Chatham holiday lettings

We found 3,392 holiday rentals — enter your dates for availability
Select from 280 homes, 31 cottages and other holiday rentals in Chatham to find one that's perfect for your trip. Holiday homes offer the best amenities for your family, friends or furry companion, such as a fireplace and a washer and dryer. At the end of the day, you'll be sure to find a property to rent that has what everyone needs, including accessible or non-smoking choices.

Holiday rentals with weekly discounts – Chatham

Showing deals for:9 Oct - 16 Oct

Image gallery for Private heated pool, minutes to beach

Pool
10 out of 10, Exceptional, (32 reviews)
Exceptional
(32 reviews)

Private heated pool, minutes to beach

Brewster

7% off
Price is £3,793
for 7 nights, 1 home
£542 per night
includes taxes & fees
Private heated pool, minutes to beach

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Why visit Chatham

  • Pristine Beaches: Enjoy the beautiful sandy shores of Chatham, perfect for sunbathing and water activities.
  • Historic Lighthouses: Explore iconic lighthouses that offer stunning views and a glimpse into the town's maritime heritage.
  • Charming Streets: Stroll through picturesque streets lined with local boutiques and delightful eateries serving fresh seafood.
  • Scenic Trails: Discover scenic walking trails that showcase Chatham's natural beauty and coastal landscapes.
  • Family-Friendly Atmosphere: Experience a welcoming community ideal for families and couples seeking a relaxing getaway.

Popular types of accommodation in Chatham

Chatham, Massachusetts, is a charming coastal town that offers a delightful blend of natural beauty and rich history. Visitors can explore pristine beaches, picturesque lighthouses, and scenic walking trails. Popular vacation rentals include private homes, cosy cottages, and stylish condos, perfect for families or couples seeking a relaxing getaway. Enjoy fresh seafood dining, local boutiques, and the serene atmosphere that makes Chatham a top choice for your next holiday retreat.

  • Houses: The top choice for visitors seeking a home-away-from-home experience in Chatham, offering spacious living and personalised amenities.
  • Cottages: Quaint and charming, cottages provide a cosy retreat, perfect for a romantic getaway or family holiday.
  • Condos: Ideal for those wanting modern convenience, condos often come with shared facilities and are close to local attractions.
  • Apartments: Offering flexibility and practicality, apartments are great for longer stays with all the comforts of home.
  • Cabins: Embrace nature in a rustic cabin, providing a serene escape amidst Chatham’s beautiful landscapes.**

Top attractions in and around Chatham

Chatham, Massachusetts, is a charming coastal town perfect for beach lovers and outdoor enthusiasts. Visitors can enjoy stunning beaches, scenic views, and a variety of outdoor experiences. Popular attractions include picturesque beaches, historic houses, and golf courses, catering to those seeking culture and recreation. Whether you're exploring the beautiful shoreline or indulging in local history, Chatham provides a delightful escape for travellers wanting to immerse themselves in the natural beauty and heritage of Cape Cod.

  • Ocean Edge Golf Club: A beautifully designed golf course set within a stunning resort, offering picturesque landscapes and a challenging game for golfers of all levels.
  • Chatham Lighthouse Beach: A charming beach with serene vibes, perfect for sunbathing, swimming, or taking leisurely strolls along the shoreline, all framed by the iconic lighthouse.
  • Chatham Windmill: A historic windmill that adds character to the town, showcasing traditional architecture and providing a lovely backdrop for photos amidst trendy surroundings.

Things to do recommended for couples

Chatham offers a charming escape for couples. Enjoy a romantic walk along the picturesque beaches, explore quaint shops in the town centre, or take a sunset sail on the calm waters of Cape Cod. Don't miss a candlelit dinner at a local bistro for a perfect end to your day.

Things to do recommended for families

Families visiting Chatham can delight in a day at the Cape Cod National Seashore, where children can explore sandy beaches and tidal pools. For a unique experience, take a scenic whale-watching tour to witness these magnificent creatures up close. Enjoy local ice cream shops for a sweet treat.

Things to do recommended for groups

Groups visiting Chatham can enjoy a whale watching tour off Cape Cod, explore the charming Main Street shops, and relax on the beautiful beaches. Don't miss a visit to the Chatham Lighthouse for stunning coastal views and local history.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

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

When travelling with a group, family, pets, or seeking extended stays, it's essential to filter your options according to your priorities. Here are some helpful Vrbo booking tips for you.

