House vacation rentals in Chatham

A bright bedroom showcases a spacious bed with white linens and decorative pillows. A wooden dresser and bedside tables are positioned nearby. Nautical-themed decor, including a wall sign and a decorative ship's wheel, enhances the coastal ambiance. Natural light enters through a window overlooking the peaceful surroundings.

4.94 out of 5 average rating, 127 reviews

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.

A charming cottage is situated on a gravel driveway, framed by greenery and featuring a flagpole adorned with the American flag. A front porch with steps leads to the entrance, complemented by well-kept landscaping and a peaceful atmosphere.

4.89 out of 5 average rating, 132 reviews

Cute cottage - walking distance to Ridgevale Beach

Retreat to this very quiet and peaceful residential shore neighbored on a dead end street. If LOCATION is what you're looking for, look no further! This year round cottage will serve as a comfortable and relaxing home away from home for your vacation, with walking rights to Ridgevale Beach about 300 yards from the front door. Provided in your home away from home vacation house are linens, towels, fully equipped kitchen, spacious out door shower, 2 roomy bedrooms, & 4 season porch to relax on.

4.87 out of 5 average rating, 211 reviews

A wooden dock extends into a serene freshwater pond, surrounded by lush green foliage. The calm water reflects the clear blue sky and distant tree line, creating a tranquil setting for relaxation and outdoor activities.

Home in Brewster

Water Front Pond House - 3 acre Cape Cod Sanctuary

Extraordinary pondfront sanctuary on Cape Cod. 1300 sq.ft. home sleeps 8 in 3 bedrooms and 1 bath. Private dock and beach area. House is on the Pond and sited on 3 pristine acres - this property offers exceptional privacy with full water recreation opportunities while also being close to everything "Cape Cod". Centrally located in laid-back Brewster, 5 minutes to Bayside beaches, 10 mins to Chatham, Harwich Port, and Orleans. Local owners have 22 years of online vacation rental experience.

5 out of 5 average rating, 40 reviews

Downtown Chatham Home w/ Patio - Near Oyster Pond

This stunning historical home is the perfect getaway for those who want to be near downtown Chatham & the beach. Walk to shops, restaurants, Oyster Pond, movie theater, Veterans Field for Chatham A’s games & more! This cozy home is perfect for a family, group of friends, or couples with two living areas, an outdoor patio with lounge areas, a large dining table, grill & fire pit. 1 Min Walk to Downtown Chatham 9 Min Walk to Oyster Pond Beach Experience Chatham with us & Learn More Below!

An open living space showcases a light beige sectional sofa paired with vibrant red and white decorative pillows. A wooden coffee table is centered on a blue area rug, while a dining area is visible in the background, featuring a round table with muted grey chairs under a chandelier.

5 out of 5 average rating, 9 reviews

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!

A gravel driveway leads up to a charming two-bedroom home surrounded by lush greenery. A white picket fence outlines manicured garden beds, while a spacious front porch is visible through large windows, allowing for natural light to enter the inviting living space.

4.93 out of 5 average rating, 28 reviews

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 miles 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

A spacious dining area features a long white table adorned with a runner and decorative centerpiece. Overhead, a chandelier adds elegance, while large windows frame views of the water. Natural light brightens the room, complemented by charcoal slate flooring and a cozy seating arrangement nearby.

4.95 out of 5 average rating, 282 reviews

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.

Top guest favorite

The exterior of the cottage is framed by a lush green lawn and manicured shrubbery. A welcoming pink door serves as the focal point. Shade is provided by a large tree in the foreground, enhancing the serene atmosphere of the setting.

5 out of 5 average rating, 70 reviews

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.

A modern kitchen features white cabinetry and stainless steel appliances. A large island with seating for two is positioned next to a dining table with light wood chairs. Natural light fills the space through sliding glass doors leading to the outdoor area.

4.97 out of 5 average rating, 103 reviews

Chatham Charm

Welcome to our newly renovated 4-bed, 2-bath Cape house close to downtown Chatham and beaches! The house is equipped with central air, wifi, a living room TV with cable, smart TVs in bedrooms, and a washer/dryer set. The property also includes a large deck and back yard, great for grilling and outdoor activities. We have a contractor nearby to help with any needs you may have during your stay. Sat-Sat 7-night minimum stay last 2 weeks of June through end of August.

The exterior of the renovated Chatham home features a white picket fence and a gravel driveway. The house showcases a gabled roof and large windows, surrounded by greenery and trees. The clear blue sky above emphasizes the peaceful neighborhood setting.