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Chatham Massachusetts Vacation Rentals - Estate
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Chatham Estate
9 BR / 5 BA / Sleeps 20 9 20 Min stay varies
Estate / 9 Bedrooms / Sleeps 20
9 bedrooms 5 bathrooms Sleeps 20
High Speed Internet • Dishwasher • Microwave
"Shore Acres" Cape Cod Premier Chatham Harbor 5 Acre Seaside Elegant Estate with Oceanfront, Ocean View, Own Beach, Walk to Town, Sleeps 7- 20. Summary: Extremely Spacious Executive- Quality Special Occasions Cap...
(1) Excellent (1 review)
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Chatham Home
9 BR / 5 BA / Sleeps 20 9 20 Min stay varies
Home / 9 Bedrooms / Sleeps 20
9 bedrooms 5 bathrooms Sleeps 20
High Speed Internet • Dishwasher • Microwave
Perfect Family / Reunion / Retreat Beachhouse Style, Oceanview, Best Beach, Sleeps up to 16 Adults, Families to 20. Perfect for multi generational Wedding Family Lodging... Combine Wedding Lodging and Reunion! Child...
(1) Excellent (1 review)
Unique Chatham Villager
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Chatham Home
3 BR / 3 BA / Sleeps 8 3 8 Min stay varies
Home / 3 Bedrooms / Sleeps 8
3 bedrooms 3 bathrooms Sleeps 8
High Speed Internet • Dishwasher • Microwave
3 Bedrooms (Master w/ Ensuite), 3 Bathrooms, Sleeps 8 - Sofa Sleeps 2 Addl Newly renovated (March 2016), quaint and charming in the heart of Chatham Village Center. Enjoy the full benefit of being steps away from ...
Chatham Massachusetts Vacation Rentals - Home
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Chatham Home
3 BR / 2 BA / Sleeps 8 3 8 Min stay varies
Home / 3 Bedrooms / Sleeps 8
3 bedrooms 2 bathrooms Sleeps 8
High Speed Internet • Dishwasher • Microwave
This newly renovated, quaint and charming home is set in the heart of Chatham village. Enjoy the full benefit of being steps away from Main Street, the scenic beaches, and the ocean. There are 3 bedrooms/2 baths and p...
Chatham Massachusetts Vacation Rentals - Home
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Chatham Home
2 BR / 3 BA / Sleeps 4 2 4 No min stay
Home / 2 Bedrooms / Sleeps 4
2 bedrooms 3 bathrooms Sleeps 4
Dishwasher • Washer/Dryer • Air Conditioning
Enjoy staying in the heart of Chatham Village in this brand new, tastefully appointed 2 bedroom, 2. 5 bath 1, 300 sq. ft. home. Downtown Chatham is just steps away where you can enjoy shopping, fine restaurants, ban...
Chatham Massachusetts Vacation Rentals - Home
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Chatham Home
3 BR / 3 BA / Sleeps 8 3 8 No min stay
Home / 3 Bedrooms / Sleeps 8
3 bedrooms 3 bathrooms Sleeps 8
Dishwasher • Washer/Dryer • Air Conditioning
Panoramic views of Nantucket Sound and a pristine salt marsh await you from this 3 bedroom, 2. 5 bathroom South Chatham home. The back deck offers a commanding view of the estuary and wildlife including osprey and egret...
Chatham Massachusetts Vacation Rentals - Home
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Chatham Home
3 BR / 2 BA / Sleeps 10 3 10 Min stay varies
Home / 3 Bedrooms / Sleeps 10
3 bedrooms 2 bathrooms Sleeps 10
High Speed Internet • Dishwasher • Microwave
Completely renovated, this year round quaint Cape Cod open concept 1500 sq ft home has 3 bedrooms, 2 baths with a large two level outdoor deck overlooking beautifully landscaped yard. Sleeps 6- 8 comfortably. Up to 10 ...
(1) Excellent (1 review)
Chatham Massachusetts Vacation Rentals - Home
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Chatham Home
3 BR / 2 BA / Sleeps 6 3 6 No min stay
Home / 3 Bedrooms / Sleeps 6
3 bedrooms 2 bathrooms Sleeps 6
Dishwasher • Washer/Dryer • Air Conditioning
