Photo by George Sykes

Chatham Holiday Rentals

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Check prices for these dates

In two weeks
23 Jan - 25 Jan
In two months
6 Mar - 8 Mar
In three months
3 Apr - 5 Apr
In four months
1 May - 3 May

Our top choices for Chatham holiday rentals

Terrace/patio
Darling, secluded cottage with large yard - walk to Chatham & Lighthouse Beach

Darling, secluded cottage with large yard - walk to Chatham & Lighthouse Beach

Darling, secluded cottage with large yard - walk to Chatham & Lighthouse Beach
Chatham
9.6 out of 10, Exceptional, (30 reviews)
"CutePrivateGreat outdoor showe "
United States
Stephanie D.
The price is HK$623
HK$2,556 total
includes taxes & fees
10 Jan - 11 Jan
Darling, secluded cottage with large yard - walk to Chatham & Lighthouse Beach
TV, fireplace, books
Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK

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)
"House was as advertised. Very clean and comfortable.we loved the fireplace and the large deck was great.we walked to Hardings beach in the morning.Highly recommend this vacation home"
United States
Linda W.
The price is HK$693
HK$3,249 total
includes taxes & fees
14 Jan - 15 Jan
Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK
Exterior
Quaint & Cozy Downtown Chatham Home, Walk to Town and Beaches

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, (117 reviews)
"Clean, lovely cottage. Excellent location. "
United States
Dottie P.
The price is HK$1,401
HK$3,841 total
includes taxes & fees
19 Jan - 20 Jan
Quaint & Cozy Downtown Chatham Home, Walk to Town and Beaches
TV, books
Beautiful, cozy ranch home w/ a deck - walking distance to Downtown Chatham

Beautiful, cozy ranch home w/ a deck - walking distance to Downtown Chatham

Beautiful, cozy ranch home w/ a deck - walking distance to Downtown Chatham
Chatham
8.6 out of 10, Excellent, (26 reviews)
"This was a very nice place to stay, the location was perfect. A short walk to town and centrally located on the Cape as a whole. This home had all of the amenities need for a comfortable stay."
United States
Jeffrey A.
The price is HK$1,558
HK$4,214 total
includes taxes & fees
12 Jan - 13 Jan
Beautiful, cozy ranch home w/ a deck - walking distance to Downtown Chatham
Indoor pool, seasonal outdoor pool
The Cove at Yarmouth by Westgate Resorts

The Cove at Yarmouth by Westgate Resorts

The Cove at Yarmouth by Westgate Resorts
3.0 star property
West Yarmouth
9.2 out of 10, Wonderful, (244 reviews)
"The staff are amazing! Love the amenities - the pool, recreation center, activities for the kids such as windchime arts and crafts. The arcade is always a hit. The Loft makes it so easy to not have to stress about a place to go to for dinner. The Cove is a great place for everyone! "
United States
Lauren
The price is HK$1,003
HK$1,148 total
includes taxes & fees
11 Jan - 12 Jan
The Cove at Yarmouth by Westgate Resorts
Indoor spa tub
Brewster Green Resort

Brewster Green Resort

Brewster Green Resort
3.5 star property
Brewster
9.4 out of 10, Exceptional, (123 reviews)
"The front desk staff are So pleasant to deal with. Pool is huge and the kids loved the game room"
United States
PAUL
The price is HK$1,083
HK$1,240 total
includes taxes & fees
10 Jan - 11 Jan
Brewster Green Resort
Interior
The Nantucket Room Unit - #2

The Nantucket Room Unit - #2

The Nantucket Room Unit - #2
Harwich port
9.8 out of 10, Exceptional, (49 reviews)
"amazing location and cute place to stay!"
United States
Adriana A.
The price is HK$771
HK$1,489 total
includes taxes & fees
20 Jan - 21 Jan
The Nantucket Room Unit - #2
Beach nearby
Quaint condo near private beach access with fireplace - close to dining

Quaint condo near private beach access with fireplace - close to dining

Quaint condo near private beach access with fireplace - close to dining
Dennis Port
9.0 out of 10, Wonderful, (63 reviews)
"Clean, beautiful, great location "
United States
Jennifer B.
The price is HK$467
HK$2,463 total
includes taxes & fees
10 Jan - 11 Jan
Quaint condo near private beach access with fireplace - close to dining
Outdoor dining
Spectacular Private Waterfront Cottage on Bayside. Panoramic Views. Pet Friendly

