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Vacation Rentals near Skaket Beach

192 Skaket Beach Rd, Orleans, Massachusetts 02653-3008
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    Travelers to Orleans are booking May dates now. Secure your vacation rental today, and have the perfect trip.
    All 236 Rentals in Orleans
    Walk to Beach, Beautiful Brewster Home! Crosby1 / 26
    (4)Very good
    1.4 miles from Skaket Beach
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    On the Banks of Rock Harbor Creek1 / 36
    (1)Excellent
    0.6 miles from Skaket Beach
    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Cozy Cottage Overlooking Rock Harbor Creek1 / 22
    (1)Excellent
    0.7 miles from Skaket Beach
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    17 Center Place 183741 / 10
    (3)Excellent
    1.4 miles from Skaket Beach
    2 Bedrooms, Sleeps 4 Quick View
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    Orleans Center (ID# 18374) Close to town, waterfront to pond Orleans Center! 2022 Season! Charming waterfront cottage on scenic Boland Pond. A good location, only a short distance to the center of Orleans, not far from the bike trails and to Skaket and Nauset Beaches! 2 Bedrooms, 1 Bath. Sleeps a...
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    Orleans, Cape Cod
    Rental Home - 2 Bedrooms, Sleeps 4
    1.7 miles from Skaket Beach
    4 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Private Outdoor Pool (Heated)
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    • Private Yard
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    Smoking allowed
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    Come to your very own private resort on Cape Cod. Located directly on Nauset Harbor on the Eastham\Orleans town line, The Jeremiah House is the place to be for your quintessential Cape Cod getaway. This luxury home is the perfect convergence of classic old Cape Cod architecture and charm with...
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    Orleans, Cape Cod
    Rental Home - 4 Bedrooms, 5 Bathrooms, Sleeps 10
    0.4 miles from Skaket Beach
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    5 Blueberry Island Road, Orleans, MA (ID# 18404) .Bright and spacious home just a short distance to Cape Cod Bay and Skaket Beach! This wonderful home provides all amenities and has cathedral ceilings in the living, dining and kitchen areas. 3 Bedrooms (2 Queens, 2 Twins) and 2 Baths. A/C units in...
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    Orleans, Cape Cod
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    0.9 miles from Skaket Beach
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    28 Kings Way, Orleans MA (ID# 95117) 2022 Season! Adorable 3 Bedroom, 2 Bath Cape style home close to Skaket Beach. Convenient to Nauset Beach, Orleans Town Center, and the bike trail. Main level includes large living area, eat in kitchen, bedroom with two twins and full bath. Second level has main...
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    Orleans, Cape Cod
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Path to Skaket Beach1 / 33
    (3)Very good
    0.4 miles from Skaket Beach
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Contemporary home with private setting just 3/10 mile walk through a private neighborhood association path to Skaket Beach. Back yard overlooks an active cranberry bog! Near the Cape Cod Bike Trail and less than a mile to Rock Harbor fishing fleet. There are 3 decks and a fully screened porch with...
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    Orleans, Cape Cod
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 10
    0.8 miles from Skaket Beach
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Three bedroom with A/C * Wireless Internet * NO Pets Accepted 2022 Season! Located on a quiet street in a private setting this 3 bedroom, 3 bath tri-level home is just 1/2 mile to Rock Harbor & a short drive to Skaket Beach and the local shops and restaurants in Orleans! There is an split AC...
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    Orleans, Cape Cod
    Rental Home - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    1.1 miles from Skaket Beach
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    15504 Harbor Haven: This classic Cape Cod cottage is located just under 1 minute drive to Rock Harbor and 2 minutes to Orleans Town Center! This picture perfect cottage has been newly renovated with all the essentials to enjoy a great vacation just a short distance away from beautiful Rock Harbor...
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    Orleans, Cape Cod
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    0.8 miles from Skaket Beach
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    This beautiful split ranch is only .5 miles to Rock Harbor Beach and less than 1 mile to Cape Cod Rail Trail. Entry level bedroom #1 has double bed, TV and en-suite bath with tub/shower. There is also access to the basement for the washer and dryer. Go up a few steps to the main level. Large sunny...
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    Orleans, Cape Cod
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    0.9 miles from Skaket Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    171 Sunset Avenue (117506) ~ Bayside ~ Boat Meadow Beach Area Bright and sunny home offering central air conditioning and around the corner from an association beach at Boat Meadow. This beautiful home has an open floor plan with great kitchen featuring stainless appliances, granite countertops,...
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    Eastham, Cape Cod
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    0.6 miles from Skaket Beach
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    *Please note: all bookings for June, July, and August must span Saturday-Saturday and be a minimum of 7 days. During the Fall, Winter, and Spring, our minimum stay is frequently 2 days and occasionally 3 days for holiday weekends; changeovers can be any day of the week. If you have any additional...
