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Holiday Rentals in Chatham

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Our top choices for Chatham holiday rentals

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, (103 reviews)
"Our second year in a row staying here. Cute house and great location! "
United States
Erin M.
The price is €624
includes taxes & fees
14 Jul - 15 Jul
Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK

Waterfront Chatham Village, Short Walk to Town & Lighthouse Beach

Waterfront Chatham Village, Short Walk to Town & Lighthouse Beach
Chatham
10.0 out of 10, Exceptional, (136 reviews)
"Wonderful house, wonder view and fantastic location!"
United States
shelly c.
The price is €2,492
includes taxes & fees
18 Jul - 19 Jul
Waterfront Chatham Village, Short Walk to Town & Lighthouse Beach

Main Street Hyannis 1-bedroom Apartment Walk Everywhere!

Main Street Hyannis 1-bedroom Apartment Walk Everywhere!
Barnstable
The price is €467
includes taxes & fees
15 Jul - 16 Jul
Main Street Hyannis 1-bedroom Apartment Walk Everywhere!

The Nantucket Room Unit - #2

The Nantucket Room Unit - #2
Harwich port
9.8 out of 10, Exceptional, (56 reviews)
"amazing location and cute place to stay!"
United States
Adriana A.
The price is €369
includes taxes & fees
12 Jul - 13 Jul
The Nantucket Room Unit - #2

Private Cape Cod Cottage. Walk to Ellis Landing Beach!

Private Cape Cod Cottage. Walk to Ellis Landing Beach!
Brewster
10.0 out of 10, Exceptional, (42 reviews)
"Great location - privacy, comfy, and close to the beach!"
United States
Samantha K.
The price is €471
includes taxes & fees
21 Jul - 22 Jul
Private Cape Cod Cottage. Walk to Ellis Landing Beach!

Family-friendly house w/gas grill, deck, streaming services - near Haigis Beach

Family-friendly house w/gas grill, deck, streaming services - near Haigis Beach
Dennis Port
The price is €466
includes taxes & fees
15 Jul - 16 Jul
Family-friendly house w/gas grill, deck, streaming services - near Haigis Beach

Beach Walks, Books & Bay Sunsets

Beach Walks, Books & Bay Sunsets
Brewster
The price is €879
includes taxes & fees
15 Jul - 16 Jul
Beach Walks, Books & Bay Sunsets

Ocean Edge Resort ground-floor condo with access to pools, hot tub, & tennis

Ocean Edge Resort ground-floor condo with access to pools, hot tub, & tennis
Brewster
9.0 out of 10, Wonderful, (20 reviews)
"Facility was excellent"
United States
Joe K.
The price is €596
includes taxes & fees
13 Jul - 14 Jul
Ocean Edge Resort ground-floor condo with access to pools, hot tub, & tennis

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, (115 reviews)
"perfect for couples, clean and pet friendly"
Canada
Jonathan
The price is €371
includes taxes & fees
24 Jul - 25 Jul
Stay in a TINY HOUSE!★0.4mi to Beach★Village★Restaurants★Pet Friendly ★ 2 bikes!

Pondside/Kayak/Firepit/Dog Friendly~Willow Haven

Pondside/Kayak/Firepit/Dog Friendly~Willow Haven
Eastham
10.0 out of 10, Exceptional, (4 reviews)
"Great hideaway location on the Cape. Well equipped rental."
United Kingdom
Richard F.
The price is €520
includes taxes & fees
12 Jul - 13 Jul
Pondside/Kayak/Firepit/Dog Friendly~Willow Haven

Relaxing Cape Cod Cottage Getaway

Relaxing Cape Cod Cottage Getaway
Dennis
The price is €535
includes taxes & fees
13 Jul - 14 Jul
Relaxing Cape Cod Cottage Getaway

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

1 Mi to Ferry: 'Sea Street Cottage' in Hyannis
Hyannis
8.8 out of 10, Excellent, (19 reviews)
"Perfect weekend getaway- super location. Cozy spot! Loved the area "
United States
Jill S.
The price is €349
includes taxes & fees
21 Jul - 22 Jul
1 Mi to Ferry: 'Sea Street Cottage' in Hyannis