This 3 bedroom, 2 bath house is in a quiet neighborhood abutting a wooded backyard. You'll be 7/10ths of a mile from Pleasant Street Beach and just a smidge further to Red River Beach. Amenities include window AC units ...
House exterior
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Chatham Cottage
2 BR / 1 BA / Sleeps 5 2 5 7 night min stay
Cottage / 2 Bedrooms / Sleeps 5
2 bedrooms 1 bathroom Sleeps 5
High Speed Internet • Dishwasher • Microwave
$1150/week–High Season–lower other times Foote- steps Chatham Charmer - Weekly Rentals The charm of a Cape Cod cottage with all the amenities of home. Relaxation and conveniences on a private circle with idyllic ...
(5) Excellent (5 reviews)
Enjoy the Calm Waters of our Private Beach . . . Little Beach - Great for kids!
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Chatham Condo
2 BR / 2 BA / Sleeps 6 2 6 Min stay varies
Condo / 2 Bedrooms / Sleeps 6
2 bedrooms 2 bathrooms Sleeps 6
High Speed Internet • Dishwasher • Microwave
“Cozy Condo on the Beach” is a bright and airy, immaculately- maintained beach condo with plenty of charm and location, location, location . . . walk/bike just 1 mile to the quaint seaside village of Chatham to al...
Chatham Massachusetts Vacation Rentals - Home
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Chatham Home
4 BR / 2 BA / Sleeps 8 4 8 3 night min stay
Home / 4 Bedrooms / Sleeps 8
4 bedrooms 2 bathrooms Sleeps 8
High Speed Internet • Dishwasher • Microwave
Charming house completely renovated in the perfect location - central to all that Chatham and the Cape have to offer. Enjoy the downtown Main Street, restaurants, beaches, Chatham A's baseball, outdoor concerts and ...
PLEASANT STREET - NORTHERN VIEW
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Chatham Home
3 BR / 2 BA / Sleeps 8 3 8 Min stay varies
Home / 3 Bedrooms / Sleeps 8
3 bedrooms 2 bathrooms Sleeps 8
High Speed Internet • Dishwasher • Microwave
This charming Cape Cod style home is an attractively- furnished 6 room, 3 bedroom, 2 bath home that is only a 2 minute walk from the Pleasant Street Beach, for which a sticker is not required. It has a rooftop deck wi...
(11) Excellent (11 reviews)
Front View of Cranberry Way, South Chatham
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Chatham Home
2 BR / 2 BA / Sleeps 6 2 6 Min stay varies
Home / 2 Bedrooms / Sleeps 6
2 bedrooms 2 bathrooms Sleeps 6
High Speed Internet • Dishwasher • Microwave
This charming Cape Cod style cottage is a delight! It is a 2 bedroom, 2 bath home (one large new one) on a large lot with much privacy. It has A/C, hi- speed wireless internet, a new wide- screen HD TV, new carpetin...
(13) Excellent (13 reviews)
DINING SALT WATERFRONT! IT DOESN'T GET ANY BETTER
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Chatham Home
3 BR / 3 BA / Sleeps 8 3 8 Min stay varies
Home / 3 Bedrooms / Sleeps 8
3 bedrooms 3 bathrooms Sleeps 8
High Speed Internet • Dishwasher • Microwave
Located SALT WATERFRONT on the Oyster Pond River, a salt water Nantucket Sound inlet, this charming, beautifully updated home, has views of both Nantucket Sound and the Village of Chatham. The private neighborhood is...
Chatham Massachusetts Vacation Rentals - Apartment
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Chatham Apartment
2 BR / 2 BA / Sleeps 5 2 5 7 night min stay
Apartment / 2 Bedrooms / Sleeps 5
2 bedrooms 2 bathrooms Sleeps 5
High Speed Internet • Dishwasher • Microwave
Conveniently located South of Route 28 and less than a mile to popular Ridgevale Beach, this 2 bedroom, 2 bathroom Town House style condominium is absolutely pristine. The unit has been totally renovated with features ...
