Orleans, Massachusetts

Vacation Rentals in Orleans, Massachusetts

Discover 55 vacation rental properties in Orleans. From 1 to 5 bedrooms. Average $336/night. 100% have pools.

55 verified listings Book securely on VRBO Prices updated March 2026

55 properties available

East Orleans - walk to Nauset Beach

East Orleans - walk to Nauset Beach

2 beds 1 bath
PoolA/CWiFiBalcony
$224/night
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Comfy Cape Cod studio, 5-minute walk to beach - great weekend getaway

Comfy Cape Cod studio, 5-minute walk to beach - great weekend getaway

1 bath
PoolA/CWiFiBalcony
$224/night
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Bright and Inviting, close to Jacknife Beach!

Bright and Inviting, close to Jacknife Beach!

4 beds 3 baths
PoolA/CWiFiBalcony
$321/night
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Beachfront on Skaket Beach!

Beachfront on Skaket Beach!

2 beds 1 bath
PoolA/CWiFiBalcony
$325/night
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Beachfront on Skaket Water Views!

Beachfront on Skaket Water Views!

3 beds 1 bath
PoolA/CWiFiBalcony
$406/night
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Charming home within walking distance to Nauset Beach and National Seashore

Charming home within walking distance to Nauset Beach and National Seashore

2 beds 1 bath
PoolA/CWiFiBalcony
$193/night
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Pristine Cottage in Orleans: AC, outdoor shower+ firepit, walk to Bakers Pond

Pristine Cottage in Orleans: AC, outdoor shower+ firepit, walk to Bakers Pond

2 beds 1 bath
PoolA/CWiFiBalcony
$239/night
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Comfy Studio Cottage, Walk to Beach & Dining - 300 Yards to Nauset Beach

Comfy Studio Cottage, Walk to Beach & Dining - 300 Yards to Nauset Beach

1 bath
PoolA/CWiFiBalcony
$211/night
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Amazing location! Quiet, picturesque neighborhood!

Amazing location! Quiet, picturesque neighborhood!

3 beds 2 baths
PoolA/CWiFiBalcony
$255/night
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Spacious Home with Sprawling Yard!

Spacious Home with Sprawling Yard!

4 beds 2 baths
PoolA/CWiFiBalcony
$253/night
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Romantic Orleans Waterfront Cottage!

Romantic Orleans Waterfront Cottage!

1 bed 1 bath
PoolA/CWiFiBalcony
$210/night
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The Perfect Beach Getaway!

The Perfect Beach Getaway!

3 beds 2 baths
PoolA/CWiFiBalcony
$347/night
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Come enjoy Orleans and Chatham

Come enjoy Orleans and Chatham

3 beds 1 bath
PoolA/CWiFiBalcony
$221/night
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Spacious Orleans Apartment With Private Beach Access

Spacious Orleans Apartment With Private Beach Access

1 bed 1 bath
PoolA/CWiFiBalcony
$231/night
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Cozy updated cottage!

Cozy updated cottage!

2 beds 1 bath
PoolA/CWiFiBalcony
$257/night
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1.6 mi to Nauset Beach!

1.6 mi to Nauset Beach!

4 beds 2 baths
PoolA/CWiFiBalcony
$286/night
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Walk to Skaket Beach, Great Backyard!

Walk to Skaket Beach, Great Backyard!

4 beds 2 baths
PoolA/CWiFiBalcony
$291/night
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4-5 Min to Mill Pond or Nauset Beach!

4-5 Min to Mill Pond or Nauset Beach!

4 beds 2 baths
PoolA/CWiFiBalcony
$292/night
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Spacious home with huge deck & tree-lined yard, grill, & WiFi - great location

Spacious home with huge deck & tree-lined yard, grill, & WiFi - great location

4 beds 3 baths
PoolA/CWiFiBalcony
$271/night
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Beautiful Cape Cod home!

Beautiful Cape Cod home!

3 beds 2 baths
PoolA/CWiFiBalcony
$329/night
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Beautiful home with ocean-view, patio, grill, W/D, & close to Nauset Beach

Beautiful home with ocean-view, patio, grill, W/D, & close to Nauset Beach

3 beds 1 bath
PoolA/CWiFiBalcony
$339/night
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Historic home in East Orleans

Historic home in East Orleans

3 beds 1 bath
PoolA/CWiFiBalcony
$321/night
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Classic Cape Cod home near beaches with yard, patio & outdoor fireplace

Classic Cape Cod home near beaches with yard, patio & outdoor fireplace

3 beds 2 baths
PoolA/CWiFiBalcony
$358/night
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Cape Cod Sunscape.

Cape Cod Sunscape.

