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2,216 Houses

4

Topside MainHouse

Cape Cod / South Orleans

South Orleans house

3 8 7 nights min

  • 3 bedrooms
  • sleeps 8
  • 7 nights min
  • Suitable for children age 5+

Price per night from

$1,071

Price per night from

$1,071

41

18 Scotlin Way Harwich Cape Cod

Cape Cod / South Orleans

South Orleans house

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$290

Price per night from

$290

(2) Excellent 

10

Topside BoatHouse on Pleasant Bay

Cape Cod / South Orleans

South Orleans boathouse

2 4 7 nights min

  • 2 bedrooms
  • sleeps 4
  • 7 nights min
  • Ask about children
  • Private garden

Price per night from

$429

Price per night from

$429

29

Orleans Town Landing - 3906

Cape Cod / South Orleans

South Orleans house

5 10 7 nights min

  • 5 bedrooms
  • sleeps 10
  • 7 nights min
  • Child Friendly

Price per night from

$257

Price per night from

$257

(1) Excellent 

16

Large House On Private Acre - Newly Remodeled & New Furnishings

Cape Cod / South Orleans

South Orleans house

4 10 min stay varies

  • 4 bedrooms
  • sleeps 10
  • min stay varies
  • Child Friendly

Price per night from

$399

Price per night from

$399

31

Pleasant Bay Association Beach

Cape Cod / South Orleans

South Orleans house

2 8 7 nights min

  • 2 bedrooms
  • sleeps 8
  • 7 nights min
  • Ask about children
  • Air conditioning

Price per night from

$243

Responds fast!
avg. 2 hours 4 minutes

Price per night from

$243

18

22 Little Bay Lane 18416

Cape Cod / South Orleans

South Orleans house

5 10 7 nights min

  • 5 bedrooms
  • sleeps 10
  • 7 nights min
  • Child Friendly
  • Air conditioning

Price per night from

$757

Price per night from

$757

28

Exquisite Custom Built 5BR Home in Orleans: 004-OP

Cape Cod / South Orleans

South Orleans house

5 12 min stay varies

  • 5 bedrooms
  • sleeps 12
  • min stay varies
  • Child Friendly

Price per night from

$719

Price per night from

$719

19

9 Woodridge Road 99912

Cape Cod / South Orleans

South Orleans house

4 8 7 nights min

  • 4 bedrooms
  • sleeps 8
  • 7 nights min
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$157

Price per night from

$157

(2) Very Good 

19

52 Forest Way 18423

Cape Cod / South Orleans

South Orleans house

5 8 7 nights min

  • 5 bedrooms
  • sleeps 8
  • 7 nights min
  • Child Friendly
  • Air conditioning
“We enjoyed our rental very much.” This was the second year at this house. We enjoyed the house very much. It was clean and very well equiped. It met our needs, as a family, very well. There was plenty of room for all us. We have been coming to Cape Co
…see more

Price per night from

$200

Price per night from

$200

29

Waterfront Home with Large Private Deck and Hot Tub Overlooking Pond; 054-O

Cape Cod / South Orleans

South Orleans house

3 10 min stay varies

  • 3 bedrooms
  • sleeps 10
  • min stay varies
  • Child Friendly

Price per night from

$308

Price per night from

$308

26

Large, Updated 5 Bedroom with Private Beach Access

Cape Cod / South Orleans

South Orleans house

5 10 7 nights min

  • 5 bedrooms
  • sleeps 10
  • 7 nights min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$648

Price per night from

$648

28

NEW LISTING! Beautiful home w/ entertainment - near golf courses & Pleasant Bay

Cape Cod / South Orleans

South Orleans house

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Child Friendly
  • Air conditioning

Price per night from

$128

Responds fast!
avg. 1 hour 12 minutes

Price per night from

$128

43

5 White Cedar Lane Orleans Cape Cod - White Cedar

Cape Cod / South Orleans

South Orleans house

4 12 min stay varies

  • 4 bedrooms
  • sleeps 12
  • min stay varies
  • Child Friendly
  • Air conditioning

Price per night from

$535

Price per night from

$535

Great rentals within 20 miles that match your search

Distance approx 10.55 km from South Orleans

15

Skip to beach! Condo across from beach!

