10 Best Airbnb Vacation Rentals In Chatham, Massachusetts - Updated 2024

Sheela
Sheela 
Updated
| 4 min read

Not heard of Chatham before? If so, find out why people would choose Chatham as a travel destination. With miles and miles of pristine beaches and white sand, spending time at the beaches would most definitely offer a slice of paradise. Swim in the warm water or indulge in some yoga to have a great day. There are several water sports to indulge in such as kayaking and paddle boarding. There is beautiful scenery around the area and this is evident in the vast number of nature trails and parks. If music is your thing, then many musical concerts are conducted throughout the year. There are activities for everyone in the family, regardless of age. To explore fully what this city of Chatham has to offer, come and spend a few days. To have a relaxing stay go ahead and book one of the best Airbnb vacation rentals in Chatham, Massachusetts.

We handpicked these listings carefully, considering (wherever possible) Superhost status, recent guest reviews, location, accommodation type, prices, availability of dates, decor, and amenities. The image galleries get refreshed with the latest updates regularly. They were last updated on February 04, 2024.

1. A cottage-style apartment for six (from USD 189)

Book this two-bedroom apartment which comes complete with a fully equipped kitchenette, a full bathroom, and a private deck area. In this deck area, guests can make use of the deck table, chairs, and a gas grill. Use the gas grill to make and enjoy roasts with your friends and family. Simple food items for breakfast are made available for guests. The bedrooms in this property come equipped with a king-sized bed, a queen bed and two twin beds. The rental of the apartment comes with free parking and Wi-Fi along with beach towels, linen, and beach chairs.

Stayed at this property?
Chatham, Massachusetts, United States
6.2 km (3.9 mi) from Nickerson State Park
277 reviews   Superhost Wifi Available
ENTIRE RENTAL UNIT 4 Beds 6 Guests 2 Bedrooms 1 Bathroom

Accommodates: 6

Top guest reviews
Amenities & Room:
breakfast in the fresh air was a treat
we definitely appreciated the grill the well-stocked fridge and kitchen and the deck
the space and deck are great for a small family and the beds and linens are very comfortable
we really appreciated that diane stocked the kitchen with breakfast items
diane was a thoughtful host - fridge was stocked with breakfast foods and snacks
Cleanliness:
it was very clean and cosy
it was very clean and quiet
quiet and clean
everything was sparkling clean comfy convenient
perfectly clean spacious and pleasant
Host:
diana is a wonderful host
a lovely home and great host
she is a lovely host & we really appreciated the nibbles (grapes oj eggs) she supplied
she was a great host and gave us suggestions on what to do in the area
diane was a wonderful host and took great care of them
Location:
great location & good value
great location close by to a beach and easy access to chatham's main street
wonderful location quiet beautiful neighborhood close to chatham national seashore a short 20 min drive
the location is amazing as well with just a 10 minute walk to the beach
the location is perfect for dining shopping or going to the beach
Read more reviews

2. A charming stay in downtown Chatham (from USD 314)

This apartment has recently been refurbished and is set within a historic building. As this building is located in the heart of the village of Chatham, guests are placed close to amenities like restaurants, shops, and the beach. The living room and bedroom of this property overlook the town’s main street. Basic supplies are offered with the rental of this property such as towels and bed linen. One bedroom comes with a queen-sized bed and a floor mattress. There is also a queen bed in the common area. Interestingly, free Wi-Fi is offered with the rental.

Stayed at this property?
Chatham, Massachusetts, United States
10.68 km (6.7 mi) from Nickerson State Park
203 reviews   Superhost Wifi Available
ENTIRE RENTAL UNIT 2 Beds 4 Guests 1 Bedroom 1 Bathroom

Accommodates: 4

Top guest reviews
Amenities & Room:
well maintained with comfortable furnishings
it was accurately described and comfortable
good kitchen and facilities comfortable bed plenty of room for hanging up clothes drawers etc
lovely apartment with beautiful furnishings
that the apartment comes with a parking space is super awesome in this otherwise extremely difficult parking area
Cleanliness:
very clean and spacious
very clean and nicely decorated
beautiful clean and nicely appointed apartment
the apartment was clean and spacious
clean adorable center of everything
Host:
she was also extremely helpful with all of our questions
friendly and helpful host
she was very responsive and accommodating
heather was a wonderful friendly host
heather is a lovely host
Location:
great location - so central to everything
the location was ideal for us
a great location in downtown chatham
heart of town awesome location very comfortable
the location is ideal in the heart of town
Read more reviews

