Chatham Vacation Rentals

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Vacation Rentals in Chatham

Chatham Seaside Cottage - Oceanfront Beach Cottage - Spectacular Views

Chatham Seaside Cottage - Oceanfront Beach Cottage - Spectacular Views

Chatham, MA
Nestled on the beach, this Chatham cottage is within a 5-minute walk of Ridgevale Beach and Cockle Cove Beach. Forest Beach and Hardings Beach are also within ...
5/5 Exceptional! (54 reviews)
Amazing stay
"My dad and I stayed here for thanksgiving and it was lovely! Scott was so helpful and accommodating throughout the entire process. The best part about the place is that it is right on the beach!! We saw beautiful sunsets and had a fun time exploring Chatham!!"

Reviewed on Nov 29, 2021

Chatham Seaside Cottage - Oceanfront Beach Cottage - Spectacular Views
Chatham Village - Adorable Studio Apartment in Antique Home

Chatham Village - Adorable Studio Apartment in Antique Home

Chatham, MA
Located in the heart of Chatham, this apartment building is within a 15-minute walk of Chatham Windmill, Monomoy Theatre, and Chatham Seaside Links. Chatham ...
4.5/5 Wonderful! (50 reviews)
Location Location Location
"Beautiful 19th century home located just one block from downtown, an easy walk to restaurants and shopping. Perfect for two people. Privacy low as people in the adjacent unit could be heard through door/wall. Recommended that our family put on their suggestion list for visitors."

Reviewed on Dec 7, 2021

Chatham Village - Adorable Studio Apartment in Antique Home
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, MA
The price is $134 per night from Jan 23 to Jan 24
Situated by the sea, this historic vacation home is within 1 mi (2 km) of Ridgevale Beach and Hardings Beach. Hardings Lighthouse and Monomoy Theatre are also ...
4.5/5 Wonderful! (25 reviews)
Beautiful house with great location and yard
"Beautiful house in a great location, with a great yard. I’d highly recommend it."

Reviewed on Nov 8, 2021

Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK!
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New Lavish Condo in Heart of Downtown Chatham - Walk to Dining, Shops & Beach

New Lavish Condo in Heart of Downtown Chatham - Walk to Dining, Shops & Beach

Chatham, MA
Situated by the sea, this vacation home is within a 10-minute walk of Chatham Windmill and Monomoy Theatre. Chatham Seaside Links and Chatham Railroad Museum ...
4.6/5 Exceptional! (17 reviews)
Great location and beautiful apartment
"The quality of this apartment was excellent and the location is perfect, walkable to Chatham very easily. Although we hit the visit during a nor’easter it was still a nice time."

Reviewed on Nov 8, 2021

New Lavish Condo in Heart of Downtown Chatham - Walk to Dining, Shops & Beach
Quiet, luxury retreat surrounded by serene gardens and landscaping

Quiet, luxury retreat surrounded by serene gardens and landscaping

Chatham, MA
Situated near the beach, this apartment building is within 1 mi (2 km) of Chatham Chamber of Commerce, Ridgevale Beach, and Cockle Cove Beach. Forest Beach and ...
5/5 Exceptional! (20 reviews)
Comfortable stay
"Beautiful property. Very spacious and clean We'd stay again."

Reviewed on Oct 15, 2021

Quiet, luxury retreat surrounded by serene gardens and landscaping
Breathtaking riverfront dog-friendly home w/ a lovely deck, close to the beach!

Breathtaking riverfront dog-friendly home w/ a lovely deck, close to the beach!

Chatham, MA
Nestled on the beach, this Chatham vacation home is within 3 mi (5 km) of Ridgevale Beach, Hardings Beach, and Cockle Cove Beach. Forest Beach and Chatham Seaside ...
4/5 Very Good! (19 reviews)
Cute getaway place in serene location
"Quiet and beautiful spot on Oyster River. Open first floor plan allows for sunlight and breeze. Great wraparound porch / deck. 5 minute drive to Hardings Beach. 10 minute drive to Downtown Chatham. What you see in the pictures is what you get. Some minor housekeeping items for management: 1. there ..."

Reviewed on Jul 27, 2021

Breathtaking riverfront dog-friendly home w/ a lovely deck, close to the beach!
***WALK TO RESTAURANTS, SHOPS & LIQUOR STORE***CLOSE TO DOWNTOWN CHATHAM!!!