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    Orleans, Cape Cod
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    1.6 miles from Skaket Beach
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    *Please note: all bookings for June, July, and August must span Saturday-Saturday and be a minimum of 7 days. During the Fall, Winter, and Spring, our minimum stay is frequently 2 days and occasionally 3 days for holiday weekends; changeovers can be any day of the week. If you have any additional...
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    Brewster, Cape Cod
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    1.5 miles from Skaket Beach
    5 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    14447 - The Dive In: Beautiful Spacious Family Retreat w/ Private Pool! Close to Boat Meadow Beach! Look no further than this beautiful spot for your next Cape Cod getaway, the house is spacious, clean and has everything you need to enjoy a great vacation! The star feature is its huge fenced-in...
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    Eastham, Cape Cod
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 8
    0.1 miles from Skaket Beach
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    15523 The Spyglass: Step off of your porch directly onto Skaket Beach, sleeps 6, beautiful bay views! Our small but sweet Orleans condo, located directly on famous Skaket Beach is the perfect choice for a true beachside getaway. Brew up your morning coffee in the updated kitchen (boasting new...
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    Orleans, Cape Cod
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
    0.2 miles from Skaket Beach
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    15519 - Bayview Outpost: Private beach access, Screened in dining, Wrap around porch! Imagine watching the ocean waves break onto the shore while sipping your morning coffee from your private porch! This classic Cape Cod cottage, built in the 1890s, is just steps away from Cape Cod bay - with...
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    Orleans, Cape Cod
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 6
    0.6 miles from Skaket Beach
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    15518 Time Out: Spacious Accommodations, Newly Furnished, and Minutes from Skaket Beach! Take a ‘Time Out' from the pressures of everyday life, and bring the whole family (including the dog) along to this spacious, newly furnished, Cape Cod home! Located in a quiet Orleans neighborhood, just...
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    Orleans, Cape Cod
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    #530: Amazing Nauset Heights Location, Steps to Nauset Beach, Large Private Yard1 / 45
    (8)Excellent
    3.9 miles from Skaket Beach
    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Orleans, Cape Cod
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 10
    Well Appointed Home Near Skaket Beach with Central A/C1 / 25
    (9)Excellent
    0.6 miles from Skaket Beach
    2 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Orleans, Cape Cod
    Rental Home - 2 Bedrooms, 3 Bathrooms, Sleeps 8
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    Cozy Home in Quiet & Convenient Area1 / 12
    (6)Very good
    0.9 miles from Skaket Beach
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Orleans, Cape Cod
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Featured in Boston Globe- fully renovated cape with pool & modern barn poolhouse1 / 47
    (1)Excellent
    1.1 miles from Skaket Beach
    4 Bedrooms, 4 Bathrooms, Sleeps 11 Quick View
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    Orleans, Cape Cod
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 11
    #504: Fully updated, walk to Rock Harbor, 2 min drive to downtown, central A/C!1 / 27
    (31)Excellent
    1.0 miles from Skaket Beach
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Orleans, Cape Cod
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 5
    3.5 miles from Skaket Beach
    3 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Orleans, Cape Cod
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 5
    5 BR/4 bath w/heated pool .2 miles to Nauset Beach1 / 31
    (12)Excellent
    3.7 miles from Skaket Beach
    5 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    Orleans, Cape Cod
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 12
    2.6 miles from Skaket Beach
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    East Orleans, Orleans
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 10
    2.4 miles from Skaket Beach
    5 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    Orleans, Cape Cod
    Rental Home - 5 Bedrooms, 6 Bathrooms, Sleeps 12
    Orleans Oasis on Pleasant Bay, estate with 2 homes & heated pool; 137-O1 / 50
    (9)Excellent
    3.7 miles from Skaket Beach
    6 Bedrooms, 7 Bathrooms, Sleeps 14 Quick View
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    Orleans, Cape Cod
    Rental Home - 6 Bedrooms, 7 Bathrooms, Sleeps 14
    East Orleans Colonial Style Home With Your Own Private Pool1 / 44
    (13)Excellent
    2.6 miles from Skaket Beach
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Orleans, Cape Cod
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    3.4 miles from Skaket Beach
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Orleans, Cape Cod
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    Classic Cape with access to Crystal Lake1 / 20
    (5)Very good
    2.0 miles from Skaket Beach
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Orleans, Cape Cod
    Rental Home - 2 Bedrooms, 2 Bathrooms, Sleeps 6
    Updated East Orleans 6 Bedroom Home with Heated Pool, linens incl. 004-O1 / 33
    (8)Excellent
    2.7 miles from Skaket Beach
    6 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    Orleans, Cape Cod
    Rental Home - 6 Bedrooms, 4 Bathrooms, Sleeps 12
    Stunning Property with Private Heated Pool, Walk to Ocean Beaches, Sleeps 121 / 40
    (48)Excellent
    3.7 miles from Skaket Beach
    4 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    Orleans, Cape Cod
    Rental Home - 4 Bedrooms, 5 Bathrooms, Sleeps 12
    Stunning Ocean Front Luxury Home on Nauset Beach with A/C &  WiFi1 / 48
    (25)Excellent
    3.9 miles from Skaket Beach
    6 Bedrooms, 6 Bathrooms, Sleeps 16 Quick View
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    East Orleans, Orleans
    Rental Home - 6 Bedrooms, 6 Bathrooms, Sleeps 16
    0.4 miles from Skaket Beach
    3 Bedrooms, 1 Bathroom, Sleeps 8 Quick View
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    15556 - Wait n' Sea: Walk to Skaket Beach or Bike to Rail Trail! Features Outdoor Shower, SUP Board, & Ping Pong Table! Looking for the perfect family vacation getaway? Well look no further! This sweet 3BR Cape cottage, located on the bayside of Orleans, is within walking distance of beautiful...