3. A quaint cabin for three (from USD 120)

How would you like to be located halfway between the Rails to Trails bike path as well as the gorgeous Nantucket Sound? Guests can easily fall for Chatham’s charming downtown as well as access the shops around Harwichport. The property is set within a tranquil environment which is friendly and warm as well. The property has a large backyard which guests can use to hang out at and unwind. There are two beds which can sleep up to three guests. Free parking and Wi-Fi are available on the premises.

Stayed at this property?
Chatham, Massachusetts, United States
9.27 km (5.8 mi) from Nickerson State Park
105 reviews   Wifi Available
Entire cottage 2 Beds 3 Guests 0 Bedrooms 1 Bathroom

Accommodates: 3

Top guest reviews
Amenities & Room:
the picnic table was an unexpected delight to eat our meals
the cozy chatham cottage is ideal for two adults
katie was an amazing host the cottage was cozy and charming
there is a big bed - it is pretty soft
Cleanliness:
place was clean and bed was comfy
this precious cottage was clean and fitted in such a thoughtful way
the cottage was very clean & the beach decor was perfect
the cottage is perfect for two people and nicely decorated and very clean
the cottage is very cute super clean and has everything you need
Host:
katie is a great host
katie was a fantastic host
katie is the best host ever
amazing host - incredibly thoughtful and nice
katie was a wonderful host she supplied everything you could think of
Location:
great location at a bargain price
very centrally located and close to a beautiful beach
location is everything and this cottage is perfectly located
the location is perfect just 5 min walk to a beautiful beach and a short ride to chatham
katie's place is very modest and cute it is close to restaurants and shop n stop
Read more reviews

4. A cosy nook close to Cockle Cove beach (from USD 176)

This is a cozy, two-bedroom apartment which is located in a wooded neighborhood. The property consists of a full kitchen and a living room that comes with a cable TV and air conditioning. The two bedrooms in the property are also air-conditioned. One bedroom comes with a queen-sized bed and the other bedroom comes with two single beds. Guests can get access to the screened-in porch which comes with a gas grill. Guests can enjoy a short walk from Cockle Cove beach. Free Wi-Fi is available in the property.

Stayed at this property?
Chatham, Massachusetts, United States
8.59 km (5.4 mi) from Nickerson State Park
123 reviews   Superhost Wifi Available
Entire cottage 3 Beds 5 Guests 2 Bedrooms 1 Bathroom

Accommodates: 5

Top guest reviews
Amenities & Room:
full kitchen terrific view
the cottage was outfitted with everything necessary for a comfortable and convenient stay
wonderful lighted screen porch with table & chairs and plenty of room for dining
this was our first air b&b experience and it was wonderful the cottage was so cute and cozy
beautiful and cozy cottage for any season stay
Cleanliness:
place was very clean and in a quiet neighborhood
it was very clean and the neighborhood was quiet
very clean and had everything we needed for a family of three (plus dog)
the house was very clean and perfect for our needs
the bathroom was spotless & the kitchen has a nice big refrigerator & nice dishes pots pans etc
Host:
joe was a great host
joe was very accommodating and responsive
joe was helpful in orienting us and made sure we had all we needed
joe was very responsive and accommodating
overall a fantastic host and a great place to stay
Location:
great location walking distance to beach
the location was perfect close to cockle cove
great location to get anywhere on the cape
pleasant walk to the beach
location is great and also very quiet
Read more reviews

5. A studio cottage in a beautiful setting (from USD 175)

This is a comfortable studio cottage which is best suited for one or two people. The bedroom comes equipped with a queen-sized bed and has an ensuite bathroom. The kitchenette in this property is equipped with basic amenities that guests would need to make simple meals. A gas grill is provided at the yard area which guests can use to enjoy some roasts.

