Chatham holiday rentals

We found 3,349 holiday rentals — enter your dates for availability
Select from 277 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:25 Dec - 1 Jan

Living area
Exterior
Outdoor dining
Living area
Wonderful
(19 reviews)

Cottage near bay beach- 1 Bd/1Ba

Brewster

8% off
S$1,022
for 7 nights, 1 cottage
S$146 per night
includes taxes & fees
Cottage near bay beach- 1 Bd/1Ba
Downstairs bedroom
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
S$8,881
for 7 nights, 1 home
S$1,269 per night
includes taxes & fees
Stunning Waterfront Compound with Private Beach, Private Dock, Sunset View
Interior
Exterior
Private kitchen
entrance to mallardview
Exceptional
(65 reviews)

5 bedrooms ocean view estate overlooking cape cod bay

Orleans

8% off
S$9,857
for 7 nights, 1 home
S$1,408 per night
includes taxes & fees
5 bedrooms ocean view estate overlooking cape cod bay
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
S$4,281
for 7 nights, 1 home
S$612 per night
includes taxes & fees
#Game Rm, King Bds, Wi-Fi, Bikes, Beach Supplies, Quiet Street, Central AC\Heat
Exterior
Pool
Kitchen
Living area
Exceptional
(68 reviews)

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

Orleans

8% off
S$20,060
for 7 nights, 1 home
S$2,866 per night
includes taxes & fees
Luxury 8 Bedroom Home with Heated Pool - 4 minutes to the beach! Pet Friendly!
Open concept dining room with spectacular views to the ocean.
Sunny living space with large balcony, and spectacular views to the ocean.
Elegant and bright living room with views from every window.
Reclaimed hardwood floors shipped in from an old barn taken down in the mid-west
Exceptional
(65 reviews)

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

Chatham

8% off
S$11,542
for 7 nights, 1 home
S$1,649 per night
includes taxes & fees
SeaGlass House - Beautiful Cape Cod Home. Ocean Views & High End Decor
View from second floor.
Outdoor dining
Upstairs queen in View Room
Dinner with a view.
Exceptional
(53 reviews)

Picturesque Private Beachfront House on Cape Cod Bay

Brewster

8% off
S$6,489
for 7 nights, 1 home
S$927 per night
includes taxes & fees
Picturesque Private Beachfront House on Cape Cod Bay
Second floor front bedroom with view of Cape Cod Bay
Living room looking toward front / first floor front bedroom door
Outdoor dining set overlooking the bay on deck
Kitchen
Exceptional
(28 reviews)

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

Eastham

6% off
S$4,523
for 7 nights, 1 home
S$646 per night
includes taxes & fees
Waterview, 4 BR, 100 Feet from Private Eastham Bayside Beach!
Interior
Exterior
Living area
Room
Wonderful
(23 reviews)

Charming antique Cape house

Harwich

8% off
S$3,263
for 7 nights, 1 home
S$466 per night
includes taxes & fees
Charming antique Cape house
Large dining room table.
Dusk in Chatham
Sitting area with fireplace
King bed +2 twins in "the nook".  Great room for families with kids!
Exceptional
(45 reviews)

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

South Chatham

8% off
S$5,018
for 7 nights, 1 home
S$717 per night
includes taxes & fees
Charming Family Cape, Impeccably Landscaped With Water Views Near The Beach!
Charming & cozy.
Propane fire-pit for cool nights. Evening view.
Marble counters, KitchenAid appliances & gas stove. All overlooking the water.
Like being on a cruise ship!
Exceptional
(31 reviews)

★Waterfront & On Bike Path★Firepit ★Private beach★Bikes★Kayaks★Sm.Pet OK💥Sunsets

Brewster

8% off
S$9,769
for 7 nights, 1 home
S$1,396 per night
includes taxes & fees
★Waterfront & On Bike Path★Firepit ★Private beach★Bikes★Kayaks★Sm.Pet OK💥Sunsets
Large Deck facing Bike path with great East and South Sun
Linnell Landing Beach in Brewster
Newly Refurbished Dining Area adjacent to kitchen
Family Room with East and South Sun
Exceptional
(67 reviews)

PET FRIENDLY! Right on Nickerson, with Cape Cod bike trail behind house!

