Chatham holiday lettings

We found 3,477 holiday rentals — enter your dates for availability

Select from 294 homes, 30 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:3 Oct - 10 Oct
  • 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.

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.

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

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.

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)
  • 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)
  • Captain's Cove Golf Course (4.1 mi / 6.7 km)
  • Cranberry Valley Golf Course (5.4 mi / 8.6 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)
  • Red River Beach (4.2 mi / 6.8 km)
  • Bank Street Beach (5.8 mi / 9.4 km)
  • Earle Road Beach (7.1 mi / 11.5 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 most popular type of holiday rental accommodation in Chatham?
Based on our data, houses are the most desirable property type in Chatham. But having said that, everyone's idea of an epic stay can vary. Vrbo has holiday homes of all sizes and shapes, so you're sure to find the perfect match.
How much does it cost to rent a holiday rental in Chatham?
A range of things affect how much you'll pay for a holiday rental in Chatham, like the season, type of property and length of stay. Still, all Vrbo homes have one thing in common --- unbeatable value. Just add your travel dates to find your ideal fit.
How much does it cost to rent a beach house in Chatham?
When you travel and the size and style of the property will determine the cost of your beachside stay. Enter your Chatham travel dates to view your available options on Vrbo. Can't live without a hot tub? Use our filters to choose the amenities and features you need.
Are there pet-friendly holiday rentals in Chatham?
With 78 properties that host four-legged guests, your furry friend can also come along on your Chatham getaway. Use our filter tool to search our pet-friendly holiday rentals and find your pawfect pad on Vrbo.
Can I rent a house with a pool in Chatham?
Grab your swimming gear and goggles, because there are eight houses with a private pool in Chatham. Make a booking at one of these superb holiday rentals and you'll enjoy pool days every day. Simply enter your travel dates into Vrbo, then check the "pool" filter to find a place to make a splash!
What are popular rental amenities in Chatham?
When it comes to rental amenities that people are on the lookout for in Chatham, a garden, nearby museums and an ocean view are at the top of the list. With Vrbo holiday homes, you'll discover options to fit your taste and style, whether you're travelling with family members, friends or even pets.
Are there large group holiday rentals in Chatham?
There are 20 holiday properties in Chatham that can host 10 or more people. Whether you're planning a family trip or an event like a birthday party, there's plenty of room to get your group together under one roof.
Are there holiday rentals in Chatham that welcome kids?
With 78 family-friendly holiday rentals to choose from in Chatham, now is the perfect time to introduce the little ones to the joys of travel. Just check our "Properties good for families" filter box to locate stays that come with conveniences ideal for families on the move, like full kitchens, yards, hot tubs and bunk beds.
What are the top attractions for families in Chatham?
Keeping the kids entertained during your stay in Chatham is a cinch with these top family-friendly attractions:

  • Skaket Beach
  • Sea Street Beach
  • Bank Street Beach

Are there one-bedroom holiday rentals in Chatham?
Chatham has 12 one-bedroom rentals available. Typically situated in prime spots due to their smaller size, a one-bedroom rental is great if you're travelling with a buddy or your partner. And with comforts like air conditioning and more privacy than a standard hotel, you'll be able to kick back and relax while enjoying this amazing destination.
Can I find two-bedroom holiday rentals in Chatham?
Select from 15 two-bedroom holiday homes in Chatham. Put your little ones in the second room or maybe fill it with a couple of your best friends. There's plenty of space for whoever's lucky enough to be coming along.
Are there holiday rentals with WiFi in Chatham?
You'll have a choice of 26 holiday rentals with WiFi in Chatham. If you want to disconnect from daily life while on holiday, but still need to be connected to the web, these getaways have just what you need. Narrow your search by applying the WiFi filter on Vrbo.
How can I find holiday rentals with air conditioning in Chatham?
Choose from 75 Vrbo holiday rentals with air conditioning in Chatham offering that cooling breeze and extra bit of comfort. Enter your preferred dates of travel and then use our handy filter tool to help you book stays with air conditioning.
How old do you have to be to rent a holiday rental in Chatham?
The minimum required age is usually 16, 18 or 21. It can vary from one property to another on Vrbo, so check the rules of your chosen Chatham holiday home before making a booking.
How long can I rent a holiday rental in Chatham for?
It's up to the Chatham property. To see all available options offering extended stays, just type your dates and number of guests into Vrbo's search page. Look forward to having the whole place to yourself, as well as amenities such as a kitchen, air conditioning and a yard where your little ones can play. Keep your eyes open for long-term stays that offer weekly or monthly discounts.

More Holiday Rentals ideas

People also search for