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Chatham Luxury Vacation Rentals

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    Travellers to Chatham are booking June dates now. Secure your vacation rental today, and have the perfect trip.
    60 Matching Rentals in ChathamView all 402 rentals
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    8 Bedrooms, 11 Bathrooms, Sleeps 16 Quick View
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    5 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    Chatham Cape Cod Waterfront Vacation Rental (2683)1 / 36
    (2)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    $12,700/week Peak Season (June 29 - August 30) $8,600/week for the weeks of (6/22 and 8/31) $7,800/week Shoulder Season (6/15 and 9/7) $6,200/week Shoulder Season (6/8 and 9/14) $5,600/week (before 6/8 and after 9/21) This truly unique, custom built 5 bedroom, 4.5 bathroom home is just...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    6 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Private Outdoor Pool (Unheated)
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    Pet friendly
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    About this property
    Located on its own point within exclusive and private Stage Island, this Chatham home offers both an idyllic setting and modern comforts. Enjoy stunning views over Stage Harbor throughout the home and direct water access from the private dock (boats under 20' can be brought and tied up for your...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 12
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    5 Bedrooms, Sleeps 12 Quick View
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    2019 Rental Rate (Cleaning Fee Included): In-Season: $12,950 per week Click for More Photos, Map, and Availability Calendar Fabulous home close to Lighthouse Beach! This gorgeous home offers two en-suite masters, and two more bedrooms, plus a bedroom and full bath in the apartment above the garage....
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    Chatham, Cape Cod 2633
    Holiday Rental House - 5 Bedrooms, Sleeps 12
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    4 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    COMING IN 2019: BRAND NEW HEATED SALT WATER POOL! This perfectly situated Chatham rental features everything one is looking for in a Cape Cod rental. Located close to Shore Road, you and your guests will enjoy the best of being near the ocean and close to Main Street. Stroll to town on sidewalks...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 10
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    14 Hallett Lane Chatham Cape Cod - Sand Simeon1 / 48
    (6)Excellent
    6 Bedrooms, 7 Bathrooms, Sleeps 16 Quick View
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    • Patio
    • Private Outdoor Pool (Heated)
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    Pet friendly
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    Reviewed May 12, 2017
    Wow! We were impressed from the moment we walked through the door. The home is quite large, very well appointed and was very clean. We met people there and the home was great...
    Reviewed May 12, 2017
    This home was perfect for our group! Great space to have the group all together but at the same time when rooms are spread out so the home doesn't feel crowded with large groups...
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    Come stay at: Sand Simeon. Pet Friendly! Relax and enjoy this Chatham, Cape Cod Vacation Rental Home offering 6 bedroom 6.5 bathrooms. Bonus: Linens (bed sheets and bath towels) are complimentary with this home for the Peak Summer Season. This luxury home is pet friendly with a private pool,...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 6 Bedrooms, 7 Bathrooms, Sleeps 16
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    5 Bedrooms, Sleeps 10 Quick View
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    • Patio
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    Pet friendly
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    2019 Rental Rates (Cleaning/Linen Fee Included): In-Season: $14,750 per week Off-Season: $11,750 per week (Weekly Rentals Only) Click for More Photos, Map, and Availability Calendar This elegant five bedroom home is located in the heart of downtown Chatham, and keeps the look of its original...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 5 Bedrooms, Sleeps 10
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    01/01/19 - 06/22/19 $7,300 06/22/19 - 06/29/19 $8,000 06/29/19 - 08/31/19 $10,500 08/31/19 - 09/07/19 $8,000 09/07/19 - 12/31/19 $7,300 This beautifully renovated 1850 Antique home is literally just steps to Andrew Hardings Beach and Lighthouse Beach via a path directly across...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Cape Cod / Chatham HISTORIC FAMILY ESTATE1 / 8
    (2)Excellent
    9 Bedrooms, 4 Bathrooms, Sleeps 20 Quick View
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    • Ocean Views
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    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 poet. The Gatsby sits on 1.3 acres in Chatham overlooking Nantucket Sound....
