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

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2,493 Vacation rentals

14

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
Nicely decorated 3 bedroom home on a quiet dirt lane. Bright and cheerful eat in kitchen. Master bedroom freshly decorated for 2018 with window air conditioner. Home offers wifi, dvd and cable television. Large deck off the kitchen with umbrella table, chairs and a g …see more

from $143 / night

$1,000 / week

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from $143 / 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 

24

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

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
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 high Ceilings & Skylight to the spacious livin …see more

from $172 / night

$1,200 - $1,695 / week

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from $172 / night

19

Vacation condo in Dennis Port

Dennis / Dennis Port

3 7 7 nights min

  • 3 bedrooms
  • Sleeps 7
  • 7 nights min
  • Child friendly
This a great family condominium unit! Just drop your luggage and walk down to beach (2 minutes). Bdrm #1, on the first floor has a queen bed. The upstairs has 2 Bdrms, railroad style(must walk through one to get to the other). Bdrm#2 has two twin beds; Bdrm#3 has a do …see more

from $236 / night

$1,650 / week

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from $236 / night

13

Vacation home in Dennis Port

Dennis / Dennis Port

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
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 - $1,650 / week

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from $143 / night

(1) Excellent 

15

Dennis Port Vacation home rental

Dennis / Dennis Port

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Ask about children
  • Air conditioning
Charming and picturesque Dennisport farmhouse, framed by a white picket fence, located within walking distance to Nantucket sound beaches, Sundae School Ice Cream and a number of local restaurants. This home combines old world charm with updated accomodations. Beautif …see more

from $115 / night

$800 - $1,845 / week

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from $115 / 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

$1,795 / week

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Responds fast!
avg. 1 hour 49 minutes

from $139 / 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

15

Vacation home in Dennis Port

Dennis / Dennis Port

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Ask about children
  • Ask about pets
This little cute & cozy Cape Cod Cottage cottage is located so close to the Dennis Beaches on Nantucket Sound and Restaurants and shops. Sleeps up to 4 comfortably. It features an open layout with a fully equipped kitchen area, living room, and dining table. There are t …see more

from $100 / night

$700 / week

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from $100 / 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

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
  • Ask about pets
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

26

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
  • Ask about pets
This air conditioned adorable 4 bedroom, 2 bath Cape is located within quick walking distance of a Private Association Beach on Nantucket Sound. The first level features a front to back living and dining room with fireplace and fully equipped kitchen. There are also two …see more

from $215 / night

$1,500 - $2,350 / week

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from $215 / 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

(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
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

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
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 / week

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from $214 / night

(14) Very Good 

17

Vacation cottage in Dennis Port

Dennis / Dennis Port

2 4 5 nights min

  • 2 bedrooms
  • Sleeps 4
  • 5 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.5 mi
  • Ask about children
Come escape your daily hustle and bustle - our 2 bedroom cottage has a lovely 3 season room with a vaulted ceiling that opens with French doors to an outdoor patio with a gas grill. There's even a spare propane tank should the first run out! It is within walking distanc …see more

from $150 / night

$1,100 / week

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from $150 / night

(5) 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
Hard to find four bedroom and two bath home close to Haigis and Glendon beaches. First floor has lovely hardwood floors throughout. Updated kitchen which is open to the adjacent dining area. Rear patio offers patio table, gas grill and enclosed outside shower. Well …see more

from $143 / night

$995 - $2,995 / week

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from $143 / night

(4) Excellent 

14

Vacation home in Dennis Port

Dennis / Dennis Port

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
Adorable and cozy cape cod home across from Seaview Park. Inman beach is just down the hill from your front door and Sundae school ice cream within a five minute walk. The interior is bright, clean and cheerful with hardwood floors and updated kitchen and bath. Ove …see more

from $97 / night

$675 - $1,250 / week

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from $97 / night

22

Home accommodation in Dennis Port

Dennis / Dennis Port

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Ask about children
  • Ask about pets
This quaint 4 bedroom, 3 bath Cape is located within a short distance to a Private Association Beach on Nantucket Sound, which is immediately adjacent to a town beach with lifeguard. The first level features a living room with a gas stove, dining room, full bathroom (sh …see more

from $200 / night

$1,400 - $1,775 / week

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from $200 / night

(5) Excellent 

12

Dennis Port Vacation home rental

Dennis / Dennis Port

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Ask about children
  • Air conditioning
Completely updated, meticulously maintained 4 bedroom, 2 full bath house with central air. This property sleeps 8 people and offers a washer/dryer, dishwasher, ceiling fans throughout the house, an enclosed outdoor shower, gas grill, and ping-pong table! Property is lo …see more

from $358 / night

$2,500 - $3,200 / week

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from $358 / 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
  • Ask about children
  • Air conditioning
One of our most updated baker ranches, this walk to the beach home is newly renovated! This home provides a light, airy feel around the house with its honey interior and beach decor. With three bedrooms and 1.5 baths, this home gives you and your family ample living sp …see more

from $100 / night

$700 - $1,600 / week

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from $100 / 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

