A boat on a calm river, a large house with a red roof, and dense greenery in the background.

Chatham Holiday Rentals

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Our top choices for Chatham holiday rentals

1. 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 NZ$1,036
includes taxes & fees
2 Sept - 3 Sept
Seaside condo with patio, beach access, loft, board games, gas grill, & firepit

2. 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, (104 reviews)
"Our second year in a row staying here. Cute house and great location! "
United States
Erin M.
The price is NZ$1,203
includes taxes & fees
9 Aug - 10 Aug
Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK

3. Beautiful home near Jacknife Beach and bike trail

Beautiful home near Jacknife Beach and bike trail
Chatham
9.8 out of 10, Exceptional, (83 reviews)
"This is second time to stay here! We love the location and hospitality of the hosts! Great place!"
United States
Barbara P.
The price is NZ$1,419
includes taxes & fees
1 Sept - 2 Sept
Beautiful home near Jacknife Beach and bike trail

4. Great for Families! Brewster Home 6 Mi to Beach

Great for Families! Brewster Home 6 Mi to Beach
Brewster
9.8 out of 10, Exceptional, (10 reviews)
"The kitchen was well stocked. The Beds were comfortable. "
United States
Stacey P.
The price is NZ$1,198
includes taxes & fees
23 Aug - 24 Aug
Great for Families! Brewster Home 6 Mi to Beach

5. 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 NZ$1,172
includes taxes & fees
1 Sept - 2 Sept
6 Mi to Beach: Home w/ Deck in Brewster!

6. Quiet getaway in a unique area of Cape Cod

Quiet getaway in a unique area of Cape Cod
Brewster
10.0 out of 10, Exceptional, (5 reviews)
"Perfect for a quiet getaway. Owner was in Constant contact. If I had a question replied very quickly. I highly recommend staying here."
United States
Anonymous traveller
The price is NZ$797
includes taxes & fees
30 Aug - 31 Aug
Quiet getaway in a unique area of Cape Cod

7. 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, (22 reviews)
"Facility was excellent"
United States
Joe K.
The price is NZ$1,061
includes taxes & fees
1 Sept - 2 Sept
Ocean Edge Resort ground-floor condo with access to pools, hot tub, & tennis

8. 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, (26 reviews)
"Loved this property. "
United States
Carol S.
The price is NZ$911
includes taxes & fees
2 Sept - 3 Sept
Adorable Cape Escape W/ Private Beach Access, Full Kitchen, & Perfect Location

9. Beautiful cottage, Close to Wychmere & Beach, Family relax, king bed & fire pit!

Beautiful cottage, Close to Wychmere & Beach, Family relax, king bed & fire pit!
Harwich
9.6 out of 10, Exceptional, (4 reviews)
"We had an amazing stay! The house was exactly what we were looking for when booking. The host was amazing and accommodating for our dates. Communication was easy and responsive. We look forward to booking again in the future. "
United States
Laura J.
The price is NZ$1,348
includes taxes & fees
2 Sept - 3 Sept
Beautiful cottage, Close to Wychmere & Beach, Family relax, king bed & fire pit!

10. 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
9.8 out of 10, Exceptional, (118 reviews)
"perfect for couples, clean and pet friendly"
Canada
Jonathan
The price is NZ$775
includes taxes & fees
10 Aug - 11 Aug
Stay in a TINY HOUSE!★0.4mi to Beach★Village★Restaurants★Pet Friendly ★ 2 bikes!

11. Eastham, Cape Cod - Town Cove Waterfront. Newly renovated and insulated sunporch

Eastham, Cape Cod - Town Cove Waterfront. Newly renovated and insulated sunporch
Eastham
9.0 out of 10, Wonderful, (100 reviews)
"Awesome location, private and peaceful."
United States
Kathy D.
The price is NZ$966
includes taxes & fees
1 Sept - 2 Sept
Eastham, Cape Cod - Town Cove Waterfront. Newly renovated and insulated sunporch

12. Walk to Wychmere, Beach & Downtown Harwich - Firepit, Fenced Yard & AC!

Walk to Wychmere, Beach & Downtown Harwich - Firepit, Fenced Yard & AC!
Harwich
10.0 out of 10, Exceptional, (7 reviews)
"House is adorable, sparkling clean and comfy. The backyard is wonderful! Our host was responsive and helpful. We would stay again if we visit the area. "
United States
SUSAN M.
The price is NZ$1,386
includes taxes & fees
2 Sept - 3 Sept
Walk to Wychmere, Beach & Downtown Harwich - Firepit, Fenced Yard & AC!