***WALK TO RESTAURANTS, SHOPS & LIQUOR STORE***CLOSE TO DOWNTOWN CHATHAM!!!

Chatham, MA
This family-friendly cottage is located in the city center, within 1 mi (2 km) of Monomoy Theatre, Chatham Railroad Museum, and Chatham Drama Guild. Chatham ...
4.8/5 Exceptional! (52 reviews)
Delightful cottage
"This sweet cottage is clean and comfortable, stocked with all the things needed to make our stay with our three young kids easy. We loved it!"

Reviewed on Oct 12, 2021

***WALK TO RESTAURANTS, SHOPS & LIQUOR STORE***CLOSE TO DOWNTOWN CHATHAM!!!
Old Village - The Windmill Cottage! Walk to Beach & Town!

Old Village - The Windmill Cottage! Walk to Beach & Town!

Chatham, MA
This family-friendly Chatham vacation home is located by the sea, within a 10-minute walk of Chatham Lighthouse and Chatham Lighthouse Beach. Chatham Railroad ...
4.9/5 Exceptional! (10 reviews)
Incredible Holiday Getaway
"The Windmill Cottage was such a beautiful property. We stayed for the holidays and we had a wonderful time. The cottage was as advertised and the architecture was very cool. We appreciated the great communication with the hosts and it was truly a pleasure to enjoy the Cape during the off season."

Reviewed on Jan 13, 2022

Old Village - The Windmill Cottage! Walk to Beach & Town!
Newly Renovated Chatham 3 Bedroom/2 Bath Retreat

Newly Renovated Chatham 3 Bedroom/2 Bath Retreat

Chatham, MA
Situated on a river, this vacation home is within 1 mi (2 km) of Chatham Windmill, Monomoy Theatre, and Chatham Railroad Museum. Veterans Field and Chatham Seaside ...
4.4/5 Wonderful! (23 reviews)
Excellent single story property
"We stayed off season but were able to enjoy the property nonetheless. Very clean, good water pressure and heating. No issues with the neighbors."

Reviewed on Oct 31, 2021

Newly Renovated Chatham 3 Bedroom/2 Bath Retreat
Chatham Village - Lovely 2 BR Apartment in Antique Home

Chatham Village - Lovely 2 BR Apartment in Antique Home

Chatham, MA
Located in the heart of Chatham, this historic apartment building is within a 15-minute walk of Chatham Windmill, Monomoy Theatre, and Chatham Seaside Links. ...
4.8/5 Exceptional! (31 reviews)
"Perfect in town mid week getaway. Weather was perfect, house comfortable- easy recommendation"

Reviewed on Nov 12, 2021

Chatham Village - Lovely 2 BR Apartment in Antique Home
Chatham Village:  Lovely 1-Bedroom Apartment in Antique Home

Chatham Village: Lovely 1-Bedroom Apartment in Antique Home

Chatham, MA
Located in the heart of Chatham, this apartment building is within a 15-minute walk of Chatham Windmill, Monomoy Theatre, and Chatham Seaside Links. Chatham ...
4.8/5 Exceptional! (62 reviews)
Great Winter Getaway
"Great stay! The pictures are spot on and the apartment was great. It is an easy walk to Main Street. I'd stay here again!"

Reviewed on Jan 20, 2022

Chatham Village: Lovely 1-Bedroom Apartment in Antique Home
Old Village - The Captain's House!  Walk to Beach & Town!

Old Village - The Captain's House! Walk to Beach & Town!

Chatham, MA
This family-friendly Chatham vacation home is located on the waterfront, within a 10-minute walk of Chatham Lighthouse and Chatham Lighthouse Beach. Chatham ...
4.9/5 Exceptional! (17 reviews)
Special place
"The Captains House is a very special home. Historic and very comfortable. Walking distance to Light House Beach which was my favorite part of our visit to Chatham."

Reviewed on Jan 13, 2022

Old Village - The Captain's House! Walk to Beach & Town!
8 Starfish Lane - Two Bedroom House

8 Starfish Lane - Two Bedroom House

3.5 out of 5
8 Starfish Lane, Chatham, MA
Situated in Chatham, this condo building is within a 15-minute walk of Chatham Lighthouse Beach and Chatham Lighthouse. Monomoy National Wildlife Refuge and ...
8 Starfish Lane - Two Bedroom House
Charming Downtown Chatham

Charming Downtown Chatham

Chatham, MA
Located in the heart of Chatham, this historic condo building is within a 15-minute walk of Chatham Lighthouse Beach, Chatham Seaside Links, and Chatham Windmill. ...
5/5 Exceptional! (15 reviews)
Best Vrbo experience ever!
"This property is an absolute gem for anyone looking to enjoy Chatham and Cape Cod. We (family) stayed here for a week this summer, and it was the perfect spot for us. Ideal location right downtown to walk to coffee, shops, restaurants, and beach. Kitchen was great for trying to save a few bucks on ..."

