When in Chatham, the beaches are unmissable. Make sure you head to Lighthouse Beach, Harding Beach and Oyster Pond Beach. But there’s plenty more to do besides the beaches and seafood too! Rent bikes and explore bike paths along the Cape, spot seals playing in the water by the Chatham Pier, go shopping on Main Street, catch a movie at the Orpheum theatre. As for the lighthouse, consider moving over the obvious Chatham Lighthouse and head over to the Stage Harbour Lighthouse which is even more impressive. In Chatham, you have plenty of vacation rental options to choose from ranging from small bungalows to beach mansions, depending on your budget and preferences. Also, the closer you are to the water and the time of the visit may significantly impact your costing too. We’ve curated some of the top accommodation choices for you. Check out the best VRBO accommodations in Chatham, Massachusetts here.
1. Oceanfront house within walking distance of beaches and town (from USD 800)
This 2400 sq ft (222 sqm), four-bedroom house has an ocean harbor seafront with private stairway access to the harbor and lovely elegant interiors. Perfectly seated on the bank with the backyard overlooking the harbour coupled with unobstructed views of both Little Mill Pond and Mill Pond, the views from the house are truly spectacular. It’s also an easy walk to Lighthouse Beach or Andrew Hardings Beach and Chatham’s Village which houses shops and restaurants. The house has been recently renovated and comes with a well-appointed full kitchen, centralized air-conditioning, gorgeous wood flooring, and a brick-walled patio.
Fabulous Waterfront Chatham Village Home, Walk to Town & Beaches, Panoramic View4 Homestead Lane East
2. Three-bedroom house with a private beach (from USD 1842)
This 1900 sq ft (176 sqm) home is seated on its own private beach and offers unobstructed views of Pleasant Bay and the open ocean beyond. It’s also only a five-minute walk to the dozens of shops, restaurants and art galleries that line the main street. Also, the world-famous Chatham Bars Inn and Spa is only 200 yards (182 m) to its north. The house features three bedrooms and can house up to seven people comfortably. Each of the bedrooms has full-on ocean views and the outdoors have plenty of seating and a provision for alfresco dining.
Direct Ocean Front - Private Sandy Beach - 5 Min. Walk to Town166 Shore Rd
3. Four-bedroom, pet-friendly property with huge backyard, garage and workshop (from USD 942)
This 3000 sq ft (278 sqm) property is located on the ocean side of Shore Road with an easy walk to four of Chatham’s swimming beaches, the fish pier, restaurants and more. It features four bedrooms, a full kitchen, a garage, a workshop and a huge backyard with organic vegetables and a flower garden. The outdoors also come with chairs to relax and unwind at the end of the day while enjoying a drink. Entertainment options include a television, a book collection and close proximity to golf and tennis facilities. Pets are allowed on this property.
Best Location in Chatham - Great House!72 Shore Rd
4. Bright and beautiful single-story, two-bedroom townhouse (from USD 160)
This property is a bright and beautiful two-bedroom townhouse spanning 1200 sq ft (111 sqm) The house has been newly renovated and features an open floor plan, vaulted beam ceilings, a built-in gas fireplace, and hardwood floors. The well-equipped kitchen has granite counters, tile backsplash, a dishwasher and a large island with seating for four along with an adjacent dining area with a large table perfect for meals and playing board games. The outdoors includes a patio with ample seating, a gas grill and atmospheric string lights coupled with an outdoor shower. The place is located near the shops and dining areas of Chatham, 0.5 miles (0.8 km) from Oyster Pond and 2 miles (3.2 km) from Lighthouse Beach.
Newly Renovated! Walk to Beach and Town!195 Crowell Rd
5. Dog-friendly waterfront property with two decks (from USD 428)
Featuring expansive views of Pleasant Bay, two decks, two living areas, and four bedrooms, this vacation rental has plenty of room and is an ideal choice for a peaceful retreat with family or a large group of friends. The property is also dog-friendly and you don’t need to leave your furry family member behind either. The living space features ample seating and is in the center of the home with two bedrooms on each side. The bedrooms are spacious and feature plenty of natural light. The deck and porch have plenty of outdoor furniture, tables for alfresco dining, a hammock and a gas grill. The kitchen is well-appointed with all the equipment and paraphernalia you may need.
