15 Best Vacation Rentals in South Dennis - Holiday Lettings - Cabins

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2,911 Vacation rentals

(10) Excellent 

13

South Dennis Vacation cottage rental

Cape Cod / South Dennis

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Private garden
This inviting, comfortably furnished year-round home is located in a quiet, residential neighborhood and sleeps 6. There is a private back yard with patio, gas grill, washer/dryer, outdoor hot water shower, and hammock for siestas, reading, or quiet time. Walk to Kelly …see more

from $150 / night

$1,100 / week

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Responds fast!
avg. 2 hours 10 minutes

from $150 / night

27

Vacation home in South Dennis

Cape Cod / South Dennis

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly
In the HEART OF THE MID CAPE ~ CLOSE TO EVERYTHING! First Offering 2018 season! DOG FRIENDLY CHARMER vacation getaway in a quiet neighborhood yet CLOSE to shopping, dining, public golf, BIKE TRAIL & both sides of Dennis BEACHES! Just a few miles to MAYFLOWER BEACH on C …see more

from $143 / night

$1,000 - $1,200 / week

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from $143 / night

(1) Excellent 

12

Vacation cottage in South Dennis

Cape Cod / South Dennis

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Child friendly
This 1950s-era cottage, gut-renovated in 2014, has been transformed into a beautiful retreat. Everything is new: new hardwood floors, new stainless steel appliances, new quartz counter tops, new dishwasher, new central air, new washer/drier, new flat screen TV. It has …see more

from $150 / night

$900 - $1,350 / week

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from $150 / night

13

Vacation home with swimming pool in South Dennis

Cape Cod / South Dennis

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
PRIVATE POOL AND WATER VIEWS! This 4 bedroom, 2 bath home is what you have been waiting for! Updated furnishings, washer/dryer, wifi, window a/c in each bedroom, and an in ground pool (unheated) will make your vacation memorable. Views of Bass River from your front …see more

from $250 / night

$1,750 - $3,500 / week

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from $250 / night

(2) Excellent 

27

Vacation home in South Dennis

Cape Cod / South Dennis

4 8 5 nights min

  • 4 bedrooms
  • Sleeps 8
  • 5 nights min
  • Child friendly
  • Air conditioning
  • Private garden
Our modern 4 br 2 bath Raised Ranch house is tastefully decorated with all you need for a relaxing vacation; from new brand name memory foam mattresses that will help you take a restful sleep, to a peaceful backyard. Located at the heart of Cape Cod, 4 mi from the Bay; …see more

from $240 / night

$1,700 - $1,980 / week

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Responds fast!
avg. 1 hour 4 minutes

from $240 / night

11

Vacation home in South Dennis

Cape Cod / South Dennis

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Child friendly
  • Air conditioning
WALK TO FOLLINS POND!!! This three bedroom home offers comfort and relaxation. Relax on the deck, read a book in the 4 season screened porch, or walk to the beach at Follins Pond (brackish water). This property is a short drive to either the north or south side beaches …see more

from $86 / night

$600 - $1,100 / week

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from $86 / night

(1) Excellent 

18

Vacation home rental

Cape Cod / South Dennis

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Child friendly
  • Air conditioning
A BAY SIDE HOME THAT SLEEPS 10!! New owners have taken the time to update this 4 bedroom, two and a half bath home. Fresh paint and new carpeting give this large home a "beachy" feel. Property offers five bedrooms, window AC in four of them, washer, dryer, and wifi. …see more

from $186 / night

$1,300 - $1,995 / week

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from $186 / night

18

Vacation home in South Dennis

Cape Cod / South Dennis

3 8 2 nights min

  • 3 bedrooms
  • Sleeps 8
  • 2 nights min
  • Nearest beach 0.2 mi
  • Child friendly
  • Pet friendly
This is a true Cape Cod knotty pine summer cottage. Built on the shores of Follins Pond in south Dennis, MA. Simple and wonderful, with an enclosed porch, private yard , outdoor shower and access to private beach on the salt water pond. Centrally located in a quiet fa …see more

from $275 / night

$1,295 / week

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from $275 / night

(2) Excellent 

14

Vacation home accommodation

Cape Cod / South Dennis

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Child friendly
  • Air conditioning
Another north side location with central air. This three bedroom, one bathroom home is a quick drive to Mayflower beach. Owners purchased contemporary furnishings to give this home a modern feel. Amenities include washer, dryer, wifi, and gas grill. SQUARE FOOTAG …see more

from $115 / night

$800 - $1,750 / week

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from $115 / night

(8) Excellent 

10

Vacation home in South Dennis

Cape Cod / South Dennis

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Child friendly
  • Air conditioning
Sparkling clean and newly remodeled ranch with central air conditioning and hardwood floors. Large, updated eat-in kitchen with wet bar, dishwasher, microwave, toaster oven and coffeemaker. Property includes use of shared private tennis court. Other amenities include …see more

