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Orleans Luxury Holiday Rentals

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Bedrooms

Bathrooms

Amenities

Suitability

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Distinctive Features

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5 mi
235 rentals in Orleans.
Rock Harbor Retreat- Reserve for next summer! Beautifully decorated & Landcaped, holiday rental in Orleans
Rock Harbor Retreat- Reserve for next summer! Beautifully decorated & Landcaped, holiday rental in Orleans
Rock Harbor Retreat- Reserve for next summer! Beautifully decorated & Landcaped, holiday rental in Orleans

Rock Harbor Retreat- Reserve for next summer! Beautifully decorated & Landcaped

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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1 Mile to Beach & Dogs Welcome!, holiday rental in Orleans
1 Mile to Beach & Dogs Welcome!, holiday rental in Orleans
1 Mile to Beach & Dogs Welcome!, holiday rental in Orleans

1 Mile to Beach & Dogs Welcome!

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Peaceful Nauset Beach Sanctuary, holiday rental in Orleans
Peaceful Nauset Beach Sanctuary, holiday rental in Orleans
Peaceful Nauset Beach Sanctuary, holiday rental in Orleans

Peaceful Nauset Beach Sanctuary

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Private, Recently Updated Home A Short Walk Down Private Path to Skaket Beach, holiday rental in Orleans
Private, Recently Updated Home A Short Walk Down Private Path to Skaket Beach, holiday rental in Orleans
Private, Recently Updated Home A Short Walk Down Private Path to Skaket Beach, holiday rental in Orleans

Private, Recently Updated Home A Short Walk Down Private Path to Skaket Beach

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Beautifully remodeled cottage near the beach with central AC, gas grill & lawn, holiday rental in Orleans
Beautifully remodeled cottage near the beach with central AC, gas grill & lawn, holiday rental in Orleans
Beautifully remodeled cottage near the beach with central AC, gas grill & lawn, holiday rental in Orleans

Beautifully remodeled cottage near the beach with central AC, gas grill & lawn

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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1 bedroom with den sleeps 4 in Orleans near Skaket beach, holiday rental in Orleans
1 bedroom with den sleeps 4 in Orleans near Skaket beach, holiday rental in Orleans
1 bedroom with den sleeps 4 in Orleans near Skaket beach, holiday rental in Orleans

1 bedroom with den sleeps 4 in Orleans near Skaket beach

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Central location! Bungalow for 2 + Garden, holiday rental in Orleans
Central location! Bungalow for 2 + Garden, holiday rental in Orleans
Central location! Bungalow for 2 + Garden, holiday rental in Orleans

Central location! Bungalow for 2 + Garden

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Cute Cottage Retreat 1/2 Mile to Weeset Point Beach, holiday rental in Orleans
Cute Cottage Retreat 1/2 Mile to Weeset Point Beach, holiday rental in Orleans
Cute Cottage Retreat 1/2 Mile to Weeset Point Beach, holiday rental in Orleans

Cute Cottage Retreat 1/2 Mile to Weeset Point Beach

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Cozy updated cottage!, holiday rental in Orleans
Cozy updated cottage!, holiday rental in Orleans
Cozy updated cottage!, holiday rental in Orleans

Cozy updated cottage!

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Spacious Orleans Apartment With Private Beach Access, holiday rental in Orleans
Spacious Orleans Apartment With Private Beach Access, holiday rental in Orleans
Spacious Orleans Apartment With Private Beach Access, holiday rental in Orleans

Spacious Orleans Apartment With Private Beach Access

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Quaint Post & Beam near State Park and Pond, holiday rental in Orleans
Quaint Post & Beam near State Park and Pond, holiday rental in Orleans
Quaint Post & Beam near State Park and Pond, holiday rental in Orleans

Quaint Post & Beam near State Park and Pond

Holiday Rental House
1 bedroom
2 bathrooms
Sleeps 3
Match: Sleeps
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Cape Cod Cottage on Private Family Estate minutes from the Beach,, holiday rental in Orleans
Cape Cod Cottage on Private Family Estate minutes from the Beach,, holiday rental in Orleans
Cape Cod Cottage on Private Family Estate minutes from the Beach,, holiday rental in Orleans

Cape Cod Cottage on Private Family Estate minutes from the Beach,

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Charming home within walking distance to Nauset Beach and National Seashore, holiday rental in Orleans
Charming home within walking distance to Nauset Beach and National Seashore, holiday rental in Orleans
Charming home within walking distance to Nauset Beach and National Seashore, holiday rental in Orleans

Charming home within walking distance to Nauset Beach and National Seashore

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Walk to Skaket Beach or Bike to Rail Trail!, holiday rental in Orleans
Walk to Skaket Beach or Bike to Rail Trail!, holiday rental in Orleans
Walk to Skaket Beach or Bike to Rail Trail!, holiday rental in Orleans

Walk to Skaket Beach or Bike to Rail Trail!

