Home Vacation Rentals By Owner In South Dennis, MA

Showing 42 Of 42 Vacation Rentals
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Exceptional(8)

$1495.3

/ Nightly
Private Vacation Home

Grand home with historic charm, game room & spacious outdoor living spaces

South Dennis, Massachusetts, United States

The White PillarsbrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrWelcome to 'The White Pillars,' an extraordinary 6-bedroom, 6-bath Sea Captain's home nestled on a sprawling 1.61-acre picturesque lot in South Dennis, MA. This historic Greek Revival gem, boasting 3,766 square feet of classic charm combined with modern conveniences, offers the ultimate Cape Cod lifestyle. With quick access to the coveted town landing for deep-water boating and a lovely 29-acre Fresh Pond featuring a private neighborhood beach area, your days will be filled with adventure and relaxation.brbrInside, you'll find a spacious layout perfect for family gatherings or friendly get-togethers. The home is dog-friendly, ensuring that your furry companions can join in on the fun. Enjoy the comforts of central AC, a game room with a pool table, and a cozy living room equipped with a TV for movie nights. The fully equipped kitchen features modern appliances, including a fridge, stove, oven, and dishwasher, making meal preparation a breeze.brbrStep outside to discover a beautiful deck and patio area, complete with outdoor dining furniture and a gas grill, perfect for summer barbecues. As the sun sets, gather around the firepit to share stories and create lasting memories. With the beach just minutes away and a wealth of outdoor activities at your fingertips—such as kayaking, fishing, and whale watching—this home is a true haven for adventure seekers and relaxation enthusiasts alike.brbrWhether you're exploring the nearby Nantucket Sound beaches, indulging in local dining and shopping, or simply enjoying the serene surroundings, 'The White Pillars' is the perfect retreat for families and friends. Book your stay today and experience the charm and beauty of Cape Cod!brbrThings to KnowbrCheck-in time: 4:00 p.m.brCheck-out time: 10:00 a.m.brAll guests shall abide by our good neighbor policy and shall not engage in illegal activity. Quiet hours are from 10:00 p.m. to 8:00 a.m.brNo smoking is permitted anywhere on the premises.brbrParking notes: There is free parking available for 8 vehicles.brbrbrbrDamage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.brMore information can be downloaded from the Rental Agreement on the checkout page.brbrDue to local laws or HOA requirements, guests must be at least 25 years of age to book. Guests under 25 must be accompanied by a parent or legal guardian for the duration of the reservation.
Bed 7

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Bath 5

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Sleep 12

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Exceptional(7)

$554.06

/ Nightly
Private Vacation Home

Spacious home with patio, beach gear, & W/D - central location

South Dennis, Massachusetts, United States

Cape Estate 6brbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrAn escape to the Cape is waiting for you at this spacious South Dennis estate. Perfect for a family holiday or relaxing group getaway, this gorgeous gem offers a convenient central location in the heart of Cape Cod. You'll have your choice between bay or oceanside beaches, each about four miles away. Beach chairs and an umbrella are provided for convenience during your stay. Abundant golf options can be found within easy reach of home, and outdoor enthusiasts will enjoy exploring nearby conservation lands and green spaces. The Cape Cod Rail Trail can be accessed just a mile away. brbrAt home, kick back on the private patio and fire up the gas grill for a backyard barbecue. Leather sofas and a smart TV offer casual comfort in the living room after you've had your fill of outdoor fun. The open-concept kitchen keeps the space connected for family gatherings and comes well-equipped to handle home cooking easily. The large dining table is ready for family mealtimes or game nights. Home essentials include free WiFi and a private washer/dryer.brbrThings to KnowbrCheck-in time: 4:00 p.m.brCheck-out time: 10:00 a.m.brAll guests shall abide by our good neighbor policy and shall not engage in illegal activity. Quiet hours are from 10:00 p.m. to 8:00 a.m.brNo smoking is permitted anywhere on the premises. brStreaming services are available with guests’ own account(s).brThe fireplace is non-functioning and meant for decorative display only.brcontact us for seasonal long-term stay rates (October-April).brThe maximum occupancy noted is per town regulations.brbrParking notes: There is free parking available for 4 vehicles.brbrSecurity camera details: Front and back door has camerasbrbrbrbrDamage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.brMore information can be downloaded from the Rental Agreement on the checkout page.brbrDue to local laws or HOA requirements, guests must be at least 25 years of age to book. Guests under 25 must be accompanied by a parent or legal guardian for the duration of the reservation.
Bed 4

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Bath 2

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Sleep 9

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Home Most popular vacation rentals in South Dennis

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Exceptional(7)

$717.61

/ Nightly
Private vacation home

Three bedroom home sleeping 8 on the water's edge of Swan River

South Dennis, Massachusetts, United States

Bed 3

Bed

Bath 1

Bath

Sleep 8

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Exceptional(7)

$289.34

/ Nightly
Cottage

Walk to Beach: Dennis Family Cottage w/ Deck!

South Dennis, Massachusetts, United States

Bed 3

Bed

Bath 1

Bath

Sleep 8

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Exceptional(7)

$326.71

/ Nightly
Private vacation home

Walking distance to John Kelly Park, Swan River and Kellys Bay

South Dennis, Massachusetts, United States

Bed 3

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Bath 1

Bath

Sleep 6

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Exceptional(7)

$337.74

/ Nightly
Private vacation home

Lovely north side home, only a short drive to Corporation Beach.

South Dennis, Massachusetts, United States

Bed 3

Bed

Bath 1

Bath

Sleep 6

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Exceptional(7)

$371.96

/ Nightly
Private vacation home

Cape Cod House

South Dennis, Massachusetts, United States

Bed 3

Bed

Bath 1

Bath

Sleep 6

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Exceptional(7)

$478.58

/ Nightly
Private vacation home

Charming 3 bedroom sleeping 7 with central air!

South Dennis, Massachusetts, United States

Bed 3

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Bath 1

Bath

Sleep 7

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Exceptional(7)

$510.80

/ Nightly
Private vacation home

Beautiful Waterfront-Relaxin' on the River!

South Dennis, Massachusetts, United States

Bed 3

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Bath 2

Bath

Sleep 7

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Exceptional(7)

$680.94

/ Nightly
Private vacation home

Spectacular Waterfront View! A/C - Minutes to Beauitiful Beaches & Golf Course!

South Dennis, Massachusetts, United States

Bed 4

Bed

Bath 3

Bath

Sleep 10

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Exceptional(7)

$597.90

/ Nightly
Private vacation home

Private & QUIET - Bass Riverfront - 100 yards to Beach @ Follins Pond (CapeCodProperty 194)

South Dennis, Massachusetts, United States

Bed 3

Bed

Bath 1

Bath

Sleep 6

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Exceptional(7)

$531.43

/ Nightly
Cottage

Experience relaxation at Dennis CapeCodProperty 183, a cozy 2B cottage overlooking Follins Pond.

South Dennis, Massachusetts, United States

Bed 2

Bed

Bath 1

Bath

Sleep 4

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