  • Traveling to Chatham with a group: Think about how many bedrooms you’ll require, as well as amenities like a fully equipped kitchen or outdoor space for group gatherings. Luckily, you can easily filter for all of this and more on Vrbo.
  • Traveling to Chatham with young kids: Travelling with young children can be quite demanding. It's important to prioritise their comfort and safety, along with suitable amenities, like a private swimming pool. Additionally, it's wise to think about how close you are to family-friendly attractions.
  • Taking your pets with you to Chatham: For many, a family holiday isn't truly complete without their furry companion by their side. If you can relate, take a look at Vrbo properties that welcome pets. Many of these pet-friendly accommodations offer feeding bowls and beds, ensuring that everyone feels comfortable and at home.
  • Planning for a long term stay visiting Chatham: If you're seeking holiday rentals with special offers for stays of a month or more, you've come to the right place. By using the appropriate filters, you can effortlessly discover and save on monthly rentals. Don’t forget to include options like a parking space, a well-equipped kitchen, or a private pool in your search as well.

Where to stay near Chatham

Chatham, Massachusetts, is a charming coastal town perfect for a relaxing beach holiday. Visitors can enjoy scenic strolls along its picturesque streets, explore local boutiques, and indulge in fresh seafood at delightful eateries. The town's friendly atmosphere makes it ideal for families and couples alike, while its stunning beaches offer opportunities for sunbathing and water activities. With its trendy vibe and welcoming community, Chatham promises a memorable vacation experience.

  • North Chatham: Located a mere mile from Chatham, North Chatham is a coastal gem known for its stunning beaches and breathtaking scenery. This charming neighbourhood offers a delightful outdoor experience where visitors can engage in activities like golf and explore its recreational areas. The local beaches, including family-friendly spots, provide the perfect setting for relaxation and fun in the sun. The picturesque Cape Cod landscape surrounding North Chatham makes it a favourite for those seeking a tranquil getaway amidst nature's beauty.
  • West Chatham: Just 3km from Chatham, West Chatham is another idyllic neighbourhood that attracts tourists with its captivating coastal views and vibrant outdoor activities. This area is home to several playgrounds and golf courses, making it an excellent choice for families and sports enthusiasts alike. The local beaches, particularly those suited for families, are perfect for a day of swimming and sunbathing. Visitors will also enjoy the scenic charm of the Cape, making West Chatham a delightful addition to any itinerary.
  • Brewster: Situated 13km from Chatham, Brewster is celebrated for its outdoor adventures and stunning beaches. This city offers a range of activities, including golfing and exploring its recreational areas. The local beaches are ideal for families, providing a serene environment to unwind and soak in the natural beauty. Brewster's scenic landscapes, coupled with its rich history, charm visitors looking for both relaxation and exploration. With its inviting atmosphere and array of attractions, Brewster is a must-visit on your journey through 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 CloudyAverageSlightly Low
February35.4°F (1.9°C)Light RainMostly CloudyAverageSlightly Low
March38.5°F (3.6°C)Light RainMostly CloudyAverageSlightly 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 HighSlightly High
July69.6°F (20.9°C)Light RainMostly SunnyModerately HighSlightly High
August70.3°F (21.3°C)Light RainMostly SunnyModerately HighSlightly 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 journey? Being flexible with your travel dates can make a significant difference, as prices often fluctuate. Additionally, you can enjoy considerable savings by opting for a longer stay. To discover a Vrbo property that suits your budget, utilise our filters to sort by price, location, and type of holiday rental.

Vrbo Trips: Effortless planning

Vrbo’s Trip Board offers a user-friendly platform for you to plan new trips, continue from where you last stopped, or manage your travel arrangements. You can easily find your saved or booked properties sorted into categories such as Potential, Upcoming, or Current Trips. To begin using Trip Boards, please visit: https://www.vrbo.com/en-gb/trips.

**Based on Vrbo properties bookings.

Why people love visiting trendy Chatham

Enjoy the art galleries and other features of Chatham. This trendy city is known for its seafood restaurants, seaside and beaches. Cape Cod Beaches and Cape Cod National Seashore are just a couple of the must-see attractions. If you need more space to accommodate a family holiday or a trip with friends, rental homes often come with separate dining areas and spacious living rooms.

Activities and attractions in Chatham

Are you hoping to discover attractions to visit while you're in town? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that makes Chatham a fun spot to go on holiday. Here are some of the most popular attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Cape Cod Lavender Farm (6.2 mi / 10 km)
  • Cape Cod Baseball & Bumper Boats (6.9 mi / 11.1 km)
  • Ocean Edge Golf Club (7.4 mi / 12 km)
  • Cape Cod Inflatable Park (14.3 mi / 23 km)
  • Cape Codder Water Park (18 mi / 29 km)
  • Adventure Chatham (3.6 mi / 5.8 km)

Exploring the beaches and other natural features in Chatham

Whether you're an outdoor enthusiast or just want to take in the scenery, Chatham is a great place to get out in nature. These are some of the area's most eye-catching natural features, all within 30 miles (48.2 km) of the city centre:

  • Cape Cod Beaches (16.1 mi / 25.8 km)
  • Chatham Lighthouse Beach (1.2 mi / 2 km)
  • Hardings Beach (2.2 mi / 3.5 km)
  • Ridgevale Beach (2.4 mi / 3.9 km)
  • Red River Beach (4.2 mi / 6.8 km)
  • Bank Street Beach (5.8 mi / 9.4 km)

Seasonal weather averages in Chatham

If you're planning a holiday around warm-weather activities, August, July, September and June are the hottest months to visit, when temperatures average 19°C.

