Chatham Holiday Rentals

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Our top choices for Chatham holiday rentals

Quaint & Cozy Downtown Chatham Home, Walk to Town and Beaches

Quaint & Cozy Downtown Chatham Home, Walk to Town and Beaches
Chatham
10.0 out of 10, Exceptional, (122 reviews)
"Clean, quiet, and great location."
United States
Tyler B.
The price is AU$840
includes taxes & fees
2 June - 3 June
Quaint & Cozy Downtown Chatham Home, Walk to Town and Beaches

Luxury Chatham Retreat. Walk to Main St & Beach

Luxury Chatham Retreat. Walk to Main St & Beach
Chatham
10.0 out of 10, Exceptional, (1 review)
"Beautiful house in a great location in Chatham! Walking distance to shops and restaurants. The house was well-stocked with everything we needed and the beds were so comfortable. We really enjoyed our stay here!"
United States
Maggie K.
The price is AU$1,059
includes taxes & fees
1 June - 2 June
Luxury Chatham Retreat. Walk to Main St & Beach

Town Center-Limited June, Aug, Sept Dates Still Open-2026 Total Renovation

Town Center-Limited June, Aug, Sept Dates Still Open-2026 Total Renovation
Chatham
The price is AU$1,186
includes taxes & fees
16 June - 17 June
Town Center-Limited June, Aug, Sept Dates Still Open-2026 Total Renovation

Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK

Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK
Chatham
9.6 out of 10, Exceptional, (102 reviews)
"We absolutely loved this house, very comfortable, well decorated and welcoming atmosphere. It was exactly what we needed for a weekend getaway. We will be back!"
United States
Margot C.
The price is AU$819
includes taxes & fees
2 June - 3 June
Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK

Seaside condo with patio, beach access, loft, board games, gas grill, & firepit

Seaside condo with patio, beach access, loft, board games, gas grill, & firepit
Chatham
10.0 out of 10, Exceptional, (1 review)
"Lovely spot on the water!"
United States
Elizabeth T.
The price is AU$714
includes taxes & fees
1 June - 2 June
Seaside condo with patio, beach access, loft, board games, gas grill, & firepit

Downtown Chatham Gem – Walk to Beach, Shops, C.B.I, & Dining Family-Friendly!

Downtown Chatham Gem – Walk to Beach, Shops, C.B.I, & Dining Family-Friendly!
Chatham
10.0 out of 10, Exceptional, (18 reviews)
"Downtown Chatham Gem was perfect for our girls getaway weekend. Parked the cars and walked everywhere. The house was clean, beautifully decorated, and had everything we needed. Loved everything about it and we will definitely be back. "
United States
Claire S.
The price is AU$2,220
includes taxes & fees
31 May - 1 June
Downtown Chatham Gem – Walk to Beach, Shops, C.B.I, & Dining Family-Friendly!

1 Mi to Ferry: 'sea Street Cottage' in Hyannis

1 Mi to Ferry: 'sea Street Cottage' in Hyannis
3.0 star property
Hyannis
The price is AU$507
includes taxes & fees
31 May - 1 June
1 Mi to Ferry: 'sea Street Cottage' in Hyannis

Coastal Haven in West Dennis -15

Coastal Haven in West Dennis -15
2.0 star property
West Dennis
The price is AU$1,030
includes taxes & fees
31 May - 1 June
Coastal Haven in West Dennis -15

Sweet Memories- Cozy 2 bedroom cottage in West Yarmouth

Sweet Memories- Cozy 2 bedroom cottage in West Yarmouth
Yarmouth
The price is AU$603
includes taxes & fees
1 June - 2 June
Sweet Memories- Cozy 2 bedroom cottage in West Yarmouth

On Town Cove with salt water access! Kayaks and paddle board available for use!

On Town Cove with salt water access! Kayaks and paddle board available for use!
Eastham
9.8 out of 10, Exceptional, (61 reviews)
"Clean, great location. "
United States
Peter G.
The price is AU$518
includes taxes & fees
1 June - 2 June
On Town Cove with salt water access! Kayaks and paddle board available for use!

Walk to Ocean Beach, Nat`l Seashore, WiFi, Bike Rail Trail

Walk to Ocean Beach, Nat`l Seashore, WiFi, Bike Rail Trail
South Wellfleet
10.0 out of 10, Exceptional, (68 reviews)
"We really enjoyed the location and deck."
United States
Donald W.
The price is AU$1,150
includes taxes & fees
5 June - 6 June
Walk to Ocean Beach, Nat`l Seashore, WiFi, Bike Rail Trail

Edgewood on Campground Beach/Steps to the Sand

Edgewood on Campground Beach/Steps to the Sand
Eastham
10.0 out of 10, Exceptional, (9 reviews)
"Cozy cottage right by the beach. Great area not for to restaurants and beaches. Would definitely stay again!"
United States
Melinda W.
The price is AU$664
includes taxes & fees
31 May - 1 June
Edgewood on Campground Beach/Steps to the Sand

🐚The Bay Cottage on Thumpertown Beach

🐚The Bay Cottage on Thumpertown Beach
Eastham
9.8 out of 10, Exceptional, (11 reviews)
"My group and I had another wonderful stay at the Bay Cottage! The space is sparkling clean when we arrived and the location cannot be beat. Tara is also very responsive and attentive which makes for an even better stay!"
United States
Sophia I.
The price is AU$545
includes taxes & fees
1 June - 2 June
🐚The Bay Cottage on Thumpertown Beach

Family Cottage Close to Beach!!

