50 Best Vacation Rentals in Dennis Port - Holiday Lettings - Cabins

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2,784 Vacation rentals

13

Cottage rental in Dennis Port

Dennis / Dennis Port

2 6 5 nights min

  • 2 bedrooms
  • Sleeps 6
  • 5 nights min
  • Child friendly
  • Air conditioning
  • Private garden
Welcome to Stone's Throw, just steps from the warm waters of Nantucket Sound! Under new ownership for the 2018 season! Two bedroom, one bathroom rental unit at the Stone's Throw property. Just a "Stone's Throw" to popular Sea Street Beach on Nantucket Sound. Also enjoy …see more

from $240 / night

$1,500 / week

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from $240 / night

5

Vacation condo with shared pool in Dennis Port

Dennis / Dennis Port

1 4 5 nights min

  • 1 bedroom
  • Sleeps 4
  • 5 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Air conditioning
The Breakers Resort is situated beachfront and center, just waiting for your next vacation. This cozy, beachside community is the ultimate home-away-from-home in ever-popular Cape Cod. The Breakers offers visitors every opportunity to relax and recharge, whether on the …see more

from $215 / night

$1,300 / week

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from $215 / night

(1) Excellent 

11

Vacation home in Dennis Port

Dennis / Dennis Port

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Ask about children
  • Air conditioning
Adorable Cape Cod cottage with Central A/C in Dennis Port, MA-only 250 short steps to the beach! House boasts a lovely living room and large family room each with sleeper sofas. Step out onto the lovely deck to enjoy a fun BBQ and let the kids play in the big yard. Out …see more

from $158 / night

$1,100 - $1,395 / week

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from $158 / night

(1) Very Good 

22

Vacation apartment in Dennis Port

Dennis / Dennis Port

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Child friendly
Located on the warm water shores of Nantucket Sound Seasonal cozy studio-condo, sleep (2 or 3). Available from a second week of April through third week of October. All furnished including kitchen microwave, range-oven, refrigerate, toaster. Pots and pans, silverware, …see more

from $55 / night

$385 - $600 / week

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Responds fast!
avg. 3 hours 57 minutes

from $55 / night

(1) Excellent 

18

Dennis Port Vacation home rental

Dennis / Dennis Port

4 10 7 nights min

  • 4 bedrooms
  • Sleeps 10
  • 7 nights min
  • Ask about children
  • Air conditioning
Updated home with plenty of Cape Cod Charm. This home is one house back from a shared private beach and has stunning views of Nantucket Sound from the spacious deck and master bedroom balcony. Enjoy the ocean breeze in the beautiful sun porch or relax on the comfortabl …see more

from $286 / night

$2,000 - $4,200 / week

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from $286 / night

(1) Very Good 

23

Dennis Port Vacation home rental

Dennis / Dennis Port

3 12 Min stay varies

  • 3 bedrooms
  • Sleeps 12
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
Updated, refurnished and decorated Spring 2016! Enjoy ocean views from every room of 91 Glendon Road. This large, two story home offers 3 bedrooms plus a loft, 3.5 bathrooms and a full unfinished basement. The newly updated kitchen has quartz counters, stainless stee …see more

from $200 / night

$1,300 - $4,300 / week

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Responds fast!
avg. 3 hours 53 minutes

from $200 / night

(2) Excellent 

8

Vacation home in Dennis Port

Dennis / Dennis Port

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Pet friendly
Nice 3 bedroom first floor apartment in captain's house in Dennis Port. Less than 1/2 mile walk to beaches. Central air conditioning, large private yard, gas grill, full kitchen with microwave & dishwasher, full bath, 27" color tv with cable & dvd, Wi-fi, fireplace, dec …see more

