Chatham Vacation Rentals
321 rentals with 3,510 photos.About Chatham
Chatham is the "elbow" in the arm of the peninsula. Surrounded by water on three sides, Chatham is the quintessential Cape Cod town.
Chatham Highlights and Features:
- Visit the historic, 80-foot Chatham Lighthouse circa 1808, and learn about the moveable octagonal twin towers.
- Sail over to Monomoy Wildlife Sanctuary on Monomoy Island. This island serves as the nesting, resting and feeding refuge for over 285 species of birds.
- Participate in the Cape Cod Commercial Hook Fishermen's Association (CCHFA) Pier Host Program and learn the history and about earning a living from the sea from an authentic fisherman.
- Walk through nature's beauty as you stroll through 540 acres of conse...
Chatham is the "elbow" in the arm of the peninsula. Surrounded by water on three sides, Chatham is the quintessential Cape Cod town.
Chatham Highlights and Features:
- Visit the historic, 80-foot Chatham Lighthouse circa 1808, and learn about the moveable octagonal twin towers.
- Sail over to Monomoy Wildlife Sanctuary on Monomoy Island. This island serves as the nesting, resting and feeding refuge for over 285 species of birds.
- Participate in the Cape Cod Commercial Hook Fishermen's Association (CCHFA) Pier Host Program and learn the history and about earning a living from the sea from an authentic fisherman.
- Walk through nature's beauty as you stroll through 540 acres of conservation land, with four paths to choose from you will meander past native flora, fauna, marshlands and beaches.
- Enjoy the music, sing along and dance the summer night away, every Friday night at 8pm at Kate Gould Park accompanied by the 40 member, uniformed band.
- Go seal watching by boat or by land, and watch their antics as they escort the fishing boats back to harbor.
- Go to a baseball game at Veteran's Field, home to the Chatham Anglers, one of eight teams in the NCAA sanctioned Cape Cod League.
Flexible dates? Try the dateboard.
Dateboard »
Most Popular
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South Chatham
Imagine having a beautiful Nantucket Sound beach right out your back door! This 4 bedroom/1 bath home is immaculate and nicely furnished. Very comfortable setting with open livingroom/dining area that faces the water, n...
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per night
4 beds
1 bath
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Chatham
Charming 4 bedroom cottage on a quaint quiet lane, in the Old Village, with salt water views from most rooms and within a 5 minute walk to Lighthouse Beach, one of the most beautiful beaches on Cape Cod. It is also with...
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per night
4 beds
2 baths
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Chatham
The Oyster Shack is a newly renovated, two bedroom/one bath (plus outside shower) cottage in a sought after location just off the popular "Loop" in the Stage Neck area of Chatham. Located well off the main road, everyth...
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per night
2 beds
1 bath
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Listings
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Chatham
This completely renovated and newly painted home is located on a private road and just a few minutes walk away from all that the exclusive yet family friendly seaside village of Chatham has to offer: shops and galleries...
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per night
4 beds
2 baths
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Chatham
Charming 4 bedroom cottage on a quaint quiet lane, in the Old Village, with salt water views from most rooms and within a 5 minute walk to Lighthouse Beach, one of the most beautiful beaches on Cape Cod. It is also with...
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per night
4 beds
2 baths
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Chatham
Enjoy your Chatham vacation at this prime "in town" 4 bedroom home that can easily accommodate up to 8 people. Walk to Chatham's quaint Main Street shops, restaurants and Oyster Pond Beach from this lovely home located ...
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per night
4 beds
2 baths
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Chatham
This house is ideal for family and friends and entertaining and is within walking distance of the town (about one mile), close to Chatham baseball park (1/2 mile), close to Oyster Pond and all the amenities that Chatham...
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per night
4 beds
3 baths
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West Chatham
Named for Tom's grandfather, Jon's Landing has been in the family since it was built in the 1970's. "Papa" Jon retired to Chatham, and four generations of family members continue to make memories.
Expanded and updated ...
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per night
3 beds
2 baths
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North Chatham
What could be better than a house on the water, a view, relaxed comforts, and privacy? This setting can be yours to enjoy for your well earned vacation. Sitting on 1.56 acres, this Cape Cod vintage home has one floor li...
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per night
4 beds
2 baths
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Chatham
Everything in this Chatham retreat feels fresh and new, completely rebuilt in 2008. You'll find hotel-quality accommodations for 3 couples or a family, with all the comforts of home. Our architect maximized light, air, ...
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per night
3 beds
3 baths
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South Chatham
Spacious nine room Cape style home, only 1,000 feet to Pleasant Street Beach, has 2600 square feet of vacation accommodations with private first floor master bedroom suite. House sleeps 9 using the bunk beds in bedroom ...
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per night
4 beds
3 baths
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Chatham
Your perfect retreat South of 28 in Chatham's coveted SandalWood neighborhood. Very private cul-de-sac with easy access to town, beaches, kayaking/canoeing, bike path, shopping in Chatham or charming Harwichport, and Ch...