Chatham Massachusetts Vacation Rentals - Home
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Chatham Home
9 BR / 4 BA / Sleeps 20 9 20 Min stay varies
Home / 9 Bedrooms / Sleeps 20
9 bedrooms 4 bathrooms Sleeps 20
High Speed Internet • Dishwasher • Microwave
Southwesterly ocean breezes flow over this HISTORIC family estate built in the 1930?s by Mr. & Mrs. John Peale Bishop, a classmate and best friends at Princeton of F. Scott Fitzgerald and himself a famous writer and poe...
(3) Excellent (3 reviews)
FRONT VIEW OF HOME W/ BIT OF UPPER DECK SHOWING
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Chatham Home
3 BR / 2 BA / Sleeps 6 3 6 7 night min stay
Home / 3 Bedrooms / Sleeps 6
3 bedrooms 2 bathrooms Sleeps 6
High Speed Internet • Dishwasher • Microwave
Swim, fish, bike or just plain relax at this comfortable retreat in Chatham. In a quiet, wooded setting, cooled by the breezes from the pond, window AC's and ceiling fans, the home's open floor plan is well suite...
(1) Excellent (1 review)
Chatham Massachusetts Vacation Rentals - Home
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Chatham Home
3 BR / 1 BA / Sleeps 5 3 5 Min stay varies
Home / 3 Bedrooms / Sleeps 5
3 bedrooms 1 bathroom Sleeps 5
High Speed Internet • Dishwasher • Microwave
Discounts: Labor Day Wkend 9/3- 5 $450! ! Or 9/3- 6 $550! ! Fall- Check It Out Our Rates! Off Season Discount Is $125/night For 2 People. Please See "rates. " The ''chatham Retreat'' Is Clean, Charming, A...
Chatham Massachusetts Vacation Rentals - Home
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Chatham Home
4 BR / 6 BA / Sleeps 10 4 10 7 night min stay
Home / 4 Bedrooms / Sleeps 10
4 bedrooms 6 bathrooms Sleeps 10
High Speed Internet • Dishwasher • Microwave
2016 Rental Rate: $10, 675 per week with the cleaning and linens included. Weekly rentals from mid- JUNE to mid- SEPTThe views from this sprawling Crows Pond waterfront Cape, are incredible. You can see water from almo...
Chatham Massachusetts Vacation Rentals - Home
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Chatham Home
8 BR / 11 BA / Sleeps 16 8 16 7 night min stay
Home / 8 Bedrooms / Sleeps 16
8 bedrooms 11 bathrooms Sleeps 16
High Speed Internet • Dishwasher • Microwave
Two Weeks Rate: $56, 000. 00Monthly Rate: $112, 000. 00Season Rate: $224, 000. 00Rising majestically over Eldridge Point, overlooking Oyster River, Harding’s Beach, and Nantucket Sound, this extraordinary estate...
Chatham Massachusetts Vacation Rentals - Home
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Chatham Home
3 BR / 2 BA / Sleeps 8 3 8 7 night min stay
Home / 3 Bedrooms / Sleeps 8
3 bedrooms 2 bathrooms Sleeps 8
High Speed Internet • Dishwasher • Microwave
Beautiful Chatham Vacation Rental Home just 7/10ths of a mile to Cockle Cove Beach adjacent to Ridgevale Beach. This home is nicely done with all the amenities you need to enjoy your Cape Cod vacation here in Chatham. Th...
Chatham Massachusetts Vacation Rentals - Home
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Chatham Home
5 BR / 4 BA / Sleeps 10 5 10 7 night min stay
Home / 5 Bedrooms / Sleeps 10
5 bedrooms 4 bathrooms Sleeps 10
High Speed Internet • Dishwasher • Microwave
2016 Rental Rate: $6950 plus a mandatory $300 cleaning fee for one week, and $450 cleaning fee for a two week lease~~ Off- Season: $4000 per week, plus same cleaning fees as above. Weekly rentals from mid- JUNE to mid-...
Chatham Massachusetts Vacation Rentals - Home
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Chatham Home
4 BR / 4 BA / Sleeps 8 4 8 Min stay varies
Home / 4 Bedrooms / Sleeps 8
4 bedrooms 4 bathrooms Sleeps 8
High Speed Internet • Dishwasher • Microwave
