Vacation 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!

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

Overlooking Chatham's beautiful Oyster Pond, this home is the perfect location for your vacation. Take advantage of the beach just outside your door or wander down the street into Chatham center! Enjoy so much of Chatham - without getting in your car! This Sea Captain's house includes five bedrooms (sleeps three on first flr and six on second flr), four and a half bathrooms, full kitchen and dining area, two living room areas with two TVs, laundry room, water view porch and patio w/ BBQ grill.

Downtown Chatham Home w/ Patio - Near Oyster Pond

This stunning historical home is the perfect getaway for those who want to be near downtown Chatham & the beach. Walk to shops, restaurants, Oyster Pond, movie theater, Veterans Field for Chatham A’s games & more! This cozy home is perfect for a family, group of friends, or couples with two living areas, an outdoor patio with lounge areas, a large dining table, grill & fire pit. 1 Min Walk to Downtown Chatham 9 Min Walk to Oyster Pond Beach Experience Chatham with us & Learn More Below!

Luxury Home- Chatham Center- Walk to Town + Beach

Enjoy easy access to everything from this centrally located condo in the heart of downtown Chatham. This luxury condo is perfect for families, couples, or a group of friends looking to be walking distance to restaurants, boutiques, the beach & so much more! Enjoy an extremely spacious home with almost 2,700 sq ft of living space, 3 ensuites, & a large roof deck. In Downtown Chatham .3 Miles to Oyster Pond .5 Miles to Seaside Links Golf Course Experience Chatham with us & learn more below!

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.

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.

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.

Chatham Cottage | Pond Views & Fire Pit

Amazing getaway with a delightful blend of comfort and convenience. Imagine the tranquil beauty of a nearby pond unfolding right before your eyes. The land in front of the house offers not only a captivating view but also a constant connection to the natural wonders that make Cape Cod so special. This property is a bird watcher's dream come true. You're also just a short distance from the inviting sands of the beach and downtown Chatham.