Family Cottage Close to Beach!!
Harwichport
9.8 out of 10, Exceptional, (75 reviews)
"Everything was exactly as described - they provided beach towels and chairs which we used - the property was perfect for our stay"
United States
John N.
The price is AU$1,124
includes taxes & fees
1 June - 2 June
Family Cottage Close to Beach!!

Stay in a TINY HOUSE!★0.4mi to Beach★Village★Restaurants★Pet Friendly ★ 2 bikes!

Stay in a TINY HOUSE!★0.4mi to Beach★Village★Restaurants★Pet Friendly ★ 2 bikes!
Dennis
9.6 out of 10, Exceptional, (113 reviews)
"perfect for couples, clean and pet friendly"
Canada
Jonathan
The price is AU$439
includes taxes & fees
5 June - 6 June
Stay in a TINY HOUSE!★0.4mi to Beach★Village★Restaurants★Pet Friendly ★ 2 bikes!

2021 CONSTRUCTION 3BR 3BA. Close to Bike Trail & Beaches. Central AC, Firepit.

2021 CONSTRUCTION 3BR 3BA. Close to Bike Trail & Beaches. Central AC, Firepit.
Eastham
10.0 out of 10, Exceptional, (45 reviews)
"Great place, very clean. Host was accessible and accommodating. "
United States
Christopher M.
The price is AU$1,345
includes taxes & fees
31 May - 1 June
2021 CONSTRUCTION 3BR 3BA. Close to Bike Trail & Beaches. Central AC, Firepit.

6 Mi to Beach: Home w/ Deck in Brewster!

6 Mi to Beach: Home w/ Deck in Brewster!
3.0 star property
Brewster
The price is AU$959
includes taxes & fees
11 June - 12 June
6 Mi to Beach: Home w/ Deck in Brewster!

Gorgeous lake beachfront private apartment with canoe, kayaks, & home theatre

Gorgeous lake beachfront private apartment with canoe, kayaks, & home theatre
Harwich
10.0 out of 10, Exceptional, (113 reviews)
"Just as we expected we were greeted with happy pup barks and smiling faces.Our stay in Mike and Joe’s home was extremely comfortable. "
United States
Michael C.
The price is AU$539
includes taxes & fees
1 June - 2 June
Gorgeous lake beachfront private apartment with canoe, kayaks, & home theatre

The Breeze on Minister's Pond

The Breeze on Minister's Pond
Eastham
10.0 out of 10, Exceptional, (25 reviews)
"The Breeze is the cutest, warmest, comfiest home. We thoroughly enjoyed our stay and will definitely book again!"
United States
MelanieC
The price is AU$646
includes taxes & fees
12 June - 13 June
The Breeze on Minister's Pond

Cnxl Special 6-27 - 7-17 ★ WATERFRONT Kayaks & SUP’s ★ Pets OK ★HOT TUB★King bed

Cnxl Special 6-27 - 7-17 ★ WATERFRONT Kayaks & SUP’s ★ Pets OK ★HOT TUB★King bed
Bass River
10.0 out of 10, Exceptional, (108 reviews)
"Nice quiet neighborhood but close to a lot of different attractions. The home was perfect for our needs."
United States
Ryan T.
The price is AU$1,166
includes taxes & fees
11 June - 12 June
Cnxl Special 6-27 - 7-17 ★ WATERFRONT Kayaks & SUP’s ★ Pets OK ★HOT TUB★King bed
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Chatham Hotel Reviews

Find out more about Chatham

Everything you need to know about Chatham holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Chatham holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chatham holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Chatham holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chatham. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chatham holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chatham holiday rentals we have selected for you start as low as AU$221 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Chatham rentals

At Expedia, we put the best Chatham holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Chatham rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chatham holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chatham. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find a holiday rental in Chatham?

Yes, there are holiday rentals in Chatham close to Chatham Railroad Museum, or you can select a more secluded option if you're looking for a relaxing stay. Visitors like the popular beaches and waterfront in Chatham. While you're here, grab a bite or have a drink at the seafood restaurants.

What are some of the best holiday rentals that Chatham has to offer?

Quaint & Cozy Downtown Chatham Home, Walk to Town and Beaches: This highly rated holiday home rental in Chatham is located in the city centre, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. You can relax into your holiday with a garden and a selection of games.

How many holiday rentals are there in Chatham?

With 277 Expedia holiday rentals, you're guaranteed to find just the right place for your Chatham stay.

What can I see and do in Chatham?

Cultural attractions include Gallery Antonia and Chatham Drama Guild, whereas Cape Cod Beaches and Chatham Lighthouse Beach are a couple of picturesque spots to enjoy the outdoors. While here, Chatham Lighthouse and Cape Cod National Seashore are other places worth a visit.

What are holiday rentals like in Chatham?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Chatham. Holiday rentals offer extras such as hot tubs, fire pits and patios to help you enjoy your stay. If you're concerned about a clean environment, a holiday rental can offer a sense of safety away from public hotel lifts and lobbies bustling with people while still allowing you the enjoyment of travel. You'll also have more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is an attractive choice for families.