Vacation rentals with a patio in Chatham

Red Door Retreat in Chatham is 80% full for summer

Grab 1 of the last 2 summer weeks of 2025 before they're all gone at this beautiful 3bed/2.5 bath house. Cathedral L/R w/fireplace. Sunroom w/sectional and 65" TV. Dining room table for 9. Queen guest room plus "kids" bedroom with twin/full bunks & addl twin. King suite w/daybed, tv, & office area. Loft w/60" TV & Queen Sleeper. Water view deck w/dining table. Pool Table, Ping Pong, Shuffleboard, Outdoor shower, W/D, bikes, BBQ, Solo fire pit, kayaks, Wifi, A/C, Kid's gear, Access to Oyster Pond

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!

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.

Charming Chatham Home! Less than Mile To Beach !

Cozy,comfortable and completely renovated this cottage has everything you need for a relaxing stay. Central air, outdoor shower, deck with Weber grill, fire pit, fully stocked kitchen. All linens provided, including beach towels. Less than a mile to Forest Beach and bike path. Short drive to all popular beaches. 10 minutes to Chatham Center, 5 minutes to Harwichport Center. We are nearby should you need anything during your stay , however you have complete privacy. Keyless entry.

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

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!

Jean's Dream - Renovated Chatham House

Escape to Jean's Dream a charming Cape house in South Chatham, MA. A delightful newly renovated home features 2 bedrooms, 1 bathroom, and sleeps up to 7 guests. Convenient Main St (Route 28) location! Cockle Cove Beach just 0.9 mi away. Step into the backyard and access the Cape Cod bike trail. Unwind with an outdoor shower, fire up the grill, and take advantage of ample parking. Your perfect vacation retreat awaits!--

Charming Chatham Cottage

Prepare to be charmed by this quintessential Cape Cod beach cottage, tucked into a quiet residential neighborhood equidistant from both Harwich Port and central Chatham, with tons of entertainment, dining, and shopping opportunities. Explore on two wheels via the Old Colony Rail Trail bike path, just up the street, or hop in your car to explore the rest of the Cape’s charms, all an easy drive away.