors can relax and enjoy the pleasant coastal weather. Additionally, a coffee or tea maker is commonly found in these rentals, great for starting the day with a warm beverage.
When is the best time to visit Chatham for a vacation rental?
The best time to visit Chatham for a vacation rental is during the peak season from June to August, particularly in July when the town comes alive with vibrant summer energy. This period is superb for families and beachgoers looking to soak up the sun on Chatham's picturesque shores, enjoy fresh seafood at local eateries, and partake in various outdoor activities like kayaking and paddleboarding.

During the summer months, you can expect warm temperatures ranging from the mid-60s to the low 80s Fahrenheit, creating an inclusive setting for all kinds of outdoor adventures. The town is bustling with visitors, making it an ideal time for those seeking a lively community vibe and plenty of social activities, including local festivals and art fairs.

If you're looking for a more budget-friendly option, consider visiting in November.
How early should I book a Chatham vacation rental?
Book your Chatham vacation rental at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price.

*Based on analysis of Vrbo booking and occupancy data for 2024 stays.
What are the top attractions in Chatham?
In Chatham, visitors can enjoy a charming coastal experience with several attractions. The picturesque Chatham Lighthouse, located at the entrance of Chatham Harbor, offers stunning views and is a great spot for photography. Nearby, the Chatham Fish Pier provides an authentic glimpse into the local fishing industry and is superb for watching boats come in with their daily catch.

The town's beautiful beaches, such as Lighthouse Beach and Harding's Beach, are ideal for sunbathing, swimming, and beachcombing. Additionally, the quaint downtown area features unique shops, restaurants, and art galleries that reflect the town's New England charm.
Can I change or cancel my Chatham home rental booking on Vrbo?
To find Chatham vacation rentals with free cancellation, just use Vrbo's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Vrbo rentals give you the privacy of having the entire place to yourself, and for extra flexibility, some travelers can choose to pay over time with Affirm. Whether you're adjusting your plans or looking for flexible payment options, Vrbo makes it easy to book with confidence.
Why should I join Vrbo as a host?
Joining Vrbo as a host opens the door to a global community of travelers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Vrbo makes it easy to list, manage, and succeed. Whether it's a cozy flat or a countryside retreat, you can turn your space into a standout destination---become a host and let Vrbo handle the heavy lifting to help you thrive.

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