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Elder Access Holiday Rentals in Chatham, MA

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    1 / 45
    5 of 5 bubbles (3) Excellent
    South Chatham
    3 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    1 / 47
    5 of 5 bubbles (16) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    1 / 48
    5 of 5 bubbles (1) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    3 Bedrooms, 4 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Location, location, location!! New, lovely furnished home in a quaint little Cape Cod village off Main Street. Minute(s) walk to shops, restaurants, movie theater, library, Chatham Bars Inn, Oyster Pond, Claflin Landing and Lighthouse Beach. Won't need to get in your car to vacation here! Chatham... View all property information
    Location Information
    Chatham, Cape Cod 02633
    1 / 14
    5 of 5 bubbles (2) Excellent
    West Chatham
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Washer
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    Chatham Beach house... walk to Harding's Beach in Chatham. Wonderful home, great for families! Outdoor Shower, wrap-around porch with patio furniture and grill, hammock to relax, Cable TV, DVD player (family movies on site), wifi included, full kitchen, laundry, garage, plenty of parking. Just... View all property information
    Location Information
    West Chatham, Chatham 02633
    5 of 5 bubbles Reviewed 8 October 2016
    I had no idea how large my family had grown until I set out to organize a weekend in Chatham, MA. We started as a family of 3; 2 little girls and a dad. Now we're a family of 10...
    5 of 5 bubbles Reviewed 19 August 2016
    What a perfect rental! From the beginning, owner Sue was extremely helpful and responsive. The beautiful pictures on the website don't even do it justice- the house was beautiful...
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    1 / 14
    5 of 5 bubbles (5) Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    About this property
    OYSTER POND AT CHATHAM consists of 32 privately owned townhomes set on 17.5 acres on beautiful Oyster Pond in Chatham, Cape Cod, Massachussetts. Incredible two bedroom, three full bathroom end-unit with gorgeous direct water views of Oyster Pond. Beautifully decorated with charming interior decor.... View all property information
    Location Information
    Chatham, Cape Cod 02633
    5 of 5 bubbles Reviewed 21 February 2017
    Great property & perfectly located. Close to beaches, shopping & restaurants. The house is very beautiful and spacious. Quick check in and check out & quiet & secluded property.
    5 of 5 bubbles Reviewed 17 February 2017
    Our family visited Chatham numerous times over the years. We stayed at Chatham Bars Inn, Wequassett Resort, and other rentals. By far, Oysterpond Townhome Unit 32 was the best...
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    1 / 24
    South Chatham
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    #602 - Port View Home:  Nantucket sound awaits you in this sweetie beach house. Pull in the driveway, look to the left ... All you see is OCEAN. Magnificent Nantucket Sound with white sandy beach just waiting on you to put down the beach blanket and take a dip! Port view home offers great living... View all property information
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    South Chatham, Chatham 02659
    1 / 20
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    About this property
    Walk to Chatham Main St., boutiques, restaurants, galleries, and nightlife! Welcome to The Chatham Bars Carriage House, located within walking distance to Historic Main St. with it's endless variety of boutiques, restaurants, galleries, and nightlife! Enjoy this traditional, yet well-appointed... View all property information
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    Chatham, Cape Cod 02633
    1 / 21
    South Chatham
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Outdoor Dining Area
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    • Child-friendly
    • x
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    About this property
    Enjoy this adorable, classic 2 bedroom and 1 full bath Cape beach cottage only a 10 minute walk to Nantucket Sound beaches. Amenities include dishwasher, washer/dryer, one window air conditioning unit, cable TV (with basic cable) with VCR & DVD, microwave, board games, children's books and videos,... View all property information
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    South Chatham, Chatham 02659
    1 / 13
    5 Bedrooms, 3 Bathrooms, Sleeps 11 | Quick View
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    • Grill
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    • x
    • Smoking allowed
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    About this property
    NOTE - Not available to book until mid Feb deadline for family and friends to sign up. Wonderful, family-friendly, 5- bedroom house close to town. One ground-floor bed/bath. Fenced-in, flower filled, back yard with outdoor shower, grille, table and chairs, deck/patio. Walking distance to town or... View all property information
    Location Information
    Chatham, Cape Cod 02633
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    1 / 12
    5 of 5 bubbles (5) Excellent
    4 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    • Washer
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    • Secure Parking
    • Patio
    • Satellite TV
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    • Grill
    • DVD Player
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    OYSTER POND AT CHATHAM consists of 32 privately owned townhomes set on 17.5 acres on beautiful Oyster Pond in Chatham, Cape Cod, Massachussetts. This is a stunning four bedroom, four and a half bath spacious end-unit townhouse with spectacular views of Oyster Pond. Unit 25 is the largest... View all property information
    Location Information
    Chatham, Cape Cod 02633
    5 of 5 bubbles Reviewed 2 August 2016
    Chatham was a fabulous location and own home 25 was our beautiful home away from home. It had every amenity that we could ask for in the home and outside. It was a great property...
    5 of 5 bubbles Reviewed 8 October 2015
    We recently celebrated our son's commencement from graduate school and could not think of an "easy" location to travel to over the long Labor Day weekend. We were able to secure...