Spectacular Private Waterfront Cottage on Bayside. Panoramic Views. Pet Friendly

Spectacular Private Waterfront Cottage on Bayside. Panoramic Views. Pet Friendly
Wellfleet
10.0 out of 10, Exceptional, (76 reviews)
"Beautiful views in a quiet and private location. Cottage had everything we needed and nicely appointed."
United States
Janice H.
The price is HK$1,207
HK$3,547 total
includes taxes & fees
11 Jan - 12 Jan
Spectacular Private Waterfront Cottage on Bayside. Panoramic Views. Pet Friendly
Property grounds
Cottage Oasis by Lake with Kayaks, Fire Pit & a Huge Yard

Cottage Oasis by Lake with Kayaks, Fire Pit & a Huge Yard

Cottage Oasis by Lake with Kayaks, Fire Pit & a Huge Yard
2.0 star property
Dennis
9.0 out of 10, Wonderful, (2 reviews)
"Very cute cottage. Very clean and grounds well manicured. "
United States
Anonymous traveller
The price is HK$1,004
HK$2,526 total
includes taxes & fees
20 Jan - 21 Jan
Cottage Oasis by Lake with Kayaks, Fire Pit & a Huge Yard
Interior
Eazy Breezy Beach Home

Eazy Breezy Beach Home

Eazy Breezy Beach Home
Dennis
9.4 out of 10, Exceptional, (3 reviews)
"Great location"
United States
alyssa w.
The price is HK$981
HK$1,791 total
includes taxes & fees
11 Jan - 12 Jan
Eazy Breezy Beach Home
Smart TV, books
Coastal Cape Cod 3 bedroom close to the beach, bike path & ponds!

Coastal Cape Cod 3 bedroom close to the beach, bike path & ponds!

Coastal Cape Cod 3 bedroom close to the beach, bike path & ponds!
2.0 star property
West Brewster
10.0 out of 10, Exceptional, (25 reviews)
"Lovely house with nice location."
United States
amy d.
The price is HK$1,168
HK$5,605 total
includes taxes & fees
17 Jan - 18 Jan
Coastal Cape Cod 3 bedroom close to the beach, bike path & ponds!
Exterior
Lovely House 5 Min to Beach with Deck, Grill, Garage

Lovely House 5 Min to Beach with Deck, Grill, Garage

Lovely House 5 Min to Beach with Deck, Grill, Garage
Eastham
10.0 out of 10, Exceptional, (2 reviews)
"Great house with comfy beds. Would consider staying again. "
United States
Susan C.
The price is HK$1,160
HK$3,740 total
includes taxes & fees
20 Jan - 21 Jan
Lovely House 5 Min to Beach with Deck, Grill, Garage
Beach
Relaxed coastal cottage close to the beach with e-bikes, firepit, deck & AC

Relaxed coastal cottage close to the beach with e-bikes, firepit, deck & AC

Relaxed coastal cottage close to the beach with e-bikes, firepit, deck & AC
2.0 star property
Dennis Port
The price is HK$982
HK$3,511 total
includes taxes & fees
11 Jan - 12 Jan
Relaxed coastal cottage close to the beach with e-bikes, firepit, deck & AC
Beach nearby
Charming House by the Beach with Patio, Grill, FirePit

Charming House by the Beach with Patio, Grill, FirePit

Charming House by the Beach with Patio, Grill, FirePit
Bass River
9.8 out of 10, Exceptional, (7 reviews)
"Great location, walk to beach. Close to restaurants and pirate's cove mini golf. Beds were comfy. In-house laundry was convenient. Great outdoor shower. "
United States
Amanda W.
The price is HK$1,549
HK$4,673 total
includes taxes & fees
20 Jan - 21 Jan
Charming House by the Beach with Patio, Grill, FirePit
Beach nearby
The Alpine/Walk to Beach for 2 or more!

The Alpine/Walk to Beach for 2 or more!

