Chatham Holiday Rentals from AU$279: Search Short-Term Rentals

Q: What are some of the best holiday rentals that Chatham has to offer?

Cape Cod's "Beach Rose" : This holiday home rental outside of Chatham offers a patio, a selection of games and a BBQ to help you feel perfectly comfortable 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.

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Our top choices for Chatham holiday rentals

A spacious living area with a large window, a wooden ceiling, a television, and a sofa.

1. Seaside condo with patio, beach access, loft, board games, gas grill, & firepit

Chatham

Elizabeth T.

includes taxes & fees

2 Sept - 3 Sept

A room with a blue sofa, wicker chairs, a round table, a wall-mounted lamp, and a glass door leading outside.

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

Chatham

Erin M.

includes taxes & fees

29 Sept - 30 Sept

A kitchen with white cabinets, a dining table with chairs, a grill outside, and a view of trees through the window.

3. Chatham Break! 3 BR, A/C, Outdoor Shower + Deck, Near Beaches, Large Quiet Yard

Chatham

Will M.

includes taxes & fees

10 Sept - 11 Sept

A lighthouse with a cylindrical tower and a white building with a red roof.

4. Quaint & Cozy Downtown Chatham Home, Walk to Town and Beaches

Chatham

Corinne J.

includes taxes & fees

29 Sept - 30 Sept

5. Town Center-Full Reno 2026-Steps To Shops & Eateries-Walk To Lighthouse Beach

Chatham

Claudine

A sandy beach with a grassy path leading to the water.

6. Beautiful home near Jacknife Beach and bike trail

Chatham

Barbara P.

includes taxes & fees

1 Oct - 2 Oct

A lakeside setting with a wooden bench, chairs, and a picnic table.

7. Spacious 4BR house in perfect Chatham with AC

Chatham

A two-story house with a covered porch and a stone staircase leading to the entrance.

8. Stunning Beach Retreat - Walk to Beach - Chatham Bars Inn - Town + Game Room

Chatham

Sally S.

includes taxes & fees

21 Sept - 22 Sept

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Top Chatham Hotel Reviews

The Villages at Ocean Edge

10/10 Excellent

"Okokokok"

Lighthouse Inn

10/10 Excellent

"Excellent location! You’re right on the beach and right next to West Dennis beach for long walks. Lots of activities available for kids & adults. Enjoyed the Meridian Restaurant. Ate there multiple times and both my husband and I had a very good meal every time. I marveled at the amount of help they have to make things run smoothly. Based on some of the reviews I had read, this apparently had been problematic initially but certainly isn’t the case now. All staff were delightful to deal with."

Queen Anne Inn

8/10 Good

"7/10 — Charming property with room for improvement We stayed for two nights this past weekend and overall had a pleasant stay. We were in the back cottage, and the room itself was totally fine. I especially liked the hardwood floors, and we had no major concerns with the room during our stay. The bathroom could use some updating, but everything was functional. The main building has a cute, eclectic New England feel, with some really charming sitting areas and common spaces. There’s definitely a lot of character to the property, and with a few updates and a little more attention to the grounds, I think it could be a really lovely place. One area that stood out was the upkeep of the outdoor spaces. There were tables and chairs with quite a few fallen leaves sitting on them throughout the weekend, which made the outdoor areas feel a bit less inviting than they could have been. A little more regular maintenance would make a noticeable difference. The front desk receptionist was wonderful. She was very friendly and checked in with us a couple of times throughout the weekend to make sure everything was going well and that we didn’t need anything, which we really appreciated. Overall, we had a good stay and everything went smoothly. The property has a lot of charm and potential, and I think some updates to the bathrooms and a bit more attention to the outdoor grounds could really elevate the experience."

Pleasant Bay Village Resort

10/10 Excellent

"A wonderful place to stay in Chatham. Literally a five minute drive to the pier fish market, Main Street and the beach. Check in was easy and the staff person was very helpful in pointing out places to eat and places to go both in Chatham and nearby Orleans. The room was very clean, spacious and the turn down service was excellent. They have a great pool and hot tub. They also have a koi fish pond that is beautiful. We especially enjoyed the outdoor tables in the courtyards of each area. We were able to bring back lobster rolls from the fish market and enjoy a nice al fresco dinner. We then ran into the cleaning who offered to take our garbage from us, which was so helpful as it prevented us from stinking up the room. I would definitely recommend this resort to anyone staying n Chatham. Well worth it!"

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 favourite 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 depend 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 AU$279 per night. Entering your travel dates in the search wizard might find you 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?

Cape Cod's "Beach Rose": This holiday home rental outside of Chatham offers a patio, a selection of games and a BBQ to help you feel perfectly comfortable 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.

How many holiday rentals are there in Chatham?

With 277 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 Railroad Museum and Chatham Drama Guild, 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.

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Check prices for these dates

Our top choices for Chatham holiday rentals

1. 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

3. Chatham Break! 3 BR, A/C, Outdoor Shower + Deck, Near Beaches, Large Quiet Yard

4. Quaint & Cozy Downtown Chatham Home, Walk to Town and Beaches

5. Town Center-Full Reno 2026-Steps To Shops & Eateries-Walk To Lighthouse Beach

6. Beautiful home near Jacknife Beach and bike trail

7. Spacious 4BR house in perfect Chatham with AC

8. Stunning Beach Retreat - Walk to Beach - Chatham Bars Inn - Town + Game Room

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

10. 6 Mi to Beach: Home w/ Deck in Brewster!

11. Brewster Green Resort

12. Cozy Large Home in Harwich with Patio near Wequassett Resort

13. The Beachcomber Unit - #9

14. Stay in a TINY HOUSE!★0.4mi to Beach★Village★Restaurants★Pet Friendly ★ 2 bikes!

15. Harbor Hideaway Unit- #6

16. Family Cottage Close to Beach!!

17. On Town Cove with salt water access! Kayaks and paddle board available for use!

18. Cheery house with deck, sunroom & patio - short walk to pond, beach & Rail Trail

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

Find holiday rentals that suit your style

Top Chatham Hotel Reviews

The Villages at Ocean Edge

Lighthouse Inn

Cape Sands Inn

Holiday Hill Inn & Suites

Queen Anne Inn

Holiday Inn Express Hyannis Cape Cod by IHG

Sunbird Cape Cod Resort

Pleasant Bay Village Resort

Freebird Motor Lodge by Reverie Boutique Collection

Find out more about Chatham

Frequently asked questions

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