Great location! Oyster Pond & Chatham Village! ! At this home you will be just apprx. 500 ft to private Oyster Pond access, 7/10ths of a mile to the the public beach at Oyster Pond and just 6/10ths of a mile to Chatha...
Chatham Massachusetts Vacation Rentals - Home
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Chatham Home
3 BR / 3 BA / Sleeps 7 3 7 7 night min stay
Home / 3 Bedrooms / Sleeps 7
3 bedrooms 3 bathrooms Sleeps 7
High Speed Internet • Dishwasher • Microwave
2016 Rental Rate: $3165 per week, including the cleaning fee~~~~ Off- Season: $1715 per week, including the cleaning fee~~Weekly rentals from mid- JUNE to mid- SEPTBright, spacious 3 bedroom home located in South Chat...
Chatham Massachusetts Vacation Rentals - Home
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Chatham Home
4 BR / 3 BA / Sleeps 8 4 8 Min stay varies
Home / 4 Bedrooms / Sleeps 8
4 bedrooms 3 bathrooms Sleeps 8
High Speed Internet • Dishwasher • Microwave
2016 Rental Rate: $2100 per week including the cleaning fee~~ Off- Season: $1575 per week including the cleaning feeWeekly rentals from mid- JUNE to mid- SEPTGreat four bedroom home located close to Chatham's Bike Trail,...
Chatham Massachusetts Vacation Rentals - Home
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Chatham Home
5 BR / 3 BA / Sleeps 10 5 10 7 night min stay
Home / 5 Bedrooms / Sleeps 10
5 bedrooms 3 bathrooms Sleeps 10
High Speed Internet • Microwave • Washer/Dryer
2016 Rental Rate: $3625 per week including the cleaning fee~~ Off Season: $2325 per week including the cleaning feeWeekly rentals from mid- JUNE to mid- SEPTEnjoy fabulous views from this adorable family compound overloo...
Chatham Massachusetts Vacation Rentals - Home
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Chatham Home
3 BR / 2 BA / Sleeps 6 3 6 7 night min stay
Home / 3 Bedrooms / Sleeps 6
3 bedrooms 2 bathrooms Sleeps 6
High Speed Internet • Dishwasher • Microwave
2016 Rental Rate: $2350 per week, including the cleaning fee~~Off- Season: $1650/week, including the cleaning feeTHIS IS A FRIDAY TO FRIDAY RENTALWeekly rentals from mid- JUNE to mid- SEPTLight and bright cottage just ...
Chatham Massachusetts Vacation Rentals - Home
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Chatham Home
4 BR / 3 BA / Sleeps 10 4 10 7 night min stay
Home / 4 Bedrooms / Sleeps 10
4 bedrooms 3 bathrooms Sleeps 10
High Speed Internet • Dishwasher • Microwave
2016 Rental Rate: $2000 per week including the cleaning fee~~ Off- season $1600 per week including the cleaning feeWeekly rentals from mid- JUNE to mid- SEPTCharming home located in terrific central area of North Chatham...
Chatham Massachusetts Vacation Rentals - Home
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Chatham Home
3 BR / 2 BA / Sleeps 6 3 6 7 night min stay
Home / 3 Bedrooms / Sleeps 6
3 bedrooms 2 bathrooms Sleeps 6
High Speed Internet • Dishwasher • Microwave
2016 Rental Rate: $3575 per week including the cleaning fee. ~~ Off- season: $2575 per week including the cleaning feeWeekly rentals from mid- JUNE to mid- SEPTCharming home right on Seaview Street - a short walk to dow...
Chatham Massachusetts Vacation Rentals - Home
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Chatham Home
3 BR / 2 BA / Sleeps 6 3 6 7 night min stay
Home / 3 Bedrooms / Sleeps 6
3 bedrooms 2 bathrooms Sleeps 6
High Speed Internet • Dishwasher • Microwave
2016 Rental Rate: $3075 per week including the cleaning fee~ Off- Season Rate: $1775 per week including the cleaning feeWeekly rentals from mid- JUNE to mid- SEPTSummer rental one block from the popular Harding's Beach! ...
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About Chatham

