Holiday rentals with outdoor seating in Chatham

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!

Large Sunny Deck, Harbor View, Walk to Town.

Classic little Cape cottage in an ideal location. Less than ten minute drive to amazing ponds and bayside or ocean beaches. Views of the harbor from the large sunny deck with attached outdoor shower. Ten minute walk into town along Duck Creek marsh & over scenic Uncle Tim’s Bridge. Visit the shops & galleries, have lunch or grab a drink at one of the many restaurants in town. Walk to the fish market and come home grill dinner on the deck. 15 minutes bike ride to the closest ocean beach.

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.

Close to Beach Renovated Dog Friendly Cape Cottage

Welcome to our enchanting Cape Cottage in the heart of Chatham, where timeless charm meets modern comfort. 4 minutes from the beach and nestled on a spacious half acre, this newly revitalized and renovated home provides an authentic Cape Cod vacation experience. As you step into our home, you'll immediately sense the true heart and soul of a Cape Cod getaway. Our cottage boasts a warm and inviting atmosphere, perfect for families, couples, or friends seeking a luxurious escape to Chatham.

Spacious Moonhouse Studio - Chatham

Spacious studio apartment located above attached garage, with separate entrance and a relaxing private outdoor space. Perfect retreat for 1-2 people. Property is quietly situated off of a private road. Located one half mile from Ridgevale Beach along Nantucket Sound, also including nearby bike trail access. Short drive to Schoolhouse Pond, three miles from downtown Chatham. Three miles from popular Chatham Bars Inn and the Wychmere Beach Club Generally, a three night minimum.

Romantic getaway suite

GENEROUS DISCOUNT FOR LONG TERM OFF SEASON STAYS. ( February, March, November, and December) Contact direct. Ten year old private one bedroom lavish suite over two car attached garage with private entrance, deck, and parking in a quiet neighborhood central to all the Cape has to offer. Beautifully furnished with central air, gas fireplace, hardwood floors, double slipper clawfoot soaking tub, separate subway tiled shower, wireless internet and Sony 49 inch 4KUHD edge -lit streaming TV.

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!

Walk to beach! Chatham Luxury near downtown, CBI!

Chatham Searenity! BEACH ACCESS! Walk to beautiful beach overlooking monomoy! 2 minutes from Chatham Bars Inn, Chatham links golf & downtown! Luxury 2 bedroom, 2 bath condo with full kitchen & cookware. Quiet, comfy space centrally located. Peaceful, relaxing private space with large queen bed, daybed w/ pull out trundle, A/C, washer dryer, Wifi & ample parking. Hulu live tv, Netflix, Prime video, HBO max, Disney+. Central to everything! Perfect Cape escape. IG @chatham_searenity

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.

Beautiful Downtown Chatham 1 Bed, Near Oyster Pond

This gorgeous home is the perfect getaway for those who want to be near downtown Chatham & the beach. Walk to shops, restaurants, the beach, a movie theater, Veterans Field for summer Chatham A’s games, The Squire, & more! This cozy, modern, & newly renovated apartment is ideal for a couple or two friends with an open living room & kitchen space + private patio. 1 Min Walk to Downtown Chatham 9 Min Walk to Oyster Pond Beach Experience Chatham with us & Learn More Below!

Spacious Pet Friendly Cape, Large Yard

Our home is located in a quiet neighborhood close to beaches, golf courses and bike trails. It is a short drive to Chatham town center and is the perfect location to be close to all attractions but secluded enough to unwind. Take advantage of the outdoors on a new deck and large backyard. Large, mature plants and trees surround the property on three sides. Blackberry, raspberry and blueberry bushes in the backyard provide ripe fruit in the summer months.

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.