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

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2,592 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

(6) Excellent 

38

Vacation condo in Dennis Port

Dennis / Dennis Port

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.1 mi
  • Swimming pool
Adorable condo with ocean views! We are across the street from Glendon Beach, the waves and sand are less than 500 feet away! Condo was freshly renovated and updated this spring. Condo has one bedroom with a queen bed and a full size futon in the living room that sleeps …see more

from $150 / night

$1,200 - $1,300 / week

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Responds fast!
avg. 3 hours 36 minutes

from $150 / 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 

9

Dennis Port Vacation apartment rental

Dennis / Dennis Port

1 4 4 nights min

  • 1 bedroom
  • Sleeps 4
  • 4 nights min
  • Beach/lakeside relaxation
  • Child friendly
Ocean view from every room. Large lawn with private ocean beach. Kitchen, full bath with shower, bedroom, and living room. Close to shopping, Cape Cod Rail Trail, and Swan River Inlet. Canoe and kayak rental and ferry to Nantucket nearby. 1 bedroom, living room, kitche …see more

from $200 / night

$975 / week

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from $200 / night

18

Dennis Port Vacation home rental

Dennis / Dennis Port

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Child friendly
Welcome to our brand new, gut-renovated, Cape house. The 3 bed rooms have 2 queen beds and 1 set of bunk beds as well as a pull out couch in the living room. Central air with one full bathroom, as well as an outdoor shower. Half mile walk to Haigis Beach. 3/4 mile to Gl …see more

from $215 / night

$1,500 / week

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Responds fast!
avg. 3 hours 47 minutes

from $215 / night

(1) Excellent 

26

Vacation home in Dennis Port

Dennis / Dennis Port

3 10 Min stay varies

  • 3 bedrooms
  • Sleeps 10
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
Completely renovated home located directly across from the ocean. Enjoy the gorgeous ocean views from the living room, kitchen, new paver patio, two decks and plenty of outdoor seating at 134 Old Wharf Road! The newly renovated fully equipped kitchen has ocean views …see more

from $175 / night

$1,150 - $3,850 / week

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from $175 / night

(1) Very Good 

22

Vacation apartment in Dennis Port

Dennis / Dennis Port

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • 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 $85 / night

$600 / week

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from $85 / night

(3) 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

(2) Very Good 

14

Vacation home in Dennis Port

Dennis / Dennis Port

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
Come and relax at a beautiful beach cottage just a minute walk to the beach. This 2 bedroom cottage sleeps 6 and has 1 full bathroom. The cottage also includes an outdoor shower to easily rinse off after your day at the beach. The cottage is cable and wifi ready. Air …see more

from $150 / night

$700 - $1,400 / week

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Responds fast!
avg. 1 hour 22 minutes

from $150 / 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
  • Child friendly
  • Air conditioning
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

16

Vacation home in Dennis Port

Dennis / Dennis Port

3 7 7 nights min

  • 3 bedrooms
  • Sleeps 7
  • 7 nights min
  • Child friendly
  • Air conditioning
Great 3 bedroom, 2.5 bathroom home, with central ac (wall unit in master bedroom) Home offers a living room, a den, and a screened porch for lots of room to spread out. Only .3 miles to Sea Street beach. Amenities include eat in kitchen with dishwasher, washer and dr …see more

from $243 / night

$1,700 - $2,100 / week

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from $243 / night

(1) Very Good 

11

Dennis Port Vacation cottage rental

Dennis / Dennis Port

1 6 7 nights min

  • 1 bedroom
  • Sleeps 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Child friendly
Enjoy a quiet day at the beach or take in a gorgeous sunset while building lifelong memories in this adorable cottage. Cottage 49 is located steps away from a private beach on the Nantucket Sound. It is a freestanding cottage in Chases Ocean Grove, a small resort colony …see more

from $165 / night

$1,150 / week

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from $165 / night

(1) Excellent 

15

Vacation home in Dennis Port

Dennis / Dennis Port

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Child friendly
  • Air conditioning
Oceanviews from this contemporary split level home with a shared private ocean beach maintained daily by owner. Lower level in-law suite with queen size bed, separate living area, small second kitchen and bathroom with Jacuzzi tub. Front to back living room, dining ro …see more

from $362 / night

$2,534 - $6,200 / week

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from $362 / 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 40 minutes

from $172 / 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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from $275 / 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