Dennis / Dennis Port

Dennis Port condo

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Child Friendly

Price per night from

$100

Responds fast!
avg. 2 hours 47 minutes

Price per night from

$100

Distance approx 9.91 km from South Orleans

12

Beach House

Dennis / Dennis Port

Dennis Port house

3 4 7 nights min

  • 3 bedrooms
  • sleeps 4
  • 7 nights min
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$121

Price per night from

$121

Distance approx 5.14 km from South Orleans Show on Map

(17) Excellent 

16

IVY Cottage - 3 Bedroom, Secluded and Comfortable

Cape Cod / Eastham

Eastham cottage

3 6 3 nights min

  • 3 bedrooms
  • sleeps 6
  • 3 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly
“AMAZING!!!!!” My husband, 7 month old son, father & I stayed for 4 nights in this amazing cottage. Location was perfect. Nice & quiet the cottage was equipped with absolutely everything you can think of. 2 bath rooms was a really nice bonus. I can not
…see more

Price per night from

$100

Responds fast!
avg. 3 hours 8 minutes

Price per night from

$100

Distance approx 16.81 km from South Orleans

9

Best Location Private Beach/Pool/3 BRs Hyannis

Cape Cod / Hyannis

Hyannis condo

3 6 7 nights min

  • 3 bedrooms
  • sleeps 6
  • 7 nights min
  • Child Friendly

Price per night from

$141

Price per night from

$141

Distance approx 2.96 km from South Orleans Show on Map

(3) Excellent 

16

Rock Harbor Getaway

Cape Cod / Orleans

Orleans house

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Nearest beach 2 mi
  • Child Friendly
  • Air conditioning

Price per night from

$225

Responds fast!
avg. 46 minutes

Price per night from

$225

Distance approx 7.56 km from South Orleans

(1) Excellent 

28

Whale's Tale Cottage

Harwich / Harwich Port

Harwich Port house

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Child Friendly
  • Air conditioning
  • Pet Friendly

Price per night from

$172

Responds fast!
avg. 33 minutes

Price per night from

$172

Distance approx 3.7 km from South Orleans Show on Map

18

Your perfect Cape Cod Getaway! Fully renovated cottage minutes from the beach!

Cape Cod / Orleans

Orleans house

2 5 3 nights min

  • 2 bedrooms
  • sleeps 5
  • 3 nights min
  • Child Friendly
  • Air conditioning

Price per night from

$202

Price per night from

$202

Distance approx 4.73 km from South Orleans Show on Map

28

Cape Cod Home w/ Fire Pit & Grills - Near Beaches!

Chatham / South Chatham

South Chatham house

3 10 min stay varies

  • 3 bedrooms
  • sleeps 10
  • min stay varies
  • Child Friendly
  • Air conditioning

Price per night from

$330

Responds fast!
avg. 8 minutes

Price per night from

$330

Distance approx 11.05 km from South Orleans

15

Perfect Family Cottage w/ Amazing Private Beach

Dennis / West Dennis

West Dennis house

3 6 7 nights min

  • 3 bedrooms
  • sleeps 6
  • 7 nights min
  • Child Friendly

Price per night from

$295

Price per night from

$295

Distance approx 6.26 km from South Orleans

46

Waterfront 6 Bedroom with Pool and Private Dock

Cape Cod / Chatham

Chatham house

6 12 7 nights min

  • 6 bedrooms
  • sleeps 12
  • 7 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$1,786

Price per night from

$1,786

Distance approx 15.43 km from South Orleans

19

Water View Hibiscus Beach House Pet friendly

Cape Cod / Yarmouth

Yarmouth house

3 6 2 nights min

  • 3 bedrooms
  • sleeps 6
  • 2 nights min
  • Nearest beach 0.3 mi
  • Child Friendly
  • Air conditioning

Price per night from

$302

Responds fast!
avg. 3 hours 39 minutes

Price per night from

$302

Distance approx 6.68 km from South Orleans

(1) Excellent 

22

Looking for a Great Summer Vacation? Eastham is Beautiful!!!

