Chatham holiday lettings

We found 3,252 holiday rentals — enter your dates for availability

Select from 273 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:15 May - 22 May

Image gallery for Charming Cabin for 2 w pool, 1mile to ocean, BBQ, Pet ok, walk to mini golf/food

Queen bed, porch, bathroom, kitchenette, ac, café table+chairs.
8.8 out of 10, Excellent, (53 reviews)
Excellent
(53 reviews)

Charming Cabin for 2 w pool, 1mile to ocean, BBQ, Pet ok, walk to mini golf/food

South Yarmouth

8% off
Price is £987
for 7 nights, 1 cabin
£141 per night
includes taxes & fees
Charming Cabin for 2 w pool, 1mile to ocean, BBQ, Pet ok, walk to mini golf/food

Find spaces that suit your style

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Why visit Chatham

  • Picturesque beaches: Chatham boasts stunning, pristine beaches ideal for relaxation and family-friendly activities.
  • Charming neighbourhoods: The local areas offer a romantic and inviting atmosphere, perfect for couples and families.
  • Historic attractions: Explore the town's rich history through its beautifully preserved historic houses.
  • Outdoor activities: Enjoy a variety of outdoor pursuits, from beachcombing to scenic waterfront strolls.
  • Diverse accommodation options: Choose from quaint cottages, spacious holiday homes, or modern condos for your stay.

Popular types of accommodation in Chatham

Planning a getaway to Chatham? The next step is selecting the perfect accommodation. Explore a variety of options, from charming cottages and spacious houses to modern condos. Whether you're searching for Chatham holiday rentals or house rentals in Chatham, you're sure to find something that suits your needs. Enjoy the beauty of the area while having a comfortable base to return to after your adventures!

  • Houses: The top choice for visitors to Chatham, offering spacious and comfortable stays perfect for families or groups.
  • Cottages: A delightful second option, these quaint retreats provide a charming escape close to nature.
  • Condos: A popular third choice, condos offer modern amenities and convenient access to local attractions.
  • Apartments: Fourth in popularity, apartments are ideal for a self-catering experience in the heart of Chatham.
  • Cabins: Fifth on the list, cabins offer a rustic, cosy atmosphere for those seeking solitude in nature.**

Top attractions in and around Chatham

Chatham is an ideal destination for those seeking beach, outdoor, and scenic experiences. Its most popular attractions include beautiful beaches, historic houses, and charming neighbourhoods. Visitors can enjoy a rich blend of culture and outdoor activities, making it a perfect location for a relaxing getaway or an adventurous holiday.

  • Harwich Port: A charming seaside town offering a vibrant atmosphere, Harwich Port features quaint shops, delightful eateries, and picturesque views of the waterfront. Enjoy leisurely strolls along the marina and immerse yourself in the local culture.
  • Chatham Lighthouse: This historic lighthouse stands as a symbol of Chatham's maritime heritage. Visitors can explore the surrounding area and appreciate the stunning coastal views while learning about its rich history.
  • Chatham Lighthouse Beach: A beautiful sandy beach perfect for relaxation and sunbathing, Chatham Lighthouse Beach boasts serene waters and breathtaking scenery. It's an ideal spot for a refreshing dip or a leisurely picnic.

Things to do recommended for couples

Searching for a romantic escape in Chatham? Indulge in a rejuvenating experience at Sol Spa, only 4.3km away, or treat yourselves to the serene atmosphere of The E Spa, 5.0km from town. Both promise a blissful retreat for couples seeking relaxation and wellness.

Things to do recommended for families

During your family holiday in Chatham, explore the vibrant Veterans Field for sports activities, enjoy thrilling rides at Cape Cod Baseball & Bumper Boats, and experience the excitement of karting at Bud's Go Karts, all within a short drive of your accommodation.

Things to do recommended for groups

Experience the local charm at Chatham Fish Pier, where you can soak up the bustling market atmosphere. Enjoy a round at Chatham Seaside Links for some outdoor sports, or embark on an adventure along the scenic Cape Cod Rail Trail, just 6.2km away.