Waterfront in North Chatham300 Whidah Road
6. Four-bedroom house with stylish interiors, private yard and water views (from USD 240)
This four-bedroom property is a comfortable family home sitting near the end of a quiet dead-end road. Located just five minutes’ from the Ridgevale Beach and a quick drive to Downtown Chatham or Harwich Port, this home can comfortably sleep up to eight people. The main floor has a wide open floor plan with two separate living areas, one bedroom with twin beds, a well-equipped kitchen, and a dining area. It also comes with a large deck to enjoy lovely views of Buck’s creek while just taking in the sunset or barbecuing. The second floor has three bedrooms - one with a king size bed, one with a queen size bed and one with twin beds. The house comes with a large private yard and an outdoor shower. The house is centrally air-conditioned, has laundry equipment in the basement, is Wi-Fi enabled and allows dogs.
#611: Amazing views of Buck's Creek, 2 decks, walk to Ridgevale Beach!90 Ridgevale Road South
7. Large vacation home on Morris Island, close to the best of nature (from USD 714)
This vacation home is located on 2 acres (0.8 hectares) of a prime oceanfront real estate on Morris Island. Offering panoramic views of the Nantucket Sound and Monomoy Islands, the sunsets from here are truly sublime. The house spans 5000 sq ft (464 sqm) and hints at Asian-style decor. With five bedrooms, three bathrooms, two powder rooms, and multiple living and dining spaces, it comes with plenty of space to accommodate larger groups up to 13 people. The outdoor space features sun loungers, a barbecue, a fire pit and plenty of seating with a provision for alfresco dining. Wake up to the sounds of songbirds and the sight of whitetail deer gracefully moving through the grass then head on to hike on the Monomoy National Refuge trails.
2 Weeks Left in August! 30% Discount! Oceanfront Luxury Home127 Wapoos Trail
8. Furnished property in a townhouse complex with tennis court, swimming pool shared access (from USD 750)
This 2500 sq ft (232 sqm) picture-perfect townhouse is set on 17.5 acres (7 hectares) and is beautifully and meticulously designed for the best of style and comfort. The elegantly furnished house features four bedrooms, a spacious area, dining space for eight, a well-appointed kitchen with an island and breakfast bar and luxury bathroom fittings. The guests at the property have access to the tennis court, swimming pool, huge lawn and more. There are also plenty of excellent restaurants nearby, ranging from casual to fine dining, for when you do not wish to cook. The location also puts you in close proximity of Chatham Main Street’s eclectic shopping options, sightseeing, whale watching, golf, movies, concerts and more.
Brand New Waterfront Townhome1233 Main St
9. Cozy, one-bedroom vacation rental for a couple (from USD 225)
This vacation home is a one-bedroom rental cottage with tasteful nautical decor that’s perfect for a couple’s retreat or a small family getaway. With breathtaking views of the Oyster Pond and the town beach just a short walk away, water babies will love the place. The sleeping arrangements include a king bed in the master bedroom and a pullout bed in the living room. The cozy living room features plush couches and a flat-screen television as well. The house comes with central heating, Wi-Fi access and shared laundry machine access. The outdoor area comes with a private furnished patio and a gas grill.
NEW! Darling 1BR Chatham Windmill Cottage!133 Queen Anne Rd. Windmill
10. Beautiful townhouse with two bedrooms and in proximity to all attractions (from USD 185)
This beautiful townhouse sits on the main street and is close to all of downtown’s attractions. It comes with two master bedrooms and additional sleeping arrangements in the living room. The house features air-conditioning in each room, heating, Wi-Fi access, and laundry equipment. Indoor entertainment options include a television, a DVD player and a book collection. The outdoors comes with a sun deck, a barbecue grill and a provision for alfresco dining. The place is only a short walk to restaurants, shops, Oyster Pond Beach, the movie theatre, a baseball field, and the village market.
Beautiful Townhouse in Downtown Chatham , Walk to Oyster Pond & Baseball Field791 Main Street
Explore the architecture and homes in Chatham
Chatham is home to some mansions that can rival even the best European chalets. Spend some time strolling around and check out some truly spectacular seaside homes.
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