from $72 / night

$500 - $1,495 / week

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from $72 / night

(1) Very Good 

13

Home rental in South Dennis

Cape Cod / South Dennis

3 7 7 nights min

  • 3 bedrooms
  • Sleeps 7
  • 7 nights min
  • Child friendly
  • Air conditioning
Lovely well maintained home located in a peaceful, quiet residentail area in South Dennis. Just a quick drive to popular West Dennis and South Village Beaches. Home has a spacious fenced in back yard with a nice deck to help you relax. Amenities include central a/c, cei …see more

from $115 / night

$800 - $1,750 / week

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from $115 / night

15

South Dennis Vacation home rental

Cape Cod / South Dennis

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Child friendly
Sleeps 6 - 8+; (1 King, 1 Queen, 1 Full, 2 Twins, 1 Full Sleeper). 3 Bedrooms + Loft, 2 Full Baths. Fully equipped kitchen, living room, dining area, cable TV, DVD, telephone, and WiFi Internet access. Laundry, outside shower, natural gas grill, and huge deck with panor …see more

from $368 / night

$2,575 / week

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Responds fast!
avg. 1 hour 14 minutes

from $368 / night

(1) Excellent 

4

Vacation home rental

Cape Cod / South Dennis

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Private garden
Rent this charming vacation home with Central A/C in a quiet neighborhood with a short drive to several Dennis beaches on the north side, Mayflower and the south side, West Dennis beach. It is close proximity to the Johnnie Kelly Recreation park, minutes to the Cape Cod …see more

from $250 / night

$1,600 / week

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from $250 / night

(5) Very Good 

21

Home accommodation in South Dennis

Cape Cod / South Dennis

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Child friendly
  • Air conditioning
Set way, way back from the road with fabulous views of beautiful Swan River and the wetlands beyond. The great room has floor to ceiling glass with multiple decks overlooking the river and wetlands. There are two large bedroom suites with water views. Other amenities i …see more

from $133 / night

$925 - $1,950 / week

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from $133 / night

21

Vacation home rental

Cape Cod / South Dennis

4 7 2 nights min

  • 4 bedrooms
  • Sleeps 7
  • 2 nights min
  • Child friendly
  • Air conditioning
  • Private garden
Perfect house. Perfect location.Perfect for your vacation. This cute home features 4 bedrooms and 2 bathrooms. It offers fully equipped kitchen, fire place, beautiful patio with grill station, cable TV, wi-fi and coziness. You can hardly imagine better location. Play y …see more

from $525 / night

$3,000 / week

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Responds fast!
avg. 3 hours 44 minutes

from $525 / night

(4) Very Good 

9

Vacation home rental

Cape Cod / South Dennis

3 7 7 nights min

  • 3 bedrooms
  • Sleeps 7
  • 7 nights min
  • Child friendly
  • Air conditioning
Ranch home with eat-in-kitchen and hardwood floors. Remodeled bathrooms for 2018 season. Includes a dishwasher, microwave, toaster, toaster oven, coffeemaker and washer and dryer. Owner adding wifi and a new couch for 2015. A 12’x18’ deck is located directly off of t …see more

from $143 / night

$1,000 - $1,750 / week

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from $143 / night

14

Vacation home in South Dennis

Cape Cod / South Dennis

3 9 7 nights min

  • 3 bedrooms
  • Sleeps 9
  • 7 nights min
  • Child friendly
  • Private garden
Sleeps 8; (1 King, 2 Queens, 1 Twin, 1 Full Sleeper). 3 Bedrooms, 2 Full Baths. Beautifully renovated, spacious living room overlooking the scenic panorama of Swan River and your dock for kayaking, canoeing, fishing and swimming. Fully appliance kitchen, window A/C unit …see more

from $415 / night

$2,900 / week

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Responds fast!
avg. 1 hour 14 minutes

from $415 / night

16

South Dennis Vacation home rental

Cape Cod / South Dennis

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Child friendly
  • Air conditioning
  • Private garden
Sleeps 8; (1 King, 1 Queen, 2 Twins, 1 Queen Sleeper), three (3) bedrooms and two (2) full baths. Spacious living room overlooking the scenic panorama of Swan River and your own private dock for kayaking, canoeing, fishing and swimming. Fully equipped eat-in kitchen, wa …see more

from $415 / night

$2,900 / week

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Responds fast!
avg. 1 hour 14 minutes

from $415 / night

25

Vacation home with swimming pool in South Dennis

Cape Cod / South Dennis

3 9 7 nights min

  • 3 bedrooms
  • Sleeps 9
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
This 3 bedroom, 2.5 bath home is what you have been waiting for! Property was recently purchased. New furnishings, fresh paint, washer/dryer, wifi, window a/c in master bedroom, and in ground pool will make your vacation memorable. Home is at the end of a cul-de-sac …see more

from $250 / night

$1,750 - $3,400 / week

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from $250 / night