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Vacation rentals in Chatham

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Top-rated vacation rentals in Chatham

Guests agree: these stays are highly rated for location, cleanliness, and more.

Main Suite - Chatham Guest Rooms
SUPERHOST
Hotel room · 4 guests · 1 bed · 1 bath

Main Suite - Chatham Guest RoomsThis welcoming two-room guest suite has a queen bed and a separate living room with an impressive library, cathedral ceilings, and a full-sized sofa bed (additional fees apply for use of extra bed). Kitchen features granite counter tops and is stocked with dishes, silverware, cooking utensils, coffee & tea makers, a microwave, and a dishwasher! The bathroom includes a tub, shower, and built-in vanity. Children lodging with an attentive adult must be at least 7 years old to stay in this unit.

Modern Cottage with All Your Needs
Entire cottage · 5 guests · 4 beds · 1 bath

Modern Cottage with All Your NeedsWelcome to Our Beautiful South Chatham Cottage, next to Cape Cod bike trail and beaches. 1 mile to Cockle Cove Beach, 2 miles to Red River Beach. Center located near shopping, activities and restaurants. All new Interior, large outdoor patio with grill. Outdoor shower. First floor living area with kitchen and bathroom, second floor bedroom. Parking for 5 car. Bicycles and beach accessories available.

Cape Cod Classic Cottage Near Forest Beach
PLUS
Entire residential home · 5 guests · 3 beds · 1 bath

Cape Cod Classic Cottage Near Forest BeachSee Cape Cod at its most traditional in this cozy, fully renovated cottage. Get a good night's sleep in the cozy bedrooms with central a/c and blackout shades. Prepare for the day in the clean and bright interior, as the ocean breeze drifts through the windows. Pack up your beach chairs and cooler and take a short walk down to Forest Beach. Grab your bike and hop on the Cape Cod Rail trail nearby or take a short drive into charming downtown Chatham. After a day in the sun, unwind in the hammock or enjoy a BBQ on the deck. End your evening snuggled up on the couch watching Netflix.

Vacation rentals for every style

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Popular amenities for Chatham vacation rentals

  • Kitchen
  • Wifi
  • Pool
  • Free parking on premises
  • Air conditioning

Other great vacation rentals in Chatham

  1. Entire guest suite
  2. Harwich
BB's Hideaway (A Cape Cod Experience)
  1. Entire rental unit
  2. Orleans
Modern Cape Apartment in Orleans, Private Entrance
SUPERHOST
  1. Entire guest suite
  2. Harwich
Romantic getaway suite
SUPERHOST
  1. Entire cottage
  2. Chatham
Cozy Cottage
SUPERHOST
  1. Hotel room
  2. Chatham
East Room - Chatham Guest Rooms
SUPERHOST
  1. Entire rental unit
  2. Brewster
Ocean Edge Resort 2 bed/2 bath 2nd floor golf view
SUPERHOST
  1. Entire residential home
  2. Chatham
Peaceful Beach House with Amazing Views
SUPERHOST
  1. Entire guest suite
  2. Chatham
Couples Retreat in Beautiful Chatham Cape Cod!
SUPERHOST
  1. Entire guest suite
  2. Orleans
Private Beach, Cozy Cape Cottage
SUPERHOST
  1. Entire condominium (condo)
  2. Brewster
Ocean Edge Resort Condo, 4 beds, sleeps 5 Brewster
SUPERHOST
  1. Entire guest suite
  2. Brewster
Sheep Pond Get-Away
  1. Entire condominium (condo)
  2. Chatham
Cozy Chatham Condo Steps to Downtown and Beaches

Top-rated things to do in Chatham

Unique activities hosted by local experts vetted for quality

  • Discover Chatham Bike Tour
    We will meet at my home on Seaview Street to get set up with bikes talk a little bit about the surrounding homes in the neighborhood. We will start off the bike tour visiting two landmarks (Chatham Bars Inn and Chatham Lighthouse) and a secret beach! The second half of the tour covers some history of Chatham, the increased shark activity in these waters, and information about clamming and fishing in the town. We will end with the picturesque Oyster Pond and Veteran’s field and talk about the local community. I'll provide some nearby recommendations for delicious lunch. This is an easy to medium difficulty bike ride. It is 3 miles in total and more of a means to easily see a lot of places than you would on foot. Please note that there are some roads with traffic, but cars are generally respectful of bikes in Chatham. I am fully vaccinated.
    From Price:$50/person
  • Beachside seafood or chicken paella
    I will greet my guest and tell them about myself I will give a tour of the property, beach, personal facilities to use in my home and make everyone feel comfortable. I will give a detail to the evening. I will have everyone watch my demonstrate and offer for anyone to participate in the meal. We will all sit around the large tables that are beautifully set and eat dinner. After or before dinner, depending on the time of day, I will encourage guests to take a walk along the water or watch the most amazing sunset over the water,
    From Price:$88/person
  • Harbor Seal and Boat Tour - Cape Cod
    A booking provides fare passage to explore the rivers and bays of Orleans, North Chatham; the haul out area of Cape Cod's large gray seal population; the waters of Chatham Harbor including the Chatham fishing fleet and the Chatham fish pier. View Chatham lighthouse and the shores of the beautiful Cape Cod National Seashore barrier beach with its vibrant bird and marine life. Water is provided. The tour is 2 hours long and is 22 miles round trip. Our trip remains within the calm protected waters of Orleans and Chatham and does not go into the ocean. If you haven't seen this part of Cape Cod from the water, then you are missing its true beauty. Due to the substantial cost of operating the vessel, a tour trip can only run if there are a minimum of three booked fares. Other things to note Children 12 and under must wear life jackets. Children of all ages are welcome if accompanied by their parent. Unaccompanied children must be 18 years of age or older. Capt. may cancel if bad weather
    From Price:$156/person
  • Relax and enjoy beauty of salt cave.
    A unique Himalayan Salt Cave experience, Here in the middle of Cape Cod. The facility was recently built by the pioneer of Salt Therapy and the founder of Salt Cave Inc., Dr. Margaret Smiechowski. In just one 45 minute session, you will learn about the history and benefits of salt therapy. Relaxing in a zero gravity chair, you will experience salt-saturated air pumped into the cave by our salt generator. Other things to note Please wear loose clothing, and bring white socks to wear in our cave. Please notice this is a group experience. You might be in the salt cave with other groups of people. No refund will be issued if canceled less than 24 hours before the event.
    From Price:$44/person
  • Fat tire biking on the beach
    The tidal flats in Dennis are one of the most unique features that you will see while on Cape Cod. The tidal flats wrap around the inner elbow of Cape Cod and extend all the way to North Eastham, making this the largest tidal flat in North America. At it's best, the beach at low tide extends over a mile from the high tide line. We will begin with an orientation to the riding area, including safety considerations and points of interest. We will then ride one mile over packed sand to the nearby oyster farms, where we will talk about the process and business of shellfish farming as well as it's environmental and economic benefits. Then we will ride over the beach and through small shin-deep tide pools to the low tide line, approximately 1/2 mile depending on tidal conditions. From here, feel free to dismount your bike, walk around on the beach, or continue biking along the coast for a bit before riding back to the parking area. Other things to note: You do not have to be an athlete to participate in this experience, but a moderate level of physical fitness will help you enjoy it. Also, your feet will get wet, so bring an extra pair of shoes.
    From Price:$100/person

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