Holiday rentals with a patio in Chatham

Central AC, Pet-friendly, Walk to water & town!

Sunnyside Escape is a bright, spacious retreat ideally located near freshwater ponds, bike path, beaches, and downtown Chatham. Just across the street, a “paper road” leads directly to the Chatham bike path, and White Pond is only minutes away on foot. Beaches are close by and downtown is a quick bike ride or walk away! This pet-friendly home features central A/C, a gas fireplace, sunny deck, gas grill, fire pit, & game room with ping pong & foosball -everything you need for a relaxing escape!

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.

Lovely Cape Cottage Home < 1 mile to the beach!

Relax at this charming South Chatham coastal retreat! Situated just 0.8 miles to Forest Beach & close proximity to the Cape Bike Trail - get away & enjoy the fall colors in a serene, private setting. The extensive outdoor space includes a custom fire pit, composite deck, stone patio & gas grille. Walking distance to several restaurants including Drifters, Bucas, Pisces & a short drive or bike ride to Chatham center. Located on a private drive & overlooking acres of beautiful conservation land.

Private Bay Beach and Sunset Views! Dog friendly.

The beauty of Cape Cod awaits in this meticulous cottage with water views. Access to a private bayside beach is just steps away, across from the driveway and down a short sandy path. Beach chairs and beach towels included. Ride or walk 1 mi away to a great bike trail, or to National Seashore beaches, shops and restaurants. Or, relax at the cottage with updated amenities, appliances, comfortable beds, and a wonderful outdoor space with deck, fire pit, outdoor shower, lawn games and a hammock!

2 BR w A/C, near beach, Main St., CBI, Wequossett

Welcome to our delightful 2 BR 1 BA home, a mile to the beach and CBI, 1.2 miles to Main Street, .5 mile to the bike path, and 3 miles to Wequosset. This dog-friendly retreat perfectly combines peace and accessibility, making it an ideal destination for your vacation in the picturesque Chatham. Inside, you'll find a bright and welcoming ambiance, complete with tasteful decor & furnishings. An expansive outdoor space features a fully fenced-in yard, perfect for outdoor games and activities

Charming 3b/2ba House close to Downtown/Pier/Beach

Relax in this charming 3 bedroom, 2 full bath house located at the end of a quiet cul de sac, close to downtown, Chatham Bars Inn, Lighthouse beach! Beautiful home that features coastal classic interior with all of the modern amenities to make your vacation that much more enjoyable. Enjoy abundant outdoor space for lawn games, fenced in yard, a fire pit with seating, lawn games, patio with table, appointed chef's kitchen, full linens, towels, beach chairs and more. Permit - STR 626

Apartment suite|pond access|Firepit|Private Deck

Enjoy a stylish experience at this centrally-located spot. Our newly built apartment suite is within walking distance of Dennis Port for restaurants, yoga, and an organic market. Private parking, entrance, and deck along w/ water access to Swan Pond. A full kitchen & Bath equipped with a new LG washer + dryer makes this space feel like your home away from home. Explore, play, rest & relax. We have all you need for a wonderful retreat to make your trip to the Cape an enjoyable one.

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!