Brewster

6% off
S$2,409
for 7 nights, 1 home
S$344 per night
includes taxes & fees
PET FRIENDLY! Right on Nickerson, with Cape Cod bike trail behind house!
Exterior
Marina
Interior
Outdoor dining
Exceptional
(44 reviews)

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

South Dennis

7% off
S$2,081
for 7 nights, 1 home
S$297 per night
includes taxes & fees
Rates just lowered for last week of July and Aug with 5 night min accepted.
Dining
Interior
Living area
Room
Exceptional
(9 reviews)

Charming 4-bedroom house in enchanting Yarmouth

South Yarmouth

7% off
S$5,519
for 7 nights, 1 home
S$788 per night
includes taxes & fees
Charming 4-bedroom house in enchanting Yarmouth
Bathroom
Front Entrance
Private kitchen
Private kitchen
Exceptional
(9 reviews)

Cozy, vacation home in a charming duplex cottage

West Yarmouth

7% off
S$2,213
for 7 nights, 1 cottage
S$316 per night
includes taxes & fees
Cozy, vacation home in a charming duplex cottage
Living area
Private kitchen
Exterior
Outdoor dining
Exceptional
(12 reviews)

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

Dennis

7% off
S$4,006
for 7 nights, 1 home
S$572 per night
includes taxes & fees
3-bedroom house in charming Dennis minutes to Corporation Beach. Relax & unwind.
Updated Kitchen for Summer 2020
Fully equipped
Outdoor dining
Seating for 3 at kitchen counter
Living room has vaulted ceiling, skylight & ceiling fan. Central AC
Exceptional
(57 reviews)

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

South Dennis

12% off
S$4,865
for 7 nights, 1 home
S$695 per night
includes taxes & fees
3 BR Cape-short drive to Mayflower & other bay beaches-A/C, Wi-Fi, Linens Incl.
Private kitchen
Living area
Dining
Exterior detail
Exceptional
(30 reviews)

Steps to the beach!

Dennis Port

8% off
S$3,210
for 7 nights, 1 cottage
S$459 per night
includes taxes & fees
Steps to the beach!
Fire pit with seating area to enjoy cool starlit cape cod evenings
Interior
Dining
Private kitchen
Wonderful
(10 reviews)

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

West Yarmouth

11% off
S$5,329
for 7 nights, 1 home
S$761 per night
includes taxes & fees
Newly renovated Seagull Beach, coastal retreat, charm, comfort, outdoor living.
Living area
Dining room with water views
Room
Terrace/patio
Exceptional
(36 reviews)

Steps to Paine's Creek-The Perfect Vacation Home

Brewster

7% off
S$5,152
for 7 nights, 1 home
S$736 per night
includes taxes & fees
Steps to Paine's Creek-The Perfect Vacation Home
Room
The Chatham downtown is filled with cute shops and restaurants.
Living area
Dining
Exceptional
(7 reviews)

Charming Chatham Bungalow- Minutes to Beaches and Downtown Chatham

North Chatham

8% off
S$4,740
for 7 nights, 1 home
S$677 per night
includes taxes & fees
Charming Chatham Bungalow- Minutes to Beaches and Downtown Chatham
Living area
Dining
Terrace/patio
Interior
Exceptional
(11 reviews)

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

South Chatham

8% off
S$8,117
for 7 nights, 1 home
S$1,160 per night
includes taxes & fees
Enjoy a relaxing retreat. Easy access: Beaches, Bike Path, & Great restaurants.
Master (View 2)
Dining Patio (other side of house)
Front of House
Family room - access to backyard
Exceptional
(16 reviews)

Charming 3-bedroom + 3-full bath house in S. Yarmouth with AC - walk to beach!

South Yarmouth

8% off
S$5,351
for 7 nights, 1 home
S$764 per night
includes taxes & fees
Charming 3-bedroom + 3-full bath house in S. Yarmouth with AC - walk to beach!
Kids love the slides and swingset
Exterior detail
Carriage house recreation with 82inch 4K TV. Ping pong, billiards and pinball!!
Hot Tub has lights, waterfall, massage jets and Bluetooth stereo to stream.
Exceptional
(54 reviews)

Huge Family Compound Near Beach Hot Tub, Basketball Court,Pinball. Linens incl

South Yarmouth

7% off
S$4,385
for 7 nights, 1 home
S$626 per night
includes taxes & fees
Huge Family Compound Near Beach Hot Tub, Basketball Court,Pinball. Linens incl
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    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 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 ideas