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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Our top choices for Chatham vacation 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.
$452 nightly
The price is $518
Sep 14 - Sep 15
Total with taxes and fees
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.
$575 nightly
The price is $659
Aug 31 - Sep 1
Total with taxes and fees
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

Chatham Break! 3 BR, A/C, Outdoor Shower + Deck, Near Beaches, Large Quiet Yard
Chatham
10.0 out of 10, Exceptional, (106 reviews)
"Great stay. House is in a great location and is well maintained. Bonnie was super helpful. "
United States
Will M.
$596 nightly
The price is $682
Sep 10 - Sep 11
Total with taxes and fees
Chatham Break! 3 BR, A/C, Outdoor Shower + Deck, Near Beaches, Large Quiet Yard

4. Beautiful home near Jacknife Beach and bike trail

Beautiful home near Jacknife Beach and bike trail
Chatham
9.8 out of 10, Exceptional, (84 reviews)
"This is second time to stay here! We love the location and hospitality of the hosts! Great place!"
United States
Barbara P.
$615 nightly
The price is $704
Sep 15 - Sep 16
Total with taxes and fees
Beautiful home near Jacknife Beach and bike trail

5. 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.
$1,773 nightly
The price is $2,029
Sep 8 - Sep 9
Total with taxes and fees
Stunning Beach Retreat - Walk to Beach - Chatham Bars Inn - Town + Game Room

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 23 - Aug 24
Total with taxes and fees
6 Mi to Beach: Home w/ Deck in Brewster!

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.
$496 nightly
The price is $549
Sep 7 - Sep 8
Total with taxes and fees
Cozy Large Home in Harwich with Patio near Wequassett Resort

8. Brewster Green Resort

Brewster Green Resort
3.5 star property
Brewster
9.4 out of 10, Exceptional, (141 reviews)
"Nice resort. Well maintained, very quiet, off the beaten path. Everything in good working order, Staff very nice. Will stay here again. Great location!"
United States
Kevin
$239 nightly
The price is $274
Sep 15 - Sep 16
Total with taxes and fees
Brewster Green Resort

9. 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 29 - Aug 30
Total with taxes and fees
Quiet getaway in a unique area of Cape Cod

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

On Town Cove with salt water access! Kayaks and paddle board available for use!
Eastham
9.8 out of 10, Exceptional, (63 reviews)
"Clean, great location. "
United States
Peter G.
$365 nightly
The price is $418
Sep 12 - Sep 13
Total with taxes and fees
On Town Cove with salt water access! Kayaks and paddle board available for use!

11. 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

12. 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!!

13. 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, (5 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.
$686 nightly
The price is $786
Sep 2 - Sep 3
Total with taxes and fees
Beautiful cottage, Close to Wychmere & Beach, Family relax, king bed & fire pit!

14. 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, (120 reviews)
"perfect for couples, clean and pet friendly"
Canada
Jonathan
$306 nightly
The price is $350
Sep 17 - Sep 18
Total with taxes and fees
Stay in a TINY HOUSE!★0.4mi to Beach★Village★Restaurants★Pet Friendly ★ 2 bikes!

15. 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, (200 reviews)
"Superb stay! Everything was perfect for our family of 6. Close location to everything we had planned for the week. Thank you for the great experience! "
United States
Matt D.
2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill

16. 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)
"Excellent location "
United States
Norman Y.
$646 nightly
The price is $739
Sep 8 - Sep 9
Total with taxes and fees
Walk to Wychmere, Beach & Downtown Harwich - Firepit, Fenced Yard & AC!

17. 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)
"House was perfect for our family reunion! "
United States
Gregg H.
$654 nightly
The price is $748
Sep 16 - Sep 17
Total with taxes and fees
Cheery house with deck, sunroom & patio - short walk to pond, beach & Rail Trail

18. The Brewster Pearl

The Brewster Pearl
Brewster
10.0 out of 10, Exceptional, (2 reviews)
"The home is so beautiful and the decor is like out of a magazine. Immaculately clean, our standards are high, being hosts ourselves. Every amenity thoughtfully provided. The furnishings, bedding, towels are of premium quality and top brand. Our host was incredible, responsive, kind and helpful. This home is perfectly located to many beaches , excellent restaurants and coffee shops. Brewster is a special place. I can understand why the owner chose it. Our family was immensely blessed to have the...
United States
PAULA
$629 nightly
The price is $720
Sep 17 - Sep 18
Total with taxes and fees
The Brewster Pearl

19. 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.
$436 nightly
The price is $500
Sep 16 - Sep 17
Total with taxes and fees
Adorable Cape Escape W/ Private Beach Access, Full Kitchen, & Perfect Location

20. Beach Chic Chatham 5 Star 5 Min Walk to Beach-Newly Renovated Private Retreat AC

Beach Chic Chatham 5 Star 5 Min Walk to Beach-Newly Renovated Private Retreat AC
Chatham
10.0 out of 10, Exceptional, (88 reviews)
"Loved our stay. The location is a perfect central point for exploring Cape Cod. Plenty of amenities in the home, bikes, beach supplies. Well equipped home and John was so helpful the entire stay. "
United States
Ed N.
$1,164 nightly
The price is $1,332
Sep 7 - Sep 8
Total with taxes and fees
Beach Chic Chatham 5 Star 5 Min Walk to Beach-Newly Renovated Private Retreat AC
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 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 $274 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.

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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.