Chatham holiday homes

We found 3,373 holiday rentals — enter your dates for availability
Select from 277 homes, 32 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:20 Nov - 27 Nov

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

Cottage near bay beach- 1 Bd/1Ba

Brewster

8% off
NZ$1,358
for 7 nights, 1 cottage
NZ$194 per night
includes taxes & fees
Cottage near bay beach- 1 Bd/1Ba
Second Deck Bar Sitting/Dining Area
Breakfast Nook with Pool View
New Chefs Kitchen
Breakfast Nook With Pool and Tranquil Forest View
Exceptional
(35 reviews)

Modern Cape, Private Heated Salt Water Pool, Minutes to Beaches/Golf/Lakes

Brewster

7% off
NZ$8,413
for 7 nights, 1 home
NZ$1,202 per night
includes taxes & fees
Modern Cape, Private Heated Salt Water Pool, Minutes to Beaches/Golf/Lakes
Full view of backyard with in ground pool
Backyard view of house
Pool house: a quiet hideaway or remote office
Large family room with lots of seating; perfect for family game night
Exceptional
(29 reviews)

Immaculately maintained, large beach home with heated swimming pool

Eastham

8% off
NZ$9,736
for 7 nights, 1 home
NZ$1,391 per night
includes taxes & fees
Immaculately maintained, large beach home with heated swimming pool
Living room
Private beach/dock area
Living room - French doors
View of property
Exceptional
(18 reviews)

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

South Chatham

8% off
NZ$12,028
for 7 nights, 1 home
NZ$1,718 per night
includes taxes & fees
Stunning Waterfront Compound with Private Beach, Private Dock, Sunset View
Mudroom and laundry
Eat-in kitchen with oversized island is great for entertaining
Hot tub spa
Primary bedroom (king bed)
Exceptional
(28 reviews)

Family friendly luxury home with heated pool and spa

Chatham

7% off
NZ$13,551
for 7 nights, 1 home
NZ$1,936 per night
includes taxes & fees
Family friendly luxury home with heated pool and spa
Kitchen with island
Deck with teak table and chairs
Living room with cathedral ceiling - open floor plan
Interior
Exceptional
(90 reviews)

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

Chatham

7% off
NZ$6,290
for 7 nights, 1 home
NZ$899 per night
includes taxes & fees
Unique Oyster Pond 3bd-2ba home in private setting close to downtown.
Light & bright second floor great room
Deeded access to nearby Mill Pond to launch your Kayak
Large island, comfortable seating area
Well equipped chef's kitchen w. stainless steel appliances
Exceptional
(119 reviews)

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

Chatham

26% off
NZ$10,158
for 7 nights, 1 home
NZ$1,451 per night
includes taxes & fees
Water View-Walk town/beach, pets considered, Linen Option
rear view of house
Exterior
Private kitchen
entrance to mallardview
Exceptional
(60 reviews)

5 bedrooms ocean view estate overlooking cape cod bay

Orleans

8% off
NZ$13,850
for 7 nights, 1 home
NZ$1,979 per night
includes taxes & fees
5 bedrooms ocean view estate overlooking cape cod bay
Interior
Marina
Outdoor dining
Pine Room/Family room with queen pull out couch
Exceptional
(43 reviews)

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

South Dennis

7% off
NZ$2,484
for 7 nights, 1 home
NZ$355 per night
includes taxes & fees
Rates just lowered for last week of July and Aug with 5 night min accepted.
Fire pit & couch
Center island with seating for 4
2000+ SF multi level patio, pool, pool house, outdoor kitchen, fire pit & more!
Pool house
Exceptional
(43 reviews)

Chatham Loop/Stage Neck/5 Bed/6 Bath

Chatham

8% off
NZ$15,875
for 7 nights, 1 home
NZ$2,268 per night
includes taxes & fees
Chatham Loop/Stage Neck/5 Bed/6 Bath
View from second floor.
Outdoor dining
The Woolrych House sits above a private Brewster beach.
Upstairs queen in View Room
Exceptional
(50 reviews)

Picturesque Private Beachfront House on Cape Cod Bay

Brewster

8% off
NZ$8,835
for 7 nights, 1 home
NZ$1,262 per night
includes taxes & fees
Picturesque Private Beachfront House on Cape Cod Bay
Living area
Private kitchen
Outdoor dining
Interior
Exceptional
(10 reviews)