Reviewed on Aug 23, 2021

Charming Downtown Chatham
504 Old Harbor Road - Six Bedroom House

504 Old Harbor Road - Six Bedroom House

4 out of 5
504 Old Harbor Road, Chatham, MA
Situated in Chatham, this vacation home is within 1 mi (2 km) of Chatham Fish Pier, Chatham Seaside Links, and Chatham Railroad Museum. Veterans Field and Chatham ...
504 Old Harbor Road - Six Bedroom House
#613: Close to Hardings & Ridgevale Beach, Game Room, Dog Friendly!

#613: Close to Hardings & Ridgevale Beach, Game Room, Dog Friendly!

Chatham, MA
This family-friendly Chatham vacation home is located by the sea, within 2 mi (3 km) of Hardings Beach, Ridgevale Beach, and Chatham Chamber of Commerce. Chatham ...
5/5 Exceptional! (24 reviews)
Chillin in Chatham
"Property was far out, and close to everything we needed. Fire pit was perfect for s’mores and we got a blazer going. Very short drive to multiple beaches. Our favorite was cockle cove. Would stay here again. Rock and roll."

Reviewed on Nov 6, 2021

#613: Close to Hardings & Ridgevale Beach, Game Room, Dog Friendly!
#620: FULL RENOVATION - Amazing Location on Main St, Central A/C, Deck w/ Views!

#620: FULL RENOVATION - Amazing Location on Main St, Central A/C, Deck w/ Views!

Chatham, MA
Located in the heart of Chatham, this condo building is within a 15-minute walk of Chatham Windmill, Chatham Seaside Links, and Chatham Lighthouse Beach. Monomoy ...
4.9/5 Exceptional! (20 reviews)
Great place.
"Loved our time there. Location is great and property is cute and clean. Will be returning. Property management staff was awesome as well."

Reviewed on Oct 30, 2021

#620: FULL RENOVATION - Amazing Location on Main St, Central A/C, Deck w/ Views!
Chatham Village:  Charming 3 Room Apartment in Antique Home

Chatham Village: Charming 3 Room Apartment in Antique Home

Chatham, MA
Situated in Chatham, this apartment building is within a 15-minute walk of Chatham Windmill, Monomoy Theatre, and Chatham Seaside Links. Chatham Railroad Museum ...
4.4/5 Wonderful! (36 reviews)
Very convenient place
"Place was less than a block from Chatham town center, but still quiet. I like to run in the mornings, and there were several small roads around where I could easily get a decent workout in. We generally don't stay inside much when we travel so we didn't spend a lot of time in the place, but it definitely ..."

Reviewed on Sep 7, 2021

Chatham Village: Charming 3 Room Apartment in Antique Home
Waterfront Chatham Village, Short Walk to Town & Lighthouse Beach

Waterfront Chatham Village, Short Walk to Town & Lighthouse Beach

Chatham, MA
This family-friendly Chatham vacation home is located on the waterfront, within a 15-minute walk of Chatham Lighthouse Beach, Chatham Seaside Links, and Monomoy ...
5/5 Exceptional! (61 reviews)
Winter Weekend
"We had a perfect weekend! The house was exactly as advertised and perfect for the Chatham stroll."

Reviewed on Dec 28, 2021

Waterfront Chatham Village, Short Walk to Town & Lighthouse Beach
#601: Private, great location, new outdoor dining, outdoor shower, dog friendly!

#601: Private, great location, new outdoor dining, outdoor shower, dog friendly!

Chatham, MA
This family-friendly Chatham vacation home is located by the sea, within 2 mi (3 km) of Monomoy Theatre, Chatham Railroad Museum, and Ridgevale Beach. Hardings ...
4.4/5 Wonderful! (17 reviews)
Wonderful spot!
"This home is in a great location and has great amenities. The yard is very private and we enjoyed spending family time there with our dogs."

Reviewed on Aug 22, 2021

#601: Private, great location, new outdoor dining, outdoor shower, dog friendly!
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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.

Large Group Rentals Chatham

26 Mousehole Lane - Four Bedroom House

26 Mousehole Lane - Four Bedroom House

4.5 out of 5
26 Mousehole Lane, Chatham, MA
26 Mousehole Lane - Four Bedroom House
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.

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 months, such as . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year. is the cheapest month to visit, with the most expensive. 

Your chosen location, property type, and amenities will impact the cost of your trip, too. Right now, Chatham vacation rentals range between $134 per night and $134 per night.

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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