Chatham holiday rentals

We found 3,373 holiday rentals — enter your dates for availability
Select from 276 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:18 Dec - 25 Dec

Living area
Exterior
Living area
Private kitchen
Wonderful
(19 reviews)

Cottage near bay beach- 1 Bd/1Ba

Brewster

8% off
AU$1,095
for 7 nights, 1 cottage
AU$156 per night
includes taxes & fees
Cottage near bay beach- 1 Bd/1Ba
Living room - French doors
Private beach/dock area
Living room
View of property
Exceptional
(19 reviews)

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

South Chatham

8% off
AU$9,856
for 7 nights, 1 home
AU$1,408 per night
includes taxes & fees
Stunning Waterfront Compound with Private Beach, Private Dock, Sunset View
Well equipped chef's kitchen w. stainless steel appliances
Deeded access to nearby Mill Pond to launch your Kayak
Large island, comfortable seating area
Fabulous family room, a magnet for family gatherings
Exceptional
(121 reviews)

Water View-Walk town/beach, pets considered, Linen Option

Chatham

20% off
AU$8,475
for 7 nights, 1 home
AU$1,211 per night
includes taxes & fees
Water View-Walk town/beach, pets considered, Linen Option
Private kitchen
Exterior
Interior
entrance to mallardview
Exceptional
(64 reviews)

5 bedrooms ocean view estate overlooking cape cod bay

Orleans

8% off
AU$10,885
for 7 nights, 1 home
AU$1,555 per night
includes taxes & fees
5 bedrooms ocean view estate overlooking cape cod bay
Living room with cathedral ceiling - open floor plan
Deck with teak table and chairs
Kitchen with island
Interior
Exceptional
(92 reviews)

Unique Oyster Pond 3bd-2ba home in private setting close to downtown.

Chatham

7% off
AU$5,175
for 7 nights, 1 home
AU$739 per night
includes taxes & fees
Unique Oyster Pond 3bd-2ba home in private setting close to downtown.
Open concept dining room with spectacular views to the ocean.
Sunny living space with large balcony, and spectacular views to the ocean.
Reclaimed hardwood floors shipped in from an old barn taken down in the mid-west
Huge gourmet kitchen with 2 SubZero fridges, and high end appliances.
Exceptional
(64 reviews)

SeaGlass House - Beautiful Cape Cod Home. Ocean Views & High End Decor

Chatham

8% off
AU$12,624
for 7 nights, 1 home
AU$1,803 per night
includes taxes & fees
SeaGlass House - Beautiful Cape Cod Home. Ocean Views & High End Decor
Master Bedroom - King Bed, TV, Bureau and ensuite bath
Shuffle Board
Living Room
Kitchen, Dining area: Fridge, Stove, Dishwasher
Exceptional
(138 reviews)

#Game Rm, King Bds, Wi-Fi, Bikes, Beach Supplies, Quiet Street, Central AC\Heat

Harwich

6% off
AU$3,883
for 7 nights, 1 home
AU$555 per night
includes taxes & fees
#Game Rm, King Bds, Wi-Fi, Bikes, Beach Supplies, Quiet Street, Central AC\Heat
Living area
Pool
Kitchen
Exterior
Exceptional
(68 reviews)

Luxury 8 Bedroom Home with Heated Pool - 4 minutes to the beach! Pet Friendly!

Orleans

8% off
AU$17,934
for 7 nights, 1 home
AU$2,562 per night
includes taxes & fees
Luxury 8 Bedroom Home with Heated Pool - 4 minutes to the beach! Pet Friendly!
View from second floor.
Outdoor dining
The Woolrych House sits above a private Brewster beach.
Upstairs queen in View Room
Exceptional
(52 reviews)

Picturesque Private Beachfront House on Cape Cod Bay

Brewster

8% off
AU$6,626
for 7 nights, 1 home
AU$947 per night
includes taxes & fees
Picturesque Private Beachfront House on Cape Cod Bay
Outdoor dining set overlooking the bay on deck
Living room looking toward front / first floor front bedroom door
Kitchen
Second floor front bedroom with view of Cape Cod Bay
Exceptional
(28 reviews)

Waterview, 4 BR, 100 Feet from Private Eastham Bayside Beach!

Eastham

6% off
AU$4,812
for 7 nights, 1 home
AU$687 per night
includes taxes & fees
Waterview, 4 BR, 100 Feet from Private Eastham Bayside Beach!
Sitting area with fireplace
Dusk in Chatham
Large dining room table.
Kitchen
Exceptional
(44 reviews)

Charming Family Cape, Impeccably Landscaped With Water Views Near The Beach!

South Chatham

8% off
AU$5,568
for 7 nights, 1 home
AU$795 per night
includes taxes & fees
Charming Family Cape, Impeccably Landscaped With Water Views Near The Beach!
Interior
Exterior
Dining
Living area
Wonderful
(5 reviews)

Newly Renovated Chatham Home overlooking Cranberry Bog.

West Chatham

7% off
AU$6,735
for 7 nights, 1 home
AU$962 per night
includes taxes & fees
Newly Renovated Chatham Home overlooking Cranberry Bog.
Outdoor dining
Marina
Pine Room/Family room with queen pull out couch
Interior
Exceptional
(43 reviews)

Rates just lowered for last week of July and Aug with 5 night min accepted.

