Chatham Holiday Rentals

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Holiday Rentals in Chatham

Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK

9.6 out of 10, Exceptional, (96)
"Great location"
Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK

Chatham 3 Bedroom/2 Bath Retreat

9.0 out of 10, Wonderful, (44)
"Pam was an excellent host. The house is in a great location and served as a perfect home base for my group over 4th of July Weekend."
The price is NZ$1,476
includes taxes & fees
15 July - 16 July
Chatham 3 Bedroom/2 Bath Retreat

Walk to Chatham Main St., boutiques, restaurants, galleries, and nightlife!

10.0 out of 10, Exceptional, (96)
"Place was amazing! Host was so great and very helpful. Location was fantastic. Can’t wait to come back to Chatham and stay here! "
Walk to Chatham Main St., boutiques, restaurants, galleries, and nightlife!

Quiet South Chatham 2-Bedroom House, Close To Beaches

9.4 out of 10, Exceptional, (3)
"We had a great stay. The location was perfect for visiting family, beach, and downtown Chatham. The house was spotless. We wouldn't hesitate to stay again!"
The price is NZ$1,251
includes taxes & fees
18 July - 19 July
Quiet South Chatham 2-Bedroom House, Close To Beaches

Jaws Nest~Dog Friendly~Oceanside Beauty

The price is NZ$1,275
includes taxes & fees
15 July - 16 July
Jaws Nest~Dog Friendly~Oceanside Beauty

Beachside Bliss: Modern Comfort Steps from Scenic Trails, Sleeps 10!

9.0 out of 10, Wonderful, (2)
"Nice, clean property. We all slept comfortably and had a great, fun stay at a quiet location. The hosts were very informative, kind and communicative. We will definitely be staying here in the future. Thank you again for a pleasurable experience from beginning to end!"
The price is NZ$2,581
includes taxes & fees
14 July - 15 July
Beachside Bliss: Modern Comfort Steps from Scenic Trails, Sleeps 10!

National Seashore/Updated/Game Room~Blue Pearl

10.0 out of 10, Exceptional, (7)
"This house is like brand new and so clean. Well stocked with basics like glasses, dishes, pots and pans. The owner is very responsive and helpful!!"
The price is NZ$1,059
includes taxes & fees
17 July - 18 July
National Seashore/Updated/Game Room~Blue Pearl

Newly Renovated Guest House For 10 Near The Beach!

10.0 out of 10, Exceptional, (4)
"Space was great for our family/friends gathering Location perfect for events we were attending on the Cape"
The price is NZ$2,270
includes taxes & fees
14 July - 15 July
Newly Renovated Guest House For 10 Near The Beach!

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

10.0 out of 10, Exceptional, (13)
"Property was clean and as described in the listing, owner was communicative and easy to check in"
The price is NZ$5,196
includes taxes & fees
14 July - 15 July
Beautiful home in Orleans. Park, Beach, Lake & Ocean. Telsa charge

Cape Cod Sunscape.

10.0 out of 10, Exceptional, (15)
"The property was very nice and the host was very responsive. Would definitely stay there again."
The price is NZ$1,779
includes taxes & fees
7 Aug - 8 Aug
Cape Cod Sunscape.

Pond House~Waterfront Oasis W/Jacuzzi Tub

10.0 out of 10, Exceptional, (6)
"We had a great stay at the Pond House. Everything was clean and functional. Beds were extremely comfortable! Nice spot for a two night stay."
The price is NZ$1,177
includes taxes & fees
24 July - 25 July
Pond House~Waterfront Oasis W/Jacuzzi Tub

Eastham is Cape Cod’s best kept secret!

9.8 out of 10, Exceptional, (7)
"This house is beautifully decorated, especially the main floor. The screened-in porch was so relaxing. We all enjoyed the pool and the lovely patio area surrounding it. The beds were all uncomfortable. The sheets on one of the beds were very dirty upon arrival. "
The price is NZ$2,935
includes taxes & fees
15 July - 16 July
Eastham is Cape Cod’s best kept secret!

Gray Whale - 3 bedrm/2 bath/gameroom

The price is NZ$1,479
includes taxes & fees
16 July - 17 July
Gray Whale - 3 bedrm/2 bath/gameroom

Beachfront~Seaside Sea-duction-Dog Friendly

10.0 out of 10, Exceptional, (8)
"Quick winter getaway with another couple celebrating a birthday, also. Everything was perfect. The view was gorgeous.The house was adorable, even in the dead of winter.Can't even imagine how great it would be in the summertime."
Beachfront~Seaside Sea-duction-Dog Friendly

Ebb Tide~3b/2b and dog friendly for 2-10

10.0 out of 10, Exceptional, (1)
"Great stay. Kind extra touches of hospitality appreciated!"
The price is NZ$1,469
includes taxes & fees
17 July - 18 July
Ebb Tide~3b/2b and dog friendly for 2-10

Modern Family Getaway In Harwich

9.8 out of 10, Exceptional, (6)
"The house was very comfortable, we had a great time. The fire pit and game room were fun,location was great for us. "
The price is NZ$3,600
includes taxes & fees
10 Aug - 11 Aug
Modern Family Getaway In Harwich

New! Island Pines-A Dog Friendly Boutique Oasis

9.6 out of 10, Exceptional, (8)
"Very well kept host was charming."
The price is NZ$1,956
includes taxes & fees
22 July - 23 July
New! Island Pines-A Dog Friendly Boutique Oasis

🐚Shell City on Lt Island

9.4 out of 10, Exceptional, (6)
"We had a perfect three night stay. The house is well appointed with comfortable beds, sheets, and towels. We used the bikes and kayaks and everything was in working order. We would gladly stay again!"
The price is NZ$1,903
includes taxes & fees
28 July - 29 July
🐚Shell City on Lt Island

New! High Tide Hideaway: Waterfront/Dog-Friendly

10.0 out of 10, Exceptional, (3)
"We had a lovely stay at the Hideaway beach front property! This property is in a breathtaking location, with gorgeous views from the house and deck, along with easy access to the beach for leisurely walks and sunset views. We were so happy to be able to bring our dog along , he absolutely loved it as well! Very easy check in/out process, along with easy and personable communication with our host! Thank you, Tara, we would definitely recommend and would love to come back!"
The price is NZ$1,896
includes taxes & fees
17 July - 18 July
New! High Tide Hideaway: Waterfront/Dog-Friendly

Luxe Lakefront Retreat ★ Sauna ★ Media Rm ★ Kayaks ★ Bikes ★ Steps to Bike-Path★

The price is NZ$2,309
includes taxes & fees
31 July - 1 Aug
Luxe Lakefront Retreat ★ Sauna ★ Media Rm ★ Kayaks ★ Bikes ★ Steps to Bike-Path★
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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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?

Breathtaking Riverfront Home with a Lovely Deck, Close to Beach - Dogs OK: This highly rated holiday home rental in Chatham is located on a river, and has a patio, a selection of games and air conditioning to put you at ease 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. Some other top choices in Chatham are Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK and Cozy Retreat in South Chatham (2374).

How many holiday rentals are there in Chatham?

With 294 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 Atwood House Museum and Gallery Antonia, whereas Chatham Lighthouse Beach and Ridgevale Beach are a couple of picturesque spots to enjoy the outdoors. While here, Chatham Fish Pier 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.