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 centre. If you can't find a flight that works for your travel itinerary, you can also fly into Nantucket, MA (ACK-Nantucket Memorial), which is 29.9 mi (48.1 km) away.

Frequently asked questions

What is the best area to stay in Chatham when booking a holiday rental?
When considering a holiday rental in Chatham, Massachusetts, a popular area to stay is near the charming downtown district. This vibrant locale offers a delightful blend of shops, galleries, and eateries, making it a great base for exploring the town's unique character. You'll find a variety of properties available, from quaint cottages to more spacious homes, suiting different preferences and group sizes.

A popular attraction in the area is the Chatham Lighthouse, which not only provides stunning views but also holds historical significance as a guiding beacon for sailors. Additionally, the nearby Chatham Pier offers a picturesque spot to watch the fishing boats come in and enjoy fresh seafood from local vendors.
How much does it cost to rent a holiday home in Chatham?
Prices for holiday 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 holiday 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, the area around Chatham Lighthouse Beach is particularly appealing, offering stunning views of the Atlantic and easy access to the sandy shore. Properties in this vicinity often come with amenities such as outdoor decks, great for enjoying morning coffee or evening sunsets, as well as spacious living areas ideal for families or groups. Many houses here also feature modern kitchens, allowing guests to prepare their own meals with fresh local seafood.

Another popular area is the stretch along Hardings Beach, which is known for its gentle waves and picturesque scenery. Rentals here frequently include private outdoor spaces, like patios or gardens, where visitors can relax after a day at the beach. This location is also close to local shops and eateries, providing convenience for those looking to explore the culinary scene.

For a more tranquil experience, the area near Monomoy National Wildlife Refuge offers a quieter setting, with properties often boasting scenic views of the marshland and easy access to nature trails. Many accommodations here come equipped with amenities such as outdoor showers, great for rinsing off after a day spent on the nearby beaches.
What is the most popular type of holiday rental accomodation in Chatham?
In Chatham, holiday houses are the most popular type of holiday rental, with approximately 944 available throughout the charming coastal town. These houses often feature spacious layouts, multiple bedrooms, fully equipped kitchens, and outdoor areas great for enjoying the picturesque surroundings. Many are situated close to local attractions such as Chatham Lighthouse, the beautiful beaches, and the scenic Cape Cod Rail Trail.

Cottages are also a great option, with around 96 available, providing a quaint and cosy atmosphere typically equipped with essential amenities for a comfortable stay. Condos and apartments, while fewer in number—about 60 and 32 respectively—offer a more compact alternative for those seeking convenient access to local dining and shopping.
Are there any family house rentals in Chatham?
In Chatham, Massachusetts, there are numerous family-friendly house rentals available, with about 188 options to choose from. This charming coastal town offers a variety of accommodations suitable for families, particularly in neighbourhoods close to the beach and local attractions. Many properties boast spacious living areas, full kitchens for preparing family meals, and outdoor decks or patios superb for enjoying the fresh sea air.

Visitors can expect amenities like laundry facilities, Wi-Fi, and often outdoor showers, which are convenient after a day at the beach. The area is known for its picturesque beaches, such as Lighthouse Beach and Chatham Lighthouse Beach, ideal for sandcastle building and swimming. Additionally, families can explore the nearby Chatham Fish Pier, where children can watch the boats come in and enjoy fresh seafood dining.
Can I rent a holiday home with a pool or hot tub in Chatham?
In Chatham, Massachusetts, there are many holiday homes available for rent that come with pools or hot tubs, with around 29 options to choose from. This charming coastal town offers a range of neighbourhoods where these properties can be found, including the picturesque Chatham Village, known for its historic charm and proximity to beautiful beaches, as well as the serene areas near Monomoy National Wildlife Refuge that provide a more tranquil setting.

Travellers can expect a variety of amenities in these rentals, including private swimming pools, inviting hot tubs, outdoor patios for al fresco dining, and fully equipped kitchens ideal for family meals. Many properties also offer spacious living areas, superb for relaxation after a day of exploring the stunning Cape Cod scenery.
Can I find long-stay holiday rentals in Chatham?
A long-stay holiday rental in Chatham is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your travel dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Are there pet-friendly house rentals in Chatham?
In Chatham, Massachusetts, there are numerous pet-friendly house rentals available, offering a range of amenities and comfortable living spaces for both guests and their furry companions. Many of these rentals come equipped with fully stocked kitchens, spacious living areas, and outdoor spaces such as patios or decks, great for enjoying the coastal atmosphere.

