50 Best Dennis Apartments on Holiday Lettings - Vacation rentals

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2,596 Vacation rentals

25

Vacation home in West Dennis

Dennis / West Dennis

4 9 Min stay varies

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies
  • Child friendly
  • Air conditioning
Experience the rich history and unique culture of Cape Cod from the comfort of this 4-bedroom, 1.5-bath vacation rental home in West Dennis. Located just steps from the crystal clear waters of Grand Cove, this 19th century home for 9 allows guests to canoe, swim, and pa …see more

from $250 / night

$1,750 - $4,375 / week

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Responds fast!
avg. 13 minutes

from $250 / 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

11

Home rental in Dennis

Cape Cod / Dennis

3 5 7 nights min

  • 3 bedrooms
  • Sleeps 5
  • 7 nights min
  • Ask about children
Walk to Kelly's Bay & Johnny Kelly Park, Central to North & Southside Beaches This affordable 3 bedroom, 1 bath home features hardwood floors throughout and a central location that is convenient to shopping plazas, a theater, and the entrance to the Cape Cod Rail Tra …see more

from $128 / night

$890 - $1,240 / week

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from $128 / night

12

Vacation home in Dennis

Cape Cod / Dennis

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
Convenient location, close to Dennis Village and Golf, 3ACs "Ready to Rent for the 2018 Season" This 2 bedroom (sleeps 6), 1.5 bath Cape-Style home is located just over 2 miles to the shops & restaurants of Dennis Village on 6A. It is 2.5 miles to Scargo Observation …see more

from $120 / night

$840 - $1,040 / week

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from $120 / 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

13

Dennis Vacation home rental

Cape Cod / Dennis

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
1 Mile To South Village Beach AC's Ready to Rent for the 2018 Season This ranch-style home with 3 bedroms, 1 1/2 baths is located 1 mile from South Village Beach. The master bedroom offers a full size bed and A/C. The 2nd bedroom has 2 twins, while the 3rd bedroom …see more

from $120 / night

$840 - $1,090 / week

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from $120 / 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

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

21

Home rental in East Dennis

Dennis / East Dennis

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
  • Air conditioning
Lovely north side home in established year round neighborhood. Short drive to the popular Corporation Beach. Minutes to historic route 6A. Convenient to antique shops, restaurants and the Dennis playhouse. Private back yard setting with patio, outdoor dining table, g …see more

from $143 / night

$1,000 - $1,650 / week

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from $143 / 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 - $1,250 / week

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from $150 / night

15

Vacation home rental

Cape Cod / Dennis

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Child friendly
  • Air conditioning
  • Private garden
Enjoy this home away from home with a lot of natural light centrally located on Cape Cod, MA. If relaxing is your style enjoy the private beach on Follins Pond only a short 4 minute walk from the house or a scenic view of Bass River from the Mayfair Boat Yard a quick …see more

from $258 / night

$1,800 / week

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Responds fast!
avg. 58 minutes

from $258 / 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

(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 

Certificate of Excellence

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

Certificate of Excellence

from $125 / night

$1,200 / week

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Responds fast!
avg. 1 hour 41 minutes

from $125 / night

6

Vacation cottage rental

Dennis / Dennis Port

1 2 7 nights min

  • 1 bedroom
  • Sleeps 2
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.48 mi
  • Child friendly
Cute, clean beach house just .3 miles from the beach. House has 1 bedroom with a queen bed, living room and kitchen with a new smooth top stove. Bathroom has a shower, or shower in our enclosed outdoor shower. There is a patio with a gas grill and outdoor patio set. Use …see more

from $80 / night

$675 / week

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from $80 / night

(4) Excellent 

20

Vacation home in Dennis

Cape Cod / Dennis

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 5 mi
  • Child friendly
Completely renovated to make bright open spaces with stunning views of Flax Pond (rated 2nd best pond on the Cape). Swim, kayak or have lunch on the beautiful private dock. Surrounded by miles of conservation nature trails, 5 minute drive to beautiful beaches. A relaxin …see more

from $179 / night

$999 - $3,950 / week

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Responds fast!
avg. 1 hour 43 minutes

from $179 / night

14

Home rental in West Dennis

Dennis / West Dennis

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
  • Ask about pets
Relax and enjoy Cape Cod at this West Dennis unit! This 3 bedroom, 1 bath unit is one of two in a duplex situated within walking distance to a private, association beach at the end of Fiddlers Green Lane. Cozy & cute, it offers an open layout with a living area with fla …see more

from $158 / night

$1,100 - $1,260 / week

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from $158 / night

27

Home rental in Dennis

Cape Cod / Dennis

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Child friendly
Make this Dennis vacation rental your yearly retreat on Cape Cod. At Retro Beach Escape, you'll enjoy must-have amenities such as a wood fireplace and an outdoor shower along with fabulous decor that just may inspire you. Situated only 400 yards from quaint Bayview Be …see more

from $89 / night

$623 / week

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Responds fast!
avg. 1 hour 28 minutes

from $89 / night

16

Vacation home rental

Dennis / Dennis Port

4 10 7 nights min

  • 4 bedrooms
  • Sleeps 10
  • 7 nights min
  • Ask about children
  • Air conditioning
Spacious four bedroom, two bathroom home with views, located in one of the most sought after locations in Dennis Port. Just steps away from a private association beach. This two story home is equipped with central air conditioning on bottom level and window air conditio …see more

from $543 / night

$3,800 / week

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from $543 / 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

