Search Vacation Homes in Chatham

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Vacation Homes in Chatham

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

9.6 out of 10, Exceptional, (93)
"Great location"
The price is ¥25,955
¥83,066 total
includes taxes & fees
Jun 25 - Jun 26
Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK

Charming 2 bedroom condo on Private Beach by Outer Most Marina

9.4 out of 10, Exceptional, (3)
"Good to be near the water. Very pretty. "
The price is ¥42,775
¥84,304 total
includes taxes & fees
Jul 5 - Jul 6
Charming 2 bedroom condo on Private Beach by Outer Most Marina

The Pet-Friendly Surf Shack Hideaway on the Cove

10.0 out of 10, Exceptional, (15)
"Beautiful home, great location , quiet , pictures do not convey how nice the property is. "
The price is ¥43,822
¥99,441 total
includes taxes & fees
Jun 24 - Jun 25
The Pet-Friendly Surf Shack Hideaway on the Cove

Jaws Nest~Dog Friendly~Oceanside Beauty

The price is ¥43,187
¥99,214 total
includes taxes & fees
Jun 24 - Jun 25
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 ¥93,164
¥178,650 total
includes taxes & fees
Jun 23 - Jun 24
Beachside Bliss: Modern Comfort Steps from Scenic Trails, Sleeps 10!

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

10.0 out of 10, Exceptional, (11)
"Property was clean and as described in the listing, owner was communicative and easy to check in"
The price is ¥261,000
¥454,877 total
includes taxes & fees
Jun 22 - Jun 23
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 ¥76,560
¥147,533 total
includes taxes & fees
Jul 14 - Jul 15
Cape Cod Sunscape.

Pondside/Kayak/Firepit/Dog Friendly~Willow Haven

10.0 out of 10, Exceptional, (2)
"Cosy retreat with pond view. Great for canoeing with the dog. Sweet porch for reading and morning coffee. Tara was an excellent host who communicated immediately and went well above and beyond to correct an issue that was out of her control.A great central location that allowed us to roam freely to our favorite beaches, hikes, and restaurants. We will gladly return in the future. "
The price is ¥27,786
¥60,014 total
includes taxes & fees
Jun 25 - Jun 26
Pondside/Kayak/Firepit/Dog Friendly~Willow Haven

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 ¥67,480
¥126,353 total
includes taxes & fees
Jul 2 - Jul 3
Pond House~Waterfront Oasis W/Jacuzzi Tub

Cozy Large Home in Harwich with Patio near Wequassett Resort

9.8 out of 10, Exceptional, (7)
"We had a great time here - the kids’ room is truly special!"
Cozy Large Home in Harwich with Patio near Wequassett Resort

Eastham is Cape Cod’s best kept secret!

9.8 out of 10, Exceptional, (6)
"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 ¥144,855
¥255,732 total
includes taxes & fees
Jul 15 - Jul 16
Eastham is Cape Cod’s best kept secret!

Gray Whale - 3 bedrm/2 bath/gameroom

The price is ¥31,437
¥83,773 total
includes taxes & fees
Jun 25 - Jun 26
Gray Whale - 3 bedrm/2 bath/gameroom

Driftmoor~Dog Frndly 3bd/2 bth~Luxe

The price is ¥48,745
¥108,397 total
includes taxes & fees
Jun 25 - Jun 26
Driftmoor~Dog Frndly 3bd/2 bth~Luxe

The Alpine/Walk to Beach for 2 or more!

8.8 out of 10, Excellent, (8)
"This home was in an amazing location. The beach is fantastic. The home has everything you need. Best part was outside space, great outdoor shower and big table in screened in porch for family games and cards!"
The price is ¥73,354
¥132,246 total
includes taxes & fees
Jun 23 - Jun 24
The Alpine/Walk to Beach for 2 or more!

New! Sandy Point-Private beach/Dog Friendly

The price is ¥48,427
¥113,010 total
includes taxes & fees
Jun 30 - Jul 1
New! Sandy Point-Private beach/Dog Friendly

Beachfront~Seaside Sea-duction-Dog Friendly

10.0 out of 10, Exceptional, (7)
"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."
The price is ¥154,329
¥244,505 total
includes taxes & fees
Jul 12 - Jul 13
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 ¥45,887
¥96,496 total
includes taxes & fees
Jun 26 - Jun 27
Ebb Tide~3b/2b and dog friendly for 2-10

Sand Bar-Dog Friendly on Cooks Brook Beach

10.0 out of 10, Exceptional, (16)
"Hope to be back soon!"
Sand Bar-Dog Friendly on Cooks Brook Beach

🐚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 ¥51,285
¥119,932 total
includes taxes & fees
Jun 25 - Jun 26
🐚Shell City on Lt Island

New! High Tide Hideaway: Waterfront/Dog-Friendly

10.0 out of 10, Exceptional, (2)
"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 ¥80,232
¥171,526 total
includes taxes & fees
Jun 25 - Jun 26
New! High Tide Hideaway: Waterfront/Dog-Friendly
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.
Save an average of 15% on thousands of hotels when you're signed in