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    1 / 24
    South Chatham
    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    • Porch
    • Wi-Fi
    • Satellite TV
    • DVD Player
    • Washer
    • Grill
    • Waterfront
    • Air Conditioning
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    This gorgeous sprawling home on 3 acres is surrounded by 50 acres of conservation land. It is extremely private, very quiet, has its own pond, and plenty of space for sunbathing and outside play, large, expansive decks, lots of room for entertainment inside and out. It is completely equipped with... View all property information
    Location Information
    South Chatham, Chatham 02659
    1 / 24
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    #604 The Hideaway: Less than a mile to one of the best beaches in Chatham! Feel the warm sand between your toes at Cockle Cove beach, just .8 mile walk/bike ride. Downtown Chatham just minutes away. The Hideaway lives up to its name with being tucked away at the end of a private road, completely... View all property information
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    Chatham, Cape Cod 02633
    1 / 22
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    #603 - Lovers Holley Home: Lovely renovated home less than one mile from Chatham's famous downtown shopping and overlooking Lover's Lake - which is a walk around corner in a few minutes. All Chatham beaches are within two miles.  This home, located in the Great Hills Estates, provides a very... View all property information
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    Chatham, Cape Cod 02633
    1 / 20
    3 of 5 bubbles (1) Average
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Patio
    • Internet Access
    • Satellite TV
    • Air Conditioning
    • Washer
    • DVD Player
    • Grill
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    You will enjoy easy times in this 3 bedroom 2 bath Cape set on a hilltop. This very well-equipped house is at the end of a cul-de-sac and offers complete privacy, a large deck with grill, outdoor shower, and ample parking. It has a contemporary open and airy floor plan with cathedral ceilings and... View all property information
    Location Information
    Chatham, Cape Cod 02633
    3 of 5 bubbles Reviewed 19 August 2016
    We are a family of four travelling from the UK and stayed at the property for one week in July. Chatham was a relaxing week after our whirlwind tour of Florida and New York. We...
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    1 / 9
    South Chatham
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Pet-friendly
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    • x
    • Smoking allowed
    • x
    About this property
    Yes, the price is low but that's why so many customers have come for decades! <BR>Looking for a nice clean quiet cottage close to Nantucket Sound beaches? And one that you can afford on a tight budget with some money left for gas & dining?<BR><BR>Well, then...Pleasant Forest Shores just may be the... View all property information
    Location Information
    South Chatham, Chatham 02659 1525
    1 / 13
    5 of 5 bubbles (7) Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Balcony
    • Shared Outdoor Pool...
    • Parking
    • Wi-Fi
    • Grill
    • Outdoor Dining Area
    • Washer
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    OYSTER POND AT CHATHAM consists of 32 privately owned townhomes set on 17.5 acres on beautiful Oyster Pond in Chatham, Cape Cod, Massachussetts. Beautiful two bedroom plus a den and a loft, two and a half bathroom townhome with gorgeous direct water views of Oyster Pond. Beautifully decorated with... View all property information
    Location Information
    Chatham, Cape Cod 02633
    5 of 5 bubbles Reviewed 20 February 2017
    The location on Oyster Pond in Chatham is amazing, with close proximity to beaches and the attractions of the town center. The newly renovated unit is sparklingly clean and...
    5 of 5 bubbles Reviewed 28 June 2016
    This was the most perfect house for our vacation. It really is beautiful with every facility you could possibly want. Everything in the property details is as described but even...
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    1 / 11
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    About this property
    Chatham, 3 bedroom, 2 bath, walk to Ridgevale Beach and the warm waters of Nantucket Sound, south side of 28, whirlpool, stainless appliances, deck, gas grill, outdoor shower, all the amenities, fully stocked. Clean and comfortable, large yard, color cable, wi-fi. Enjoy all Chatham has to offer... View all property information
    Location Information
    Chatham, Cape Cod 02659
    1 / 7
    1 Bedroom, 2 Bathrooms, Sleeps 2 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    This property is not available after August 15, 2016. Charming Carriage House in fabulous location one street off Main St. near ball fields in quaint fishing village of Chatham, MA. Leave you car here as downtown is just a 10 minute walk, as is Oyster Pond. Also a short drive to the famous... View all property information
    Location Information
    Chatham, Cape Cod 02633
    1 / 11
    4.5 of 5 bubbles (12) Very good
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    • DVD Player
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    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    At this quiet lakeside cottage you can experience classic Cape Cod with all the modern amenities -- wireless internet, cable TV, air conditioning. Enjoy beautiful sunsets as well as swimming and canoeing at the lake---and only be a short trip to the beach or Chatham center. The cottage features... View all property information
    Location Information
    Chatham, Cape Cod 02633
    5 of 5 bubbles Reviewed 16 September 2016
    I loved the cottage, the location, and all the amenities. Helen thought of everything I would need for a restful stay. The cottage is airy and clean. The space is used very...
