Chatham holiday rentals

We found 3,338 holiday rentals — enter your dates for availability
Select from 281 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:6 Nov - 13 Nov

Room
Exterior
Living area
Living area
Wonderful
(18 reviews)

Cottage near bay beach- 1 Bd/1Ba

Brewster

8% off
AU$1,112
for 7 nights, 1 cottage
AU$159 per night
includes taxes & fees
Cottage near bay beach- 1 Bd/1Ba
Lights for Swimming and Bocce Etc.
Pool
Pool
Pool
Exceptional
(34 reviews)

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

Brewster

7% off
AU$6,933
for 7 nights, 1 home
AU$990 per night
includes taxes & fees
Modern Cape, Private Heated Salt Water Pool, Minutes to Beaches/Golf/Lakes
Living room
View of property
Private beach/dock area
Dock at sunset
Exceptional
(17 reviews)

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

South Chatham

8% off
AU$9,848
for 7 nights, 1 home
AU$1,407 per night
includes taxes & fees
Stunning Waterfront Compound with Private Beach, Private Dock, Sunset View
Eat-in kitchen with oversized island is great for entertaining
10' x 30' pool w/hot tub
Hot tub spa
Exterior
Exceptional
(28 reviews)

Family friendly luxury home with heated pool and spa

Chatham

8% off
AU$9,879
for 7 nights, 1 home
AU$1,411 per night
includes taxes & fees
Family friendly luxury home with heated pool and spa
Deck with teak table and chairs
Living area
Flowering plantings including blue hydrangea, lilac and magnolia
SoloStove fire-it and patio with Adirondack chairs and tables
Exceptional
(90 reviews)

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

Chatham

8% off
AU$5,155
for 7 nights, 1 home
AU$736 per night
includes taxes & fees
Unique Oyster Pond 3bd-2ba home in private setting close to downtown.
The entry to your next vacation home.
Elegant and bright living room with views from every window.
Grand approach to the West facing front facade.
Extensive parking space, and wonderful covered wrap around porch.
Exceptional
(62 reviews)

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

Chatham

8% off
AU$12,657
for 7 nights, 1 home
AU$1,808 per night
includes taxes & fees
SeaGlass House - Beautiful Cape Cod Home. Ocean Views & High End Decor
Rear of house with 400+ square foot roof deck
Aerial view
Water, water everywhere-Mill Pond, Mitchell River, Stage Harbor, Atlantic Ocean
Front of 12 Room House with Roof Deck
Exceptional
(119 reviews)

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

Chatham

26% off
AU$7,174
for 7 nights, 1 home
AU$1,025 per night
includes taxes & fees
Water View-Walk town/beach, pets considered, Linen Option
Bathroom
Exterior
Back yard and patio
18 inch wide dishwasher
Exceptional
(42 reviews)

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

South Dennis

7% off
AU$1,944
for 7 nights, 1 home
AU$278 per night
includes taxes & fees
Rates just lowered for last week of July and Aug with 5 night min accepted.
Exterior
entrance to mallardview
Exterior
Exterior
Exceptional
(58 reviews)

5 bedrooms ocean view estate overlooking cape cod bay

Orleans

8% off
AU$11,058
for 7 nights, 1 home
AU$1,580 per night
includes taxes & fees
5 bedrooms ocean view estate overlooking cape cod bay
Fire pit & couch
2000+ SF multi level patio, pool, pool house, outdoor kitchen, fire pit & more!
Ariel view of the entire property.
Outdoor kitchen: grill, fridge, sink
Exceptional
(43 reviews)

Chatham Loop/Stage Neck/5 Bed/6 Bath

Chatham

8% off
AU$13,259
for 7 nights, 1 home
AU$1,894 per night
includes taxes & fees
Chatham Loop/Stage Neck/5 Bed/6 Bath
Master Bedroom - King Bed, TV, Bureau and ensuite bath
Shuffle Board
Living Room
Kitchen, Dining area:  Fridge, Stove, Dishwasher
Exceptional
(137 reviews)

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

Harwich

7% off
AU$3,285
for 7 nights, 1 home
AU$469 per night
includes taxes & fees
#Game Rm, King Bds, Wi-Fi, Bikes, Beach Supplies, Quiet Street, Central AC\Heat
Kitchen and dining area.
4 Minute walk to Oyster River
Looking towards Oyster River from Ocean Port Lane
4 Minutes walk from our house....boat ramp on Oyster River.
Exceptional
(105 reviews)

