South Dennis Vacation Rentals

1-42 of 54 rentals
USA Massachusetts South Dennis

On The Water

$186 - $888  per night
3D Tour
NEW!
4 Bed | 2.5 Bath | Sleeps 10

Monarch Haven

$174 - $610  per night
3D Tour
NEW!
3 Bed | 1 Bath | Sleeps 6

Dream in Orleans

$184 - $1,025  per night
3D Tour
4 Bed | 5 Bath | Sleeps 8

South Chatham Sunshine

$89 - $813  per night
3D Tour
3 Bed | 2 Bath | Sleeps 6

Meet Me at the Cape

$89 - $396  per night
3 Bed | 1 Bath | Sleeps 6

A Chatham Pearl on Oyster River

$113 - $719  per night
3D Tour
3 Bed | 2 Bath | Sleeps 6

Cape Escape

$89 - $433  per night
3D Tour
3 Bed | 1.5 Bath | Sleeps 6

The Waterfront Penthouse

$125 - $1,711  per night
3D Tour
3 Bed | 2 Bath | Sleeps 6

Bayside Cape Codder

$129 - $1,018  per night
3D Tour
3 Bed | 2 Bath | Sleeps 8

Hyannis Hideaway

$103 - $498  per night
3D Tour
3 Bed | 2 Bath | Sleeps 7 (5 Adults Max)

Provincetown Dunes

$399 - $2,006  per night
3D Tour
4 Bed | 3.5 Bath | Sleeps 8

The Harbor Breeze

$64 - $471  per night
3D Tour
2 Bed | 1 Bath | Sleeps 4

Harwich Port Perfection

$89 - $750  per night
3D Tour
3 Bed | 3.5 Bath | Sleeps 8

Chic Antique in Wellfleet Village

$124 - $628  per night
3D Tour
4 Bed | 3 Bath | Sleeps 10

Bayside Retreat

$114 - $1,116  per night
3D Tour
4 Bed | 2.5 Bath | Sleeps 8

Weeks Pond Charmer

$64 - $396  per night
3D Tour
2 Bed | 2 Bath | Sleeps 6

Cerulean Cottage

$103 - $527  per night
3D Tour
2 Bed | 1 Bath | Sleeps 6

Cape Tip Townhouse

$89 - $730  per night
3D Tour
3 Bed | 3.5 Bath | Sleeps 6

One Love - Eastham

$99 - $770  per night
3D Tour
3 Bed | 1.5 Bath | Sleeps 5

Nest on the Namequoit

$158 - $656  per night
3D Tour
4 Bed | 3 Bath | Sleeps 8

The Mary Alden

$200 - $564  per night
3D Tour
2 Bed | 2 Bath | Sleeps 4

Bayview Cottage

$100 - $421  per night
3D Tour
2 Bed | 1 Bath | Sleeps 6

Cranberry Hill

$89 - $337  per night
3D Tour
3 Bed | 1 Bath | Sleeps 6

Narragansett Cottage

$89 - $404  per night
3D Tour
3 Bed | 1 Bath | Sleeps 6

The Beauty of Brewster

$114 - $336  per night
3D Tour
4 Bed | 2.5 Bath | Sleeps 6

Brewster Beaches

$150 - $347  per night
3D Tour
NEW!
1 Bed | 2 Bath | Sleeps 6

Harwich Tranquility

$300 - $634  per night
3D Tour
3 Bed | 3 Bath | Sleeps 6

The Sea Chest in The South of Chatham

$300 - $966  per night
3D Tour
4 Bed | 2 Bath | Sleeps 8

Cranberry Lane Retreat

$200 - $411  per night
3D Tour
2 Bed | 2 Bath | Sleeps 7

Provincetown Perfection

$85 - $466  per night
3D Tour
1 Bed | 1 Bath | Sleeps 2

Cape Cod Bliss

$201 - $1,324  per night
NEW!
4 Bed | 3.5 Bath | Sleeps 8

Ocean Hideaway

$113 - $493  per night
3D Tour
1 Bed | 1 Bath | Sleeps 3 (2 Adults Max)

Sandpiper's Saltbox

$250 - $952  per night
3D Tour
4 Bed | 2 Bath | Sleeps 8

Endless Summer

$160 - $485  per night
3D Tour
2 Bed | 1 Bath | Sleeps 4

Nauset Beach Dream

$95 - $344  per night
3D Tour
3 Bed | 1 Bath | Sleeps 6

"Sampsons Folly"

$196 - $2,439  per night
3D Tour
6 Bed | 6 Bath | Sleeps 14 (8 Adults Max)

SeaWind Guest Studio

$94 - $285  per night
3D Tour
1 Bed | 1 Bath | Sleeps 3

Almost Outermost

$170 - $271  per night
3D Tour
3 Bed | 2 Bath | Sleeps 7

Couple's Paradise by the Sea

$108 - $356  per night
3D Tour
1 Bed | 1 Bath | Sleeps 2

Escape in Dennis

$126 - $524  per night
3D Tour
3 Bed | 2 Bath | Sleeps 7

Sandwich Family House

$120 - $149  per night
3D Tour
3 Bed | 2 Bath | Sleeps 6

Truro Beach Dunes Cottage

$714 - $714  per night
3D Tour
5 Bed | 1 Bath | Sleeps 8
Page 1 of 2
Related Destinations
East Dennis   |   Dennis   |   South Yarmouth   |   West Dennis   |   Dennis Port   |   Yarmouth Port   |   West Harwich   |   Yarmouth   |   Cummaquid   |   Harwich   |   Harwich Port   |   Brewster   |   West Yarmouth   |   South Harwich   |   South Chatham   |   Barnstable   |   Hyannis   |   Hyannis Port   |   West Chatham   |   South Orleans   |   East Orleans   |   West Hyannisport   |   North Chatham   |   Orleans   |   Chatham   |   Centerville   |   West Barnstable   |   Eastham   |   Osterville   |   North Eastham   |   Marstons Mills   |   Cotuit   |   South Wellfleet   |   East Sandwich   |   Wellfleet   |   Sandwich   |   Mashpee   |   Forestdale   |   Sagamore   |   Sagamore Beach   |   Truro   |   Buzzards Bay   |   East Falmouth   |   North Truro   |   Monument Beach   |   Pocasset   |   Cataumet   |   Provincetown   |   North Falmouth   |   Manomet   |   Silver Beach   |   Falmouth   |   East Wareham   |   Onset   |   West Falmouth   |   White Horse Beach   |   Oak Bluffs   |   Edgartown   |   Vineyard Haven   |   West Chop   |   Woods Hole   |   Wareham   |   Tisbury   |   Nantucket   |   Massachusetts
show more  
About South Dennis
Attractions
South Dennis
42 of 54