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    South Chatham, Chatham 02659
    Holiday Rental House - 9 Bedrooms, 4 Bathrooms, Sleeps 20
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    5 Bedrooms, 6 Bathrooms, Sleeps 16 Quick View
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    • Cable/satellite TV
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    About this property
    Chatham Resort Feel: Sleeps 16, Heated Pool/Spa, Renovated, Roomy, Upscale. Peak Summer Weekly Rates: $13,500 - $15,000 Rents Saturday to Saturday in peak season Linens Included Please click on the 'Virtual Tour'tab to take a 3D tour of the home PLEASE NOTE: The new Massachusetts state and...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 16
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    4 Bedrooms, 6 Bathrooms, Sleeps 8 Quick View
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    • DVD Player
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    • Private Outdoor Pool (Unheated)
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    • Waterfront
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    Pet friendly
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    Robert Paul Properties Luxury collection rental home. Imagine walking through the front door to a stunning view of the Harbor overlooking Chatham Pier and your own heated pool. Relax in the hot tub or sit on the back patio and take it all in. This waterfront vacation home has magnificent views...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 6 Bathrooms, Sleeps 8
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    $9,800/week Peak Season (7/27 - 8/16) $9,400/week Shoulder Season (Weeks of 7/20 and 8/17) $8,900/week Shoulder Season (Weeks of 7/13 and 8/24) $8,400/week Shoulder Season (Week of 7/6) $7,900/week Shoulder Season (Weeks of 6/29 and 8/31) $6,500/week Off Season (Week of 9/7) $6,000/week Off...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    4 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    Spectacular seaside views from almost every room in this beautiful 4 bedroom, 3 bathroom Chatham rental home which rests below the watchful gaze of Chatham Light. This Chatham rental home is ideally situated between scenic Lighthouse Beach and the edge of Monomoy National Wild Life Refuge, a beach...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 12
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    4 Bedrooms, Sleeps 8 Quick View
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    2019 Rental Rates (Cleaning/Linens Fee Included): In-Season: $13,000 per week Off-Season: Call for Availability Click for More Photos, Map, and Availability Calendar Stunning four bedroom home on Holway Street, with fabulous water views from almost every room in the house! Filled with gorgeous...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, Sleeps 8
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    5 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    • Cable/satellite TV
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    About this property
    Updated Chatham Family Compound Sleeps 14, Large Heated Pool with Spa, Walk to Town Peak Summer Rates: $12,500 - $14,000 Rents Saturday to Saturday in Peak Season Linens Included PLEASE NOTE: The new Massachusetts state and local taxes apply to stays starting July 1 or later. Book in June and...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 14
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    7 Bedrooms, 5 Bathrooms, Sleeps 20 Quick View
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    Historic North Chatham Estate. Sleeps 20, private beach! Linens included and new beds/furniture for 2018 Peak Summer Weekly Rates: $12,500 - $14,000 Rents Saturday to Saturday during peak season Two-night rentals available in the offseason   Please click on the 'Virtual Tour' to see a 3D tour of...
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    North Chatham, Chatham 02650
    Holiday Rental House - 7 Bedrooms, 5 Bathrooms, Sleeps 20
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    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Extraordinary Chatham Waterfront Home.  Private Beach, Sleeps 10 Peak Summer Weekly Rates: $8,650 Rents Saturday to Saturday during peak season Linens included PLEASE NOTE: The new Massachusetts state and local taxes apply to stays starting July 1 or later. Book in June and save! Come enjoy all...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    About this property
    This gorgeous 3 bedroom, 3.5 bath custom home is located less than 300 feet from Ridgevale Beach by neighborhood footbridge. This lovingly detailed and beautifully appointed home features both first and second floor master bedrooms, three living areas, a gourmet kitchen with a piano shaped island,...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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    5 Bedrooms, 5 Bathrooms, Sleeps 16 Quick View
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    • Grill
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    Pet friendly
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    About this property
    Only 4 miles from popular Chatham town center with its many shops and eateries, this house sits along the lovely private Eastward Ho! golf course with rolling hills and nearby Pleasant Bay. Also, 5 miles to the north is Orleans center. A large semi-circular driveway swings behind tall oaks and...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 16
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
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    Pet friendly
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    Smoking allowed
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    Beautiful Home on Morris Island! This exquisite property is set facing Monomoy on Morris Island in Chatham. Beautiful water views from every room set the tone for a relaxing and peaceful retreat. The interior is bathed in natural light and with 4 bedrooms and 3 1/2 bathrooms has plenty of space...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Robert Paul Properties Luxury Collection Condo. Four bedroom, four and a half bath spacious townhouse with spectacular views of Oyster Pond. Unit 25 is the largest condominium in the complex. Four well-appointed bedrooms (including a 1st floor king master and a 2nd floor king master), plus four and...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    $5,000/week (6/1 - 6/14) $5,600/week (6/15 - 6/28) $7,500/week (6/29 - 8/30) $5,600/week (8/31 - 9/13) $5,000/week (9/14 - 9/27) Enjoy the picturesque water views of Nantucket Sound from this brand new, custom built 4 bedroom, 4 full and 2 half bath home just steps away from Forest Beach...