from $100 / night

$495 - $1,195 / week

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from $100 / night

10

Vacation home in Dennis Port

Dennis / Dennis Port

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Ask about children
  • Air conditioning
  • Ask about pets
Well kept, two bedroom home with sleeping for 4. Only 2/10 of a mile to Sea Street Beach in Dennis Port! This cottage offers a washer and dryer, a portable window air conditioner, enclosed outdoor shower, gas grill and front deck. Bedroom 1: Full Bedroom 2: 2 Twins …see more

from $72 / night

$500 - $1,095 / week

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from $72 / night

(1) Excellent 

9

Vacation home in Dennis Port

Dennis / Dennis Port

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
  • Air conditioning
  • Ask about pets
Clean and cute home less than 1 mile to popular South Village and West Dennis beaches. Located on a quiet street, this is an ideal spot for children and families. This 3 bedroom 2 bathroom home leaves plenty of space to spread out. Amenities include window A/C in two o …see more

from $100 / night

$700 - $1,450 / week

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from $100 / night

(1) Excellent 

25

Vacation home in Dennis Port

Dennis / Dennis Port

2 7 7 nights min

  • 2 bedrooms
  • Sleeps 7
  • 7 nights min
  • Ask about children
  • Air conditioning
  • Pet friendly
Walk to the beach in 5 minutes from this charming 2+ bedroom, 1 bath cottage in Dennis Port with Central Air! Dog friendly! You will be overjoyed by this beautifully renovated cottage. Inside, it features an open kitchen/dining/living area that is vacation-comfortable w …see more

from $275 / night

$1,925 - $2,370 / week

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Responds fast!
avg. 3 hours 29 minutes

from $275 / night

(3) Excellent 

16

Cottage rental in Dennis Port

Dennis / Dennis Port

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.32 mi
  • Child friendly
This charming two-bedroom cottage is your perfect Cape Cod getaway! The Captain's Quarters has a queen size bed and the Crew's Quarters has a twin bed and bunk beds. The cottage features a cathedral ceiling and full kitchen with nautical and seaside decor throughout. T …see more

from $172 / night

$1,200 / week

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Responds fast!
avg. 2 hours 33 minutes

from $172 / night

(1) Very Good 

10

Hotel apartment rental in Dennis Port with shared pool

Dennis / Dennis Port

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool
Two bedroom condo with large balcony steps from the beautiful sandy beaches on Nantucket Sound at the Breakers North Resort on Cape Cod. Relax on the private beach or in outdoor pool with an indoor pool available for any fair weather day. Eight hundred square feet of …see more

from $300 / night

$2,100 / week

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from $300 / night

(1) Excellent 

16

Vacation home in Dennis Port

Dennis / Dennis Port

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
  • Air conditioning
  • Ask about pets
This spacious 3 bedroom home offers central air and plenty of living space! Bring your Bocce and Croquet sets and take advantage of all the yard space this home offers, or play a game of Ping Pong or Foosball in the basement on a rainy day. Other amenities include 3 T …see more

from $165 / night

$1,150 - $1,495 / week

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from $165 / night

(1) Excellent 

16

Vacation home rental

Dennis / Dennis Port

3 7 7 nights min

  • 3 bedrooms
  • Sleeps 7
  • 7 nights min
  • Ask about children
  • Air conditioning
This three bedroom home sleeps 7 and offers hardwood floors throughout. Newly renovated kitchen for 2017 including all new appliances and stackable washer and dryer. Just an easy 1/2 mile to Sea Street beach. Amenities include window a/c in kitchen and each of the thre …see more

from $93 / night

$650 - $1,300 / week

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from $93 / night

14

Home rental in Dennis Port

Dennis / Dennis Port

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
  • Air conditioning
One of our most updated baker ranches, this home is newly renovated and provides a light, airy feel around the house. Three bedrooms, this home provides ample living area with its partially finished basement and extra den. Central AC, gas grill, wifi, washer, and drye …see more