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

Dennis

7% off
NZ$5,069
for 7 nights, 1 home
NZ$724 per night
includes taxes & fees
3-bedroom house in charming Dennis minutes to Corporation Beach. Relax & unwind.
Kitchen
Living room looking toward front / first floor front bedroom door
Living room looking toward front
Outdoor dining set overlooking the bay on deck
Exceptional
(28 reviews)

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

Eastham

6% off
NZ$6,006
for 7 nights, 1 home
NZ$858 per night
includes taxes & fees
Waterview, 4 BR, 100 Feet from Private Eastham Bayside Beach!
Dining
Living area
Room
Property grounds
Exceptional
(15 reviews)

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

Chatham

10% off
NZ$4,668
for 7 nights, 1 home
NZ$667 per night
includes taxes & fees
Updated 4BR close to downtown Chatham, Beaches, Bike Path & Tennis Pickleball
Exterior
Interior
Dining
Living area
Exceptional
(9 reviews)

Charming 4-bedroom house in enchanting Yarmouth

South Yarmouth

7% off
NZ$7,379
for 7 nights, 1 home
NZ$1,054 per night
includes taxes & fees
Charming 4-bedroom house in enchanting Yarmouth
Living area
The Chatham downtown is filled with cute shops and restaurants.
Dining
Room
Exceptional
(7 reviews)

Charming Chatham Bungalow- Minutes to Beaches and Downtown Chatham

North Chatham

8% off
NZ$6,395
for 7 nights, 1 home
NZ$914 per night
includes taxes & fees
Charming Chatham Bungalow- Minutes to Beaches and Downtown Chatham
Living area
Dining room with water views
Terrace/patio
Room
Exceptional
(35 reviews)

Steps to Paine's Creek-The Perfect Vacation Home

Brewster

7% off
NZ$6,809
for 7 nights, 1 home
NZ$973 per night
includes taxes & fees
Steps to Paine's Creek-The Perfect Vacation Home
Living room has vaulted ceiling, skylight & ceiling fan. Central AC
Outdoor dining
Dining
Updated Kitchen for Summer 2020
Fully equipped
Exceptional
(55 reviews)

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

South Dennis

12% off
NZ$6,439
for 7 nights, 1 home
NZ$920 per night
includes taxes & fees
3 BR Cape-short drive to Mayflower & other bay beaches-A/C, Wi-Fi, Linens Incl.
Built in microwave and range.
Welcome to the porch where you can relax after a day at the beach or golfing!
A place to rest your head after all the fun you will have here!
Eat in kitchen. Enjoy the lobsters!
Wonderful
(65 reviews)

Delightful Cottage for Two

Chatham

8% off
NZ$2,792
for 7 nights, 1 cottage
NZ$399 per night
includes taxes & fees
Delightful Cottage for Two
Room
Living area
Private kitchen
Exterior detail
Exceptional
(28 reviews)

Steps to the beach!

Dennis Port

8% off
NZ$4,275
for 7 nights, 1 cottage
NZ$611 per night
includes taxes & fees
Steps to the beach!
Living room off kitchen sports two big picture glass window, great bird watching
Enjoy bug-free dining on brand new floor-to-ceiling screen porch & ceiling fan
Living room full of family history, British memorabilia, antiques and books!
Outdoor cedar shower - with detachable hand shower sprayer.
Exceptional
(10 reviews)

Short Walk to Private Beach! Fully-Appointed House w New Screened Porch.

Brewster

8% off
NZ$7,588
for 7 nights, 1 home
NZ$1,084 per night
includes taxes & fees
Short Walk to Private Beach! Fully-Appointed House w New Screened Porch.
Property grounds
Interior
Dining
Living area
Exceptional
(21 reviews)

Make Memories on Mansion- location perfect for beaches, bars & bbq’s

West Harwich

8% off
NZ$6,669
for 7 nights, 1 home
NZ$953 per night
includes taxes & fees
Make Memories on Mansion- location perfect for beaches, bars & bbq’s
Living area
Property grounds
Room
Dining
Exceptional
(15 reviews)

3-bedroom cape house in South Yarmouth.

