Chatham holiday lettings

We found 3,236 holiday rentals — enter your dates for availability

Select from 274 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:17 Apr - 24 Apr

Image gallery for ⭐️ STUNNING WATERFRONT ⭐️Pet Friendly 3BDRM/2BTH*FIREPIT*KAYAKS*GAS FIREPLACE*

Stunning waterfront home on Flax Pond. Rated 2nd best pond on Cape Cod (by Cape Cod Online).
10 out of 10, Exceptional, (77 reviews)
Exceptional
(77 reviews)

⭐️ STUNNING WATERFRONT ⭐️Pet Friendly 3BDRM/2BTH*FIREPIT*KAYAKS*GAS FIREPLACE*

Dennis

11% off
Price is £2,646
for 7 nights, 1 cottage
£378 per night
includes taxes & fees
⭐️ STUNNING WATERFRONT ⭐️Pet Friendly 3BDRM/2BTH*FIREPIT*KAYAKS*GAS FIREPLACE*

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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)
  • 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:

  • 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, the area around Chatham Village is an excellent choice. This charming centre boasts a delightful blend of historic architecture and modern amenities, making it a vibrant hub for visitors. Staying here places you within walking distance of the iconic Chatham Lighthouse, where you can enjoy stunning views of the ocean and the picturesque coastline. The nearby Chatham Fish Pier offers a fantastic opportunity to watch the local fishermen at work and sample some fresh seafood from the market stalls.

Another fantastic option is the area near Stage Harbor, which is particularly appealing for its serene waterfront views and proximity to the beautiful Stage Harbor Lighthouse. This tranquil neighbourhood provides a peaceful retreat while still being close enough to the village's shops, restaurants, and galleries. In terms of holiday rentals, both areas offer a range of properties, with numerous options available to suit various tastes and budgets.
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, Massachusetts, the area around Chatham Lighthouse Beach is particularly appealing. This picturesque beach is known for its stunning views and soft sands, making it a favourite among families and beachgoers. Properties in this vicinity often feature amenities such as outdoor decks for sunbathing, spacious living areas, and fully equipped kitchens ideal for preparing fresh seafood from local markets.

The area near Stage Harbor also offers delightful options, where you can find charming cottages and larger homes with private beaches or easy access to the water. Many of these properties come with outdoor showers, patios equipped with grills, and sometimes even kayaks or paddleboards for guests to use. The proximity to local shops and restaurants enhances the convenience for travellers looking to enjoy the coastal lifestyle.
What is the most popular type of holiday rental accomodation in Chatham?
In Chatham, holiday houses are the predominant type of rental, with approximately 258 available throughout the charming coastal town. These houses often provide ample space, featuring multiple bedrooms, fully equipped kitchens, and outdoor patios or decks where guests can enjoy the pleasant seaside atmosphere. Many are situated close to local attractions such as Chatham Lighthouse and the picturesque beaches along the Cape Cod coastline.
Are there any family house rentals in Chatham?
In Chatham, Massachusetts, there is a wide selection of family-friendly holiday rentals—around 220 available throughout the area. This charming coastal town is superb for families, offering an array of properties in picturesque neighbourhoods. Many homes come with spacious living areas, fully equipped kitchens, and outdoor spaces for barbecues or relaxation. Visitors can also expect amenities such as Wi-Fi, air conditioning, and laundry facilities to enhance their stay.
Can I rent a holiday home with a pool or hot tub in Chatham?
In Chatham, there are plenty of holiday homes available for rent that come with pools or hot tubs, with around 33 options to choose from. This charming town on Cape Cod offers a variety of neighbourhoods, each providing its special environment and proximity to the beautiful coastline. Popular areas include the serene Chatham Village, with its historic charm, and the picturesque waterfront properties along the shores of Stage Harbor.
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, there are many pet-friendly house rentals available, with around 136 options for travellers looking to bring their furry friends along. The charming coastal town offers a variety of holiday homes, often featuring amenities such as fully equipped kitchens, spacious gardens, and outdoor patios, great for enjoying the pleasant weather. Many properties are designed with families in mind, providing comfortable living spaces and easy access to local attractions.
Are there any remote work holiday rentals in Chatham?
In Chatham, Massachusetts, there are numerous remote work holiday rentals available, with around 295 options to choose from. This charming coastal town offers a serene environment conducive to productivity, with many properties featuring dedicated workspaces equipped with desks, ergonomic desk chairs, and high-speed Wi-Fi.

Travellers can expect amenities such as comfortable living areas, fully equipped kitchens for preparing meals, and outdoor spaces where one can unwind after work. The proximity to stunning beaches and scenic attractions like the Chatham Lighthouse adds to the appeal, providing opportunities for relaxation and leisure during breaks. 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 well-equipped kitchens, which are essential for those wishing to prepare their own meals during their stay. Many properties also feature outdoor patios, great for enjoying the pleasant coastal weather. Additionally, travellers can expect rooms with microwaves, stovetops, and toasters, making it easy to whip up quick meals or snacks.
When is the best time to visit Chatham for a holiday rental?
The most popular time to visit Chatham for a holiday rental is during the peak season from June to August. This charming coastal town comes alive with families and travellers looking to soak up the sun on its beautiful beaches and partake in various outdoor activities. Expect vibrant summer days where you can enjoy swimming, sailing, and exploring the stunning Cape Cod National Seashore.

July stands out as the busiest month, offering a lively atmosphere filled with local events, festivals, and the chance to mingle with fellow visitors. The warm temperatures, typically in the mid-20s Celsius, create great conditions for al fresco dining and leisurely strolls along the picturesque harbour.

For those seeking a more budget-conscious option, November presents a wonderful opportunity to enjoy Chatham's tranquil charm. During this shoulder season, you can experience the beauty of the autumn landscape and enjoy a quieter pace, making it ideal for reflective walks along the beach or exploring the quaint shops without the summer crowds.
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 highlight the town's coastal charm and rich history. The Chatham Lighthouse, which offers scenic views of the Atlantic Ocean, is a must-see landmark, and the surrounding beaches, such as Lighthouse Beach, are great for sunbathing and swimming.

The charming Main Street is lined with quaint shops, galleries, and eateries, making it an ideal spot for a leisurely stroll. Nearby, the Chatham Fish Pier provides a glimpse into the local fishing industry and offers opportunities for fresh seafood dining.
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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