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    South Chatham, Chatham 02659
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    • Cable/satellite TV
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    • Private Garden
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    Pet friendly
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    Smoking allowed
    About this property
    If you're fond of sand dunes and salty air.....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...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    Chatham Cape Cod Vacation Rental (102)1 / 19
    (1)Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Reviewed September 13, 2017
    My family of 5 has been vacationing in the Ridgevale Beach area of Chatham for many years now. Chatham is our favorite town on the Cape, and Ridgevale is the most family...
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    About this property
    $7,200/week Peak Season (7/20 -8/16) $6,800/week On Season (6/29 -7/19 and 8/17 - 8/30) $5,000/week Off Season (6/22 - 6/28 and 8/31 - 9/6) $4,300/week Off Season (6/15 - 6/21 and 9/7 - 9/13) $3,600/week Off Season (1/1 - 6/14 and 9/14 - 12/31) Spectacular 3+ bedroom, 3.5 bath home in one of...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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    8 Bedrooms, 6 Bathrooms, Sleeps 16 Quick View
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    Chatham Family Compound Sleeps 16   Walk to Public Beach – Linens Included Peak Summer Weekly Rates: $13,500 - $13,900  Rents Saturday - Saturday during peak season   Please click on the 'Virtual Tour' to see a 3D tour of the home PLEASE NOTE: The new Massachusetts state and local taxes apply to...
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    North Chatham, Chatham 02650
    Holiday Rental House - 8 Bedrooms, 6 Bathrooms, Sleeps 16
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    5 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    • Waterfront
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    About this property
    Spacious Custom Chatham Home Plus Guest House Linens included, new furnishings, hot tub, bocce court Peak Summer Weekly Rates: $12,500-$13,900/week Rents Saturday to Saturday in peak season PLEASE NOTE: The new Massachusetts state and local taxes apply to stays starting July 1 or later. Book in...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 14
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    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    • Grill
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    Pet friendly
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    Smoking allowed
    About this property
    Come enjoy easy, breezy Highwood Cottage, tucked away off of N. Chatham's prettiest street. Enjoy the quiet calm and fresh air after a busy day of shopping downtown, away from the noise and crowds (but not too far). Sit on your beach and read while the boats glide by or play games with the kids...
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    North Chatham, Chatham 02650
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 7
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    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Pet friendly
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    About this property
    2019 Rental Rates (Cleaning Fee Included): In-Season: $7,050 per week No Off-Season Click for More Photos, Map, and Availability Calendar Main Street in Chatham! Spend your summer vacation relaxing on the front porch of this charming, quintessential Cape Cod home in downtown Chatham. This highly...
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    Chatham, Cape Cod 2633
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Beautiful Home on Main Street in Downtown Chatham! This gracious and comfortable home has all you could ask for and more in a summer vacation home! Located on Main Street in downtown Chatham, this house is ideally situated for enjoying town and beaches and all the rest this area has to offer....
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    Chatham, Cape Cod 02633
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    About this property
    One of the most photographed Wind Mill homes on Cape Cod. Classic old world charm, coupled with all modern conveniences located near the beach and town. The Stony Hill Mill, constructed with 100 year old beams, river rock and barn board, is truly Cape Cod at its finest. This large stately home is...
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    North Chatham, Chatham 02650
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    About this property
    2019 Rental Rates (Cleaning Fee Included): In-Season: $6800 per week No Off-Season Click for More Photos, Map, and Availability Calendar Gorgeous home, located just steps to the center of downtown Chatham, is filled with upscale furnishings and custom amenities and is everything you want for the...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    1 Bedroom, 4 Bathrooms, Sleeps 8 Quick View
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    Beautiful, Spacious and Bright Home in North Chatham! This lovely home is located in the Canon Hill Association area of North Chatham and has a private association beach on Pleasant Bay just a short ways down the road! With 4 bedrooms, 3 full baths, 2 half baths and many different living spaces,...
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    North Chatham, Chatham 02650
    Holiday Rental House - 1 Bedroom, 4 Bathrooms, Sleeps 8
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    394 Barn Hill Road1 / 25
    (1)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Reviewed August 21, 2018
    Our 2 weeks at the Kenneys’ Barn Hill Rd home couldn’t have been better. It was perfect for our sons and grandchildren’s comings and goings. We all loved having breakfast on the...
