Chatham holiday rentals

We found 3,328 holiday rentals — enter your dates for availability
Select from 283 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

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

Cottage near bay beach- 1 Bd/1Ba

Brewster

8% off
S$1,019
for 7 nights, 1 cottage
S$146 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
(34 reviews)

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

Brewster

7% off
S$6,491
for 7 nights, 1 home
S$927 per night
includes taxes & fees
Modern Cape, Private Heated Salt Water Pool, Minutes to Beaches/Golf/Lakes
Living room - French doors
Private beach/dock area
View of property
Downstairs bedroom
Exceptional
(17 reviews)

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

South Chatham

8% off
S$9,171
for 7 nights, 1 home
S$1,310 per night
includes taxes & fees
Stunning Waterfront Compound with Private Beach, Private Dock, Sunset View
Primary bedroom (king bed)
Eat-in kitchen with oversized island is great for entertaining
Family room with TV enclosed in built-in millwork
Mudroom and laundry
Exceptional
(28 reviews)

Family friendly luxury home with heated pool and spa

Chatham

7% off
S$8,838
for 7 nights, 1 home
S$1,263 per night
includes taxes & fees
Family friendly luxury home with heated pool and spa
Large island, comfortable seating area
Deeded access to nearby Mill Pond to launch your Kayak
Light & bright second floor great room
Fabulous family room, a magnet for family gatherings
Exceptional
(119 reviews)

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

Chatham

25% off
S$6,775
for 7 nights, 1 home
S$968 per night
includes taxes & fees
Water View-Walk town/beach, pets considered, Linen Option
Private kitchen
Exterior
Interior
entrance to mallardview
Exceptional
(58 reviews)

5 bedrooms ocean view estate overlooking cape cod bay

Orleans

8% off
S$10,311
for 7 nights, 1 home
S$1,473 per night
includes taxes & fees
5 bedrooms ocean view estate overlooking cape cod bay
Elegant and bright living room with views from every window.
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
(62 reviews)

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

Chatham

8% off
S$11,501
for 7 nights, 1 home
S$1,643 per night
includes taxes & fees
SeaGlass House - Beautiful Cape Cod Home. Ocean Views & High End Decor
Pool house
Center island with seating for 4
Fire pit & couch
Front Den looking in to kitchen
Exceptional
(43 reviews)

Chatham Loop/Stage Neck/5 Bed/6 Bath

Chatham

8% off
S$12,296
for 7 nights, 1 home
S$1,757 per night
includes taxes & fees
Chatham Loop/Stage Neck/5 Bed/6 Bath
Living room with cathedral ceiling - open floor plan
Deck with teak table and chairs
Interior
Kitchen with island
Exceptional
(90 reviews)

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

Chatham

7% off
S$4,799
for 7 nights, 1 home
S$686 per night
includes taxes & fees
Unique Oyster Pond 3bd-2ba home in private setting close to downtown.
Front Door
Upstairs master bedroom
Master bedroom upstairs with TV.
Kitchen
Exceptional
(105 reviews)

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

West Chatham

7% off
S$2,624
for 7 nights, 1 home
S$375 per night
includes taxes & fees
Near Harding's Beach, 4 min walk to Oyster River. 3BR, 2Bath, enclosed deck area
Dinner with a view.
Outdoor dining
Upstairs queen in View Room
View from second floor.
Exceptional
(50 reviews)

Picturesque Private Beachfront House on Cape Cod Bay

Brewster

8% off
S$4,395
for 7 nights, 1 home
S$628 per night
includes taxes & fees
Picturesque Private Beachfront House on Cape Cod Bay
Dining
Living area
Private kitchen
Room
Exceptional
(15 reviews)

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

Chatham

10% off
S$3,491
for 7 nights, 1 home
S$499 per night
includes taxes & fees
Updated 4BR close to downtown Chatham, Beaches, Bike Path & Tennis Pickleball
Updated Kitchen for Summer 2020
Fully equipped
Outdoor dining
Dining
Seating for 3 at kitchen counter
Exceptional
(55 reviews)

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

South Dennis

12% off
S$4,888
for 7 nights, 1 home
S$698 per night
includes taxes & fees
3 BR Cape-short drive to Mayflower & other bay beaches-A/C, Wi-Fi, Linens Incl.
Living area
Interior
Exterior
Dining
Exceptional
(8 reviews)

Charming 4-bedroom house in enchanting Yarmouth

South Yarmouth

7% off
S$5,604
for 7 nights, 1 home
S$801 per night
includes taxes & fees
Charming 4-bedroom house in enchanting Yarmouth
Exterior
Private kitchen
Outdoor dining
Interior
Exceptional
(10 reviews)

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

Dennis

7% off
S$3,820
for 7 nights, 1 home
S$546 per night
includes taxes & fees
3-bedroom house in charming Dennis minutes to Corporation Beach. Relax & unwind.
Dining
Living area
Exterior detail
Private kitchen
Exceptional
(27 reviews)

Steps to the beach!

Dennis Port

7% off
S$3,350
for 7 nights, 1 cottage
S$479 per night
includes taxes & fees
Steps to the beach!
Room
Property grounds
Living area
Exterior
Exceptional
(6 reviews)

Cozy, vacation home in a charming duplex cottage

West Yarmouth

7% off
S$2,281
for 7 nights, 1 cottage
S$326 per night
includes taxes & fees
Cozy, vacation home in a charming duplex cottage
Partial kitchen view to dining / living rooms
Dining Patio (other side of house)
Front of House
Master (View 2)
Exceptional
(13 reviews)

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

South Yarmouth

8% off
S$5,469
for 7 nights, 1 home
S$781 per night
includes taxes & fees
Charming 3-bedroom + 3-full bath house in S. Yarmouth with AC - walk to beach!
Private kitchen
Interior
Property grounds
Living area
Exceptional
(19 reviews)

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

West Harwich

7% off
S$5,188
for 7 nights, 1 home
S$741 per night
includes taxes & fees
Make Memories on Mansion- location perfect for beaches, bars & bbq’s
Exterior detail
Property grounds
Interior
Private kitchen
Exceptional
(52 reviews)

Ocean Front, Private Beach, Ocean View , Private patio

Dennis Port

16% off
S$4,714
for 7 nights, 1 apartment
S$673 per night
includes taxes & fees
Ocean Front, Private Beach, Ocean View , Private patio
Room
Living area
Living area
Private kitchen
Exceptional
(5 reviews)

Charming Waterfront Cape Cottage with Private Beach and Beautiful Water Views

South Yarmouth

7% off
S$4,443
for 7 nights, 1 home
S$635 per night
includes taxes & fees
Charming Waterfront Cape Cottage with Private Beach and Beautiful Water Views
Dining
Room
Living area
Property grounds
Exceptional
(28 reviews)

Step onto your private beach, Dennisport, MA

Dennis Port

7% off
S$3,950
for 7 nights, 1 apartment
S$564 per night
includes taxes & fees
Step onto your private beach, Dennisport, MA
Exterior
Living area
Private kitchen
Dining
Exceptional
(57 reviews)

Renovated Dennis Port cottage

Dennis Port

7% off
S$3,136
for 7 nights, 1 home
S$448 per night
includes taxes & fees
Renovated Dennis Port cottage
Private kitchen
Interior
Dining
Interior
Exceptional
(52 reviews)

5BR Brewster Home - Private Pond Beach - Cape Rail Trail Access

Brewster

7% off
S$4,850
for 7 nights, 1 home
S$693 per night
includes taxes & fees
5BR Brewster Home - Private Pond Beach - Cape Rail Trail Access
  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support
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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 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 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