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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Beachfront on Skaket Water Views!, holiday rental in Orleans
Beachfront on Skaket Water Views!, holiday rental in Orleans
Beachfront on Skaket Water Views!, holiday rental in Orleans

Beachfront on Skaket Water Views!

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
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Beautiful home with ocean-view, patio, grill, W/D, & close to Nauset Beach, holiday rental in Orleans
Beautiful home with ocean-view, patio, grill, W/D, & close to Nauset Beach, holiday rental in Orleans
Beautiful home with ocean-view, patio, grill, W/D, & close to Nauset Beach, holiday rental in Orleans

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

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Dreamy Duplex Near Beach with Spacious Patio, Grill, & Outdoor Shower, holiday rental in Orleans
Dreamy Duplex Near Beach with Spacious Patio, Grill, & Outdoor Shower, holiday rental in Orleans
Dreamy Duplex Near Beach with Spacious Patio, Grill, & Outdoor Shower, holiday rental in Orleans

Dreamy Duplex Near Beach with Spacious Patio, Grill, & Outdoor Shower

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Private beach access Wrap around porch!, holiday rental in Orleans
Private beach access Wrap around porch!, holiday rental in Orleans
Private beach access Wrap around porch!, holiday rental in Orleans

Private beach access Wrap around porch!

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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15 min Walk to Nauset Beach!, holiday rental in Orleans
15 min Walk to Nauset Beach!, holiday rental in Orleans
15 min Walk to Nauset Beach!, holiday rental in Orleans

15 min Walk to Nauset Beach!

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Highly Rated Cottage in Orleans, Cape Cod, holiday rental in Orleans
Highly Rated Cottage in Orleans, Cape Cod, holiday rental in Orleans
Highly Rated Cottage in Orleans, Cape Cod, holiday rental in Orleans

Highly Rated Cottage in Orleans, Cape Cod

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Dream Waterfront A-Frame in Orleans!, holiday rental in Orleans
Dream Waterfront A-Frame in Orleans!, holiday rental in Orleans
Dream Waterfront A-Frame in Orleans!, holiday rental in Orleans

Dream Waterfront A-Frame in Orleans!

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Mid-Century Contemporary | 2 Bed, 2 Bath, holiday rental in Orleans
Mid-Century Contemporary | 2 Bed, 2 Bath, holiday rental in Orleans
Mid-Century Contemporary | 2 Bed, 2 Bath, holiday rental in Orleans

Mid-Century Contemporary | 2 Bed, 2 Bath

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Captain's Quarters by Nauset Beach, holiday rental in Orleans
Captain's Quarters by Nauset Beach, holiday rental in Orleans
Captain's Quarters by Nauset Beach, holiday rental in Orleans

Captain's Quarters by Nauset Beach

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Nestled by Nauset, holiday rental in Orleans
Nestled by Nauset, holiday rental in Orleans
Nestled by Nauset, holiday rental in Orleans

Nestled by Nauset

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Skaket Beach escape: Corner-lot home with big yard - walk to Warm Bayside Shore, holiday rental in Orleans
Skaket Beach escape: Corner-lot home with big yard - walk to Warm Bayside Shore, holiday rental in Orleans
Skaket Beach escape: Corner-lot home with big yard - walk to Warm Bayside Shore, holiday rental in Orleans

Skaket Beach escape: Corner-lot home with big yard - walk to Warm Bayside Shore

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Nauset Beach Retreat | 4 Bed, 3 Bath, holiday rental in Orleans
Nauset Beach Retreat | 4 Bed, 3 Bath, holiday rental in Orleans
Nauset Beach Retreat | 4 Bed, 3 Bath, holiday rental in Orleans

Nauset Beach Retreat | 4 Bed, 3 Bath

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Walk to Nauset Beach NEW AC System!, holiday rental in Orleans
Walk to Nauset Beach NEW AC System!, holiday rental in Orleans
Walk to Nauset Beach NEW AC System!, holiday rental in Orleans

Walk to Nauset Beach NEW AC System!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Bike to Nauset Beach or Walk to Mill Pond!, holiday rental in Orleans
Bike to Nauset Beach or Walk to Mill Pond!, holiday rental in Orleans
Bike to Nauset Beach or Walk to Mill Pond!, holiday rental in Orleans

