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Rentals for Seniors in Chatham, MA

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    1 / 46
    5 of 5 bubbles (16) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    1 / 14
    5 of 5 bubbles (2) Excellent
    West Chatham
    4 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    1 / 20
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    1 / 47
    5 of 5 bubbles (1) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    • Patio
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    • x
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    About this property
    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 including a pullout sleeper sofa. All rooms are bright and nicely appointed with... View all property information
    Location Information
    Chatham, Cape Cod 02659
    5 of 5 bubbles Reviewed 5 weeks ago
    We loved our stay and our vacation was one to remember! The home was great. It was very clean, well kept and comfortable. It was conveniently located and we were on the go every...
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    1 / 17
    5 of 5 bubbles (1) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    Location, location, location! Charming cottage-like apartment right across the street from the Cape Cod Coast and Lighthouse Beach. The unit is also within a ten minutes walk to the vibrant downtown area abound with eclectic shops and restaurants. This Hammond House unit has a beautiful water view... View all property information
    Location Information
    Chatham, Cape Cod 02633
    5 of 5 bubbles Reviewed July 7, 2016
    My husband and I booked this vacation rental for the Fourth of July week and we really enjoyed our stay! Your right in the middle of the excitement a five minute walk to the beach...
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    1 / 44
    5 of 5 bubbles (3) Excellent
    South Chatham
    3 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    • DVD Player
    • Grill
    • Patio
    • Satellite TV
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    • Wi-Fi
    • Secure Parking
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    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 including a pullout sleeper sofa. All rooms are bright and nicely appointed with... View all property information
    Location Information
    South Chatham, Chatham 02659
    5 of 5 bubbles Reviewed 5 weeks ago
    We loved our stay and our vacation was one to remember! The home was great. It was very clean, well kept and comfortable. It was conveniently located and we were on the go every...
    5 of 5 bubbles Reviewed September 15, 2016
    What a unique & wonderful house in Chatham!  John & Ruby are really superb hosts, very accommodating, making sure we were all set… to our delight, John even texted to let us know...
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    1 / 7
    North Chatham
    4 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    • x
    About this property
    Spacious four bedroom ranch in Riverbay, a quiet neighborhood that is great for walking, and is only 1 mile from the calm waters of Jackknife Beach on Pleasant Bay! The house is cheerfully decorated with bright colors and upscale furnishings. The finished basement provides extra space for playing... View all property information
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    North Chatham, Chatham 02633
    1 / 7
    1 Bedroom, 2 Bathrooms, Sleeps 2 | Quick View
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    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 / 14
    5 of 5 bubbles (2) Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Grill
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    • Balcony
    • Porch
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    • Shared Outdoor Pool...
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
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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 November 18, 2014
    We had an amazing time in Chatham. My family (wife and two young kids) greatly enjoyed all the activities the area had to offer. The townhome far exceeded our expectations. The...
    5 of 5 bubbles Reviewed October 19, 2014
    This was intended as a romantic getaway with my wife. The townhouse was simply spectacular, and it was truly a great location and with amazing views. It was peaceful, very...
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    1 / 13
    5 of 5 bubbles (6) Excellent
    2 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Balcony
    • Shared Outdoor Pool...
    • Parking
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    • Air Conditioning
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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. 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 June 28, 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...
    5 of 5 bubbles Reviewed September 13, 2015
    Great location.The facilities were top notch; clean, spotless We really appreciated having everything provided from beach chairs, towels, toiletries, grill high chair for our...
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    1 / 13
    5 Bedrooms, 3 Bathrooms, Sleeps 11 | Quick View
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    • Pet-friendly
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    • x
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    About this property
    Wonderful, family-friendly, 5- bedroom house close to town. One ground-floor bed/bath.<BR>Fenced-in, flower filled, back yard with outdoor shower, grille, table and chairs, deck/patio. Walking distance to town or take extra bikes to ride to Lighthouse Beach/ Oyster Pond.<BR>Kitchen table has room... 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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    • x
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    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 September 16, 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 July 20, 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 / 12
    5 of 5 bubbles (5) Excellent
    4 Bedrooms, 5 Bathrooms, Sleeps 10 | Quick View
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    • Washer
    • Air Conditioning
    • Secure Parking
    • Patio
    • Satellite TV
    • Internet Access
    • Grill
    • DVD Player
    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. 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 August 2, 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 October 8, 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 / 21
    South Chatham
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Private Yard
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    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
    Location Information
    South Chatham, Chatham 02659
    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 October 17, 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 July 17, 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 / 20
    3 of 5 bubbles (1) Average
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Patio
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    • 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 August 19, 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 / 22
    5 Bedrooms, 5 Bathrooms, Sleeps 12 | Quick View
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    • x
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    About this property
    Ideal for extended families or larger groups. Walking distance from popular Ridgevale Beach (less than half of a mile), and only two miles from downtown Chatham, this 3,500 square foot home is a luxurious retreat for those who enjoy quality. Spacious modern kitchen, multiple eating areas for large... View all property information
    Location Information
    Chatham, Cape Cod 02633
    1 / 11
    South Chatham
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Satellite TV
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    • Waterfront
    • Patio
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Recently renovated cottage in sought after Cockle Cove beach neighborhood. Walk or bike 4/10ths mile to warm, sandy & family friendly town beach on Nantucket Sound. Direct waterfront location on tidal Taylors Pond, with stunning views and access to owner's private dock for kayaking & boating into... View all property information
    Location Information
    South Chatham, Chatham 02360
    1 / 11
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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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 / 21
    3 Bedrooms, 4 Bathrooms, Sleeps 6 | Quick View
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    • Patio
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    • Central Heating
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    • x
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    • x
    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
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    1 / 9
    South Chatham
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Parking
    • Porch
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    • Pet-friendly
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    • x
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    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 / 16
    4 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Air Conditioning
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    • Pet-friendly
    • Child-friendly
    • x
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    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 / 22
    6 Bedrooms, 5 Bathrooms, Sleeps 12 | Quick View
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    • Grill
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    • Pet-friendly
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    • x
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    About this property
    The ultimate setting for a relaxing vacation, this historic home is sited at the end of a 900 ft. seashell driveway on three secluded acres offering fantastic views of Strong Island and Pleasant Bay. Step out of the 6 person hot tub on the 1200 sq ft deck, pick up your beach chairs and walk across... View all property information
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    Chatham, Cape Cod 02633
    1 / 14
    South Chatham
    3 Bedrooms, 2 Bathrooms, Sleeps 9 | Quick View
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    • Terrace
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    • Pet-friendly
    • Child-friendly
    • x
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    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 / 7
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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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
    Location Information
    Chatham, Cape Cod 02633
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