13. Cape Cod Oceanside Condo across from beach!

Cape Cod Oceanside Condo across from beach!
Dennis
8.8 out of 10, Excellent, (20 reviews)
"Checkin was easy. Very friendly staff. Location was across the street from the beach. If you parked at the beach, it would cost $35. Had a nice pool if you did not use the beach."
United States
philip
The price is NZ$435
includes taxes & fees
3 Sept - 4 Sept
Cape Cod Oceanside Condo across from beach!

14. 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, (8 reviews)
"Lovely property with attentive hosts "
United States
marian t.
The price is NZ$2,650
includes taxes & fees
3 Sept - 4 Sept
Cape Cod Villa pond front vacation home, retreat, spa, venue, film location

15. Cape Cod Beach Cottage-2 bdrm, 1 bath, full kitchen and two minute walk to beach

Cape Cod Beach Cottage-2 bdrm, 1 bath, full kitchen and two minute walk to beach
Dennisport
10.0 out of 10, Exceptional, (31 reviews)
"We had a wonderful time and great weather!!!"
United States
Peter C.
The price is NZ$969
includes taxes & fees
3 Sept - 4 Sept
Cape Cod Beach Cottage-2 bdrm, 1 bath, full kitchen and two minute walk to beach

16. Harwich Port Hideaway: 3-bedroom pet-friendly house with AC for relaxing stays

Harwich Port Hideaway: 3-bedroom pet-friendly house with AC for relaxing stays
Harwich
10.0 out of 10, Exceptional, (2 reviews)
"We loved staying at this beautiful house in Harwich. The property was clean, cozy and felt just like home. There was a fenced in back yard which was perfect for our dog and kids. Very private and close to shops, restaurants and the beach. We look forward to visiting again in the future!"
United States
Nicole M.
The price is NZ$1,247
includes taxes & fees
16 Aug - 17 Aug
Harwich Port Hideaway: 3-bedroom pet-friendly house with AC for relaxing stays

17. The Captain's Quarters Suite Unit - 10

The Captain's Quarters Suite Unit - 10
Harwich
10.0 out of 10, Exceptional, (17 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 NZ$772
includes taxes & fees
20 Aug - 21 Aug
The Captain's Quarters Suite Unit - 10

18. Luxury Romantic 'Studio by the Beach' Free WiFi, Central Air and Heat

Luxury Romantic 'Studio by the Beach' Free WiFi, Central Air and Heat
Dennis
9.6 out of 10, Exceptional, (105 reviews)
"Had a great Cape Cod vacation. The location was perfect for our needs."
United States
Jessica M.
The price is NZ$655
includes taxes & fees
1 Sept - 2 Sept
Luxury Romantic 'Studio by the Beach' Free WiFi, Central Air and Heat

19. 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
4.0 out of 10, (1 review)
"Excellent vacation in a great spot but the property needs some care."
United States
Art E.
The price is NZ$953
includes taxes & fees
2 Sept - 3 Sept
Family-friendly house w/gas grill, deck, streaming services - near Haigis Beach

20. The Beachcomber Unit - #9

The Beachcomber Unit - #9
Harwich
9.8 out of 10, Exceptional, (20 reviews)
"We had an amazing time staying here, great location and it was very clean. "
United States
Mike B.
The price is NZ$828
includes taxes & fees
13 Aug - 14 Aug
The Beachcomber Unit - #9
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$913 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?

Private Sandy Beach, Truly Oceanfront,Private Decks, Free Kayak, Sleeps 5: This holiday home rental outside of Chatham is located on the beach, and has a balcony, a selection of games and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave.

How many holiday rentals are there in Chatham?

With 281 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 Chatham Drama Guild and Caleb Nickerson House, 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.