The Alpine/Walk to Beach for 2 or more!
Eastham
9.2 out of 10, Wonderful, (11 reviews)
"The location was awesome, the house was clean and spacious, and overall it was terrific! I would highly recommend."
United States
Jennifer G.
The price is HK$1,347
HK$4,055 total
includes taxes & fees
20 Jan - 21 Jan
The Alpine/Walk to Beach for 2 or more!
Pool
Cozy Large Home in Harwich with Patio near Wequassett Resort

Cozy Large Home in Harwich with Patio near Wequassett Resort

Cozy Large Home in Harwich with Patio near Wequassett Resort
Harwich
9.8 out of 10, Exceptional, (11 reviews)
"Host was very responsive and the house provided everything we needed. Great location! "
United States
Ashley M.
The price is HK$1,238
HK$4,035 total
includes taxes & fees
18 Jan - 19 Jan
Cozy Large Home in Harwich with Patio near Wequassett Resort
Smart TV, fireplace
The Pet-Friendly Surf Shack Hideaway on the Cove

The Pet-Friendly Surf Shack Hideaway on the Cove

The Pet-Friendly Surf Shack Hideaway on the Cove
Eastham
10.0 out of 10, Exceptional, (21 reviews)
"We loved the luxury bed linens, large kitchen & living area & the fact that it was pet friendly in a lovely neighborhood!"
United States
Jennifer G.
The price is HK$1,253
HK$3,840 total
includes taxes & fees
20 Jan - 21 Jan
The Pet-Friendly Surf Shack Hideaway on the Cove
Beach nearby
Ocean Edge Cape Cod 2 Bed 2 Bath, Golf & Free Resort Access - Brewster, MA

Ocean Edge Cape Cod 2 Bed 2 Bath, Golf & Free Resort Access - Brewster, MA

Ocean Edge Cape Cod 2 Bed 2 Bath, Golf & Free Resort Access - Brewster, MA
Brewster
10.0 out of 10, Exceptional, (41 reviews)
"Great clean place. Host was very quick to respond. I would definitely recommend staying here. "
United States
Ginnie W.
The price is HK$1,465
HK$2,639 total
includes taxes & fees
11 Jan - 12 Jan
Ocean Edge Cape Cod 2 Bed 2 Bath, Golf & Free Resort Access - Brewster, MA
On the beach
Sand Bar-Dog Friendly on Cooks Brook Beach

Sand Bar-Dog Friendly on Cooks Brook Beach

Sand Bar-Dog Friendly on Cooks Brook Beach
Eastham
10.0 out of 10, Exceptional, (23 reviews)
"The beach view was wonderful. The beds are comfy. Local restaurants are abundant. It was easy to feel comfortable in this cottage. "
United States
Gerard B.
The price is HK$1,604
HK$4,092 total
includes taxes & fees
11 Jan - 12 Jan
Sand Bar-Dog Friendly on Cooks Brook Beach
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

Margaritaville Resort Cape Cod

Margaritaville Resort Cape Cod

10/10 Excellent
"We are very happy with all the people at margaritaville, they are awesome 💝"
Ewerton 2-night trip
Posted 2 days ago
Margaritaville Resort Cape Cod

Find out more about Chatham

Search for holiday rentals in Chatham on Expedia! You can easily find your home rentals, villas, holiday apartments in Chatham using one of the methods below:

  • View our selection of featured holiday rentals in Chatham
  • Use the map to find apartments and other holiday homes in the Chatham neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Chatham while they last

Look no further and take a look at our great range of rental properties in Chatham!

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?

Downtown Chatham Luxury 9 BR Home with Heated Pool. Pets welcome!: This highly rated holiday home rental in Chatham is located in the city centre, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 9 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a patio, a garden and a selection of games so that you can immerse yourself in your holiday. Some other top choices in Chatham are Breathtaking Riverfront Home with a Lovely Deck, Close to Beach - Dogs OK and Walk to Chatham Main St., boutiques, restaurants, galleries, and nightlife!.

How many holiday rentals are there in Chatham?

With 274 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 Monomoy Theatre, whereas Chatham Lighthouse Beach and Ridgevale Beach are a couple of picturesque spots to enjoy the outdoors. While here, Chatham Lighthouse and Cockle Cove Beach 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.