Cape Cod / Eastham

Eastham house

3 6 7 nights min

  • 3 bedrooms
  • sleeps 6
  • 7 nights min
  • Beach / lakeside relaxation
  • Child Friendly
  • Car not necessary
“Second Yr Renting - Lovely Clean Family Home” This is my family's 2nd year of renting this beautifully decorated immaculately clean and upscale family style home with all the extras you would have in your own home. We had such good memories there the
…see more

Price per night from

$300

Price per night from

$300

Distance approx 18.54 km from South Orleans

(1) Excellent 

9

Hideaway Saltbox Colonial

Cape Cod / Centerville

Centerville house

3 8 3 nights min

  • 3 bedrooms
  • sleeps 8
  • 3 nights min
  • Child Friendly
  • Private garden

Price per night from

$227

Price per night from

$227

Distance approx 18.53 km from South Orleans

12

Cape Cod Deluxe Hideaway

Cape Cod / Centerville

Centerville b and b

2 4 2 nights min

  • 2 bedrooms
  • sleeps 4
  • 2 nights min
  • Nearest beach 5 mi
  • Child Friendly
  • Air conditioning

Price per night from

$150

Responds fast!
avg. 24 minutes

Price per night from

$150

Distance approx 10.15 km from South Orleans

19

200 feet from Sea Street beach

Dennis / Dennis Port

Dennis Port house

2 5 min stay varies

  • 2 bedrooms
  • sleeps 5
  • min stay varies
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$110

Price per night from

$110

Distance approx 14.94 km from South Orleans

18

Amazing CapeCod Location:Lewis Bay with Private beach & Sensational water views!

Cape Cod / West Yarmouth

West Yarmouth house

3 6 5 nights min

  • 3 bedrooms
  • sleeps 6
  • 5 nights min
  • Nearest beach 0.2 mi
  • Child Friendly
  • Pet Friendly

Price per night from

$425

Price per night from

$425

Distance approx 2.01 km from South Orleans Show on Map

16

Open-Plan Cape close to quiet beach, 3 miles from Nauset Beach

Cape Cod / Orleans

Orleans house

4 10 min stay varies

  • 4 bedrooms
  • sleeps 10
  • min stay varies
  • Child Friendly

Price per night from

$350

Price per night from

$350

Distance approx 4.01 km from South Orleans Show on Map

20

Eastham Cottage Vacation Rental

Cape Cod / Eastham

Eastham house

2 6 3 nights min

  • 2 bedrooms
  • sleeps 6
  • 3 nights min
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$182

Price per night from

$182

Distance approx 8.94 km from South Orleans

10

Beautiful Brand New Condos Close to Beach

Dennis / Dennis Port

Dennis Port condo

2 10 5 nights min

  • 2 bedrooms
  • sleeps 10
  • 5 nights min
  • Child Friendly

Price per night from

$433

Price per night from

$433

Distance approx 3.13 km from South Orleans Show on Map

13

Charming Classic Cape with Ocean Views

Cape Cod / Orleans

Orleans house

3 6 7 nights min

  • 3 bedrooms
  • sleeps 6
  • 7 nights min
  • Child Friendly

Price per night from

$129

Price per night from

$129

Distance approx 10.44 km from South Orleans

16

"MERMAID COTTAGE"

Cape Cod / Dennis

Dennis house

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Child Friendly
  • Air conditioning
  • Private garden

Price per night from

$165

Price per night from

$165

Distance approx 12.69 km from South Orleans

17

Wellfleet 5 Bedroom Captain's House Near Cahoon Hollow

Cape Cod / Wellfleet

Wellfleet house

5 10 7 nights min

  • 5 bedrooms
  • sleeps 10
  • 7 nights min
  • Child Friendly
  • Pet Friendly

Price per night from

$244

Price per night from

$244

Distance approx 17.92 km from South Orleans

18

Contemporary Hilltop Home Next to National Seashore Park

Cape Cod / Truro

Truro house

3 10 7 nights min

  • 3 bedrooms
  • sleeps 10
  • 7 nights min
  • Child Friendly
  • Pet Friendly

Price per night from

$259

Price per night from

$259

Distance approx 2.16 km from South Orleans Show on Map

19

Perfect Summer Retreat ~Steps away from town dock and boat ramp~

Cape Cod / Orleans

Orleans house

4 9 7 nights min

  • 4 bedrooms
  • sleeps 9
  • 7 nights min
  • Child Friendly

Price per night from

$355

Price per night from

$355