from $150 / night

$1,050 - $1,600 / week

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from $150 / night

(2) Very Good 

10

Home rental in Dennis Port

Dennis / Dennis Port

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Ask about children
This 2 bedroom duplex is available to rent on its own or rent both sides and invite the whole family! This unit has been updated and looks fantastic. Only 1/2 mile to beautiful Haigis Beach! 1 minute walk to your deeded access to Swan River so bring your kayak or canoe. …see more

from $108 / night

$750 - $975 / week

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from $108 / night

11

Dennis Port Vacation home rental

Dennis / Dennis Port

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
  • Air conditioning
Fully renovated three bedroom, two bathroom home located less than 1/2 mile to Glendon and Haigis beaches. Enjoy your summer vacation in this immaculate, well maintained home with central air conditioning. Open floor plan with recessed lighting, hardwood and ceramic ti …see more

from $100 / night

$700 - $1,650 / week

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from $100 / night

(2) Excellent 

18

Home rental in Dennis Port

Dennis / Dennis Port

3 7 7 nights min

  • 3 bedrooms
  • Sleeps 7
  • 7 nights min
  • Ask about children
  • Air conditioning
  • Ask about pets
Well maintained three bedroom home just one half mile to Inman Rd beach in Dennisport. Located on quiet dead end street. Easy walk to Seaview park and playground. Close to local restaurants and Sundae School ice cream parlor. Window a/c's in living room and bedrooms …see more

from $115 / night

$800 - $1,600 / week

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from $115 / night

17

Vacation home in Dennis Port

Dennis / Dennis Port

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
  • Air conditioning
  • Ask about pets
Pleasant, well maintained home! All new updated kitchen appliances and freshly painted throughout. Enjoy a relaxing morning cup of coffee, the paper and fresh pastries from one of our local bakeries on the screened porch decorated in pretty wicker. Enjoy a sit down m …see more

from $86 / night

$600 - $1,250 / week

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from $86 / night

8

Dennis Port Vacation home rental

Dennis / Dennis Port

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Ask about children
  • Air conditioning
Lovely two bedroom home located 2/10 miles to Sea Street Beach!! Amenities include window air conditioning in the living room and master bedroom, WiFi, enclosed outdoor shower and gas grill. Enjoy your vacation relaxing on the spacious deck or in the comfortable sunny p …see more

from $143 / night

$995 - $1,195 / week

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from $143 / night

6

Vacation home in Dennis Port

Dennis / Dennis Port

1 2 7 nights min

  • 1 bedroom
  • Sleeps 2
  • 7 nights min
  • Ask about children
  • Air conditioning
  • Ask about pets
Adorable and clean one bedroom condo unit across the street from Glendon Beach. Hardwood floors throughout, recently updated kitchen. Window A/C. One bath with shower only. Shared patio with chairs and beach views. Condo offers cable television. Land line. Owner also of …see more

from $72 / night

$500 - $600 / week

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from $72 / night

7

Vacation home in Dennis Port

Dennis / Dennis Port

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Ask about children
Inviting ocean breezes and Nantucket Sound views from the upper level of this home. Located at the end of a dead end road, this house is only .3 miles from the beach! Great lawn to play games, and small patio area with table and umbrella, along with gas grill. Amenitie …see more

from $108 / night

$750 - $1,350 / week

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from $108 / night

(1) Excellent 

12

Vacation home in Dennis Port

Dennis / Dennis Port

3 7 7 nights min

  • 3 bedrooms
  • Sleeps 7
  • 7 nights min
  • Ask about children
  • Air conditioning
This very bright and cheerful ranch is a delightful addition to our rental inventory. Wood floors throughout and updated furnishings. Central AC added for 2017. Televisions in the living room, sun porch and two bedrooms. WIFI and DVD player included. Nice side deck …see more

from $214 / night

$1,495 / week

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from $214 / night

(8) Excellent 

21

Vacation home in Dennis Port

Dennis / Dennis Port

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
Beautiful new 5 bedroom, 4 bath home complete with a private pool, central air conditioning,and 2 washers and 2 dryers, Air Hockey, ping pong table, arcade basketball! This is the perfect home for 2 familes or 1 large family. Inman Rd. Beach at only 4/10 of a mile away! …see more