South Yarmouth

16% off
NZ$3,133
for 7 nights, 1 cottage
NZ$448 per night
includes taxes & fees
3-bedroom cape house in South Yarmouth.
Private kitchen
Property grounds
Exterior
Room
Exceptional
(7 reviews)

Cozy, vacation home in a charming duplex cottage

West Yarmouth

7% off
NZ$2,956
for 7 nights, 1 cottage
NZ$422 per night
includes taxes & fees
Cozy, vacation home in a charming duplex cottage
  • Peace of mind

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  • More quality time

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  • 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 visit Chatham

  • Pristine Beaches: Enjoy sun, sand, and surf along Chatham's unspoilt coastline.
  • Historic Charm: Wander through picturesque streets lined with heritage homes and local landmarks.
  • Coastal Culture: Experience the warm, inviting New England spirit in every nook and cranny.
  • Outdoor Activities: Tee off at local golf courses and explore scenic walking trails.
  • Family-Friendly Ambience: Relish a relaxed getaway perfect for families, couples, or a leisurely solo escape.

Top attractions in and around Chatham

Chatham, Massachusetts, offers a delightful escape for those seeking beachside relaxation and scenic outdoor adventures. Visitors can enjoy pristine beaches, explore local historic houses, and engage in outdoor activities like golf. With its charming coastal atmosphere, Chatham caters to travellers looking for a blend of culture and nature, making it an ideal destination for memorable experiences.

  • Chatham Lighthouse Beach: Enjoy coastal charm with beach vibes, located 2km from Chatham, perfect for a seaside stroll and sunset views.
  • Chatham Windmill: Discover trendy vibes at this historic windmill situated in Chatham, offering a unique glimpse of local heritage.
  • Skaket Beach: Experience expansive shoreline and inviting beach vibes at this scenic beach, located 13km from Chatham, ideal for a relaxed day by the sea.

Things to do recommended for couples

Looking for a romantic getaway in Chatham? Explore the charming streets hand-in-hand, enjoy a sunset picnic at Lighthouse Beach, or take a scenic boat tour to spot seals. Don't miss dining at a cozy seafood restaurant overlooking the water for a perfect evening.

Things to do recommended for families

Families will love exploring the Cape Cod National Seashore, where they can enjoy stunning beaches and nature trails. Don't miss the Chatham Lighthouse Beach for a picnic and swimming, or visit the Monomoy National Wildlife Refuge to spot local wildlife and enjoy a bit of hiking.

Things to do recommended for groups

Groups visiting Chatham can enjoy a whale watching tour off the coast, explore the charming streets lined with shops and eateries, and visit the picturesque Chatham Lighthouse. Don't miss a relaxing day at the local beaches, perfect for beach games and picnics with friends.

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

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

Whether you're travelling with a group, as a family, with your pets, or looking for extended stays, be sure to use the appropriate filters. Here are some Vrbo booking tips for you.

  • Traveling to Chatham with a group: Think about how many bedrooms you require, along with features like a full kitchen or outdoor areas for group gatherings. Fortunately, you can easily filter for these options and many more on Vrbo.
  • Traveling to Chatham with young kids: Traveling with young ones can be a challenge. You must prioritise their comfort and safety, ensuring they have age-appropriate facilities like a private pool. It's also wise to consider how close you are to attractions that cater to families.
  • Taking your pets with you to Chatham: For some, a family holiday isn’t complete without their four-legged companion by their side. If that sounds like you, have a look at Vrbo properties that welcome pets. Most pet-friendly properties offer feeding bowls and beds, ensuring everyone feels right at home.
  • Planning for a long term stay visiting Chatham: If you're seeking holiday rentals offering deals for a month or more, you've come to the right spot. With the appropriate filter, you can effortlessly locate and save on monthly rentals. Also, consider including extras like a parking space, a well-equipped kitchen, or a private pool in your search.

Where to stay near Chatham

Chatham, Massachusetts offers a perfect blend of scenic coastal beauty and vibrant local charm. Enjoy a leisurely stroll through its picturesque streets, relax on pristine beaches, and savour the trendy yet friendly atmosphere. Ideal for a family-friendly, romantic, or luxury break, Chatham promises holiday fun and stunning natural vistas, making it a top choice for travellers seeking a quintessential New England experience.

