Holiday houses in Chatham

LOCATION! Sea Captain's House, Walk to Beach/Town

**Airbnb service fees are now included in nightly rate.** -----Overlooking Chatham's beautiful Oyster Pond, this home is perfect location for your vacation. Take advantage of beach outside your door or wander down the street into Chatham Ctr! Enjoy Chatham without getting in your car! Sea Captain's house has 5 bedrooms (sleeps 3 on first flr and 6 on second flr), 4 1/2 bathrooms, full kitchen and dining area, 2 living room areas with 2 TVs, laundry room, water view porch and patio w/ BBQ grill.

Private Beach in Chatham - Sleeps 5

Welcome to 6 Starfish Lane! Rare for Chatham - flexible stays perfect for a long weekend and last minute getaways (2-4 night min, varies). This is a 2 Bedroom condo (King + Full + Twin) with views of the beach, ocean and marina. We have a private beachfront/oceanfront steps away and easy for the whole family! We are also within a mile of beautiful downtown Chatham and within a short walk to Chatham’s famous Lighthouse Beach and Monomoy Wildlife refuge. This is a great place to make memories!

Slate House - a modern waterfront getaway

Water front on Frost Fish Creek! This recently renovated 3 bedroom (sleeps 9) 2 bath home is tucked off the road in a private oasis with panoramic water front views from almost every room. The bright open floor plan with fireplace, blue slate floors, high open ceilings to second floor, three pairs of sliders that boast nature, water views, fire pit, and screened in lounge and abundant sunlight. Walking distance to a small private dog friendly beach. Driving distance to many great beaches.

Cozy Cottage

Our 3 room cottage in the Old Village is within steps of Lighthouse beach and a 15 minute stroll to town along charming streets. Its location in an ample yard insures comfort and privacy for your stay. The kitchen is equipped for stay-at-home dining. The owners live in a separate house on the property and are ready to provide you with knowledge of Chatham’s history and assist you in your explorations of the town or Cape Cod. The owner welcomes your visit to his art studio on the property

Meadow + Main

Welcome to Meadow + Main – A Boutique Coastal Retreat in South Chatham Nestled between the peaceful Twine Field Meadows conservation area and South Chatham's Main Street, you'll be just a short walk from the Old Colony Rail Trail while some of Cape Cod's most beautiful beaches, restaurants, golf courses, and villages are only minutes away. The home is notably tucked away from the main road and surrounded by mature trees, creating a peaceful and private setting where you can truly unwind.

Charming Chatham Home! Less than Mile To Beach !

Cozy,comfortable and completely renovated this cottage has everything you need for a relaxing stay. Central air, outdoor shower, deck with Weber grill, fire pit, fully stocked kitchen. All linens provided, including beach towels. Less than a mile to Forest Beach and bike path. Short drive to all popular beaches. 10 minutes to Chatham Center, 5 minutes to Harwichport Center. We are nearby should you need anything during your stay , however you have complete privacy. Keyless entry.

Beachfront Charmer! Newly Renovated.

Steps to a beautiful sandy beach and just a mile to the heart of Chatham! This charming, newly renovated beach house has the amenities you need to make the most of your time with friends & family. Just 300 ft from Little Beach & a 5 minute walk to Chatham Lighthouse and Lighthouse Beach, we've made our new home the perfect place to gather and relax. All BRs and Living room have AC. Grill on the back deck, stroll to town, rinse off in the outdoor shower...this house has it all!

Spacious cottage beach Wychmere < 4 min Central AC

Entire spacious newly renovated modern cottage in Harwich Port. Open concept living room with a large kitchen island. Great space for families ! Bank street Beach and Wychmere Beach Club wedding venue are 4 min drive from us ! We’re very close to Harwich Port downtown with great restaurants. We’re centrally located, close to Chatham, Brewster and Dennis. Freedom Cruise Line ferry to Nantucket at the end of our street. Enjoy the bike trail nearby with rental location if needed.

The Osprey Nest - Beach house with stunning views

The Osprey Nest is a classic Cape Cod beach house just steps to the ocean with panoramic views across the protected marsh. A cozy and timeless retreat, with modern amenities and spacious and light-filled rooms. This home has been in my family since the 1960’s and you will feel the warmth and charm the minute you step in the door. The location is perfect for nature lovers but within 10 minutes of stores, restaurants, and charming towns. A perfect base for Cape Cod sightseeing.

The Chatham Bars White Foam House Steps From Beach

Settle back in one of the rocking chairs on the front patio and take in the views of the harbor. Charm and warmth abound in this Cape Cod cottage with Chatham Seaside Links located across the street. Leave the car and walk to local restaurants and shops. Watch band concerts at the park and bask in the views from the Chatham Lighthouse. Go for a long stroll along Claflin Landing Beach all the way to the Fish Pier and buy the day's fresh catch.

Chatham House Near Town and Beach

Comfortable and colorful 3 bedroom, summer home in beautiful Chatham! Walking distance to downtown main street shops, restaurants, as well as Oyster Pond. Our summer home is perfect for a family vacation, a couples get-away, girl's weekend, and a family of 4 with in-laws. We love our home and invite you to come explore downtown Chatham, beautiful beaches, and all Cape Cod has to offer for a special New England summer vacation.

Oceanfront Chatham Village Home

Quiet Peaceful Oceanfront Home, Short Walk to Chatham Village and Walk to Lighthouse Beach. Sleeps 12. Large kitchen, stainless steel appliances, gas stove. Every Room except one room has amazing ocean views! Stone patio overlooks Ocean Harbor on Little Mill Pond. A Video Walkthrough of the house, featured by Eileen Cotter of Pure Wander: https://www.youtube.com/watch?v=_tqi6m8-1zs&t