Chatham is well-known for its picturesque beaches and charming New England architecture. The area is not only pet-friendly but also offers various parks and natural attractions where pets are welcome. For instance, the nearby Monomoy National Wildlife Refuge is a wonderful spot for outdoor adventures, featuring scenic trails and opportunities to observe local wildlife.

Additionally, the town's beaches, like Lighthouse Beach, often allow dogs during certain hours or off-season, giving pet owners a chance to enjoy the sand and surf together.
Are there any remote work holiday rentals in Chatham?
In Chatham, Massachusetts, remote work holiday rentals are plentiful, with around 1,096 options available. This charming coastal town offers a variety of properties that cater to the needs of remote workers. Many rentals provide essential amenities such as high-speed internet and Wi-Fi, ensuring a seamless work experience.

Travellers can expect comfortable living spaces equipped with dedicated office areas, which are superb for focusing on tasks while enjoying the serene surroundings. Properties often feature fully stocked kitchens, allowing for home-cooked meals during breaks, and some may even include outdoor spaces where one can unwind after a productive day.

Chatham is known for its picturesque beaches, quaint shops, and vibrant local dining scene, making it an excellent choice for those looking to blend work and leisure. The nearby Chatham Lighthouse and scenic walking paths along the coast add to the area's appeal, providing opportunities to explore and relax during downtime. To help narrow your search, insert your dates and apply the "WiFi" filter on Vrbo.
Are there any Chatham holiday rentals with parking?
Vrbo offers a wide selection of holiday rentals in Chatham with parking available—perfect for families or travellers 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 fully equipped kitchens, allowing guests to prepare their own meals while enjoying the comforts of home. Many properties feature outdoor spaces such as decks or patios, great for soaking up the sun or enjoying a meal al fresco. Onsite parking is commonly available, making it convenient for those travelling by car. Additionally, rentals often come with coffee and tea makers, ensuring that guests can savour their morning beverages in a relaxed setting.
When is the best time to visit Chatham for a holiday rental?
The peak season for visiting Chatham is during the summer months of June to August, with July being particularly popular among holidaymakers. This vibrant period welcomes a flurry of visitors eager to enjoy the stunning beaches, charming shops, and delicious seafood that Chatham has to offer. With temperatures typically ranging from 18 to 26 degrees Celsius, the warm weather makes it great for outdoor activities such as swimming, sailing, and exploring the picturesque coastline.

If you prefer a quieter experience, consider visiting in November. While this month might be outside the bustling summer season, it presents a unique opportunity to enjoy the serene beauty of Chatham. The cooler temperatures, averaging around 5 to 12 degrees Celsius, create a peaceful atmosphere ideal for leisurely walks along the beach and taking in the stunning autumn colours.

For those who cherish a blend of comfort and convenience, planning your stay during the shoulder months of late spring or early autumn can offer you a fantastic balance. You'll find that the crowds have thinned, allowing for more personalised experiences while still enjoying the beauty of Chatham's natural surroundings.
How early should I book a Chatham holiday rental?
Book your Chatham holiday 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 holiday 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, Massachusetts, visitors can enjoy a variety of attractions that showcase the charm of this picturesque coastal town. The Chatham Lighthouse, with its iconic white tower, offers stunning views of the Atlantic Ocean and is a popular spot for photographs. Nearby, the Chatham Fish Pier is a bustling hub where visitors can watch local fishermen at work and perhaps even sample fresh seafood from nearby vendors.

The quaint Main Street is lined with charming shops, art galleries, and restaurants, making it an excellent place to stroll and soak up the local atmosphere. For those interested in history, the Chatham Historical Society Museum provides insights into the town's maritime heritage and showcases various artefacts.

Outdoor enthusiasts will appreciate the scenic beauty of Cape Cod National Seashore, which is just a short drive away, offering hiking trails, beautiful beaches, and opportunities for birdwatching. Additionally, the Monomoy National Wildlife Refuge is ideal for nature lovers looking to explore the diverse ecosystems and see local wildlife.
Can I change or cancel my Chatham home rental booking on Vrbo?
To find Chatham holiday 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 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 travellers 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 cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Vrbo handle the heavy lifting to help you thrive.

Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.
Are all fees included in the Chatham holiday rental prices shown on Vrbo?
Vrbo provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
What is VrboCare™ and how does it work?
Vrbo's mission is to help guests relax, reconnect, and enjoy precious time together. With VrboCare™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable.

If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
What can I expect from Vrbo customer service and VrboCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, VrboCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Vrbo customer service is available 24/7 to support you every step of the way.

Vrbo also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
Can I plan a group trip on Vrbo?
Vrbo's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favorites, and build the perfect itinerary together.

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