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, (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 €447
includes taxes & fees
26 May - 27 May
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 €440
includes taxes & fees
27 May - 28 May
Seaside condo with patio, beach access, loft, board games, gas grill, & firepit

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, (120 reviews)
"Clean, quiet, and great location."
United States
Tyler B.
The price is €502
includes taxes & fees
26 May - 27 May
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.
Luxury Chatham Retreat. Walk to Main St & Beach

Town Center-Summer Dates Still Available-Walk To Stores-2026 Total Renovation

Town Center-Summer Dates Still Available-Walk To Stores-2026 Total Renovation
Chatham
The price is €752
includes taxes & fees
16 Jun - 17 Jun
Town Center-Summer Dates Still Available-Walk To Stores-2026 Total Renovation

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

🐚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 €341
includes taxes & fees
31 May - 1 Jun
🐚The Bay Cottage on Thumpertown Beach

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

Sweetbriar ~ Charming Cape Cottage ~ Dog-Friendly!

Sweetbriar ~ Charming Cape Cottage ~ Dog-Friendly!
Eastham
10.0 out of 10, Exceptional, (5 reviews)
"Welcoming, cozy and ergonomic cottage equiped with everything you need for a summer vacation! We enjoyed our stay very much! Thank you!"
United States
Kate D.
Sweetbriar ~ Charming Cape Cottage ~ Dog-Friendly!

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 €419
includes taxes & fees
27 May - 28 May
Edgewood on Campground Beach/Steps to the Sand

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 €333
includes taxes & fees
1 Jun - 2 Jun
On Town Cove with salt water access! Kayaks and paddle board available for use!

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, (112 reviews)
"The hosts were so accommodating and lovely. The property is adorable and well appointed! Would stay again 100 percent. "
United States
rachel n.
The price is €339
includes taxes & fees
1 Jun - 2 Jun
Gorgeous lake beachfront private apartment with canoe, kayaks, & home theatre

The Blue Crab Unit 7

The Blue Crab Unit 7
Harwich
9.6 out of 10, Exceptional, (15 reviews)
"Nice place, decent central location "
United States
hannah k.
The price is €183
includes taxes & fees
27 May - 28 May
The Blue Crab Unit 7

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 €529
includes taxes & fees
26 May - 27 May
Cheery house with deck, sunroom & patio - short walk to pond, beach & Rail Trail

The Captain's Quarters Suite Unit - 10

The Captain's Quarters Suite Unit - 10
Harwich
10.0 out of 10, Exceptional, (16 reviews)
"It was perfect for what I needed, hosts were helpful and accommodating. I would definitely stay here again!"
United States
Julienne
The price is €203
includes taxes & fees
28 May - 29 May
The Captain's Quarters Suite Unit - 10

Solace in the Sun- Adj. Beds/Game Rm/Soakng Tub/Dog Ok

Solace in the Sun- Adj. Beds/Game Rm/Soakng Tub/Dog Ok
Eastham
10.0 out of 10, Exceptional, (2 reviews)
"The house was beautiful, tucked away, and clean. It was spacious for two families with room for more comfortably. "
United States
michele I.
The price is €573
includes taxes & fees
27 May - 28 May
Solace in the Sun- Adj. Beds/Game Rm/Soakng Tub/Dog Ok

Sleeps 2-8/Soaking Tub/FirePit~Burrows

Sleeps 2-8/Soaking Tub/FirePit~Burrows
Eastham
10.0 out of 10, Exceptional, (8 reviews)
"We went with a small group of friends and everything was amazing. The property is beautiful and well located. We had everything that we needed and the communication con the owner was good."
United States
Lourdes P.
The price is €445
includes taxes & fees
27 May - 28 May
Sleeps 2-8/Soaking Tub/FirePit~Burrows

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 €594
includes taxes & fees
29 May - 30 May
6 Mi to Beach: Home w/ Deck in Brewster!

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 €293
includes taxes & fees
5 Jun - 6 Jun
Stay in a TINY HOUSE!★0.4mi to Beach★Village★Restaurants★Pet Friendly ★ 2 bikes!

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, (23 reviews)
"Our host was very responsive and all the instructions were clear. The house was immaculate and a perfect spot of a winter getaway. Would stay again!"
United States
Anna P.
The price is €433
includes taxes & fees
27 May - 28 May
The Pet-Friendly Surf Shack Hideaway on the Cove
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 €157 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?

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 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 Caleb Nickerson House and Gallery Antonia, whereas Chatham Lighthouse Beach and Cape Cod Beaches 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.