$485 - $1,195 / week

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from $100 / night

(1) Excellent 

9

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 two bedroom cottage with central air conditioning. Totally remodelled kitchen and bath. New wood flooring and furnishings. Fenced in yard with deck and gas grill. Wifi available. Less than one mile to Glendon Road beach. Square Footage 650 Bedroom #1: 1 Q …see more

from $72 / night

$500 - $1,050 / week

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from $72 / 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
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

24

Cottage rental in Dennis Port

Dennis / Dennis Port

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Child friendly
  • Air conditioning
Clean and comfortable 2 duplex units- each has 2 bedrooms (twin beds, full bed), 1 full bath (shower only), outdoor enclosed shower, TV, cable, fully equipped kitchen (including coffee maker, microwave, and toaster oven). Gas grill and picnic table on deck. Provided: p …see more

from $143 / night

$995 / week

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from $143 / night

(4) Very Good 

9

Vacation home with swimming pool in Dennis Port

Dennis / Dennis Port

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Swimming pool
  • Ask about children
This cozy cape cod cottage with a 5x8 front screened porch is located just 150 feet to Sea Street beach. Full Bath with tub and outdoor enclosed shower. Property has a shared swimming pool for tenant use only. Other amenities include premium cable TV (HBO, Showtime a …see more

from $208 / night

$1,450 - $1,560 / week

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from $208 / night

12

Vacation home rental

Dennis / Dennis Port

3 7 7 nights min

  • 3 bedrooms
  • Sleeps 7
  • 7 nights min
  • Ask about children
  • Air conditioning
This clean and bright home is located close to Dennisport beaches, town and Sundae School Ice Cream. You will enjoy endless hours relaxing on the great screened porch overlooking a private and ample rear yard with picnic area and gas grill. The interior is tastefully …see more

from $115 / night

$800 - $1,695 / 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
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

(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

(6) Excellent 

13

Dennis Port Vacation home rental

Dennis / Dennis Port

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Ask about children
  • Air conditioning
Newer contemporary cape, meticulously maintained inside and out. Perfectly located on quiet cul-de-sac, just an easy 3-block walk to Inman Beach and Sundae School Ice Cream Shop. Large, private yard with four tables, two umbrellas, lawn chairs and gas grill for enjoyi …see more

from $200 / night

$1,400 - $3,200 / week

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from $200 / night

11

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
Completely renovated top to bottom! Meticulously maintained two bedroom home located less than ½ mile to Hagis Beach. Decor is bright and cheerful with beautiful hardwood floors. Amenities include window air conditioning in both living room and master bedroom, WiFi, gas …see more

from $72 / night

$500 - $1,050 / week

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from $72 / 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

(4) Very Good 

10

Vacation home in Dennis Port

Dennis / Dennis Port

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
Well maintained, bright and cheerfull, two story Cape just 2/10 miles to Raycroft or Sea Street beach. New flat screen T.V., DVD player, Plush beauty rest mattresses on every bed. Fully fenced in yard on a lightly traveled dirt road. Two picnic tables in the yard an …see more

from $204 / night

$1,425 - $1,525 / week

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from $204 / 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 59 minutes

from $172 / night

(3) Excellent 

10

Dennis Port Vacation home rental

Dennis / Dennis Port

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
This gently used and well maintained home offers beautiful, shining hardwood floors. Galley kitchen with breakfast bar and adjacent dining area. Cozy living room. There is an additional half bath off of the main bedroom. Amenities include wahser and dryer, dishwashe …see more

from $86 / night

$600 - $1,600 / week

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from $86 / night

(1) Very Good 

16

Dennis Port Vacation home rental

Dennis / Dennis Port

3 5 7 nights min

  • 3 bedrooms
  • Sleeps 5
  • 7 nights min
  • Ask about children
  • Air conditioning
Central air conditioning added in 2017! Charming well maintained cottage close to Sea Street beach. Sunny, small front deck and nicely landscaped front yard with stone patio area and a lovely mix of pretty perennials and annuals. Amenities include TV, DVD, cable, micr …see more

from $193 / night

$1,350 / week

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from $193 / 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

11

Vacation home in Dennis Port

Dennis / Dennis Port

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
Well maintained ranch with a 10x14 screened, enclosed sunroom. Open living room, kitchen and dining area with vaulted ceiling and skylight. 2013 Remodeled bathroom. Stainless steel appliances. Fenced in yard with a wrap around deck, gas grill and patio furniture. Home …see more

from $150 / night

$1,050 / week

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from $150 / night

(2) Excellent 

7

Home accommodation in Dennis Port

Dennis / Dennis Port

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Ask about children
  • Air conditioning
Cozy Cape Cod Comfort.Cozy Cape Cod Comfort. This lovely 2 bedroom, bath and a half cottage will underwent a major update in 2017. The living room was expanded out to the current porch with large glass windows and a vaulted ceiling. A deck will be added in the front f …see more

from $122 / night

$850 - $1,475 / week

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from $122 / night