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Holiday Rentals in Chatham

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    Travellers to Chatham are booking September dates now. Secure your holiday rental today, and have the perfect trip.
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    2017 Rental Rate: $2825 per week including the cleaning fee ~~~ Off-Season: $2225 per week including the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT Charming, antique home located in North Chatham with a pretty, private yard and distant views of the ocean from large deck. Short walk to...
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    North Chatham, Chatham 02650
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    2017 Rental Rates: $4425 per week, including cleaning Off-Season: $3125 per week cleaning Weekly rentals from mid-JUNE to mid-SEPT Stunning, new home located on Oyster River with breathtaking views of the river and marsh. Enjoy your afternoons after the beach watching the birds and wildlife from...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    This recently updated 4 bedroom, 2 bathroom home is located in the desirable Stage Harbor area of Chatham. On the ?loop,' this home is just a short walk to Battlefield Landing on Stage Harbor and only 1 mile to the shops and restaurants in downtown Chatham or to the warm waters of Oyster Pond. This...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    2017 Rental Rate: $1950 per week including the cleaning fee FRIDAY TO FRIDAY RENTAL! ~~ Off-Season: $1400 per week including the cleaning fee !!! Weekly rentals from mid-JUNE to mid-SEPT Charming cottage just steps to Ridgevale Beach. Upstairs addition is fabulous. It has a separate bathroom and...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    A "Shore Thing" in Chatham!1 / 17
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Cape Cod Dreaming by the Beach - Perfect for families to share! Relax by escaping to our newly refurbished and decorated classic Cape Cod cottage, just a short walk, 4/10 of a mile, to sandy Pleasant Street Beach on Nantucket Sound. It is walkable to Forest Street and Red River Beaches. Swim,...
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    Chatham, Cape Cod 02659
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    2017 Rental Rate: $2175 per week, including the cleaning fee Off Season: $1575 per week, including the cleaning fee Wonderful, updated ranch located in a private neighborhood and centrally located to all that Chatham has to offer! Open and airy floor plan with newer furnishings throughout. Tons of...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Enjoy a timeless beach vacation in this lovely Chatham home, 3-bed 2-bath, set near the beach with beautiful private gardens. Here, you’re only a mile from the beach, close to biking trails, and surrounded by fishing opportunities. Not to mention the shops and restaurants on Main Street! There’s a...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    2017 Rental Rate: $1725 per week, including the cleaning fee ~~ Off Season: $1125 per week, including the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT Recently remodeled cottage with central air is close to shopping and restaurants in downtown Chatham, baseball games at Veteran's Field,...
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    North Chatham, Chatham 02650
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    2017 Rental Rate $3875 per week, including the cleaning fee Off Season, $2725 per week, including the cleaning fee Light and bright, this spacious beach home is located right down the street from family-friendly Hardings Beach. Plenty of room to spread out and relax as you enjoy your Chatham...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    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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    Chatham, Cape Cod 02650
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 12
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Charming renovated home with central a/c in North Chatham! Charming renovated home in North Chatham, approx. .5 mile to Chatham Fish Pier, less than 2 miles to Chatham Lighthouse Beach and convenient to Scatteree Beach and the Cow Yard Landing! Approx. 1 mile to Main St., Chatham for shopping,...
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    North Chatham, Chatham 02650
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Lovely home with a/c near Ridgevale Beach RIDGEVALE BEACH 7/10 of a mile on Nantucket Sound!! Comfortably sleeps 10!! Cape Cod Bike Trail 8/10 of a mile away. Located at the end of a cul-de-sac and approximately 2 miles to the Village of Chatham for great dining, shopping, Cape Cod League Baseball...
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    South Chatham, Chatham 02659
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    16 SEA STRAND LANE (ID#109551) CHATHAM Charming and comfortable! Located in a quiet area within a short driving distance to both Hardings and Ridgevale Beaches. Air conditioning cools the home with units in every bedroom, including first floor master bedroom. WiFi, outdoor shower, washer/dryer,...
