Dennisport, Massachusetts

Vacation Rentals in Dennisport, Massachusetts

Discover 27 vacation rental properties in Dennisport. From 1 to 6 bedrooms. Average $313/night. 100% have pools.

27 verified listings Book securely on VRBO Prices updated March 2026

27 properties available

Beautiful Ocean View Studio !!

Beautiful Ocean View Studio !!

1 bath
PoolA/CWiFiBalcony
$185/night
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Ocean Winds Resort - (Previously Seawinds Resort)

Ocean Winds Resort - (Previously Seawinds Resort)

2 beds 2 baths
PoolA/CWiFiBalcony
$207/night
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Walk to beach-Ocean Drive, Updated Cottage

Walk to beach-Ocean Drive, Updated Cottage

2 beds 1 bath
PoolA/CWiFiBalcony
$274/night
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Cape Cod Beach Cottage-2 bdrm, 1 bath, full kitchen and two minute walk to beach

Cape Cod Beach Cottage-2 bdrm, 1 bath, full kitchen and two minute walk to beach

2 beds 1 bath
PoolA/CWiFiBalcony
$168/night
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<br>Walk to Private Beach, 2 Br Cottage, AC, WiFi

<br>Walk to Private Beach, 2 Br Cottage, AC, WiFi

2 beds 1 bath
PoolA/CWiFiBalcony
$155/night
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Charming Cape Cottage - Central heat. Walk to Swan Pond for kayaking.

Charming Cape Cottage - Central heat. Walk to Swan Pond for kayaking.

2 beds 1 bath
PoolA/CWiFiBalcony
$291/night
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Pool & 300 yards to the beach , 4 Bedroom/ 1.5 bath Cape sleeps 8-9

Pool & 300 yards to the beach , 4 Bedroom/ 1.5 bath Cape sleeps 8-9

4 beds 1 bath
PoolA/CWiFiBalcony
$512/night
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Brand new Ocean View Condo with private balcony, steps from the beach!

Brand new Ocean View Condo with private balcony, steps from the beach!

1 bed 1 bath
PoolA/CWiFiBalcony
$142/night
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Cute 1 Bedroom efficiency Condo At Glendon Beach With Inground Pool

Cute 1 Bedroom efficiency Condo At Glendon Beach With Inground Pool

1 bed 1 bath
PoolA/CWiFiBalcony
$131/night
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Cape cottage close to all attractions! 117 Captain Chase Road, Dennisport<br>

Cape cottage close to all attractions! 117 Captain Chase Road, Dennisport<br>

2 beds 1 bath
PoolA/CWiFiBalcony
$193/night
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Driftwood Cottage- Cozy Gas Fireplace - Walk to beach

Driftwood Cottage- Cozy Gas Fireplace - Walk to beach

3 beds 1 bath
PoolA/CWiFiBalcony
$359/night
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Walk to beach - three bedroom cottage

Walk to beach - three bedroom cottage

3 beds 1 bath
PoolA/CWiFiBalcony
$386/night
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1/2 Mile to Beach / Central AC with Whole House Filter - Reme Halo / Deck

1/2 Mile to Beach / Central AC with Whole House Filter - Reme Halo / Deck

3 beds 1 bath
PoolA/CWiFiBalcony
$243/night
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Brand new Ocean View Condo with private balcony, steps from the beach!

Brand new Ocean View Condo with private balcony, steps from the beach!

1 bed 1 bath
PoolA/CWiFiBalcony
$215/night
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Central air, walk to beach , great location on Captain Chase Rd Dennisport

Central air, walk to beach , great location on Captain Chase Rd Dennisport

3 beds 1 bath
PoolA/CWiFiBalcony
$326/night
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Updates Throughout! Walk to Dennisport beaches! Private landscaped backyard!

Updates Throughout! Walk to Dennisport beaches! Private landscaped backyard!

3 beds 2 baths
PoolA/CWiFiBalcony
$251/night
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Secluded, Family-friendly Beach House - walk to Beach; adjacent to Swan River

Secluded, Family-friendly Beach House - walk to Beach; adjacent to Swan River

2 beds 1 bath
PoolA/CWiFiBalcony
$300/night
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1 min walk from private beach - 4 bd main house, 2 bd carriage house!

1 min walk from private beach - 4 bd main house, 2 bd carriage house!

6 beds 2 baths
PoolA/CWiFiBalcony
Price on request
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Step onto your private beach, Dennisport, MA

Step onto your private beach, Dennisport, MA

2 beds 1 bath
PoolA/CWiFiBalcony
$314/night
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Cottage Amongst the Pines, Short Walk to Beach

Cottage Amongst the Pines, Short Walk to Beach

3 beds 1 bath
PoolA/CWiFiBalcony
$235/night
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SHORT WALK TO BEACH Central A/C

SHORT WALK TO BEACH Central A/C

4 beds 2 baths
PoolA/CWiFiBalcony
$400/night
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Steps to Beach 4-5 Bedrooms w/Central A/C

Steps to Beach 4-5 Bedrooms w/Central A/C

4 beds 3 baths
PoolA/CWiFiBalcony
$343/night
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WATER FRONT BEACH FRONT CENTRAL A/C 180 DEGREE OCEAN VIEW

WATER FRONT BEACH FRONT CENTRAL A/C 180 DEGREE OCEAN VIEW

4 beds 2 baths
PoolA/CWiFiBalcony
$1,097/night
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Discounted rate of 280/night from June 18th-30th in Dennis Port,4 nights minimum

Discounted rate of 280/night from June 18th-30th in Dennis Port,4 nights minimum

3 beds 1 bath
PoolA/CWiFiBalcony
$282/night
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Short stroll to public and private beaches, cottage in Dennisport

Short stroll to public and private beaches, cottage in Dennisport

3 beds 2 baths
PoolA/CWiFiBalcony
$401/night
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Farmhouse near Sea Street Beach

Farmhouse near Sea Street Beach

4 beds 2 baths
PoolA/CWiFiBalcony
$300/night
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Charming 4 bedroom 2 1/2 bath Cape house

Charming 4 bedroom 2 1/2 bath Cape house

4 beds 2 baths
PoolA/CWiFiBalcony
$422/night
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Boston (1034) Nantucket (637) Provincetown (428) Falmouth (348) Wellfleet (288) Cambridge (276) Brewster (271) Chatham (258) Plymouth (247) Gloucester (203) Yarmouth (164) Sandwich (163) Rockport (158) Barnstable (155) Eastham (143) Dennis (139) Dennis Port (129) North Truro (126) Hyannis (121) South Yarmouth (115)