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    About this property
    Comfort and charm abound in this updated 18th Century seaside farmhouse (four bedrooms and three baths) situated on more than 3/4 of an acre of land. Brand new kitchen with stainless appliances, granite counter tops and cherry cabinets. Enjoy your morning cup of coffee while taking in the...
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    Location Information
    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    103 Bellamy Lane1 / 30
    (1)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Parking
    • Wi-Fi
    • Cable/satellite TV
    • Grill
    • DVD Player
    • Private Outdoor Pool (Unheated)
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 6, 2018
    5 stars. We had a great family vacation in this house. The pool area is fantastic. The house is clean and comfortable. It was large enough for 10 of us. The kitchen is very well...
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    About this property
    Tucked in the private Cannon Hill setting, this enchanting 4 bedroom, 3 full and 1 half bathroom home with a large 40 x 20 heated salt-water pool offers tons of comfort and is perfect for your summer getaway. Just a short 3 minute stroll away, on the calm waters of Pleasant Bay, a private...
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    Location Information
    Chatham, Cape Cod 02650
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Parking
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Patio
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Looking for a property which is located in one of the most desirable towns on Cape Cod and features amenities that you usually have to drive to and pay extra for? Well look no further... welcome to 324 Deer Meadow Lane in Chatham. Featuring five bedrooms, three full and one half baths, a heated...
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    Location Information
    Chatham, Cape Cod 02633
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 12
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    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Washer
    • Grill
    • Cable/satellite TV
    • DVD Player
    • Internet Access
    • Air Conditioning
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    2019 Rental Rates (Cleaning Fee Included): In-Season: $6775 per week No Off-Season Rate Click for More Photos, Map, and Availability Calendar Gorgeous four bedroom home located in a prestigious North Chatham neighborhood! Offering plenty of room to spread out, this lovely home features upscale...
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    Location Information
    North Chatham, Chatham 2650
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 8
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    5 Bedrooms, Sleeps 11 Quick View
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    Amenities & Details
    • Internet Access
    • Patio
    • Washer
    • Air Conditioning
    • DVD Player
    • Cable/satellite TV
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    2019Rental Rates (Cleaning Fee Included): In-Season: $8600 per week Off-Season: $6650 per week Click for More Photos, Map, and Availability Calendar This gorgeous home offers over 5000 square feet of living space spanning three levels, and manages to be both elegant and comfortable. It features...
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    Location Information
    Chatham, Cape Cod 02633
    Holiday Rental House - 5 Bedrooms, Sleeps 11
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    201 Main Street Chatham Cape Cod - Sandpiper1 / 42
    (1)Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Hot Tub
    • Parking
    • DVD Player
    • Wi-Fi
    • Cable/satellite TV
    • Grill
    • Air Conditioning
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Experience the Sandpiper! Pet Friendly! 4 bedroom, 4.5 bath Vacation Rental located in the heart of Chatham's historic village!! BONUS: LINENS INCLUDED IN SEASON. Whether you are soaking in the hot tub on the private patio or enjoying an outdoor shower after you've come home from Lighthouse or...
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    Location Information
    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    Quintessential Cape Cod Vacation Home in N.Chatham1 / 41
    (1)Excellent
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
    • Air Conditioning
    • Patio
    • Washer
    • Balcony
    • Grill
    • Internet Access
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 23, 2014
    Amazing home with a great owner who was 100 percent accessible our whole trip. Huge house, our party of 10 didn't even know one another was there. Highly recommend the...
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    About this property
    Welcome to the Whydah Figawai - a privately-owned five bed room vacation home in exclusive North Chatham, just a few steps away from the private beach on Pleasant Bay. This traditional Cape Cod home is located in a serene setting and offers the perfect combination of quiet and accessibility for...
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    Location Information
    Chatham, Cape Cod 02650
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    South Chatham Cape Cod Waterfront Vacation Rental (1841)1 / 19
    (1)Excellent
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Waterfront
    • Washer
    • Grill
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 2, 2017
    Great location right on Nantucket Sound. Upstairs you'd think you were on a boat; the water's THAT close. Lovely and very well equipped cottage. Kitchen was recently and...
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    About this property
    Spectacular panoramic water views from this 4 bedroom, 2 bath Chatham rental situated right on Cockle Cove Beach on Nantucket Sound. This is one of very few homes where you can step out your door and take only a few steps to the water's edge. The living room, dining room, kitchen and a full...