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per night
3 beds
2 baths
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Chatham
This Cape Cod charmer south of Rt. 28 is situated at the end of a dead end private lane with 1/2 a mile walk to Ridgevale Beach. Bright & clean Cape with open floor plan, kitchen open to dining room with slider to large...
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per night
3 beds
2 baths
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Chatham
Welcome to our bright, clean, central air conditioned home only a stone's throw to bike paths and tennis courts and a mile to town. We offer ample off street parking, a well-equipped kitchen, updated bathrooms, new matt...
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per night
3 beds
2 baths
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Chatham
This enchanting 4 bedroom cottage with a Queen, Double, Two twins (adaptable to a king sized bed), set of bunk beds, a cot and full size crib is well located close to all activities and within walking distance of 2 beau...
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per night
4 beds
2 baths
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North Chatham
This beautifully maintained property is located in prestigious North Chatham, and close to all Chatham has to offer. This home is virtually across the street from Ryder's Cove, a popular marina with access to Pleasant B...
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per night
4 beds
2 baths
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Chatham
This charming newer Cape Cod home offers new central air (06), professionally landscaped property, hardwood(wide plank) floors, new kitchen and appliances including washer, dryer, refrigerator, and microwave. Living roo...
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per night
4 beds
2 baths
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Chatham
Inviting beach house with expansive views of Nantucket Sound. Sleeps 6-7.
Three levels, with water views from each level
Large front deck with picnic table & umbrella
Adjoining brick patio with lounge chairs
Large bedr...
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per night
3 beds
2 baths
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Chatham
A few feet from the water on Ryder's Cove with direct boat access to the Atlantic Ocean. A charming two bedroom apartment on the second floor of an authentic Cape Cod boat house. The large front deck gives you a beautif...
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per night
2 beds
1 bath
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Chatham
Swim, fish, bike or just plain Relax at this private, comfortable retreat in Chatham. In a quiet, wooded setting, cooled by the breezes from the pond, the open floor plan is well suited for gathering. This 12 year old h...
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per night
3 beds
2 baths
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Chatham
Located within walking distance (4/10 mile) of freshwater White Pond - great for swimming, kayaking & canoeing - and all other beaches are within a 2-5 minute drive. This beautifully decorated, 4 bedroom 2 bath home has...
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per night
4 beds
2 baths
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Chatham
Located on the banks of the Monomoy tidal river that flows to Pleasant Bay, this 3-bedroom gettaway is the perfect retreat for kayakers and birders. View the swans and other waterfowl from the the new 6 person Hot Tub o...
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per night
3 beds
2 baths
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Chatham
Sunny and breezy property with plenty of living space. Close to beaches and Cape Cod Rail/Bike Trail with deeded rights to Taylors Pond, if you want to kayak or boat to the beach. Large air conditioned family room/dinin...
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per night
3 beds
2 baths
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Blog Posts
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October 05, 2012
Coves, ponds, bays, lakes, inlets, harbors - seems like there is water everywhere you turn both in and around Chatham - and boats, boats, and more boats. Nice place to get married - the Chatham Bars I...
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October 04, 2012
Strolling in downtown Chatham - it wasn't really as cold as these folks are dressed - but fall weather has definitely arrived. Chatham real estate average is more than half a million dollars (accordin...
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October 03, 2012
The Town of Chatham enjoys a wonderful location at the elbow of the Cape Cod arm and is about as pretty an area as one can imagine. The Fish Pier hosts many working boats and is a popular spot for fo...
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September 07, 2012
Although this restaurant, that serves breakfast and lunch, isn’t new to Chatham, we had never been (probably because we love Hangar B so much . . .). However, when we showed up to Hangar B on Friday ...
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August 11, 2012
Last weekend, the weather was picture perfect and our daughters were begging to go for a boat ride. We opted for a seal cruise, a Chatham tourist tradition with several companies offering tours depar...
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July 26, 2012
It was the quintessential Cape weekend: days at the beach, nights around a campfire making s'mores. Had dinner at the beautiful Chatham Bars Inn, and caught a bit of a Cape League game at Veteran's Fi...
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July 18, 2012
One of the evenings we were away, we visited Chatham and had dinner at The Wequassett resort…a stunning waterfront location with a great vista for cape light at sunset. I can’t wait to go back to the...
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July 13, 2012
After Tommy and I got back from Nantucket, we relaxed in Chatham for another couple of days to end our vacation. We went on a couple of runs, enjoyed time on the boat and cooled off from the heat by ...
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July 06, 2012
Take Route 28 to Main Street in Chatham Village. You're going to want to head straight though the funky rotary/intersection (you'll know it when you see it!) to get to the free parking and walkable po...
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October 16, 2011
I used to manage a motel with 2 other people. It was The Ridgevale Motor Inn in West Chatham, Massachusetts, on the corner of Ridgevale Road and Route 28. We all lived in a 4 bedroom house that was at...
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