Chatham holiday rentals

We found 3,375 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:13 Nov - 20 Nov

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

Cottage near bay beach- 1 Bd/1Ba

Brewster

8% off
S$1,025
for 7 nights, 1 cottage
S$146 per night
includes taxes & fees
Cottage near bay beach- 1 Bd/1Ba
Breakfast Nook With Pool and Tranquil Forest View
Breakfast Nook with Pool View
Second Deck Bar Sitting/Dining Area
New Chefs Kitchen
Exceptional
(35 reviews)

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

Brewster

7% off
S$6,545
for 7 nights, 1 home
S$935 per night
includes taxes & fees
Modern Cape, Private Heated Salt Water Pool, Minutes to Beaches/Golf/Lakes
Living room
Private beach/dock area
Downstairs bedroom
Living room - French doors
Exceptional
(18 reviews)

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

South Chatham

8% off
S$9,265
for 7 nights, 1 home
S$1,324 per night
includes taxes & fees
Stunning Waterfront Compound with Private Beach, Private Dock, Sunset View
Hot tub spa
Eat-in kitchen with oversized island is great for entertaining
Primary bedroom (king bed)
Mudroom and laundry
Exceptional
(28 reviews)

Family friendly luxury home with heated pool and spa

Chatham

7% off
S$8,058
for 7 nights, 1 home
S$1,151 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
Well equipped chef's kitchen w. stainless steel appliances
Fabulous family room, a magnet for family gatherings
Exceptional
(119 reviews)

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

Chatham

25% off
S$6,783
for 7 nights, 1 home
S$969 per night
includes taxes & fees
Water View-Walk town/beach, pets considered, Linen Option
Interior
Exterior
rear view of house
entrance to mallardview
Exceptional
(60 reviews)

5 bedrooms ocean view estate overlooking cape cod bay

Orleans

8% off
S$10,217
for 7 nights, 1 home
S$1,460 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
(137 reviews)

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

Harwich

6% off
S$2,901
for 7 nights, 1 home
S$414 per night
includes taxes & fees
#Game Rm, King Bds, Wi-Fi, Bikes, Beach Supplies, Quiet Street, Central AC\Heat
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
S$12,310
for 7 nights, 1 home
S$1,759 per night
includes taxes & fees
Chatham Loop/Stage Neck/5 Bed/6 Bath
Interior
Marina
Exterior
Outdoor dining
Exceptional
(43 reviews)

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

South Dennis

7% off
S$1,755
for 7 nights, 1 home
S$251 per night
includes taxes & fees
Rates just lowered for last week of July and Aug with 5 night min accepted.
Living room with cathedral ceiling - open floor plan
Deck with teak table and chairs
Interior
Flowering plantings including blue hydrangea, lilac and magnolia
Exceptional
(90 reviews)

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

Chatham

7% off
S$4,869
for 7 nights, 1 home
S$696 per night
includes taxes & fees
Unique Oyster Pond 3bd-2ba home in private setting close to downtown.
Upstairs bedroom with TV
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$2,663
for 7 nights, 1 home
S$380 per night
includes taxes & fees
Near Harding's Beach, 4 min walk to Oyster River. 3BR, 2Bath, enclosed deck area
Dining
Interior
Exterior
Living area
Exceptional
(9 reviews)

Charming 4-bedroom house in enchanting Yarmouth

South Yarmouth

7% off
S$5,720
for 7 nights, 1 home
S$817 per night
includes taxes & fees
Charming 4-bedroom house in enchanting Yarmouth
Property grounds
Living area
Dining
Room
Exceptional
(15 reviews)

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

Chatham

10% off
S$4,204
for 7 nights, 1 home
S$601 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
Seating for 3 at kitchen counter
Dining
Exceptional
(55 reviews)

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

South Dennis

12% off
S$4,893
for 7 nights, 1 home
S$699 per night
includes taxes & fees
3 BR Cape-short drive to Mayflower & other bay beaches-A/C, Wi-Fi, Linens Incl.
Interior
Private kitchen
Exterior
Living area
Exceptional
(10 reviews)

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

Dennis

7% off
S$3,825
for 7 nights, 1 home
S$546 per night
includes taxes & fees
3-bedroom house in charming Dennis minutes to Corporation Beach. Relax & unwind.
Room
The Chatham downtown is filled with cute shops and restaurants.
Dining
Private kitchen
Exceptional
(6 reviews)

Charming Chatham Bungalow- Minutes to Beaches and Downtown Chatham

North Chatham

7% off
S$4,950
for 7 nights, 1 home
S$707 per night
includes taxes & fees
Charming Chatham Bungalow- Minutes to Beaches and Downtown Chatham
Study/Lounge are with water views
Dining room with water views
Terrace/patio
Living area
Exceptional
(35 reviews)

Steps to Paine's Creek-The Perfect Vacation Home

Brewster

7% off
S$5,273
for 7 nights, 1 home
S$753 per night
includes taxes & fees
Steps to Paine's Creek-The Perfect Vacation Home
Private kitchen
Living area
Dining
Exterior detail
Exceptional
(27 reviews)

Steps to the beach!

Dennis Port

7% off
S$3,354
for 7 nights, 1 cottage
S$479 per night
includes taxes & fees
Steps to the beach!
Built in microwave and range.
Welcome to the porch where you can relax after a day at the beach or golfing!
Exterior
A place to rest your head after all the fun you will have here!
Wonderful
(64 reviews)

Delightful Cottage for Two

Chatham

7% off
S$2,194
for 7 nights, 1 cottage
S$313 per night
includes taxes & fees
Delightful Cottage for Two
Front of House
Dining Patio (other side of house)
Family room - access to backyard
Partial kitchen view to dining / living rooms
Exceptional
(13 reviews)

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

South Yarmouth

8% off
S$5,476
for 7 nights, 1 home
S$782 per night
includes taxes & fees
Charming 3-bedroom + 3-full bath house in S. Yarmouth with AC - walk to beach!
Private kitchen
Property grounds
Dining
Room
Exceptional
(15 reviews)

3-bedroom cape house in South Yarmouth.

South Yarmouth

15% off
S$2,466
for 7 nights, 1 cottage
S$352 per night
includes taxes & fees
3-bedroom cape house in South Yarmouth.
Exterior
Property grounds
Room
Private kitchen
Exceptional
(6 reviews)

Cozy, vacation home in a charming duplex cottage

West Yarmouth

7% off
S$2,326
for 7 nights, 1 cottage
S$332 per night
includes taxes & fees
Cozy, vacation home in a charming duplex cottage
Private kitchen
Property grounds
Exterior detail
Property grounds
Exceptional
(53 reviews)

Ocean Front, Private Beach, Ocean View , Private patio

Dennis Port

15% off
S$4,884
for 7 nights, 1 apartment
S$698 per night
includes taxes & fees
Ocean Front, Private Beach, Ocean View , Private patio
Property grounds
Interior
Living area
Private kitchen
Exceptional
(20 reviews)

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

West Harwich

7% off
S$5,194
for 7 nights, 1 home
S$742 per night
includes taxes & fees
Make Memories on Mansion- location perfect for beaches, bars & bbq’s
  • 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 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