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    West Chatham, Chatham 02669
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    6 Bedrooms, 2 Bathrooms, Sleeps 11 Quick View
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    209 Champlain Rd Chatham MA DOG FRIENDLY Great, rambling home with an old-Cape Cod feel located on the "loop" just around the bend from Stage Harbor. Wonderful area to enjoy while here on the Cape! A tennis court is available to tenants during daytime hours from 10 am to 5 pm. The huge, grassy...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 6 Bedrooms, 2 Bathrooms, Sleeps 11
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    2017 Rental Rate: $2175 including the cleaning fee ***SPECIAL FOR 8/26 Week $1575 inc. Cleaning!!***Off-Season: $1575 per week including the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT Lovely home, on 1/2 acre wooded lot, only 1/2 mile to the warm waters of kid-friendly Ridgevale Beach!...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    2017 Rental Rate: $2100 per week including the cleaning fee ~~ Off-Season: $1575 per week including the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT Great four bedroom home located close to Chatham's Bike Trail, and near a fresh water pond. Located at the end of a cul-de-sac with a nice...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 8
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    5 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Classic Chatham Charm -- Walk to Beach & Town! (Linens included) Peak Summer Weekly Rates: $5,900 - $6,750 (Pets Considered) (Rents Saturday to Saturday during peak season) Located in a premier Chatham Village location, this classic antique home has everything to experience an idyllic Chatham...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    2017 Rental Rate: $3575 per week including the cleaning fee. ~~ Off-season: $2575 per week including the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT Charming home right on Seaview Street - a short walk to downtown Chatham, or Chatham Bars Inn! This home has lovely furnishings throughout,...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    This 3 bedroom cottage is the perfect location for your family stay in Chatham. The 3 bedrooms have one king room with a spacious en suite bathroom with Jacuzzi, and the other two with a queen sized bed in each. There are 2 sleeper sofas, one in the living room and the other in the family room. The...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    2017 Rental Rate: $2800 per week including the cleaning fee Off-Season Rate: $1800 per week including the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT You will love this 4 bedroom home near Ridgevale Beach! Located at the end of a dirt road with water views of a freshwater pond and...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Located outside of downtown Chatham sits this charming four bedroom home, known as Stones Throw. This property features great amenities such as central air conditioning, high speed wireless internet, and flat screen TVs in every bedroom. Enjoy an outdoor dinner in your central courtyard accessed...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    4 Bedrooms, 4 Bathrooms, Sleeps 11 Quick View
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    Immaculate Chatham Village Renovation, Walk to Beach & Village Peak Summer Weekly Rates: $7,900-$8,800 (Linens Included) (Rents Saturday to Saturday during peak season) JUNE Special - week of June 24th just dropped to $7,500! Your quintessential Chatham vacation awaits! This masterfully restored...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 11
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Location - Location - Location! Run, walk, or skip the loop in Chatham from this Family Cape Cod Vacation Rental home. SPECIAL 2017 LABOR DAY RATE! Stay 09/02 - 09/06 for the holiday for $900 (plus $175 processing fee). It's just a 5 minute stroll to the town landing to put your kayak or canoe in...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    4 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    Bring the whole family to Cape Cod! This sprawling 4BR, 4.5BA home sleeps 15 in comfort. Kids will love the basement entertainment and sleep area, and you’ll adore the 3-season room. Walk to Forest Beach, and drive to downtown Chatham in 10 minutes! INSIDE THE HOUSE From a drive with parking...
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    South Chatham, Chatham 02659
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 10
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    ON THE WATER ...<BR><BR>* Beautiful water views! <BR>* Back decks open to mesmerizing views of Emery Pond <BR>* Hammock and patio furniture chosen for comfort and relaxation!<BR>* Direct access to pond from backyard. <BR><BR>* Clean swimmable pond.<BR>* Bass fishing plentiful!<BR>* Gas grill.<BR>*...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    Experience Cape Cod living at our 4-bed, 2-bath Chatham vacation rental in a quiet, quaint wooded neighborhood. Hop on your bike (or into the car) and be at the beach or downtown Chatham in minutes! The home’s wooded deck/backyard and its finished basement—with a pool table, foosball, playroom and...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 10
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    190 Countryside Drive - ID# 104736. Lovely 4 bedroom home in Chatham Charming 4 bedroom home in a peaceful area with a lovely fenced in yard. Just a short drive to Jackknife Cove beach on Pleasant Bay and a short distance to Monomoy River for kayaking and canoeing. School Houe Pond is a half mile...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    2017 Rental Rate ~ $5225 per week, including the cleaning fee ~~ Off-Season: $3725, including the cleaning fee~~Weekly rentals from mid-JUNE to mid-SEPT Gorgeous home located in a secluded yet convenient area of Chatham and overlooking Oyster Pond. The house is almost surrounded by water views!...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    2017 Rental Rates: ~~~Pre-season (May 13-June 16) $1,200 per week ~~~IN SEASON: $1800 per week (June 17-Sept 9) ~~~Post-season (Sept 9-Oct 14th) $1,200 per week Off-season (subject to Owner's prior approval) $800 week $175 MANDATORY cleaning fee per lease Weekly rentals from mid-JUNE to mid-SEPT...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    Cape Cod Escape 5 min Walk to Beach! Private-Newly Renovated-Hear Waves at Night1 / 48
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    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    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...