(21) Excellent 

17

Dennis Port Vacation cottage rental

Dennis / Dennis Port

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.1 mi
  • Child friendly
Beautiful 2 bedroom Cottage located steps from Glendon Beach in Dennis Port, MA. Open year round for your enjoyment. Recently renovated and updated with modern beach decor. Master bedroom contains a Queen size bed. Second bedroom has a trundle bed which can be used as …see more

from $200 / night

$1,200 - $1,500 / week

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Responds fast!
avg. 2 hours 11 minutes

from $200 / night

(2) Excellent 

12

Vacation condo in Dennis Port

Dennis / Dennis Port

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
This charming Dennis Port condo is just steps from the beach!! (2 min walk to closest beach, 5 min walk to Sea St. Beach). Well maintained & clean condo (no musty smells that plague many cottages & homes on the Cape) has 2 bedrooms 1 bath and can sleep up to 5 people. …see more

from $150 / night

$1,000 - $1,200 / week

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from $150 / 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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from $200 / night

38

Home rental in Dennis Port

Dennis / Dennis Port

4 9 7 nights min

  • 4 bedrooms
  • Sleeps 9
  • 7 nights min
  • Child friendly
  • Air conditioning
Stunning updated home in a sought after location. Walk to a shared private beach right across the river from South Village Beach. New hardwood floors throughout the home and new kitchen appliances. Home is meticulously maintained. This two story Cape Cod home is ste …see more

from $285 / night

$1,995 - $4,500 / week

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from $285 / night

(2) Good 

17

Vacation home rental

Dennis / Dennis Port

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Child friendly
  • Air conditioning
Spectacular oceanfront home with spacious great room overlooking Nantucket Sound. Nice lawn and deck on the ocean side of the property and a private courtyard in the back. The house has everything you could want and is decorated in a nautical theme that says have a gre …see more

from $250 / night

$1,750 - $8,500 / week

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from $250 / night

24

Vacation apartment in Dennis Port

Dennis / Dennis Port

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Child friendly
  • Air conditioning
Discover the quaint villages and historical lighthouses of Cape Cod from this 2-bedroom, 1-bathroom Dennis Port vacation rental condo with sleeping accommodations for 6. Situated only a stone’s throw away from a private beach on the Nantucket Sound, this charming home o …see more

from $150 / night

$1,050 / week

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Responds fast!
avg. 50 minutes

from $150 / night

8

Vacation cottage in Dennis Port

Dennis / Dennis Port

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Child friendly
  • Pet friendly
Adorable 2 bedroom cottage in Dennis Port near the ocean. Just a few steps to private association beach. Bring your small dog with prior approval! Bedroom 1: Full Bedroom 2: Bunk Beds - 2 Twins Additional amenities include: full kitchen, sofabed, cooking utensils, fans …see more

from $136 / night

$950 / week

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from $136 / night

13

Dennis Port Vacation home rental

Dennis / Dennis Port

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Child friendly
Beautiful and very large 6 bedroom home located just 2/10 of a mile to the beach. This property is immaculate and professionally cleaned every week! There are 6 bedrooms with a total of 9 beds. There is also a large living room with fireplace, a large dining room, 1.5 …see more

from $500 / night

$2,800 / week

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from $500 / night

(1)  

14

Home rental in Dennis Port

Dennis / Dennis Port

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Child friendly
  • Air conditioning
Pristine condition! Beautifully decorated, fully renovated four bedroom home with central air. Located less than 500 feet to Sea Street Beach! This home boasts a spacious kitchen with stainless steel appliances and granite counter tops. Enjoy cookouts with your guests o …see more

from $250 / night

$1,750 - $4,500 / week

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from $250 / night

(2) Excellent 

9

Home rental in Dennis Port

Dennis / Dennis Port

2 8 7 nights min

  • 2 bedrooms
  • Sleeps 8
  • 7 nights min
  • Child friendly
  • Air conditioning
Well maintained home with large master bedroom and master bath. This home offers 2 window A/Cs and 3 ceiling fans to keep you cool and comfortable on those hot summer days. Lovely corner, shaded lot with a patio, gas grill, patio table, and retractable awning. Just . …see more

from $93 / night

$650 - $1,750 / week

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from $93 / night

8

Vacation home in Dennis Port

Dennis / Dennis Port

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Child friendly
Cozy cape home close to Haigis Beach. Large rear fenced yard with chiminea, large picnic table, and lawn swing. Screened porch for dining out or hours of evening card playing and games. Eat in kitchen and a den. Other amenities include a dishwasher, wifi, microwave …see more

from $86 / night

$600 - $1,750 / week

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from $86 / night

(4) Excellent 

18

Vacation home in Dennis Port

Dennis / Dennis Port

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
Come and relax at a beautiful beach cottage just a minute walk to the beach. This 2 bedroom cottage sleeps 6 and has 1 full bathroom. The cottage also includes an outdoor shower to easily rinse off after your day at the beach. The cottage is cable and wifi ready. Air …see more

from $150 / night

$700 - $1,400 / week

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Responds fast!
avg. 1 hour 22 minutes

from $150 / night

(1)  