    4 of 5 bubbles Reviewed 20 July 2016
    When we drove up to the cottage, our hearts sunk a bit at how close the neighboring cottages were. Once we got settled in, though, we found that the Lakeview Colony is very quiet...
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    1 / 16
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Air Conditioning
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    This Chatham vacation rental has four bedrooms and can sleep six adults with two children. Unlike much of its competition, it is very spacious. It has one king bed, one queen bed, two twin beds and one room has a futon that can sleep two children. All bedrooms, as well as most of the house, are... View all property information
    Location Information
    Chatham, Cape Cod 02633
    1 / 28
    5 of 5 bubbles (2) Excellent
    4 Bedrooms, 6 Bathrooms, Sleeps 12 | Quick View
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    • Children's Pool
    • DVD Player
    • Internet Access
    • Satellite TV
    • Hot Tub
    • Waterfront
    • Air Conditioning
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    OYSTER POND AT CHATHAM consists of 32 privately owned townhomes set on 17.5 acres on beautiful Oyster Pond in Chatham, Cape Cod, Massachussetts. Incredible four bedroom, five and a half bathroom double end townhouse with gorgeous direct water views of Oyster Pond. Townhomes 31 and 32 are rented... View all property information
    Location Information
    Chatham, Cape Cod 02633
    5 of 5 bubbles Reviewed 17 October 2014
    The house was incredible. I have rented homes across the world with our family, and we are extremely picky in terms of 1. Cleanliness 2. renovation/newness 3. Location 4. Details...
    5 of 5 bubbles Reviewed 17 July 2014
    The units we rented at Oyster Pond exceeded our expectations. These two units (31 & 32) were very well appointed with TVs in every room, modern appliances, comfortable furniture...
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    1 / 14
    South Chatham
    3 Bedrooms, 2 Bathrooms, Sleeps 9 | Quick View
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    • Parking
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    • Satellite TV
    • Balcony
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    • Washer
    • Terrace
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Come enjoy our spacious 3-bedroom, 2.5 baths home that is just a short walk to Forest Beach and the warm waters of Nantucket Sound. Our home is located on a quiet lane 0.4 mile to the beach, 0.5 to the Cape Cod bike trail, and less than 4 miles to shopping and eating in quaint Chatham Center and... View all property information
    Location Information
    South Chatham, Chatham 24151
    1 / 32
    5 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    • Pet-friendly
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    • x
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    Central Air and Pet Friendly! Updated 5 Bedroom Cape Cod Vacation Rental Family Home in Chatham on the way to Cockle Cove Beach. Peak Summer Weekly Rates:  last week of June until the first week in September: $4,500/week. Large family? No problem! Can't leave home without Fido? Bring your doggie... View all property information
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    Chatham, Cape Cod 02633
    1 / 7
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • x
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    About this property
    Adorable doll like house very light airy cape vintage. Three bedroom one full bath . Close to beaches shopping baseball fields in beautiful historic town of chatham. All linens and towels professionally done like an inn. Vintage house so cute. Full kitchen dinning room living room with fireplace... View all property information
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    Chatham, Cape Cod 02633
    1 / 4
    4 Bedrooms, 2 Bathrooms, Sleeps 9 | Quick View
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    • Terrace
    • Balcony
    • Grill
    • Housekeeping...
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    • Pet-friendly
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    • Smoking allowed
    • x
    About this property
    This charming ranch is great for two families. Home has 3 bedrooms plus a bunk room, 2 baths, and is wheelchair accessible. The expanded Master Bedroom, en suite and hallway bathrooms, and kitchen are all newly renovated. The living room and Master Bedroom have new wide-screen HD TVs, and the house... View all property information
    Location Information
    Chatham, Cape Cod 02633
    1 / 30
    South Chatham
    2 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    • Grill
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    • Private Garden
    • Central Heating
    • DVD Player
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    • Satellite TV
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Fabulous opportunity to rent this impeccably maintained home located in desirable Chatham neighborhood south of Route 28. Forest Street Beach on Nantucket Sound, a little piece of heaven, just 5/10th's of a mile, +/- down the street. This charming, upscale beach house has been beautifully updated... View all property information
    Location Information
    South Chatham, Chatham 02659
    1 / 24
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Parking
    • Patio
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    • Outdoor Dining Area
    • Air Conditioning
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Have the ultimate Chatham getaway at this 2-bedroom, 1-bathroom 'Carriage House' cottage that comfortably sleeps 4. Steps away from Oyster Pond, the home offers spectacular water views and easy access to the beach. Whether you're seeking an art-inspired getaway or outdoor excitement, you're sure to... View all property information
    Location Information
    Chatham, Cape Cod 02633
    1 / 24
    5 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    • Patio
    • Air Conditioning
    • Satellite TV
    • Porch
    • Grill
    • Internet Access
    • Washer
    • DVD Player
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Escape to this 1801 Sea Captain's House with alluring old-world charm in Chatham for the ultimate Cape Cod getaway! With 5 bedrooms,4.5 bathrooms and accommodations for 10 this vacation rental house is the ideal size for families, friends, or couples traveling together. Whether you're seeking... View all property information
    Location Information
    Chatham, Cape Cod 02633