Family-friendly holiday rentals in Chatham

Walk to Ridgevale Beach

We have done extensive renovation and remodeling to the home with attention to detail. We believe we have created a warm and inviting atomosphere. The home is decorated in a coastal style with carefully chosen accents from the edison bulbs in the dining area to the custom barn/boathouse style door and repurposed hand hewn 18th century beam that anchors the staircase. The Kitchen is equipped with the same attention to detail for those who enjoy preparing their own meals. Summerfell is an entire home rental. Both hosts live nearby, Patty and Bill will be accessible via cell, text and email. The property is in a peaceful neighborhood with a good mix of seasonal homes and full time residences. The area has a number of quiet roads perfect for evening strolls. Of course, the beach is a short 5 minute walk away. The kitchen is equipped for the guest who enjoys cooking. From small appliances (Crockpot, waffle iron, blender, hand mixer etc) to small gadgets (citrus press, microplane, garlic press, potato ricer etc) A three burner weber gas grill is on the deck.

Family · Indoor spaces · Checkout

Private Beach in Chatham - Sleeps 5

Welcome to 6 Starfish Lane! Rare for Chatham - flexible stays perfect for a long weekend and last minute getaways (2-4 night min, varies). This is a 2 Bedroom condo (King + Full + Twin) with views of the beach, ocean and marina. We have a private beachfront/oceanfront steps away and easy for the whole family! We are also within a mile of beautiful downtown Chatham and within a short walk to Chatham’s famous Lighthouse Beach and Monomoy Wildlife refuge. This is a great place to make memories!

Kitchen · Indoor spaces · Layout

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.

Indoor spaces · Family · Condition

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

Family · Indoor spaces · Condition

The Knoll

A quiet home nestled next to conservation land at the end of a dirt road. Though there are neighbors, the landscaping creates a private oasis. The downstairs apartment with private entrance is old New England with Cape Cod affects. The Bedroom has a queen bed. Second sleeping area has a Daybed with trundle and is partially open to the living area. Outside deck has a grill and shower for guest use. Close to School House pond, bike path, and 3 miles from beaches, shopping, and downtown.

Kitchen · Family · Layout

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.

Family · Kitchen · Beach

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!

Indoor spaces · Kitchen · Nearby

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.

Family · Kitchen · Bathroom

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.

Kitchen · Family · Layout

Cape Cod Classic Cottage Near Forest Beach

See Cape Cod at its most traditional in this cozy, fully renovated cottage. Get a good night's sleep in the cozy bedrooms with central a/c and blackout shades. Prepare for the day in the clean and bright interior. Pack up your beach chairs and cooler and take a short walk down to Forest Beach. Grab your bike and hop on the Cape Cod Rail trail nearby or take a short drive into charming downtown Chatham. After a day in the sun, unwind in the hammock or enjoy a BBQ on the deck.

Kitchen · Indoor spaces · Hiking

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.

Family · Kitchen · Bathroom

Quaint Downtown Chatham Home

This charming and totally renovated Chatham home is on a private road in a downtown neighborhood of exclusive homes. Its ideal location enables you to walk to Lighthouse Beach about (1/2 mile) and 1 block from downtown Chatham. Also, the house is a quick walk to Children's Beach (Oyster Pond).

Family · Kitchen · Outdoor spaces