from $429 / night

$3,000 - $8,495 / week

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from $429 / night

(5) Good 

12

Vacation home in Dennis Port

Dennis / Dennis Port

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
  • Air conditioning
  • Ask about pets
This oceanfront property has incredible views from the roof top deck, some excellent and some partially obstructed views from the living room. There is another property situated partly in front (see pictures) and to the right of the house. The house has 3 bedrooms, w …see more

from $172 / night

$1,200 - $3,495 / week

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from $172 / night

(2) Very Good 

15

Dennis Port Vacation home rental

Dennis / Dennis Port

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
  • Air conditioning
  • Ask about pets
Completly renovated, hard to find beach front cottage! Shared private beach. Non obstructive ocean views. Window air conditioner in the main bedroom, two televisions and wifi available. Updated kitchen with walk out sliders to the front deck facing the ocean with a pat …see more

from $286 / night

$2,000 - $3,995 / week

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from $286 / night

(5) Excellent 

11

Vacation home with shared pool in Dennis Port

Dennis / Dennis Port

1 4 7 nights min

  • 1 bedroom
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
SPRING, SUMMER & FALL ARE PERFECT FOR A CAPE COD VACATION! AND, Dennisport, home of the famous Cape Cod Rail Trail is located right in the middle of the Cape for easy access to the full Cape and all of its wonders and beauty. With this conveniently located rental yo …see more

from $108 / night

$750 - $1,295 / week

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from $108 / night

14

Vacation home in Dennis Port

Dennis / Dennis Port

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Private garden
*Weekly rental in July and August - Saturday to Saturday rental* Charming cottage within a 5 minute walk to the beach. Beautifully refinished 100 year old hardwood floors - newly painted and redone with the feel of a quintessential Cape cod cottage. Located on a private …see more

from $139 / night

$1,895 / week

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Responds fast!
avg. 1 hour 47 minutes

from $139 / night

(1) Excellent 

9

Vacation home in Dennis Port

Dennis / Dennis Port

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
  • Air conditioning
Quaint cottage located on dead end street, this 3 bedroom home sleeps 6. Amenities include window a/c in each bedroom, wifi, TV, gas grill, and patio. Less than a mile to Sea Street Beach. Square footage: 768 Bedroom 1: Queen Bedroom 2: 2 Twins Bedroom 3: 2 Twins Ma …see more

from $86 / night

$600 - $1,000 / week

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from $86 / night

20

Vacation home in Dennis Port

Dennis / Dennis Port

3 7 7 nights min

  • 3 bedrooms
  • Sleeps 7
  • 7 nights min
  • Ask about children
  • Air conditioning
  • Pet friendly
DEEDED BEACH RIGHTS! DENNISPORT! Dog Friendly! DENNISPORT! DEEDED RIGHTS TO PRIVATE NANTUCKET SOUND BEACH just a few doors down!! ADORABLE freshly painted 3 bedroom, 1 bath Ranch with A/C, Cable TV , & Wi-Fi bathed in natural sunlight from the open concept kitchen with …see more

from $172 / night

$1,200 - $1,695 / week

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from $172 / night

15

Vacation home in Dennis Port

Dennis / Dennis Port

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Ask about children
  • Air conditioning
This 4 bedroom, 2 bath home is located in a great neighborhood in the Dennisport area. This property sleeps 8 comfortably, 3 bedrooms with two twin sized beds and one king sized bed respectively. The outside of the house features a beautiful new large deck with sitting …see more

from $143 / night

$1,000 - $2,300 / week

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from $143 / night

(2) Excellent 

15

Vacation home in Dennis Port

Dennis / Dennis Port

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
  • Air conditioning
Cozy cape cod cottage with lovely wood floors. Central AC for comfortable sleeping on warm nights. Skylight and breakfast bar in the kitchen. Three season porch with trundle bed for additional sleeping. Sliders lead to a nice deck. Firepit with sitting area in the b …see more