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    Orleans, Cape Cod
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 8
    2.9 miles from Skaket Beach
    5 Bedrooms, 3 Bathrooms, Sleeps 11 Quick View
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    Orleans, Cape Cod
    Rental Home - 5 Bedrooms, 3 Bathrooms, Sleeps 11
    0.8 miles from Skaket Beach
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Orleans, Cape Cod
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Central AC, Spacious, 5-level, beautiful home, near lakes and beach1 / 28
    (20)Excellent
    2.6 miles from Skaket Beach
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Orleans, Cape Cod
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    4.0 miles from Skaket Beach
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    Orleans, Cape Cod
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    2.4 miles from Skaket Beach
    Studio, 1 Bathroom, Sleeps 6 Quick View
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    Location Information
    Orleans, Cape Cod
    Condo/Apartment - 1 Bathroom, Sleeps 6
    1.7 miles from Skaket Beach
    5 Bedrooms, 4 Bathrooms, Sleeps 11 Quick View
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    • Balcony
    • Waterfront
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    14478 Center Board: Expansive home with ocean views, large lawn, outdoor space, close to downtown and beach! This large, stately home boats 5 bedrooms, a massive kitchen and living area with beautiful ocean views, and a sprawling manicured lawn with a grand patio and seating. The ideal spot for a...
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    Location Information
    Eastham, Cape Cod
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 11
    Awesome Orleans Waterfront Cottage1 / 28
    (11)Excellent
    1.6 miles from Skaket Beach
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Patio
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    Orleans, Cape Cod
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 6
    3.5 miles from Skaket Beach
    5 Bedrooms, 2 Bathrooms, Sleeps 12 Quick View
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    Orleans, Cape Cod
    Rental Home - 5 Bedrooms, 2 Bathrooms, Sleeps 12
    1.7 miles from Skaket Beach
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
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    14479 Lifeboat Lights: This adorable home is located on a large property with 3 other homes, each have their own private outdoor space, water views, and a large shared yard, perfect for summer fun! The first floor of this home offers a kitchen with a small eat-in area, as well as a living room...
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    Eastham, Cape Cod
    Cabin - 1 Bedroom, 1 Bathroom, Sleeps 2
    Walk to Skaket Beach1 / 24
    (29)Excellent
    0.3 miles from Skaket Beach
    4 Bedrooms, 2 Bathrooms, Sleeps 10 Quick View
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    • Patio
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    • Central Heating
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    Location Information
    Orleans, Cape Cod
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 10
    1.0 miles from Skaket Beach
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    Darling two bedroom one full bath dog-friendly cottage has been updated and refreshed for Summer 2022! Walk to downtown Orleans, Cape Cod Rail Trail, restaurants, shops and Orleans Farmers Market. Just over a mile to Rock Harbor Beach and 1.6 miles to Skaket Beach.Cozy living room leads to fully...
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    Location Information
    Orleans, Cape Cod
    Rental Home - 2 Bedrooms, 1 Bathroom, Sleeps 5
    1.8 miles from Skaket Beach
    4 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    Pet friendly
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    Location Information
    Orleans, Cape Cod
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 8
    Family home, 2 mi to Nauset Beach, sleep 8+, perfect for 2 families1 / 34
    (17)Excellent
    3.6 miles from Skaket Beach
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Parking
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    • Housekeeping Included
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    Smoking allowed
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    Orleans, Cape Cod
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    0.8 miles from Skaket Beach
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Smoking allowed
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    Orleans, Cape Cod
    Rental Home - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Family-friendly, Colonial-style home complete w/ three-seasons patio & gas grill1 / 24
    (15)Very good
    0.7 miles from Skaket Beach
    4 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Patio
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    Location Information
    Orleans, Cape Cod
    Rental Home - 4 Bedrooms, 2 Bathrooms, Sleeps 8
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