8

Vacation home in Dennis Port

Dennis / Dennis Port

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Child friendly
  • Air conditioning
Quaint Cape Cod cottage on a lightly travelled dirt road and just 3/10 miles to shared private beach. Dine on the screened porch or el fresco on the 12 x 16 deck equipped with charcoal grill, lawn furniture and picnic table. (*Note bathroom is shower only). Charcoal …see more

from $100 / night

$700 - $1,750 / week

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from $100 / night

(1) Very Good 

13

Vacation home in Dennis Port

Dennis / Dennis Port

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Child friendly
  • Air conditioning
GEORGEOUS VIEWS OF THE SWAN RIVER. Choose to enjoy the river views from your sunny deck or large three season room with flat screen TV. Nice back yard. The interior offers two bedrooms and a full bath. Other amenities include window AC in the bedrooms, washer, dryer, …see more

from $143 / night

$1,000 - $1,750 / week

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from $143 / night

(4) Very Good 

4

Vacation cottage in Dennis Port

Dennis / Dennis Port

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly
Rustic cottage on swan river with private dock -Kayak/walk to local beach or 1 mile drive to public beach - TWO KAYAKS Pet friendly - BBQ - microwave - ladder on dock -window AC in both bedrooms - two kayaks - beach chairs - cable TV - VCR&DVD - radio - WIFI - outdoor …see more

from $200 / night

$1,400 / week

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Responds fast!
avg. 3 hours 50 minutes

from $200 / night

(3) Good 

18

Vacation home in Dennis Port

Dennis / Dennis Port

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Child friendly
Spacious two story home just one tenth mile to Glendon beach in Dennisport. Home has a large all season porch, deck and patio areas with plenty of outdoor seating. Rear yard is partially fenced and the front yard features a beach volley ball court. Home includes, 2 …see more

from $250 / night

$1,750 - $3,875 / week

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from $250 / night

(3) Very Good 

11

Vacation home in Dennis Port

Dennis / Dennis Port

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Child friendly
  • Air conditioning
Beautifully renovated cottage .2 miles to shared association beach at end of lightly travelled dirt street. Cental air conditioning, wood floors and Wifi. Eat in kitchen with dishwasher and microwave. Three TV's and DVD player. Large rear deck with umbrella table an …see more

from $100 / night

$695 - $1,750 / week

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from $100 / night

(15) Very Good 

32

Home rental in Dennis Port

Dennis / Dennis Port

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.2 mi
  • Child friendly
Our house is in the very desirable section of Dennisport south of Lower County Road. Once you step out the front door, it is a 2 minute walk (less than 2/10ths of a mile) to beautiful Sea Street Beach. This is great and saves you the daily $20 parking fee for the Dennis …see more

from $175 / night

$1,250 - $1,700 / week

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Responds fast!
avg. 3 hours 36 minutes

from $175 / 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 30 minutes

from $139 / night

11

Vacation home in Dennis Port

Dennis / Dennis Port

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Child friendly
  • Air conditioning
Just a 5 minute walk to shared private beach (.2 miles)! Charming cape cod cottage with cozy and comfortable open living room/dining area. Rear yard with patio, umbrella table, chairs and gas grill. Amenities include washer and dryer (bulkhead access only), DVD, and …see more

from $100 / night

$700 - $1,750 / week

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from $100 / night

11

Dennis Port Vacation home rental

Dennis / Dennis Port

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Child friendly
  • Air conditioning
Guests of this cozy three bedroom Dennisport cottage will enjoy the use of Oak Street shared private beach. Stack washer and dryer in the eat in kitchen. Cable TV, flatscreen, internet and window air conditioning in kitchen/living room, queen and twin bedroom. Nice ya …see more

from $214 / night

$1,495 - $1,750 / week

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from $214 / night

(3) Very Good 

10

Vacation home in Dennis Port

Dennis / Dennis Port

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Child friendly
  • Air conditioning
This Dennisport ranch offers hardwood floors in the living room and each of the three bedrooms. Nice eat in kitchen with a paddle fan and toaster oven. The porch off of the kitchen has been converted to a small den. This home offers 5 televisions, cable and wifi. A w …see more

from $129 / night

$900 - $1,750 / week

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from $129 / night

13

Vacation home in Dennis Port

Dennis / Dennis Port

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Child friendly
A Hop , Skip and a Jump to Glendon Road Beach!! This 3 bedroom, 2 full bath home offers a bonus space for spreading out. Amenities include washer, dryer, wifi, and tv in living room. 16x20 deck, gas grill, and a huge yard just screams "Summer on Cape Cod". Nice upgrad …see more

from $143 / night

$1,000 - $1,750 / week

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from $143 / night

(2) Excellent 

8

Vacation home in Dennis Port

Dennis / Dennis Port

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Child friendly
  • 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 $140 / night

$975 - $1,750 / week

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from $140 / night