from $122 / night

$850 - $1,400 / week

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from $122 / night

13

Vacation home rental

Dennis / Dennis Port

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
  • Air conditioning
  • Ask about pets
Lovely three bedroom, one bathroom home located in a quiet residential neighborhood. Access to Swan Pond, perfect for launching a canoe or kayak. Ride your bicycles on the Cape Cod Rail Trail, only .3 miles away. Bright and beachy decor with hardwood floors throughout. …see more

from $86 / night

$600 - $1,250 / week

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from $86 / night

(2) Excellent 

8

Vacation home in Dennis Port

Dennis / Dennis Port

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
  • Air conditioning
Lovely ranch home with screened in porch. 8/10 mile to Haigis Beach in Dennisport. Amenities include window air conditioning in living room and two of the bedrooms, cable TV, DVD, Wifi, washer/dryer, and microwave. Patio with table and chairs and gas gril. Square foot …see more

from $125 / night

$875 - $1,100 / week

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from $125 / night

(1) Excellent 

8

Vacation home in Dennis Port

Dennis / Dennis Port

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Ask about children
  • Air conditioning
  • Ask about pets
Absolutely adorable light and bright cottage located less than one half mile to Glendon Road Beach. This recently updated home sits behind an attached side by side duplex making it ideal for your family and friends to join you! WiFi ,one wall air conditioner in living …see more

from $86 / night

$600 - $950 / week

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from $86 / night

12

Home rental in Dennis Port

Dennis / Dennis Port

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
  • Air conditioning
  • Ask about pets
Beautifully updated three bedroom home with central air! Located only 3/10's of a mile to Sea Street Beach .Its modern and beachy decor will make you feel right at home here on the cape. Amenities include wifi, washer/dryer, dishwasher, gas grill, enclosed outdoor showe …see more

from $272 / night

$1,900 / week

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from $272 / night

(3) Very Good 

8

Home rental in Dennis Port

Dennis / Dennis Port

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
  • Air conditioning
  • Ask about pets
Ranch home with screened sunporch just 7/10 miles to Dennisport beaches. Eat in Kitchen with new pergo flooring. Amenities include washer, dryer, WIFI, flatscreen TV,two window a/c, Picnic table, charcoal grill, gas grill and enclosed outside shower. There is no land …see more

from $115 / night

$800 - $1,250 / week

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from $115 / night

(2) Excellent 

8

Home rental in Dennis Port

Dennis / Dennis Port

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
  • Air conditioning
  • Ask about pets
Affordable, cozy 2 bedroom cottage with seperate dining area, wood floors, open floor plan and vaulted ceilng. Amenities include window ac's in the bedrooms, WiFI, extended basic cable, flat screen TV, and dishwasher. Picnic table and enclosed outside shower. Square …see more

from $72 / night

$500 - $845 / week

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from $72 / night

(1) Excellent 

10

Vacation home in Dennis Port

Dennis / Dennis Port

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Ask about children
  • Air conditioning
Located near Glendon Rd Beach! You can rent one side for yourself and the attached three bedroom unit, or the detached two bedroom unit for friends and family. This completely renovated unit offers a sunny front deck with table, umbrella, chairs and gas grill. Ameniti …see more

from $93 / night

$650 - $995 / week

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from $93 / night

6

Dennis Port Vacation home rental

Dennis / Dennis Port

1 3 7 nights min

  • 1 bedroom
  • Sleeps 3
  • 7 nights min
  • Ask about children
  • Air conditioning
  • Ask about pets
Studio condominium approximately 2/10's mile to Glendon Road beach in Dennisport. This condo unit has an apartment style refrigerator and 4 burner stove, allowing you the option to cook in unit. The inside bathroom has a shower only. Wifi available. No land line avail …see more

from $72 / night

$500 - $700 / week

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from $72 / night