South Dennis Vacation Rentals

1-42 of 80 rentals
USA Massachusetts South Dennis

Bayside Beauty

$116 - $448  per night
3D Tour
1 Bed | 1.5 Bath | Sleeps 5

Pine Grove Cottage

$114 - $485  per night
NEW!
3 Bed | 1 Bath | Sleeps 6

Easy Eastham

$130 - $731  per night
3D Tour
NEW!
3 Bed | 2 Bath | Sleeps 6

Monarch Haven

$204 - $737  per night
3D Tour
3 Bed | 1 Bath | Sleeps 6

Big Pine Cottage

$85 - $278  per night
3D Tour
NEW!
2 Bed | 1 Bath | Sleeps 4

Bayside Retreat

$105 - $533  per night
3D Tour
NEW!
2 Bed | 1 Bath | Sleeps 5

Sandpiper Cottage

$161 - $665  per night
NEW!
3 Bed | 2 Bath | Sleeps 6

On The Water

$234 - $1,026  per night
3D Tour
4 Bed | 2.5 Bath | Sleeps 10

South Chatham Sunshine

$105 - $747  per night
3D Tour
3 Bed | 2 Bath | Sleeps 6

The Waterfront Penthouse

$125 - $1,654  per night
3D Tour
3 Bed | 2 Bath | Sleeps 6

Seaside Cottage #14 - Irish Mist

$100 - $405  per night
NEW!
0 Bed | 1 Bath | Sleeps 4

Seaside Cottage #23a - Seagull's Nest

$124 - $231  per night
NEW!
2 Bed | 1 Bath | Sleeps 6

Chic Antique in Wellfleet Village

$124 - $979  per night
3D Tour
4 Bed | 3 Bath | Sleeps 10

Seaside Cottage #1a - Seascape

$102 - $190  per night
3D Tour
0 Bed | 1 Bath | Sleeps 4

Seaside Cottage #29 - Stars & Stripes

$100 - $402  per night
0 Bed | 1 Bath | Sleeps 4

Seaside Cottage #23 - Seagull's Rest

$82 - $152  per night
NEW!
0 Bed | 1 Bath | Sleeps 2

Seaside Cottage #34 - The Duck House

$103 - $415  per night
1 Bed | 1 Bath | Sleeps 4

Seaside Cottage #16 Beach Cottage

$100 - $402  per night
0 Bed | 1 Bath | Sleeps 3

Meet Me at the Cape

$89 - $364  per night
3 Bed | 1 Bath | Sleeps 6

Bayside Cape Codder

$204 - $1,134  per night
3D Tour
3 Bed | 2 Bath | Sleeps 8

Dream in Orleans

$251 - $841  per night
3D Tour
4 Bed | 5 Bath | Sleeps 8

Seaside Cottage #11a - The Rabbit Patch

$100 - $405  per night
3D Tour
0 Bed | 1 Bath | Sleeps 4

Seaside Cottage #25 The Golf Shack

$100 - $402  per night
0 Bed | 1 Bath | Sleeps 4

Escape in Dennis

$126 - $584  per night
3D Tour
3 Bed | 2 Bath | Sleeps 7

Cape Escape

$109 - $441  per night
3D Tour
3 Bed | 1.5 Bath | Sleeps 6

Captain Jacks

$119 - $563  per night
3D Tour
NEW!
3 Bed | 2 Bath | Sleeps 6

Endless Summer

$158 - $473  per night
3D Tour
2 Bed | 1 Bath | Sleeps 4

Seaside Cottage #11 - The Whale Watch

$100 - $405  per night
3D Tour
0 Bed | 1 Bath | Sleeps 4

Provincetown Paradise

$88 - $383  per night
3D Tour
0 Bed | 1 Bath | Sleeps 2

"Sampsons Folly"

$164 - $2,242  per night
3D Tour
6 Bed | 6 Bath | Sleeps 14 (8 Adults Max)

Provincetown Dunes

$383 - $1,939  per night
3D Tour
4 Bed | 3.5 Bath | Sleeps 8

Cape Tip Townhouse

$128 - $722  per night
3D Tour
3 Bed | 3.5 Bath | Sleeps 6

Seaside Cottage #35 - The Bird House

$100 - $402  per night
3D Tour
0 Bed | 1 Bath | Sleeps 4 (3 Adults Max)

Perfectly Provincetown

$99 - $459  per night
3D Tour
1 Bed | 1 Bath | Sleeps 4

Seaside Cottage #21 - The Chesapeake

$102 - $410  per night
3D Tour
0 Bed | 1 Bath | Sleeps 4

Hyannis Hideaway

$103 - $559  per night
3D Tour
3 Bed | 2 Bath | Sleeps 7 (5 Adults Max)

The Harbor Breeze

$133 - $449  per night
3D Tour
2 Bed | 1 Bath | Sleeps 4

Cerulean Cottage

$96 - $485  per night
3D Tour
2 Bed | 1 Bath | Sleeps 6

Seaside Cottage #1 - Coastal Haven

$102 - $190  per night
3D Tour
0 Bed | 1 Bath | Sleeps 4

Seaside Cottage #24 - The Lighthouse

$100 - $402  per night
3D Tour
0 Bed | 1 Bath | Sleeps 4

Weeks Pond Charmer

$96 - $469  per night
3D Tour
2 Bed | 2 Bath | Sleeps 6

Harwich Port Perfection

$153 - $849  per night
3D Tour
3 Bed | 3.5 Bath | Sleeps 8
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