Dennis, Massachusetts

Vacation Rentals in Dennis, Massachusetts

Discover 139 vacation rental properties in Dennis. From 1 to 6 bedrooms. Average $355/night. 100% have pools.

139 verified listings Book securely on VRBO Prices updated March 2026

139 properties available

Perfect Location, Private, Immaculate, Affordable, East Dennis Cape Cod

Perfect Location, Private, Immaculate, Affordable, East Dennis Cape Cod

2 beds 1 bath
PoolA/CWiFiBalcony
$194/night
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August promotion - Newly renovated with pool - 6-min to beach

August promotion - Newly renovated with pool - 6-min to beach

1 bed 1 bath
PoolA/CWiFiBalcony
$171/night
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Charming Studio less than 200 steps to Glendon Beach - 200 Captain Chase Rd #18

Charming Studio less than 200 steps to Glendon Beach - 200 Captain Chase Rd #18

1 bath
PoolA/CWiFiBalcony
$160/night
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Family-friendly house w/gas grill, deck, streaming services - near Haigis Beach

Family-friendly house w/gas grill, deck, streaming services - near Haigis Beach

2 beds 1 bath
PoolA/CWiFiBalcony
Price on request
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THE BOAT HOUSE LOFT ~ THE CAPE'S BEST WATERFRONT VALUE ~ SHORT TERM STAYS AVAIL!

THE BOAT HOUSE LOFT ~ THE CAPE'S BEST WATERFRONT VALUE ~ SHORT TERM STAYS AVAIL!

1 bed 1 bath
PoolA/CWiFiBalcony
$198/night
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Compass Rose Cottage ★ Steps to Flax Pond & Nature Trails ★ Kayaks

Compass Rose Cottage ★ Steps to Flax Pond & Nature Trails ★ Kayaks

2 beds 1 bath
PoolA/CWiFiBalcony
$246/night
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Cute Cottage on Bass River in West Dennis

Cute Cottage on Bass River in West Dennis

2 beds 1 bath
PoolA/CWiFiBalcony
$231/night
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Joe's Beach Hideaway

Joe's Beach Hideaway

1 bed 1 bath
PoolA/CWiFiBalcony
$448/night
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Cozy studio only 3/10 of a mile from Nantucket Sound, Free WIFI

Cozy studio only 3/10 of a mile from Nantucket Sound, Free WIFI

1 bed 1 bath
PoolA/CWiFiBalcony
$118/night
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Stay in a TINY HOUSE!★0.4mi to Beach★Village★Restaurants★Pet Friendly ★ 2 bikes!

Stay in a TINY HOUSE!★0.4mi to Beach★Village★Restaurants★Pet Friendly ★ 2 bikes!

1 bed 1 bath
PoolA/CWiFiBalcony
$150/night
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Dennisport - Studio Condo w kitchenette - Walk to beach

Dennisport - Studio Condo w kitchenette - Walk to beach

1 bath
PoolA/CWiFiBalcony
$75/night
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Walk to DennisPort Beaches 4 min.Bars and restaurants 2min walk.Perfect Location

Walk to DennisPort Beaches 4 min.Bars and restaurants 2min walk.Perfect Location

1 bed 1 bath
PoolA/CWiFiBalcony
$199/night
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Walk to the Beach Studio

Walk to the Beach Studio

1 bed 1 bath
PoolA/CWiFiBalcony
$149/night
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Cozy 2-bedroom cottage, 0.2 mi walk to the beach and other popular attractions!

Cozy 2-bedroom cottage, 0.2 mi walk to the beach and other popular attractions!

2 beds 1 bath
PoolA/CWiFiBalcony
$189/night
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Charming Romantic Studio with Kitchenette, Private Patio. Walk to Beach!

Charming Romantic Studio with Kitchenette, Private Patio. Walk to Beach!

1 bed 1 bath
PoolA/CWiFiBalcony
$118/night
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Adorable Cottage! Wlk 2 Beach! Cntrl AC! Fire Pit!

Adorable Cottage! Wlk 2 Beach! Cntrl AC! Fire Pit!

2 beds 1 bath
PoolA/CWiFiBalcony
$213/night
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Modern & Renovated Studio Condo (Steps to the Beach!) - Pool, WiFi, Free Parking

Modern & Renovated Studio Condo (Steps to the Beach!) - Pool, WiFi, Free Parking

1 bed 1 bath
PoolA/CWiFiBalcony
$159/night
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Grandma's Cottage: Olde Cape Cod at its best. Steps to the beach. Dog-friendly!

Grandma's Cottage: Olde Cape Cod at its best. Steps to the beach. Dog-friendly!

2 beds 1 bath
PoolA/CWiFiBalcony
$216/night
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Home Away From Home!

Home Away From Home!