South Dennis

7% off
AU$1,997
for 7 nights, 1 home
AU$285 per night
includes taxes & fees
Rates just lowered for last week of July and Aug with 5 night min accepted.
Property grounds
Living area
Dining
Room
Exceptional
(16 reviews)

Updated 4BR close to downtown Chatham, Beaches, Bike Path & Tennis Pickleball

Chatham

10% off
AU$3,763
for 7 nights, 1 home
AU$538 per night
includes taxes & fees
Updated 4BR close to downtown Chatham, Beaches, Bike Path & Tennis Pickleball
Exterior
Interior
Living area
Dining
Exceptional
(9 reviews)

Charming 4-bedroom house in enchanting Yarmouth

South Yarmouth

8% off
AU$5,969
for 7 nights, 1 home
AU$853 per night
includes taxes & fees
Charming 4-bedroom house in enchanting Yarmouth
Exterior
Private kitchen
Outdoor dining
Interior
Exceptional
(12 reviews)

3-bedroom house in charming Dennis minutes to Corporation Beach. Relax & unwind.

Dennis

7% off
AU$4,333
for 7 nights, 1 home
AU$619 per night
includes taxes & fees
3-bedroom house in charming Dennis minutes to Corporation Beach. Relax & unwind.
Living area
The Chatham downtown is filled with cute shops and restaurants.
Private kitchen
Dining
Exceptional
(7 reviews)

Charming Chatham Bungalow- Minutes to Beaches and Downtown Chatham

North Chatham

8% off
AU$5,261
for 7 nights, 1 home
AU$752 per night
includes taxes & fees
Charming Chatham Bungalow- Minutes to Beaches and Downtown Chatham
Seating for 3 at kitchen counter
Outdoor dining
Dining
Updated Kitchen for Summer 2020 Fully equipped
Exceptional
(57 reviews)

3 BR Cape-short drive to Mayflower & other bay beaches-A/C, Wi-Fi, Linens Incl.

South Dennis

12% off
AU$5,192
for 7 nights, 1 home
AU$742 per night
includes taxes & fees
3 BR Cape-short drive to Mayflower & other bay beaches-A/C, Wi-Fi, Linens Incl.
Living area
Dining
Interior
Living area
Exceptional
(11 reviews)

Enjoy a relaxing retreat. Easy access: Beaches, Bike Path, & Great restaurants.

South Chatham

8% off
AU$9,060
for 7 nights, 1 home
AU$1,294 per night
includes taxes & fees
Enjoy a relaxing retreat. Easy access: Beaches, Bike Path, & Great restaurants.
Property grounds
Private kitchen
Outdoor dining
Living area
Exceptional
(5 reviews)

Adorable updated Cape in East Orleans!

Orleans

8% off
AU$6,656
for 7 nights, 1 home
AU$951 per night
includes taxes & fees
Adorable updated Cape in East Orleans!
Bathroom
Front Entrance
Private kitchen
Private kitchen
Exceptional
(8 reviews)

Cozy, vacation home in a charming duplex cottage

West Yarmouth

7% off
AU$2,079
for 7 nights, 1 cottage
AU$297 per night
includes taxes & fees
Cozy, vacation home in a charming duplex cottage
Room
Living area
Exterior detail
Private kitchen
Exceptional
(29 reviews)

Steps to the beach!

Dennis Port

8% off
AU$3,493
for 7 nights, 1 cottage
AU$499 per night
includes taxes & fees
Steps to the beach!
Exterior
Welcome to the porch where you can relax after a day at the beach or golfing!
Built in microwave and range.
A place to rest your head after all the fun you will have here!
Wonderful
(67 reviews)

Delightful Cottage for Two

Chatham

8% off
AU$2,326
for 7 nights, 1 cottage
AU$332 per night
includes taxes & fees
Delightful Cottage for Two
Private kitchen
Interior
Fire pit with seating area to enjoy cool starlit cape cod evenings
Dining
Wonderful
(10 reviews)

Newly renovated Seagull Beach, coastal retreat, charm, comfort, outdoor living.

West Yarmouth

11% off
AU$5,763
for 7 nights, 1 home
AU$823 per night
includes taxes & fees
Newly renovated Seagull Beach, coastal retreat, charm, comfort, outdoor living.

  • 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, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

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:

  • Cranberry Valley Golf Course (5.4 mi / 8.6 km)
  • 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)

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)
  • Red River Beach (4.2 mi / 6.8 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.
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.
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 Stayz.
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.
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.
Are all fees included in the Chatham holiday homes prices shown on Stayz?
Stayz 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.
Are there any Chatham holiday homes with parking?
Stayz offers a wide selection of holiday homes 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 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.
Are there any discounts for Chatham holiday homes?
You can find great discounts on holiday homes in Chatham on Stayz, 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.
Can I change or cancel my Chatham holiday home booking on Stayz?
To find Chatham holiday rentals with free cancellation, just use Stayz'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". Whether you're adjusting your plans or looking for flexible payment options, Stayz makes it easy to book with confidence.
Can I find long-stay holiday homes in Chatham?
A long-stay holiday home 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 vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Stayz?
Stayz'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 favourites, and build the perfect itinerary together.
How early should I book a Chatham holiday home?
Book your Chatham holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Stayz booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Chatham?
Prices for holiday homes 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 travelling solo, as a couple, with family, or in a group. Stayz offers something for every taste and budget, from affordable homes in Chatham to more spacious homes.
What can I expect from Stayz customer service and StayzCare™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, StayzCare™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, StayzCare™ customer service is available 24/7 to support you every step of the way. Stayz 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.
What is StayzCare™ and how does it work?
Stayz's mission is to help guests relax, reconnect, and enjoy precious time together. With StayzCare™, 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.
Why should I join Stayz as a host?
Joining Stayz 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, Stayz 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 Stayz handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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