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

Chatham Vacation Rentals

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  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Aug 28 - Aug 30
In two months
Oct 9 - Oct 11
In three months
Nov 6 - Nov 8
In four months
Dec 4 - Dec 6

Our top choices for Chatham vacation rentals

TV, offices

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.
$484 nightly
The price is $554
Sep 9 - Sep 10
Total with taxes and fees
Seaside condo with patio, beach access, loft, board games, gas grill, & firepit
TV, fireplace

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.
$642 nightly
The price is $734
Aug 30 - Aug 31
Total with taxes and fees
Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK
Sun loungers, beach towels

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.
$743 nightly
The price is $850
Sep 1 - Sep 2
Total with taxes and fees
Beautiful home near Jacknife Beach and bike trail
Exterior

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

Stunning Beach Retreat - Walk to Beach - Chatham Bars Inn - Town + Game Room
Chatham
10.0 out of 10, Exceptional, (21 reviews)
"House was wonderful with plenty of room. Great outdoor spaces with a deck and patio. Very convenient location. Host responsive to our needs. Would definitely stay again. "
United States
Sally S.
$1,814 nightly
The price is $2,076
Sep 8 - Sep 9
Total with taxes and fees
Stunning Beach Retreat - Walk to Beach - Chatham Bars Inn - Town + Game Room
Outdoor dining

5. 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.
$617 nightly
The price is $706
Aug 23 - Aug 24
Total with taxes and fees
Great for Families! Brewster Home 6 Mi to Beach
House (3 Bedrooms) | Front of property

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

6 Mi to Beach: Home w/ Deck in Brewster!
3.0 star property
Brewster
$603 nightly
The price is $690
Aug 17 - Aug 18
Total with taxes and fees
6 Mi to Beach: Home w/ Deck in Brewster!
Pool

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

Cozy Large Home in Harwich with Patio near Wequassett Resort
Harwich
9.8 out of 10, Exceptional, (13 reviews)
"Host was very responsive and the house provided everything we needed. Great location! "
United States
Ashley M.
$495 nightly
The price is $548
Sep 7 - Sep 8
Total with taxes and fees
Cozy Large Home in Harwich with Patio near Wequassett Resort
Sun loungers

8. 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 traveler
$413 nightly
The price is $473
Aug 30 - Aug 31
Total with taxes and fees
Quiet getaway in a unique area of Cape Cod
Beach nearby

9. 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, (23 reviews)
"Facility was excellent"
United States
Joe K.
$632 nightly
The price is $723
Sep 12 - Sep 13
Total with taxes and fees
Ocean Edge Resort ground-floor condo with access to pools, hot tub, & tennis
Outdoor dining

10. 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, (8 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.
$680 nightly
The price is $778
Sep 8 - Sep 9
Total with taxes and fees
Walk to Wychmere, Beach & Downtown Harwich - Firepit, Fenced Yard & AC!
Outdoor dining

11. 2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill

2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill
Dennis
9.8 out of 10, Exceptional, (199 reviews)
"Great property. So happy to find a rental welcoming to our pets. "
United States
Laura R.
$326 nightly
The price is $373
Aug 16 - Aug 17
Total with taxes and fees
2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill
TV, DVD player, offices

12. 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.
$476 nightly
The price is $544
Sep 1 - Sep 2
Total with taxes and fees
Adorable Cape Escape W/ Private Beach Access, Full Kitchen, & Perfect Location
Exterior

13. Family Cottage Close to Beach!!

Family Cottage Close to Beach!!
Harwichport
9.8 out of 10, Exceptional, (78 reviews)
"Everything was exactly as described - they provided beach towels and chairs which we used - the property was perfect for our stay"
United States
John N.
$754 nightly
The price is $863
Sep 6 - Sep 7
Total with taxes and fees
Family Cottage Close to Beach!!
Smart TV, fireplace, books

14. 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.
$706 nightly
The price is $807
Sep 2 - Sep 3
Total with taxes and fees
Beautiful cottage, Close to Wychmere & Beach, Family relax, king bed & fire pit!
Sun loungers

15. 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.
$514 nightly
The price is $588
Sep 1 - Sep 2
Total with taxes and fees
Eastham, Cape Cod - Town Cove Waterfront. Newly renovated and insulated sunporch
TV, offices

16. 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)
"We loved the house. Simple and comfortable, exactly what we needed to relax. thank you."
United States
Michael M.
$713 nightly
The price is $816
Sep 8 - Sep 9
Total with taxes and fees
Cheery house with deck, sunroom & patio - short walk to pond, beach & Rail Trail
Beach

17. Cape Cod Oceanside Condo across from beach!

Cape Cod Oceanside Condo across from beach!
Dennis
9.0 out of 10, Wonderful, (21 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
$341 nightly
The price is $390
Aug 31 - Sep 1
Total with taxes and fees
Cape Cod Oceanside Condo across from beach!
4 bedrooms, iron/ironing board, WiFi, bed sheets

18. 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, (3 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.
$849 nightly
The price is $971
Aug 23 - Aug 24
Total with taxes and fees
Harwich Port Hideaway: 3-bedroom pet-friendly house with AC for relaxing stays
Beach nearby, sun loungers, beach towels

19. 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, (33 reviews)
"We had a wonderful time and great weather!!!"
United States
Peter C.
$516 nightly
The price is $590
Sep 3 - Sep 4
Total with taxes and fees
Cape Cod Beach Cottage-2 bdrm, 1 bath, full kitchen and two minute walk to beach
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

All Seasons Resort, Trademark Collection by Wyndham

All Seasons Resort, Trademark Collection by Wyndham

8/10 Good
"A lovely, well-kept hotel. The pools and gym were a real bonus and the beds were comfy. Reception staff were very welcoming and really helpful. Only downside was breakfast. Great for waffles and coffee. One of our party needed gluten free and we accept that this isn't always possible to accommodate , but there were no ingredient lists available and the breakfast lady just gave a flat 'no' and was unhelpful. Such a shame as the other staff were so helpful and friendly. Hyannis is a nice place to visit nearby."
Kerry 2-night trip
Posted 9 hours ago
All Seasons Resort, Trademark Collection by Wyndham

Find out more about Chatham

Everything you need to know about Chatham vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Chatham vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Chatham vacation 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 low season months. For more hustle and bustle, you may prefer to visit Chatham in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $308 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Chatham rentals

At Expedia, we put the best Chatham vacation 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 vacation.

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.

Explore a world of travel with Expedia

Frequently asked questions

Can I find a vacation rental in Chatham?

Yes, you can find vacation rentals in Chatham close to Chatham Railroad Museum, or you can select a more secluded option if you'd like a relaxing place to 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 vacation rentals that Chatham has to offer?

Private Sandy Beach, Truly Oceanfront,Private Decks, Free Kayak, Sleeps 5: You might want to consider this vacation home rental near Chatham, which is located on the beach and has a balcony, a selection of games, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave.

How many vacation rentals are there in Chatham?

With 277 Expedia vacation rentals, you're sure 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 Atwood House Museum, whereas Cape Cod Beaches and Chatham Lighthouse Beach are a couple of picturesque spots to enjoy the outdoors. While here, Chatham Lighthouse and Ridgevale Beach are other places worth a visit.

What are vacation rentals like in Chatham?

Vacation rentals are privately owned properties you can stay in for several days or longer in Chatham. Vacation rentals offer amenities such as laundry facilities and kitchens so you'll be comfy for your stay. If you're concerned about a sanitized environment, a vacation rental can provide a sense of privacy away from shared hotel elevators and lobbies bustling with people while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a hotel, which makes a vacation rental an attractive option for family trips or small group gatherings.