  • North Chatham: North Chatham, a charming city only 2km away from Chatham, offers an engaging coastal experience. Visitors are drawn by its pristine beaches, captivating scenery and a variety of outdoor pursuits. The area provides access to a well-loved golf course and recreational areas, perfect for a leisurely round of golf or a peaceful day outdoors. Scenic family beaches and the iconic cape add to the allure, making North Chatham an ideal spot for those seeking a blend of nature and leisure.
  • Brewster: Brewster, located 13km from Chatham, is a delightful city celebrated for its outdoor and beachside charm. Travellers enjoy the expansive coastal views, engaging in activities such as golfing at its renowned golf course or exploring its recreational area. The local attractions, including family-friendly beaches and a picturesque cape, offer a perfect backdrop for a day out in nature, ensuring a memorable experience for visitors.
  • Harwich: Harwich is a vibrant city 11km from Chatham, known for its stunning beaches and scenic outdoor spaces. It offers a dynamic mix of leisure activities including golf, with a popular golf course contributing to its charm, and a local theatre that adds a touch of cultural excitement. With its inviting family beaches and a striking cape, Harwich provides an enriching travel experience that combines the best of coastal beauty and recreational fun.

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.

calendar iconCalendar Monthtemperature iconTemperaturerain iconPrecipitationmostly cloudy iconCloudinessoccupation rate iconOccupancyprice iconPricing
January35.6°F (2.0°C)Light RainMostly CloudyAverage
February35.4°F (1.9°C)Light RainMostly CloudyAverage
March38.5°F (3.6°C)Light RainMostly CloudyAverage
April45.3°F (7.4°C)Light RainMostly SunnyAverage
May53.1°F (11.7°C)Light RainMostly SunnyAverage
June61.7°F (16.5°C)Light RainMostly SunnyModerately High
July69.6°F (20.9°C)Light RainMostly SunnyModerately High
August70.3°F (21.3°C)Light RainMostly SunnyModerately High
September65.7°F (18.7°C)Light RainMostly SunnyAverage
October57.9°F (14.4°C)Light RainMostly SunnyModerately Low
November48.6°F (9.2°C)Light RainMostly SunnyModerately Low
December41.5°F (5.3°C)Light RainMostly CloudyModerately Low

Booking with Vrbo is a breeze

Are you keen to save on your next adventure? Being flexible with your travel dates can make a big difference, as prices often fluctuate. You can also enjoy considerable savings by opting for a longer stay. To discover a Vrbo property that suits your budget, utilise our filters to sort by price, location, and type of holiday rental. We’re here to help you find the perfect getaway.

Vrbo Trips: Effortless planning

Vrbo’s Trip Board is a handy tool that lets you start new trips, pick up where you last left off, or simply review and organise your plans. Your saved or booked properties will be neatly grouped as Potential, Upcoming, or Current Trips. To begin using Trip Boards, please visit: https://www.bookabach.co.nz/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 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)
  • Adventure Chatham (3.6 mi / 5.8 km)

Exploring the beaches and other natural features in Chatham

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

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

Seasonal weather averages in Chatham

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

How to get to and around Chatham

The nearest airport is in Hyannis, MA (HYA-Barnstable Municipal), located 16.8 mi (27 km) from the city centre. If you can't find a flight that works for your travel itinerary, you can also fly into Nantucket, MA (ACK-Nantucket Memorial), which is 29.9 mi (48.1 km) away.

Frequently asked questions

What is the most popular type of holiday home 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. Bookabach 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 home in Chatham?
A range of things affect how much you'll pay for a holiday home in Chatham, like the season, type of property and length of stay. Still, all Bookabach 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 Bookabach. Can't live without a hot tub? Use our filters to choose the amenities and features you need.
Are there pet-friendly holiday homes 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 homes and find your pawfect pad on Bookabach.
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 homes and you'll enjoy pool days every day. Simply enter your travel dates into Bookabach, then check the "pool" filter to find a place to make a splash!
What are popular home amenities in Chatham?
When it comes to home 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 Bookabach 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 homes 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 homes in Chatham that welcome kids?
With 78 family-friendly holiday homes 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 homes in Chatham?
Chatham has 12 one-bedroom homes available. Typically situated in prime spots due to their smaller size, a one-bedroom home 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 homes 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 homes with WiFi in Chatham?
You'll have a choice of 26 holiday homes 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 Bookabach.
How can I find holiday homes with air conditioning in Chatham?
Choose from 75 Bookabach holiday homes 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 home in Chatham?
The minimum required age is usually 16, 18 or 21. It can vary from one property to another on Bookabach, so check the rules of your chosen Chatham holiday home before making a booking.
How long can I rent a holiday home 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 Bookabach'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.

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