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    Location Information
    Chatham, Cape Cod 02659
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • Grill
    • DVD Player
    • Wi-Fi
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Experience 'Chatham Coastal Charm'. Popular Contemporary Cape Cod Vacation Rental home in Chatham with heated salt water gunite pool that is just a short walk to Hardings Beach (.3). Sleeps 10! Don't miss this 'fan favorite' Cape Cod Vacation Rental home in Chatham with heated pool that is very...
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    Location Information
    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    5 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    • Grill
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Chatham Village Charm Next to Chatham Light Peak summer weekly rate: $4,675 - $5,900  Rents Saturday to Saturday during peak season PLEASE NOTE: The new Massachusetts state and local taxes apply to stays starting July 1 or later. Book in June and save! NEW Kitchen coming for 2019!  This 5...
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    Location Information
    Chatham, Cape Cod 02633
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 9
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    4 Bedrooms, Sleeps 6 Quick View
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    Amenities & Details
    • DVD Player
    • Washer
    • Air Conditioning
    • Patio
    • Grill
    • Cable/satellite TV
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    2019 Rental Rates (Cleaning Fee Included): In-Season: $8,300 per week Off-Season: $6,000 per week Click for More Photos, Map, and Availability Calendar Fabulous home with all the bells and whistles, with deeded access to Stage Harbor beach. Professionally decorated, this 4 bedroom home is full of...
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    Location Information
    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, Sleeps 6
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    Spectacular Waterfront Home - Oyster Pond 31&321 / 28
    (2)Excellent
    4 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • Children's Pool
    • DVD Player
    • Internet Access
    • Cable/satellite TV
    • Hot Tub
    • Waterfront
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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...
    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...
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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 four bedroom, five and a half bathroom double end townhouse with gorgeous direct water views of Oyster Pond. Townhomes 31 and 32 are rented...
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    Location Information
    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 6 Bathrooms, Sleeps 12
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    5 Bedrooms, Sleeps 9 Quick View
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    Amenities & Details
    • Cable/satellite TV
    • Patio
    • DVD Player
    • Washer
    • Internet Access
    • Air Conditioning
    • Waterfront
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    2019 Rental Rates (Cleaning and Linen Fee Included): In-Season: $7840 per week Off-Season: $5840 per week Refundable Security Deposit - $1500 Click for More Photos, Map, and Availability Calendar This Lovely antique home overlooking the Oyster Pond Harbor has just completed a fabulous renovation!...
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    Location Information
    Chatham, Cape Cod 02633
    Holiday Rental House - 5 Bedrooms, Sleeps 9
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    55 Sears Point Road Chatham Cape Cod- The Sears Point House1 / 39
    (1)Excellent
    6 Bedrooms, 3 Bathrooms, Sleeps 12 Quick View
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    • Cable/satellite TV
    • Wi-Fi
    • Air Conditioning
    • Parking
    • Patio
    • Grill
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed August 11, 2018
    We enjoyed a lovely week at this great home. Our nine member family had plenty of room and two other family members were also able to join for a night or two. Chatham is...
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    About this property
    Enjoy this classic Cape Cod Style waterfront home with sparkling water views, a private beach, and large yard in Chatham. Over 180 degree views of Stage Harbor, Nantucket Sound, Monomoy Island, and the Atlantic Ocean beyond. Pet Friendly! Sleeping 12 there is plenty of space for everyone. Each...
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    Location Information
    Chatham, Cape Cod 02633
    Holiday Rental House - 6 Bedrooms, 3 Bathrooms, Sleeps 12
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Wi-Fi
    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    4 bedroom, 3.5 bath Cape Cod Vacation Rental home tucked up off of Bridge Street, in Chatham. BONUS: Linens included !. Privately placed on just over a half acre of land in a peaceful setting, yet just a hop, skip and a jump away you can find Lighthouse beach! It's an easy walk into the village...
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    Location Information
    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Wi-Fi
    • Air Conditioning
    • Waterfront
    • Cable/satellite TV
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Come stay at: Donnadune. Pet Friendly! (for dogs only) Waterfront Cape Cod Vacation Rental home in North Chatham on the beach with tennis court. Steps onto the large deck lead you to the entryway of this Cape home. Welcome back in time to when life was more simple-take the time to stare straight...
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    Location Information
    North Chatham, Chatham 02650
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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