Holiday Rentals in Chatham

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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, (117 reviews)
"Clean, quiet, and great location."
United States
Tyler B.
The price is €424
includes taxes & fees
13 Apr - 14 Apr
Quaint & Cozy Downtown Chatham Home, Walk to Town and Beaches

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 €403
includes taxes & fees
14 Apr - 15 Apr
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
7.8 out of 10, Good, (18 reviews)
"The property was nice and quiet getaway from the city"
United States
Jorge Z.
The price is €430
includes taxes & fees
10 May - 11 May
Seaside condo with patio, beach access, loft, board games, gas grill, & firepit

Downtown Chatham Luxury 9 BR Home with Heated Pool. Pets welcome!

Downtown Chatham Luxury 9 BR Home with Heated Pool. Pets welcome!
Chatham
10.0 out of 10, Exceptional, (40 reviews)
"We’ve stayed here 3 times and always love it. Kitchen is very well-stocked, beds are comfortable and you cannot beat the location. Owner is very responsive if there are issues. "
United States
Coleen and Brian F.
Downtown Chatham Luxury 9 BR Home with Heated Pool. Pets welcome!

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 €1,419
includes taxes & fees
12 Apr - 13 Apr
Downtown Chatham Gem – Walk to Beach, Shops, C.B.I, & Dining Family-Friendly!

Walk to Beaches & Dining: Classic Cape Cod Cottage

Walk to Beaches & Dining: Classic Cape Cod Cottage
3.0 star property
Dennis Port
Walk to Beaches & Dining: Classic Cape Cod Cottage

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, (257 reviews)
"From the moment we arrived, we was welcomed with warm hospitality and genuine friendliness The room was spotless, comfortable, and beautifully maintained, and I especially appreciated the attention to detail throughout the property. The indoor pool a plus in these cold months - The location was perfect as well—close to everything I wanted to explore, yet peaceful and relaxing. Your staff went above and beyond to ensure a pleasant experience, and it did not go unnoticed. It’s clear that you take...
United States
Angel
The price is €136
includes taxes & fees
12 Apr - 13 Apr
The Cove at Yarmouth by Westgate Resorts

The Mod Pod~2 bd/2.5 bth/dog/games/steps to beach

The Mod Pod~2 bd/2.5 bth/dog/games/steps to beach
Wellfleet
The price is €474
includes taxes & fees
12 Apr - 13 Apr
The Mod Pod~2 bd/2.5 bth/dog/games/steps to beach

Brewster Green Resort

Brewster Green Resort
3.5 star property
Brewster
9.4 out of 10, Exceptional, (128 reviews)
"Mike is the best. Very clean environment and family welcome"
United States
Catherine
The price is €224
includes taxes & fees
11 Apr - 12 Apr
Brewster Green Resort

Coastal Haven in West Dennis -15

Coastal Haven in West Dennis -15
2.0 star property
West Dennis
The price is €757
includes taxes & fees
24 Apr - 25 Apr
Coastal Haven in West Dennis -15

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, (44 reviews)
"Great place!"
United States
Michael P.
The price is €329
includes taxes & fees
12 Apr - 13 Apr
Ocean Edge Cape Cod 2 Bed 2 Bath, Golf & Free Resort Access - Brewster, MA

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)
"House was perfect for our family reunion! "
United States
Gregg H.
The price is €500
includes taxes & fees
12 Apr - 13 Apr
Cheery house with deck, sunroom & patio - short walk to pond, beach & Rail Trail

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

Coastal Cape Cod 3 bedroom close to the beach, bike path & ponds!
West Brewster
10.0 out of 10, Exceptional, (25 reviews)
"Lovely house with nice location."
United States
amy d.
The price is €619
includes taxes & fees
15 Apr - 16 Apr
Coastal Cape Cod 3 bedroom close to the beach, bike path & ponds!

Sal's Place

Sal's Place
2.0 star property
Hyannis
The price is €494
includes taxes & fees
11 Apr - 12 Apr
Sal's Place

The Nantucket Room Unit - #2

The Nantucket Room Unit - #2
Harwich port
9.8 out of 10, Exceptional, (52 reviews)
"amazing location and cute place to stay!"
United States
Adriana A.
The price is €158
includes taxes & fees
14 Apr - 15 Apr
The Nantucket Room Unit - #2

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 €589
includes taxes & fees
24 Apr - 25 Apr
6 Mi to Beach: Home w/ Deck in Brewster!

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 €416
includes taxes & fees
23 Apr - 24 Apr
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 €339
includes taxes & fees
16 Apr - 17 Apr
🐚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 €707
includes taxes & fees
13 Apr - 14 Apr
Family Cottage Close to Beach!!

Cape Cod Villa pond front vacation home, retreat, spa, venue, film location

Cape Cod Villa pond front vacation home, retreat, spa, venue, film location
Harwich - Brewster Border
10.0 out of 10, Exceptional, (6 reviews)
"Lovely property with attentive hosts "
United States
marian t.
The price is €1,093
includes taxes & fees
11 Apr - 12 Apr
Cape Cod Villa pond front vacation home, retreat, spa, venue, film location
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 €136 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?

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. Another good choice for your trip to Chatham is Quaint & Cozy Downtown Chatham Home, Walk to Town and Beaches.

How many holiday rentals are there in Chatham?

With 276 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 Railroad Museum, whereas Chatham Lighthouse Beach and Ridgevale Beach are a couple of picturesque spots to enjoy the outdoors. While here, Chatham Lighthouse and Cape Cod Beaches 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.