Adorable Cape Escape W/ Private Beach Access, Full Kitchen, & Perfect Location

Adorable Cape Escape W/ Private Beach Access, Full Kitchen, & Perfect Location
Dennis Port
9.0 out of 10, Wonderful, (25 reviews)
"Loved this property. "
United States
Carol S.
The price is €499
includes taxes & fees
26 Jul - 27 Jul
Adorable Cape Escape W/ Private Beach Access, Full Kitchen, & Perfect Location

Harbor Getaway Unit- #1

Harbor Getaway Unit- #1
Harwich
10.0 out of 10, Exceptional, (3 reviews)
"Quaint room, exactly as advertised. Easy to check in. I would recommend this inn to others."
United States
Ashley H.
Harbor Getaway Unit- #1

🐳 The Whale Song - Dog-Friendly Studio

🐳 The Whale Song - Dog-Friendly Studio
Eastham
9.6 out of 10, Exceptional, (15 reviews)
"We enjoyed our stay very much "
United States
Gregg P.
The price is €403
includes taxes & fees
21 Jul - 22 Jul
🐳 The Whale Song - Dog-Friendly Studio

Coastal Haven in West Dennis

Coastal Haven in West Dennis
Dennis
10.0 out of 10, Exceptional, (3 reviews)
"This was a great place to stay and relax, just a short walk to the beach and quick drive to great restaurants and activities. Highly recommend!!"
United States
Melissa J.
The price is €634
includes taxes & fees
13 Jul - 14 Jul
Coastal Haven in West Dennis

Charming West Yarmouth Cottage- Minutes to Beaches, Dining & Family Fun

Charming West Yarmouth Cottage- Minutes to Beaches, Dining & Family Fun
Yarmouth
10.0 out of 10, Exceptional, (2 reviews)
"Cute little cottage. Clean and pull out couch was very comfy! Great stay for a small group. Perfect location near a lot of very nice beaches. Would recommend Gray’s beach for sunset, parking is free!"
United States
Jessica Y.
The price is €506
includes taxes & fees
12 Jul - 13 Jul
Charming West Yarmouth Cottage- Minutes to Beaches, Dining & Family Fun

New! Island Pines-A Dog Friendly Boutique Oasis

New! Island Pines-A Dog Friendly Boutique Oasis
Wellfleet
9.4 out of 10, Exceptional, (12 reviews)
"Beautiful cozy home on a piney coastal island! Wish we could stay longer. Very central for exploring in all directions on the Cape. Awesome hosts with so many great recommendations and thorough info leading up to the stay."
United States
Kaden P.
The price is €830
includes taxes & fees
15 Jul - 16 Jul
New! Island Pines-A Dog Friendly Boutique Oasis

Cheery house with deck, sunroom & patio - short walk to pond, beach & Rail Trail

Cheery house with deck, sunroom & patio - short walk to pond, beach & Rail Trail
West Brewster
9.6 out of 10, Exceptional, (51 reviews)
"We loved the house. Simple and comfortable, exactly what we needed to relax. thank you."
United States
Michael M.
The price is €1,066
includes taxes & fees
22 Jul - 23 Jul
Cheery house with deck, sunroom & patio - short walk to pond, beach & Rail Trail

Secluded-Entire 2nd floor Suite with Private Bath

Secluded-Entire 2nd floor Suite with Private Bath
Barnstable
10.0 out of 10, Exceptional, (2 reviews)
"Great, very close to downtown hyannis. Charming and a nice owner. "
United States
sam s.
The price is €221
includes taxes & fees
12 Jul - 13 Jul
Secluded-Entire 2nd floor Suite with Private Bath
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, apart-hotels, 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 favorite 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 depends 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 €344 per night. Entering your travel dates in the search wizard you might find 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?

Cape Cod's "Beach Rose": This holiday home rental outside of Chatham offers a patio, a selection of games and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

How many holiday rentals are there in Chatham?

With 280 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 Caleb Nickerson House and Gallery Antonia, whereas Cape Cod Beaches and Chatham Lighthouse Beach are a couple of picturesque spots to enjoy the outdoors. While here, Cape Cod National Seashore and Chatham Lighthouse 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.