1 bed 1 bath
PoolA/CWiFiBalcony
$215/night
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Dennisport : Dog Friendly with a fenced in large yard. 1/2 mile from beach

Dennisport : Dog Friendly with a fenced in large yard. 1/2 mile from beach

2 beds 1 bath
PoolA/CWiFiBalcony
$180/night
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2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill

2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill

2 beds 2 baths
PoolA/CWiFiBalcony
$150/night
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Cape Cod Beach Cottage, only 5 minute walk to Glendon beach & local restaurants

Cape Cod Beach Cottage, only 5 minute walk to Glendon beach & local restaurants

3 beds 1 bath
PoolA/CWiFiBalcony
$220/night
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Charming 2-bedroom cottage 0.5mi to beaches and close to downtown

Charming 2-bedroom cottage 0.5mi to beaches and close to downtown

2 beds 1 bath
PoolA/CWiFiBalcony
$312/night
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Charming Home Close To Sea Street Beach, Dining, and Entertainment

Charming Home Close To Sea Street Beach, Dining, and Entertainment

2 beds 1 bath
PoolA/CWiFiBalcony
$276/night
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Luxury Romantic 'Studio by the Beach' Free WiFi, Central Air and Heat

Luxury Romantic 'Studio by the Beach' Free WiFi, Central Air and Heat

1 bath
PoolA/CWiFiBalcony
$191/night
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Cape Cod Oceanfront New Condo with Ocean View & Private Beach! capeoceanvista

Cape Cod Oceanfront New Condo with Ocean View & Private Beach! capeoceanvista

2 beds 2 baths
PoolA/CWiFiBalcony
$531/night
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Ocean Front, Private Beach, Ocean View , Private patio

Ocean Front, Private Beach, Ocean View , Private patio

2 beds 2 baths
PoolA/CWiFiBalcony
$472/night
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Walk to Beach from this 3 Bedroom Cottage!

Walk to Beach from this 3 Bedroom Cottage!

3 beds 1 bath
PoolA/CWiFiBalcony
$130/night
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*Completely Renovated Cottage Overlooking Nantucket Sound with Private Beach*

*Completely Renovated Cottage Overlooking Nantucket Sound with Private Beach*

3 beds 2 baths
PoolA/CWiFiBalcony
$1,048/night
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You, Me & the Sea - 4 Minute Walk to the Beach!

You, Me & the Sea - 4 Minute Walk to the Beach!

2 beds 1 bath
PoolA/CWiFiBalcony
$253/night
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Cozy Cape Steps from 2 Beaches + Private Beach Deeded Access

Cozy Cape Steps from 2 Beaches + Private Beach Deeded Access

3 beds 1 bath
PoolA/CWiFiBalcony
$401/night
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Lovely 2 bedroom cottage less than 500 ft to Sea Street Beach

Lovely 2 bedroom cottage less than 500 ft to Sea Street Beach

2 beds 1 bath
PoolA/CWiFiBalcony
$144/night
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3-min walk to BEACH! Private luxury Backyard!

3-min walk to BEACH! Private luxury Backyard!

2 beds 1 bath
PoolA/CWiFiBalcony
$398/night
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Quick walk to private beach. Summer 2024 dates available!

Quick walk to private beach. Summer 2024 dates available!

2 beds 1 bath
PoolA/CWiFiBalcony
$286/night
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The Cozy Cottage

The Cozy Cottage

2 beds 1 bath
PoolA/CWiFiBalcony
$352/night
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3 Bedroom Condo- 300 yards from the Beach

3 Bedroom Condo- 300 yards from the Beach

3 beds 1 bath
PoolA/CWiFiBalcony
$251/night
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"Coast" Cottage @ The Getaways- Walking distance to several Dennisport Beaches!

"Coast" Cottage @ The Getaways- Walking distance to several Dennisport Beaches!

2 beds 1 bath
PoolA/CWiFiBalcony
$345/night
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Beautiful Property Centrally Located on Cape Cod! August 17- August 23rd 2024.

Beautiful Property Centrally Located on Cape Cod! August 17- August 23rd 2024.

2 beds 2 baths
PoolA/CWiFiBalcony
$498/night
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Frank's Cozy Cape Cod Beach Cottage

Frank's Cozy Cape Cod Beach Cottage

2 beds 1 bath
PoolA/CWiFiBalcony
$401/night
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Hundred Summer Days on the Cape!

Hundred Summer Days on the Cape!

2 beds 1 bath
PoolA/CWiFiBalcony
$251/night
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Short Walk to Swan Pond, Hot Tub!

Short Walk to Swan Pond, Hot Tub!

3 beds 2 baths
PoolA/CWiFiBalcony
$253/night
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The Sweet Retreat - Less than 1/2 mile to Dennis Port beaches

The Sweet Retreat - Less than 1/2 mile to Dennis Port beaches

2 beds 1 bath
PoolA/CWiFiBalcony
$254/night
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Location!!! Beach Directly Across St from complex + Heated Pool, Sleeps 4, A/C

Location!!! Beach Directly Across St from complex + Heated Pool, Sleeps 4, A/C

1 bed 1 bath
PoolA/CWiFiBalcony
$236/night
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Cape Cod Oceanside Condominium Unit - across from beach!

Cape Cod Oceanside Condominium Unit - across from beach!

1 bed 1 bath
PoolA/CWiFiBalcony
$218/night
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Newly renovated, just steps to private beach!

Newly renovated, just steps to private beach!

3 beds 1 bath
PoolA/CWiFiBalcony
$301/night
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Enjoy your stay at Cape Cods Sea-Escape

Enjoy your stay at Cape Cods Sea-Escape

1 bed
PoolA/CWiFiBalcony
$161/night
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Beautiful Cottage on Cape Cod

Beautiful Cottage on Cape Cod

3 beds
PoolA/CWiFiBalcony
$307/night
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Steps to Oak St Private Beach!

Steps to Oak St Private Beach!

3 beds 2 baths
PoolA/CWiFiBalcony
$528/night
View Details → Book on VRBO

Showing 48 of 139 properties

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