11

Vacation home rental

Dennis / West Dennis

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
  • Air conditioning
Pleasant, bright home in West Dennis. Central air cools the home for a comfortable stay, along with "fluffy" mattress toppers for the queen and full beds. Other amenities include a washer and dryer, dishwasher, and Wifi. Spacious yard with rear patio area, including g …see more

from $115 / night

$800 - $1,600 / week

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from $115 / night

(2) Excellent 

19

Vacation home in East Dennis

Dennis / East Dennis

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
  • Air conditioning
Elegant Northside home. An easy drive to Sesuit Harbor, Princess Lake, Corporation and Mayflower beaches. Lovely, private and tranquil setting with manicured yard and mature plantings. This home offers a formal living room and dining room as well as a casual family ro …see more

from $122 / night

$850 - $1,695 / week

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from $122 / night

11

Vacation home in Dennis Port

Dennis / Dennis Port

3 6 1 night min

  • 3 bedrooms
  • Sleeps 6
  • 1 night min
  • Ask about children
Lovely ranch home with a 10x10 sunroom and a fenced yard. Home includes comcast triple play service including cable, high speed internet and unlimited calling within the U.S. and Canada. Beautiful wood floors throughout this home including new pergo flooring in the br …see more

from $86 / night

$600 - $1,200 / week

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from $86 / 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

(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

17

West Dennis Vacation home rental

Dennis / West Dennis

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
  • Ask about pets
This newly listed cozy and cute unit is part of a duplex and offers sleeping for up to 6! Situated in West Dennis within walking distance to a private association beach at the end of Fiddlers Green Lane, this 3 bedroom, 1 bath unit is a great spot for your summer vacati …see more

from $180 / night

$1,260 / week

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from $180 / night

11

Vacation home in West Dennis

Dennis / West Dennis

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Ask about children
Neat, clean and affordable 4 bedroom home with hardwood floors in West Dennis. Eat-in kitchen has dishwasher and microwave. Living room has cable TV and WiFi throughout the home. Nice shaded yard with two flagstone patios, gas grill, and hammock. Less than a mile to …see more

from $129 / night

$900 - $1,275 / week

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from $129 / 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

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

14

Home rental in West Dennis

Dennis / West Dennis

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Ask about children
  • Air conditioning
Two story home just 300 yards to shared private beach (Fiddlers Green) in West Dennis. Home has a wrap around, large upper deck with ocean views and lower level deck. Home offers central air conditioning, washer/dryer, dishwasher,37" HD Flatscreen TV, cable, HD-DVD, W …see more

from $243 / night

$1,700 - $4,500 / week

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from $243 / night

(1) Excellent 

27

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
  • Pet friendly
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

$1,100 - $3,850 / week

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from $175 / 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 

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

9

Home rental in Dennis

Cape Cod / Dennis

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Ask about children
Steps to Glendon Beach, Waterviews & WiFi Ready to Rent for the 2018 Season This adorable 2 bedroom condo unit offers waterviews from the front deck and is located across the street from Glendon Beach and the Sailing Cow restaurant. The master bedroom has 1 queen bed …see more

from $99 / night

$690 - $1,040 / week

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from $99 / 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) Very Good 

13

West Dennis Vacation home rental

Dennis / West Dennis

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
  • Air conditioning
Bright and cheerful three bedroom home with window ac units in two of the bedrooms! Located in popular West Dennis, this home sits in a quiet neighborhood, only a short drive to West Dennis Beach. This home features three bedrooms with 1.5 baths. You will enjoy the nice …see more

from $258 / night

$1,800 / week

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from $258 / 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

(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

23

Vacation home in Dennis

Cape Cod / Dennis

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
  • Air conditioning
  • Ask about pets
Spectacular water views overlooking Bayview Beach and only a short walk to Mayflower Beach! This 3 story, brand new unit features a gourmet kitchen, open floor plan with fireplaced family room, 2 bedrooms in lower level, a master suite with private balcony, and a deck f …see more

from $358 / night

$2,500 - $4,950 / week

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from $358 / night

25

Vacation home rental

Cape Cod / Dennis

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Ask about children
  • Air conditioning
BEAUTFIL BAYSIDE BEACHES ! MAYFLOWER / BAYVIEW SO CLOSE YOU CAN SMELL THE SALT AIR! With Private BEACH RIGHTS and easily accessible footpath,this perfect beach house awaits you and your guests! Less than 1/10 of a mile to two of Cape Cod s most beautiful bayside beach …see more

from $415 / night

$2,900 - $4,600 / week

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from $415 / night