Holiday rentals with a patio in Chatham

Chatham with Private Beach

Just park your car and enjoy this beautiful location. Private beach with walking paths to lighthouse beach and Monomoy. This Condo has views of the beautiful Chatham sandbars from the front Adirondack chairs, deck with grill and dining table or steps to a private beach. Inside the Condo has a fully appointed kitchen. Sofa and Love seat, wall mounted TV and dining table. Updated bathroom with full tub. First floor bedroom with queen bed and loft with queen bed, dedicated work space and twin bed

Serene Chatham cottage minutes from beach

Welcome to Cranberry Cottage, a 2 BR, 1 BA cottage centrally located & close to the best that Chatham has to offer. Perfect for couples or families! Situated at the end of a private street and overlooking a working cranberry bog, the house is surrounded by some of the Cape's best natural beauty and wildlife. The neighborhood offers walking paths to Ridgevale Beach (15-20 min; great for kids), conservation trails and the Cape Cod Rail Trail. By car, Ridgevale and Hardings Beaches are 5 min away.

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!

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.

Bright Condo on private beach

Updated condo at Outermost Harbor. Enjoy amazing views of the famous Chatham sandbars or catch a glimpse of playful seals from the association beach. Walk along the sandbar to Lighthouse Beach or to Monomoy Wildlife Refuge. Located steps away is the Outermost Marina offering boat shuttles to North and South Beaches and seal tours. Stroll a mile to town and enjoy all the local shops and restaurants. The Chatham Bars Inn restaurants and famous Chatham Fish Pier are approximately 1 mile away.

No Pet Fee, Waterfront, Fenced Yard, Close to Town

Soak up the ☀️ while enjoying the lush outdoor space at our waterfront home, Queen’s Quarters. Bring or rent a kayak or paddleboard as you have direct water access or unwind on the deck looking out for swans or our friend, the Great Blue Heron. From your morning coffee to evening cocktails, the alfresco dining space is suited for anyone at any time of day. Queen’s Quarters is multi-level with a finished basement providing ample space. Since dogs are part of the family, we consider pets.

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.

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

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!

Renovated Chatham Windmill! Walk to Beach/Town!

Newly renovated Chatham Windmill! Beautiful Water View, Steps to Oyster Pond Beach & Main Street! Complete renovation of Windmill in 2022. This unique rental has one bedroom with king bed on second floor, with small full kitchen/dining area, two sitting/TV areas and full bathroom on first floor. Private patio with BBQ grill, dining table and chairs. Enjoy the beautiful water view from Adirondack chairs, just outside your door! Perfect spot for your vacation!

Chatham Home overlooking Cranberry Bog

Beautiful home with huge back deck overlooking a cranberry bog. The house has been recently renovated with a modern but cozy beach feel. House includes 5 bedrooms, 4.5 baths, huge back deck, new kitchen, outdoor shower, fire pit and four living spaces. Very close to Ridgevale, Harding and several other Chatham beaches. Downtown Chatham a short few minutes drive away. House is within walking distance of several great restaurants/shops.

Downtown Chatham Walk to Everything: 4 Bedroom+

- 4 bedrooms (plus outbuilding with daybeds/trundles for 4 and heating/cooling) suitable for 10+ guests - 2.5 baths; enclosed outdoor shower *Stay downtown walkable to Main St. in Chatham! Central air and indoor/outdoor living at its best! Though private, it’s near the Chatham A’s baseball field, playground, beaches, and shops/bars/restaurants galore! Home sleeps 8+ & outbuilding sleeps 4 (daybeds/trundles).