Chatham Holiday Rentals

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Our top choices for Chatham holiday rentals

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 NZ$570
includes taxes & fees
25 Jan - 26 Jan
Darling, secluded cottage with large yard - walk to Chatham & Lighthouse Beach

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 NZ$711
includes taxes & fees
24 Jan - 25 Jan
Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK

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 NZ$842
includes taxes & fees
1 Feb - 2 Feb
Quaint & Cozy Downtown Chatham Home, Walk to Town and Beaches

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 NZ$922
includes taxes & fees
27 Jan - 28 Jan
Beautiful, cozy ranch home w/ a deck - walking distance to Downtown Chatham

Quaint Cape Cod Home! A/C! Firepit! Dogs Allowed

Quaint Cape Cod Home! A/C! Firepit! Dogs Allowed
Yarmouth
10.0 out of 10, Exceptional, (3 reviews)
"My wife and I stayed here four days. This house is centrally located and in a good, safe neighborhood. It was clean and had all supplies needed such as towels, dish soap, laundry soap, paper towels etc.Would stay here again. "
United States
Todd M.
The price is NZ$947
includes taxes & fees
21 Jan - 22 Jan
Quaint Cape Cod Home! A/C! Firepit! Dogs Allowed

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, (247 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 NZ$255
includes taxes & fees
27 Jan - 28 Jan
The Cove at Yarmouth by Westgate Resorts

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 NZ$1,163
includes taxes & fees
22 Jan - 23 Jan
Coastal Cape Cod 3 bedroom close to the beach, bike path & ponds!

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, (77 reviews)
"Beautiful views in a quiet and private location. Cottage had everything we needed and nicely appointed."
United States
Janice H.
The price is NZ$771
includes taxes & fees
22 Jan - 23 Jan
Spectacular Private Waterfront Cottage on Bayside. Panoramic Views. Pet Friendly

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
8.8 out of 10, Excellent, (3 reviews)
"Very cute cottage. Very clean and grounds well manicured. "
United States
Anonymous traveller
The price is NZ$539
includes taxes & fees
21 Jan - 22 Jan
Cottage Oasis by Lake with Kayaks, Fire Pit & a Huge Yard

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 NZ$791
includes taxes & fees
21 Jan - 22 Jan
Lovely House 5 Min to Beach with Deck, Grill, Garage

Beautiful home in Orleans. Park, Beach, Lake & Ocean. Telsa charge

Beautiful home in Orleans. Park, Beach, Lake & Ocean. Telsa charge
Orleans
10.0 out of 10, Exceptional, (14 reviews)
"Property was clean and as described in the listing, owner was communicative and easy to check in"
United States
Darren Y.
The price is NZ$5,210
includes taxes & fees
28 Jan - 29 Jan
Beautiful home in Orleans. Park, Beach, Lake & Ocean. Telsa charge

🦀Waterfront at The Velvet Crab~Amazing Sunsets

🦀Waterfront at The Velvet Crab~Amazing Sunsets
Eastham
9.8 out of 10, Exceptional, (23 reviews)
"Everything was great, we really enjoyed our stay!"
United States
Anna T.
The price is NZ$720
includes taxes & fees
27 Jan - 28 Jan
🦀Waterfront at The Velvet Crab~Amazing Sunsets

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 NZ$330
includes taxes & fees
30 Jan - 31 Jan
The Nantucket Room Unit - #2

New! Island Pines-A Dog Friendly Boutique Oasis

New! Island Pines-A Dog Friendly Boutique Oasis
Wellfleet
9.4 out of 10, Exceptional, (11 reviews)
"Loved the place. Very clean and updated. You have to time the tides because it is on an island, but that was fine for us. "
United States
Brian F.
The price is NZ$937
includes taxes & fees
2 Feb - 3 Feb
New! Island Pines-A Dog Friendly Boutique Oasis

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 NZ$1,084
includes taxes & fees
21 Jan - 22 Jan
Solace in the Sun- Adj. Beds/Game Rm/Soakng Tub/Dog Ok

Pond House~Waterfront Oasis W/Jacuzzi Tub

Pond House~Waterfront Oasis W/Jacuzzi Tub
Eastham
10.0 out of 10, Exceptional, (10 reviews)
"Beautiful spot ! House was clean and well equipped. "
United States
Cynthia P.
The price is NZ$871
includes taxes & fees
1 Feb - 2 Feb
Pond House~Waterfront Oasis W/Jacuzzi Tub

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 NZ$834
includes taxes & fees
22 Jan - 23 Jan
The Pet-Friendly Surf Shack Hideaway on the Cove

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 NZ$924
includes taxes & fees
1 Feb - 2 Feb
The Alpine/Walk to Beach for 2 or more!

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, (50 reviews)
"House was perfect for our family reunion! "
United States
Gregg H.
The price is NZ$909
includes taxes & fees
22 Jan - 23 Jan
Cheery house with deck, sunroom & patio - short walk to pond, beach & Rail Trail

National Seashore/Updated/Game Room~Blue Pearl

National Seashore/Updated/Game Room~Blue Pearl
Eastham
10.0 out of 10, Exceptional, (8 reviews)
"Best rental we have stayed in on Cape, and we go every year. Exceptionally clean, comfortable. I can not say enough about it. Great location as well. What stood out the most was the high quality linens, as well as comfortable mattresses. It is very well kept with attention to detail. The grill and appliances were also of a higher quality and made it a pleasure to cook. Will absolutely stay at Blue Pearl again. "
United States
Nicole V.
The price is NZ$840
includes taxes & fees
1 Feb - 2 Feb
National Seashore/Updated/Game Room~Blue Pearl
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 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 NZ$255 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. Some other top choices in Chatham are Breathtaking Riverfront Home with a Lovely Deck, Close to Beach - Dogs OK and Quaint & Cozy Downtown Chatham Home, Walk to Town and Beaches.

How many holiday rentals are there in Chatham?

With 272 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.