Stayed at this property?
Chatham, Massachusetts, United States
8.45 km (5.3 mi) from Nickerson State Park
188 reviews   Superhost Wifi Available
ENTIRE HOME 1 Bed 2 Guests 0 Bedrooms 1 Bathroom

Accommodates: 2

Top guest reviews
Amenities & Room:
the bed was comfortable the kitchen amenities perfect for a weekend getaway
the bed is comfortable there are variety of cable channels to watch and the keurig was very convenient
small but comfortable with coffee shop across the street
also a nice breakfast spot
pretty garden area outside where you can enjoy breakfast or evening drinks
Cleanliness:
so clean inside and out
it was very clean and well kept
a great stay super clean and cozy
it was so clean and well kept
clean bright and just all around lovely
Host:
david and maria are fantastic hosts
david and maria were super hosts
david and maria were great hosts to me and my husband
the hosts were very friendly and eager to help since we made the booking
he was also very responsive when we had questions
Location:
the location is ideal
the location was great
the location is brilliant very close to everything and in the nicest part of chatham
this quaint cute small home is situated in the perfect location to explore the cape
it is in a great location close to chatham and also close to some nice beaches
Read more reviews

6. A splendid home in downtown Chatham (from USD 206)

This is a charming cottage which has recently been renovated. It is located on a private road in downtown Chatham. Guests staying here get to enjoy plenty of conveniences. Guests can take an easy walk to the Lighthouse Beach which is just about a street away. The living area in the property is tastefully furnished and decorated. The kitchen is also fully equipped allowing guests to make simple meals and drinks. Two bedrooms are located on the upper level and come with a queen bed and two twin beds. Free parking and Wi-Fi are available on the premises.

Stayed at this property?
Chatham, Massachusetts, United States
10.41 km (6.5 mi) from Nickerson State Park
159 reviews   Wifi Available
ENTIRE HOME 4 Beds 5 Guests 2 Bedrooms 1 Bathroom

Accommodates: 5

Top guest reviews
Amenities & Room:
furnishings nice and comfortable
fyi only one bathroom on first floor with two bedrooms upstairs and a single bed on first floor
Cleanliness:
clean and quiet
the house was very clean and in a quiet neighborhood
the kitchen is well appointed and the whole house clean and homely
we found a very clean attractive cottage with that “beachy” feel
the house was clean and had everything you’d want from a cape house
Host:
in addition thomas is extremely responsive as a host and all of our questions were quickly answered
tom was extremely helpful and accommodating and would respond very quickly to any questions
caretaker was quick to respond and very helpful
thomas was responsive and so was damien the property manager
communication with the host was very easy and he made sure we had relevant information before our stay
Location:
the location was excellent
and the location was great
nice house with amazing location
great location walking distance to main street and the lighthouse beach
great location easy walk to town and other sites
Read more reviews

7. An artistic stay for two (from USD 170)

This spacious cottage is up for grabs should you wish to stay in a comfortable cottage that is close to major amenities. The cottage is suited for one to two people. It is also less than 5 minutes away from the beach while the Cape Cod Bike Trail is only a short walk away. The bedroom is equipped with a queen-sized bed and a full bathroom is available. The property comes equipped with two parking spaces, free Wi-Fi and other amenities like a gas grill and bikes.

Stayed at this property?
Chatham, Massachusetts, United States
8.48 km (5.3 mi) from Nickerson State Park
66 reviews   Wifi Available
ENTIRE HOME 1 Bed 2 Guests 0 Bedrooms 1 Bathroom

Accommodates: 2

Top guest reviews
Cleanliness:
super clean place
the cutest space clean lots of great local tips
very clean has everything you need for a comfortable stay
it is nicely equipped super clean warm and inviting
danielle & brett's place was great super clean and cozy would totally stay again
Host:
probably the best airbnb hosts that i have had as yet
danielle and brett were wonderful hosts
danielle greeted us warmly and gave us helpful advice about activities/restaurants/getting around
danielle and brett were great hosts
danielle & brett are great hosts and there when you need them
Location:
safe area close to the chatham hot spots
amazing location adorable cottage and great location
great place to stay very close to restaurant shops and the beach
rose arbors is a truly enchanting place and was the perfect location for our week on the cape
beaches are super close two of which you could easily bike to
Read more reviews

8. A plush haven in Cape Cod

Check out this charming cottage which is located near downtown Chatham. Here, at this property, guests will find themselves close to downtown Chatham. Staying at this property means that guests are only a short distance away from facilities like shops, beaches, and restaurants. A small cleaning fee is included in the rental.

