Vacation rentals in Oyster Pond

Walk to the Beach from a Family-Friendly Home in Chatham

Peaceful, quiet and private ocean-side neighborhood. Very short walk, 10 minutes or less, to Hardings Beach, a mile-long sandy beach. Defined by knotty wood floors and understated furnishings throughout, this home lends a muted color palette of sky blues and creamy whites, appointing a serene timbre to each room. Dine alfresco on the deck patio overlooking the conifer-clad yard. Enhanced Cleaning Protocols. All surfaces, door knobs, light switches sanitized and all bed linens, blankets and towels removed and replaced between guests. Classic Cape Cod home, perfect for family beach vacations, friends getting together and family reunions. Walk to Harding's Beach (2/10th's of a mile away), Walk to an ocean harbor (3/4 of a mile away), shop and dine in quaint Chatham Village. Enjoy the oceanside neighborhood and walks near the ocean, along the beach and along Chatham's harbors. Watch the fisherman empty their catch at the Chatham fish pier amid the watching seals. Kayak, paddle board or fish for stripers. Enjoy the hiking trails and the nature trails in Chatham's convservation areas. Bike ride on Chatham's Rail trails which connect to Harwich Port, Dennis Port, Brewster, Orleans and Nauset. Chatham is centrally located to enjoy all that the cape has to offer. We will provide everything you need before your arrival including keyless door lock information, and information about the house, the neighborhood, and local activities. Enjoy exploring Chatham, and we'll respond right away if you contact us and need anything during your stay. Set in a peaceful oceanside neighborhood, the home is nine houses down from a charming footpath down the sand dunes to arrive at Hardings Beach. Charming shops, restaurants, and supermarkets along Main Street are a short drive away. Fast Wifi, comfortable work space and child friendly. Walk to Hardings Beach, and to Oyster River's Barn Hill Landing (ocean harbor with a public dock, lobster boats and fishermen. Bike ride or walk behind the sand dunes at Hardings Beach to arrive at Stage Harbor Lighthouse. Bike on the Cape Cod Rail trail to get to Nauset Beach, which is 11 miles away. Chatham Village is only 2 miles away.

Dreamcatcher | Luxury Chatham Retreat

Ditch the car and dive into the quintessential Chatham lifestyle. > Perfectly situated, this impeccably designed 2-bedroom, 3-bath retreat offers the luxury of total walkability. Whether you’re strolling to Main Street for your morning pastry, hitting the bike path for a scenic ride, or relaxing by the gas fireplace after a day at the beach, this is your sophisticated home base for the ultimate Cape Cod escape. High-end finishes meet coastal comfort in a space designed for effortless memories.

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!

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.

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

Walk to Beach and Town, newly renovated 4/BR

Enjoy easy access to everything from this perfectly located home base. Located in historic Chatham Village, this 1850's home is a minute walk from Oyster Pond beach, down town, and the ball park. House has been completely updated and refreshed with new first floor bathroom, and new granite in kitchen. House has 4 bed rooms, three with queen sized beds, and one with twin bunks. Master bedroom has adjacent sitting room with fold out day bed providing privacy and additional sleeping area.

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!

Renovated Chatham Windmill! Walk to Beach/Town!

**Airbnb service fees are now included in nightly rate.** ----------Renovated Chatham Windmill! Beautiful Water View, Steps to Oyster Pond Beach & Main Street! 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!

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.

Private Pied-a-Terre, in-village hidden Oasis.

Great in-town location. Bright, Clean, Safe, Private and Spacious. Hidden away Above the shops, behind the Main Post Office. Great for Romantic Getaway, WEDDING GUESTS, business trips, overflow guests or just a quick get-away break. Comfortably furnished, thoughtfully outfitted. Well equipped Kitchen, Quality linens, duvet etc. Walk to everything. Private parking. **Please Note: Additional MA lodging tax of 12.45% will apply to all short term rentals**

The Chatham Bars White Foam House Steps From Beach

Settle back in one of the rocking chairs on the front patio and take in the views of the harbor. Charm and warmth abound in this Cape Cod cottage with Chatham Seaside Links located across the street. Leave the car and walk to local restaurants and shops. Watch band concerts at the park and bask in the views from the Chatham Lighthouse. Go for a long stroll along Claflin Landing Beach all the way to the Fish Pier and buy the day's fresh catch.

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).