Vacation 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

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.

Location Location Location! Beach, Bike, Ferry

STEPS to beach, bike path, trails, restaurants, shopping, bus to MV Ferry Gorgeous studio/in law apartment, private entry, own parking + patio Open plan living/sleeping area + en suite bathroom Queen bed + queen sleeper sofa: sleeps max 4 Fresh linens, towels, personal care products, first aid, hairdryer, iron Mini kitchen w fridge, air fryer, microwave, toaster oven, dishwasher, cutlery, crockery, coffee maker Our famous home baked goodies! Coffee/tea/milk/sparkling water provided

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

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.

New! Chatham Cozy Cottage on White Pond

Petite & sweet 2 room 1920s cottage in convenient location. Shared waterfront access steps away. Updated to include all essential modern comforts while maintaining its historic charm. Every detail is considered to maximize function within a small footprint. Quiet ductless A/C and heat will keep you cozy. New bathroom with shower. Queen bed. Front deck with grill and seating. Includes 1 parking spot. Linens and Bath Towels included, please bring your own beach towels and chairs.

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.

Walk to beach/Main Street/bike path/dog friendly

Welcome to your North Chatham escape — a comfortable, coastal 2-bedroom home with central A/C, a fully fenced yard, and an outdoor shower for easy beach days, with beach chairs and umbrella. Take a 15-minute walk to the beach, then enjoy quiet evenings at home grilling on the patio, or a quick trip into Main Street Chatham, just 1.2 miles away. Perfect for couples, small families, and guests traveling with dogs.