Vacation rentals in Chatham

★TINY HOUSE★4/10mi Beach & Village★Pet OK★2 Bikes

Welcome to SAND PEBBLE COTTAGE! We are PET FRIENDLY! ($25/nt) This 300sq.ft "TINY HOUSE" is 0.4 mi from the ocean beach & 1/2 mi from Dennisport village At the end of a cul-de-sac, this tiny cottage has everything you need ✅ 4/10mi to beach & village ✅ Kitchen w/marble counters ✅ 2 Bike ✅ Deck w/furniture & charcoal BBQ ✅ Parking-2 cars ✅ Separate bedroom ✅ Full A/C ✅ Bring your sheets/towels-we do not provide linens ✅ Pet friendly-only 1 pet as the cottage is tiny $25/nt

The Captain Kimball House of Christmas Joy

Experience Cape Cod while staying in this historic 1735 Salt Box built by Captain Kimball Eldredge. You will have a private entrance and the entire second floor dwelling to yourself. Conveniently located on 28 with just a short walk to the beach, this recently renovated home showcases colonial craftsmanship with the original wood floors and fireplaces. Two restaurants a stones throw away, the Cape Cod Rail Trail down the street and only a five minute drive to downtown Chatham or Harwich Port.

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

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.

Brand new, on a secret pond

Welcome to our chic guest house. This brand-new retreat includes a bedroom with king bed, a living room with a sofa bed, smart TV, sleek breakfast bar, and a contemporary bathroom with rainshower and a heated towel rail. Steps away the beach invites you to relax by the water of a semi-private pond next to the rail trail. Welcome to a retreat that strikes the perfect balance between contemporary luxury and the tranquility of nature – for those who appreciate the finer things in life.

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!

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.

Your private, in village, Pied-a-Terre.

Great in-town location. Bright, Clean, Safe, Private and Spacious. Hidden away Above the shops, behind the Main Post Office. Great for Romantic Getaway, WEDDING GUESTS, business trips, overflow guests or just a quick get-away break. Comfortably furnished, thoughtfully outfitted. Well equipped Kitchen, Quality linens, duvet etc. Walk to everything. Private parking. **Please Note: Additional MA lodging tax of 12.45% will apply to all short term rentals**

Chatham Cottage - Quiet and Quaint - Beach-Bicycle

Bicycling and the beach! My cottage is located halfway between the Rails to Trails bike path and beautiful Nantucket Sound.(free parking) It’s also equidistance to Chatham’s charming downtown or Harwichport's shops. It’s quiet setting and peaceful atmosphere calls to those who simply want to relax in the hammock or enjoy a meal on your private picnic table, complete with a gas grill. It's perfect for couples and solo adventurers.

Forbes, a South Chatham cottage

This cozy, two bedroom cottage is nestled in a wooded neighborhood and has a full kitchen, living room, 2 air conditioned bedrooms, a full bath, cable TV, Internet, a screened-in porch, shaded yard, outdoor shower, and a gas grill. Cockle Cove beach is a short walk (3/4 mile) . Weekly summer rentals only, Saturday until Saturday.

Close to everything in Chatham

3 bedrooms ( 1 King bed, 3 Queen beds, 2 Twin beds and a Queen sofa sleeper), 2 1/2 baths, sleeps 8, 3 levels of living space, yard and patio, deck bbq, lounge chairs, large patio table with umbrella, outdoor shower and washer and dryer.