Near Harding's Beach, 4 min walk to Oyster River. 3BR, 2Bath, enclosed deck area

West Chatham

7% off
AU$2,829
for 7 nights, 1 home
AU$404 per night
includes taxes & fees
Near Harding's Beach, 4 min walk to Oyster River. 3BR, 2Bath, enclosed deck area
Living area
Private kitchen
Interior
Interior
Exceptional
(10 reviews)

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

Dennis

7% off
AU$4,208
for 7 nights, 1 home
AU$601 per night
includes taxes & fees
3-bedroom house in charming Dennis minutes to Corporation Beach. Relax & unwind.
Living area
Living area
Living area
Living area
Exceptional
(15 reviews)

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

Chatham

11% off
AU$3,749
for 7 nights, 1 home
AU$536 per night
includes taxes & fees
Updated 4BR close to downtown Chatham, Beaches, Bike Path & Tennis Pickleball
Exterior
Living area
Exterior
Exterior detail
Exceptional
(8 reviews)

Charming 4-bedroom house in enchanting Yarmouth

South Yarmouth

8% off
AU$6,064
for 7 nights, 1 home
AU$866 per night
includes taxes & fees
Charming 4-bedroom house in enchanting Yarmouth
Exterior
Exterior
Room
Room
Exceptional
(6 reviews)

Charming Chatham Bungalow- Minutes to Beaches and Downtown Chatham

North Chatham

8% off
AU$5,240
for 7 nights, 1 home
AU$749 per night
includes taxes & fees
Charming Chatham Bungalow- Minutes to Beaches and Downtown Chatham
Fully equipped kitchen
Exterior
Living area
Dining room with water views
Exceptional
(35 reviews)

Steps to Paine's Creek-The Perfect Vacation Home

Brewster

7% off
AU$5,584
for 7 nights, 1 home
AU$798 per night
includes taxes & fees
Steps to Paine's Creek-The Perfect Vacation Home
Dining room with table for 6 (additional seating available on patio and counter)
Located in a quiet residential neighborhood
Bright living room with brand new sectional and chair for 2021
Living room has vaulted ceiling, skylight & ceiling fan. Central AC
Exceptional
(55 reviews)

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

South Dennis

12% off
AU$5,380
for 7 nights, 1 home
AU$769 per night
includes taxes & fees
3 BR Cape-short drive to Mayflower & other bay beaches-A/C, Wi-Fi, Linens Incl.
Enjoy watching cable T.V., reading or a nap. WIFI too!
Welcome to the porch where you can relax after a day at the beach or golfing!
Enjoy morning coffee and a meal there too!
Share conversation and a beverage with the cook!
Wonderful
(64 reviews)

Delightful Cottage for Two

Chatham

8% off
AU$2,370
for 7 nights, 1 cottage
AU$339 per night
includes taxes & fees
Delightful Cottage for Two
Outdoor dining
Exterior detail
Exterior detail
Exterior
Exceptional
(26 reviews)

Steps to the beach!

Dennis Port

8% off
AU$3,548
for 7 nights, 1 cottage
AU$507 per night
includes taxes & fees
Steps to the beach!
Living area
Exterior
Property grounds
Living area
Exceptional
(19 reviews)

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

West Harwich

8% off
AU$5,467
for 7 nights, 1 home
AU$781 per night
includes taxes & fees
Make Memories on Mansion- location perfect for beaches, bars & bbq’s
Property grounds
Outdoor dining
Terrace/patio
Dining
Exceptional
(15 reviews)

3-bedroom cape house in South Yarmouth.

South Yarmouth

16% off
AU$2,623
for 7 nights, 1 cottage
AU$375 per night
includes taxes & fees
3-bedroom cape house in South Yarmouth.
Bathroom
Exterior
Private kitchen
Private kitchen
Exceptional
(6 reviews)

Cozy, vacation home in a charming duplex cottage

West Yarmouth

7% off
AU$2,510
for 7 nights, 1 cottage
AU$359 per night
includes taxes & fees
Cozy, vacation home in a charming duplex cottage
Outside Patio for evening dining and entertaining
Exterior
Exterior
Outdoor dining
Wonderful
(8 reviews)

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

West Yarmouth

11% off
AU$5,854
for 7 nights, 1 home
AU$836 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:

  • Cape Cod Baseball & Bumper Boats (6.9 mi / 11.1 km)
  • Ocean Edge Golf Club (7.4 mi / 12 km)
  • Gold Coast Parasailing & Jet Ski (13.7 mi / 22.1 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:

  • 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. Stayz 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 Stayz 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 Stayz. 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 Stayz.
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 Stayz, 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 Stayz 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 Stayz.
How can I find holiday homes with air conditioning in Chatham?
Choose from 75 Stayz 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 Stayz, 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 Stayz'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 ideas