2 beds 2 baths
PoolA/CWiFiBalcony
$415/night
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Peaceful Nauset Beach Sanctuary

Peaceful Nauset Beach Sanctuary

3 beds 1 bath
PoolA/CWiFiBalcony
$578/night
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Your perch to the Cape's best ocean view with private Nauset access for 8!

Your perch to the Cape's best ocean view with private Nauset access for 8!

4 beds 3 baths
PoolA/CWiFiBalcony
$521/night
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Private Path to Nauset Beach!

Private Path to Nauset Beach!

4 beds 2 baths
PoolA/CWiFiBalcony
$441/night
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Pristine waterfront oasis, plus game room, jacuzzi and home office!

Pristine waterfront oasis, plus game room, jacuzzi and home office!

4 beds 3 baths
PoolA/CWiFiBalcony
$549/night
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Salty Dog Cottage In East Orleans With Access To Town Cove

Salty Dog Cottage In East Orleans With Access To Town Cove

5 beds 2 baths
PoolA/CWiFiBalcony
$411/night
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Large Heated Pool & Hot Tub - 5 Minutes from Nauset Beach

Large Heated Pool & Hot Tub - 5 Minutes from Nauset Beach

5 beds 4 baths
PoolA/CWiFiBalcony
$1,506/night
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100 Ft to Skaket Beach!

100 Ft to Skaket Beach!

5 beds 3 baths
PoolA/CWiFiBalcony
$622/night
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Cute Cottage Retreat 1/2 Mile to Weeset Point Beach

Cute Cottage Retreat 1/2 Mile to Weeset Point Beach

2 beds 1 bath
PoolA/CWiFiBalcony
$184/night
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1 bedroom with den sleeps 4 in Orleans near Skaket beach

1 bedroom with den sleeps 4 in Orleans near Skaket beach

1 bed 1 bath
PoolA/CWiFiBalcony
$189/night
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Cozy Cottage Near Rock Harbor

Cozy Cottage Near Rock Harbor

2 beds 1 bath
PoolA/CWiFiBalcony
$174/night
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Mins to Nauset Beach & Walkable to Town!

Mins to Nauset Beach & Walkable to Town!

3 beds 2 baths
PoolA/CWiFiBalcony
$215/night
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Recently reno’ed private & spacious E. Orleans 3B/2B. Close to Orleans beaches

Recently reno’ed private & spacious E. Orleans 3B/2B. Close to Orleans beaches

3 beds 2 baths
PoolA/CWiFiBalcony
$241/night
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15 min Walk to Nauset Beach!

15 min Walk to Nauset Beach!

3 beds 1 bath
PoolA/CWiFiBalcony
$343/night
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Fantastic Home by Eldridge Park!

Fantastic Home by Eldridge Park!

3 beds 2 baths
PoolA/CWiFiBalcony
$194/night
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Pet Friendly, Half Mile to Beach and Biking, AC, Recent Renovations

Pet Friendly, Half Mile to Beach and Biking, AC, Recent Renovations

4 beds 2 baths
PoolA/CWiFiBalcony
$191/night
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Walk to Water & Preservation Land!

Walk to Water & Preservation Land!

2 beds 1 bath
PoolA/CWiFiBalcony
$251/night
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Antique Cottage with King Bed, Kitchen, Bath, Private Yard & Path to Arey's Pond

Antique Cottage with King Bed, Kitchen, Bath, Private Yard & Path to Arey's Pond

1 bed 1 bath
PoolA/CWiFiBalcony
$218/night
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Bike to Nauset Beach or Walk to Mill Pond!

Bike to Nauset Beach or Walk to Mill Pond!

3 beds 1 bath
PoolA/CWiFiBalcony
$166/night
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Association Access to Nauset Beach

Association Access to Nauset Beach

3 beds 2 baths
PoolA/CWiFiBalcony
$265/night
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Lakefront retreat w/ deck, dock, sandy beach, 4 watercraft, <6 mins to 2 beaches

Lakefront retreat w/ deck, dock, sandy beach, 4 watercraft, <6 mins to 2 beaches

2 beds 1 bath
PoolA/CWiFiBalcony
$278/night
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Close to Barley Neck Landing!

Close to Barley Neck Landing!

5 beds 3 baths
PoolA/CWiFiBalcony
$269/night
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Adorable home in the heart of East Orleans!

Adorable home in the heart of East Orleans!

2 beds 1 bath
PoolA/CWiFiBalcony
$258/night
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Charming, Renovated 1870s Home with Private Beach

Charming, Renovated 1870s Home with Private Beach

3 beds 1 bath
PoolA/CWiFiBalcony
$329/night
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Beautifully Remodeled Classic Beach Home on Cape Cod Rail Trail

Beautifully Remodeled Classic Beach Home on Cape Cod Rail Trail

4 beds 2 baths
PoolA/CWiFiBalcony
$314/night
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