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    Chatham, Cape Cod 02659
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Located in Chatham, this 4 bedroom 2 bath Cape Cod vacation rental home is only 0.3 miles to Ridgevale Beach. This home has window AC units in the upstairs bedrooms as well as the 1st floor bedroom and living area to keep you cool and offers WiFi to keep you connected. Through the side door off of...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    2017 Rental Rate: $2100, including the cleaning fee Off-Season $1600 per week, including the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT This is a well maintained property located in a quiet area in W. Chatham. Spacious bedrooms, one with two double beds. Updated kitchen, with a skylight,...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    2017 Rental Rate: $6450 per week, including the cleaning fee This recently renovated antique farmhouse is filled with upscale furnishings and is practically in the center of town! Located on large lot, it offers a wonderful mixture of new and old. There is one bedroom on the first floor with a...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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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...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    FIRST FLOOR CONDO FACING CHATHAM'S LIGHTHOUSE BEACH!1 / 22
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    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Price $1445 Rates include all charges; no hidden fees! Location, Location, Location! Inviting Chatham cottage-like apartment directly across from Chatham Lighthouse beach. Downtown Chatham is just a few short blocks away. Directly across the street is a stunning sand beach with great seal...
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    Chatham, Cape Cod 2633
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Located on a quiet side street close to Pleasant Street Beach and Red River Beach this bright 3 bedroom, 2 bath home is sure to please. The open floor plan with wood floors throughout, updated kitchen and living area with cathedral ceiling flows through french doors into a large sun room with a...
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    Chatham, Cape Cod 02659
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    2017 Rental Rate: $3625 per week, including the cleaning fee ~~~~~Off-Season: $2525 with cleaning fee included ~~~~~ Fabulous updated home located in North Chatham, convenient to town and many of Chatham's beaches! High ceilings & hardwood floors throughout and a screened in porch off of the...
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    North Chatham, Chatham 02650
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 8
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    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Great Vacation Spot Right up the Road from Pleasant Street Beach in South Chatham! Well appointed and comfortable, this home is convenient to all the area has to offer. Enjoy grilling on the deck in the private backyard after a day enjoying summer on Cape Cod! Four bedrooms and 2 1/2 bathrooms...
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    South Chatham, Chatham 02659
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 10
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    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Patio
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    Lovely five bedroom home close to town and the beach! It has everything you need: a huge yard for games, central air, updated kitchen and an awesome location! The beach is just a walk across the street from this beautifully landscaped Shore Road home. This home is located on the first fairway of...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Pet Friendly! Located in a prime in-town location! This Cape Cod Vacation Rental Cottage complex offers deeded access to the Mill Pond (a saltwater inlet of Nantucket Sound) and is just a few blocks to the beautiful Lighthouse Beach in Chatham's Old Village. This desirable and newly renovated...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    2017 Rental Rate: $2300 per week, including the cleaning fee ~Off-Season: $1200 per week, including the cleaning Weekly rentals from mid-JUNE to mid-SEPT Light and bright 4 BR home, in a great central location! This recently updated home is across from the school tennis courts and playing fields,...
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    Chatham, Cape Cod 02650
    Holiday Rental House - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    Come Stay at: Chatterbox! Location! Location! Location! Luxury Chatham Vacation Rental home with 3 bedroom, 3.5 bath in the heart of Chatham and sleeps 7. Whether you enjoy cocktails on the traditional front porch, read a good book in the cozy sun room, eat outdoors on the mahogany deck, or take in...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 7
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    6 Bedrooms, 5 Bathrooms, Sleeps 13 Quick View
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    About this property
    Spend the summer on one of Chatham's most exclusive streets in this beautiful home. Located close to the beach, and to Main Street Chatham, the property at 61 Shore Road will please any discerning traveler. Graciously appointed with six bedroom and five full bathrooms, this home is well suited to...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 13
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    2017 Rental Rate: $1925 per week including the cleaning fee ~~ Off Season: $1425 per week including the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT Comfortable home in a wonderful location near Chatham Village! Let the children play in the huge yard or walk the short distance to Chatham's...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Smoking allowed
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    2017 Rental Rate: $2375 per week, including the cleaning fee ~~Off-Season: $1675/week, including the cleaning fee Weekly rentals from mid-JUNE to mid-SEPT Light and bright cottage just steps to the warm Nantucket Sound waters of Pleasant Street Beach! Tasteful, traditional furnishings throughout....
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    Chatham, Cape Cod 02659
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    5 Bedrooms, 4 Bathrooms, Sleeps 11 Quick View
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    • Patio
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    • Shared Outdoor Pool (Unheated)
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    2017 Rental Rate: $9350 per week, including the cleaning fee Call about Off-Season! The entire family will enjoy this gorgeous, newly built 4+ BR home with a private association path down to Ridgevale Beach! The beach is close, there is a path across the street that takes you to a bridge to the...
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    Chatham, Cape Cod 02633
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 11
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    3 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Waterfront
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    About this property
    Enjoy fantastic, unobstructed views of Red River Beach and Nantucket Sound from this 3 bedroom, 2 full bath traditional Chatham vacation rental only 1/10th of a mile to a semi-private beach. The property comfortably accommodates 8 people however can take up to 10 with the use of the full-size sleep...
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    Chatham, Cape Cod 02659
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 10
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