Stayed at this property?
Chatham, Massachusetts, United States
8.71 km (5.5 mi) from Nickerson State Park
54 reviews  
Entire cottage 4 Beds 3 Bedrooms 1 Bathrooms

9. A comfortable cottage for rent

This cozy Chatham cottage is beautifully decorated and is located only meters away from the bike trail and the beach. The living area adopts an open concept and a fully equipped kitchen is available for guests’ use. There are other amenities like high-speed wireless internet, a washer and dryer, air conditioning and outdoor shower facilities in the property. Guests can also make use of the gas grill to enjoy roasts. There are two bedrooms in the property, one with a double bed and the other with two single beds.

Stayed at this property?
Chatham, Massachusetts, United States
8.56 km (5.4 mi) from Nickerson State Park
81 reviews   Wifi Available
Entire cottage 3 Beds 4 Guests 2 Bedrooms 1 Bathroom

Accommodates: 4

Top guest reviews
Amenities & Room:
a very comfortable cottage in tranquil surroundings
emily's place is adorable it's got a big open space for the kitchen and living area
the patio table grill and outdoor shower are all perfect for a summer getaway
Cleanliness:
this house was impeccably clean
it was extremely clean and private
clean and comfortable both inside and out
the place is very clean and well appointed
fabulous cottage spotless and superb location
Host:
emily is a very thoughtful host
emily was a great host and responded to any questions we had promptly
our host emily was incredibly responsive and accommodating
emily was a great host and left loads of local goodies for us arriving which was just lovely
really clean and emily is a great host with quick responses to any question you might have
Location:
its an ideal location to explore the cape
great location very comfortable and cozy
the location is so convenient to the bike path and an easy walk to the beach
the location is great and is close to local beaches and the downtown area
we loved how close the place was to the bike trail
Read more reviews

10. A beachfront paradise for four

The highlight of this property is the location! Set right across the street where the Chatham Lighthouse Beach is, guests can enjoy sea views along with easy access to the happening downtown. Downtown Chatham is home to several shops and restaurants which guests will enjoy. The cottage comes with an airy living room that comes with a queen-sized sleeper sofa and a flat-screen TV. There is also a fully equipped kitchen which comes with appliances like a fridge, stove, toaster, blender and so on. The private bedroom in this property comes with a queen-sized bed which can accommodate two people. Bath towels, bed linen, blankets are included in the rental.

Stayed at this property?
Chatham, Massachusetts, United States
11.6 km (7.3 mi) from Nickerson State Park
107 reviews   Wifi Available
Entire cottage 2 Beds 2 Guests 1 Bedroom 1 Bathroom

Accommodates: 2

Top guest reviews
Amenities & Room:
had parking and wifi which was great
the cottage is so cozy and beautiful
this sweet little cottage apartment had a beautiful view and comfort all around
this place is probably best for two people as the sofa bed isn't too comfortable
the unit is well equipped reserved parking space tv wifi plenty of hotwater clean and very comfortable
Cleanliness:
it's very clean and comfortable
it was very clean and well supplied
the new bathroom is so clean
it is cozy clean tastefully decorated and in a great area
the bed was more comfortable than we expected and the bathroom was sparkling clean
Host:
the staff were great
joseph was a great host
joseph was a fantastic host
host was helpful and prompt to resolve a very minor issue
joe's an excellent host who responds to requests immediately and had ample recommendations for the area
Location:
the location is fabulous
great location close to the beach
a short walk into town is again a perfect location
great place and wonder location
great place in a great location beach within barefoot walk
Read more reviews

Incredible Chatham

After you have explored the many hiking trails and activities held in the city, enjoy the comfortable space at the rented property of your choice. With a restful night’s sleep, re-energize yourself for the next day’s exploration. Your holiday in Chatham is guaranteed to be memorable.

Stayed at this property?
Any must-sees we missed? Tell us about them in the comments section or write a post here to help out fellow travelers!
Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.

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Sheela, a devoted mother to two remarkable young children, takes immense pleasure in family travel experiences. With a well-traveled history spanning numerous countries, her passion lies in the...Read more

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