Chatham, MA Travel Tips

Situated on the southeastern tip of Cape Cod is the town of Chatham, MA. This charming town is a pleasant place for families to unwind and spend valuable and fun time together. For the most relaxing experience possible, people will want to skip hotels in favor of Chatham rentals. For the best selection of Chatham vacation rentals online, you're in the right place. Vacation Home Rentals has well-maintained properties available for rent by owner. By booking with us, you can save money and enjoy the comforts of home. When planning a trip to Chatham, there are a few tips that can make the stay more comfortable for all.
During the winter, Chatham is quieter than in the busy summer months. For families that prefer to avoid crowds, this is a good time to visit. Keep an eye on the average temperatures for the month that you'll be visiting Chatham. The warmest months of the year are July and August, with top temperatures averaging 75 degrees Fahrenheit. The coldest month of the year is January, with average lows at 24 degrees Fahrenheit and highs at 38 degrees Fahrenheit. Checking out the weather will help make packing for the family easier. When traveling in peak season, be sure to book Chatham vacation rentals in advance to save time and money.

Attractions

Rest and relaxation are two of the most important reasons why tourists stay in vacation rentals. Chatham, MA, has so many attractions that at the end of a fun-filled day, families will appreciate a good night's sleep. A popular destination for families is the Atwood House Museum. The museum is a great way to learn about the history of Cape Cod and to view the area's art while staying in Chatham, MA, rentals. Another interesting museum to visit is the Chatham Railroad Museum, which is located in an 1887 railroad depot that has been restored. The Chatham Lighthouse is another popular destination when visiting the city. To visit the lighthouse, tourists may arrange for a tour on dates that have been set aside by the Coast Guard Auxiliary. For many tourists staying in Chatham rentals, the beaches are one of the main attractions. Public beaches include Ridgevale Beach, Harding Beach, Cockle Cove Beach, and more. Parks are another way that families can enjoy their vacation. Parks such as Chase Park offer great outdoor fun and have picnic areas and charcoal grills. Also located in Chatham is the Monomoy National Wildlife Refuge, Samuel Hawes Park, Sears Park, and Volunteer Park.

Events

Hotels are often overcrowded and noisy when the city is hosting a special event. The calm atmosphere and convenience of staying in Chatham, MA, vacation rentals is a benefit for many tourists. Families on vacation will appreciate this convenience and can better enjoy the event's festivities. Festivals, fairs and other events take place throughout the year. In June, for instance, there is the annual Chatham Harbor Run and the Classic Car Invitational. For the children in the family, there are games for kids, while adults can enjoy a beer with their bratwurst and other German fare. Thanksgiving is a great time to travel to and stay in vacation rentals in Chatham, MA. Before indulging in a Thanksgiving Day meal, families can run or walk together in the annual Turkey Trot. Also during the holiday season, don't miss the annual Chatham Christmas Stroll.

When you think of a quaint New England village, of salt shaker houses and quiet, flower-edged lanes, you have Chatham. Though it’s not as sleepy as you might imagine (especially in the summer), a Chatham vacation rental provides the perfect base to explore charming Cape Cod.

Things to Do

The major draw of this area is the beaches. Cape Cod is the place Bostonites and other New Englanders flock to each summer. Cape Cod is to New England populations as Long Island is to New Yorkers. Cockle Cove and Harding’s Beaches provide excellent spots for families, while the Chatham Lighthouse Beach allows visitors to appreciate the nautical history of the area. Lighthouse Beach’s tides are some of the strongest tides in Chatham, so pay attention to posted warnings. The Monomoy National Wildlife Refuge is the ideal place to look for spotted seals and is known for its bird watching.
Seal cruises and fishing jaunts are also popular ways to enjoy the rich gifts of the sea this area is known for. If you go, bring a jacket. The Atlantic and its breezes are cold regardless of the time of year or land temperatures.   

Transit

There are a number of buses and shuttle services that take visitors from Boston to Hyannisport and connect them to other points on the cape. During the summer, you can also catch the Cape Flyer, which offers train service from Boston to the Cape. However, most people prefer to bring cars because they can visit all the delightful towns of the cape and have more room than a bike basket provides for their many treasures gathered along the way. Bikes are popular for getting around town from your Chatham vacation rental.

Climate

Most people enjoy the cape because it allows them to escape the sweltering heat of the city in the summer. Summer temps are usually in the mid 70s. Winter brings highs in the 30s and can feel bitter due to the dampness off the water.

Events

While winter is the slow time at the cape, it also brings with it the magic of quiet towns and twinkling lights. Chatham hosts a Christmas-by-the-Sea shopping event and a Christmas Stroll as well as many theater shows. July 4th is also a big holiday at the cape as neighboring towns celebrate our nation’s independence with dueling fireworks displays.

Shopping

Chatham offers a number of darling boutiques and unique shops that feature treasures that are distinctly Cape Cod. From whimsical coastal décor to delightful preppy fashions and candy kitchens with chocolate seashells to works from local artists, you can find the perfect item here to suit your fancy. The stores in Chatham are as adorable as their contents, with awnings and window boxes. Shopping is a real treat in this town.    
A Chatham vacation rental is the perfect way to try on a different style of living; one where bikes with baskets are more popular than what kind of car you drive; where high heels are traded in for sandals; and days are measured in the beauty of experience.