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

If you're travelling with a group, enjoying a family getaway, bringing along your pets, or seeking extended stays, it's important to refine your search based on your key priorities. Here are some helpful booking tips for Vrbo.

  • Traveling to Chatham with a group: Think about how many bedrooms you'll require, as well as features like a fully equipped kitchen or outdoor areas for group gatherings. Fortunately, you can easily filter for these options 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 attractions that are enjoyable for the whole family.
  • Taking your pets with you to Chatham: For many, a family holiday wouldn't be the same without their beloved pet by their side. If this resonates with you, take a look at Vrbo properties that welcome pets. Most 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 perfect spot. By using the appropriate filter, you can effortlessly discover and save on monthly rentals. Don’t forget to include preferences like a parking space, a well-equipped kitchen, or even a private pool in your search.

Where to stay near Chatham

Chatham, Massachusetts, is the perfect destination for a beach getaway, offering stunning coastal scenery and a trendy atmosphere. Visitors can relax on pristine beaches, explore the picturesque waterfront, and enjoy family-friendly activities. The charming neighbourhoods surrounding Chatham provide a romantic and welcoming vibe, making it an ideal retreat for couples and families alike. Don't miss the chance to discover local homes and cozy fireplaces that enhance the area's inviting charm.

  • North Chatham: Located a mere mile from Chatham, North Chatham is a picturesque spot renowned for its stunning beaches and vibrant outdoor scenery. Visitors flock here to enjoy the coastal charm and partake in activities such as hiking, golfing, and visiting local playgrounds. The area is surrounded by captivating landscapes, with family-friendly beaches and the iconic Cape Cod scenery just waiting to be explored. Whether you're relaxing on the sandy shores or hiking along scenic trails, North Chatham offers a delightful retreat for nature lovers.
  • Dennis Port: Situated 5.6km from Chatham, Dennis Port is a serene coastal town that beckons beachgoers and outdoor enthusiasts alike. Known for its beautiful beaches and inviting atmosphere, this area provides ample opportunities for family fun and relaxation. Popular activities include golfing and enjoying the local playgrounds, making it an ideal destination for families. The nearby beaches and the stunning Cape scenery add to the allure, ensuring visitors can unwind and soak up the sun while enjoying the picturesque surroundings.
  • West Chatham: Just 1.2km away from Chatham, West Chatham offers a delightful coastal experience rich in natural beauty. This charming city is perfect for those seeking outdoor adventures, with plenty of golfing opportunities and nearby playgrounds for the little ones. Visitors can explore the stunning beaches and scenic views that define the area, including family-friendly options that cater to all ages. The blend of outdoor activities and serene landscapes makes West Chatham a wonderful addition to your travel itinerary.

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.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
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 a breeze

Looking to save on your next escape? Consider being flexible with your travel dates, as prices can fluctuate. Moreover, opting for a longer stay can often result in significant savings. To discover the ideal Vrbo property that fits your budget, utilise our filters to search by price, location, and type of holiday rental.

Vrbo Trips: Planning as easy as it gets

Vrbo's cutting-edge Trip Board offers you a convenient platform to plan new getaways, pick up where you left off, or manage your travel arrangements with ease. You can easily locate properties you've saved or booked under Potential, Upcoming, or Current Trips. To explore Trip Boards, simply 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. 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)
  • Chatham Seaside Links (0.4 mi / 0.7 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:

  • Chatham Lighthouse Beach (1.2 mi / 2 km)
  • Hardings Beach (2.2 mi / 3.5 km)
  • Ridgevale Beach (2.4 mi / 3.9 km)
  • Cockle Cove Beach (2.6 mi / 4.3 km)
  • Bank Street Beach (5.8 mi / 9.4 km)
  • Pleasant Road Beach (7.6 mi / 12.3 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.

More holiday ideas