Bike to Nauset Beach or Walk to Mill Pond!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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The Perfect Beach Getaway!, holiday rental in Orleans
The Perfect Beach Getaway!, holiday rental in Orleans
The Perfect Beach Getaway!, holiday rental in Orleans

The Perfect Beach Getaway!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Charming Saltbox Close To Skaket Beach & OrleansTown Center (1215), holiday rental in Orleans
Charming Saltbox Close To Skaket Beach & OrleansTown Center (1215), holiday rental in Orleans
Charming Saltbox Close To Skaket Beach & OrleansTown Center (1215), holiday rental in Orleans

Charming Saltbox Close To Skaket Beach & OrleansTown Center (1215)

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Rock Harbor Hideaway | 3 Bed, 1 Bath, holiday rental in Orleans
Rock Harbor Hideaway | 3 Bed, 1 Bath, holiday rental in Orleans
Rock Harbor Hideaway | 3 Bed, 1 Bath, holiday rental in Orleans

Rock Harbor Hideaway | 3 Bed, 1 Bath

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Upscale Orleans Home w/ Deck, 1 Mi to Nauset Beach, holiday rental in Orleans
Upscale Orleans Home w/ Deck, 1 Mi to Nauset Beach, holiday rental in Orleans
Upscale Orleans Home w/ Deck, 1 Mi to Nauset Beach, holiday rental in Orleans

Upscale Orleans Home w/ Deck, 1 Mi to Nauset Beach

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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September discounts and long weekends!!Coastal Chic E. Orleans rebuilt, holiday rental in Orleans
September discounts and long weekends!!Coastal Chic E. Orleans rebuilt, holiday rental in Orleans
September discounts and long weekends!!Coastal Chic E. Orleans rebuilt, holiday rental in Orleans

September discounts and long weekends!!Coastal Chic E. Orleans rebuilt

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Central AC Close to Nauset Beach!, holiday rental in Orleans
Central AC Close to Nauset Beach!, holiday rental in Orleans
Central AC Close to Nauset Beach!, holiday rental in Orleans

Central AC Close to Nauset Beach!

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Mins to Nauset Beach & Walkable to Town!, holiday rental in Orleans
Mins to Nauset Beach & Walkable to Town!, holiday rental in Orleans
Mins to Nauset Beach & Walkable to Town!, holiday rental in Orleans

Mins to Nauset Beach & Walkable to Town!

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Nicely Renovated East Orleans Area Home Sleeps 10, holiday rental in Orleans
Nicely Renovated East Orleans Area Home Sleeps 10, holiday rental in Orleans
Nicely Renovated East Orleans Area Home Sleeps 10, holiday rental in Orleans

Nicely Renovated East Orleans Area Home Sleeps 10

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Less than .5 Miles to Rock Harbor!, holiday rental in Orleans
Less than .5 Miles to Rock Harbor!, holiday rental in Orleans
Less than .5 Miles to Rock Harbor!, holiday rental in Orleans

Less than .5 Miles to Rock Harbor!

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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1.6 mi to Nauset Beach!, holiday rental in Orleans
1.6 mi to Nauset Beach!, holiday rental in Orleans
1.6 mi to Nauset Beach!, holiday rental in Orleans

1.6 mi to Nauset Beach!

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Waterfront on Pleasant Bay!, holiday rental in Orleans
Waterfront on Pleasant Bay!, holiday rental in Orleans
Waterfront on Pleasant Bay!, holiday rental in Orleans

Waterfront on Pleasant Bay!

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Charming Family-Friendly Home On Beach Rd.  Close To Nauset Beach & Village Ctr., holiday rental in Orleans
Charming Family-Friendly Home On Beach Rd.  Close To Nauset Beach & Village Ctr., holiday rental in Orleans
Charming Family-Friendly Home On Beach Rd.  Close To Nauset Beach & Village Ctr., holiday rental in Orleans

Charming Family-Friendly Home On Beach Rd. Close To Nauset Beach & Village Ctr.

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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2 Min Walk to Private Beach & Boat Launch!, holiday rental in Orleans
2 Min Walk to Private Beach & Boat Launch!, holiday rental in Orleans
2 Min Walk to Private Beach & Boat Launch!, holiday rental in Orleans

2 Min Walk to Private Beach & Boat Launch!

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Arts and Crafts Style with Modern Amenities, holiday rental in Orleans
Arts and Crafts Style with Modern Amenities, holiday rental in Orleans
Arts and Crafts Style with Modern Amenities, holiday rental in Orleans

Arts and Crafts Style with Modern Amenities

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Classic Cape Cod home near beaches with yard, patio & outdoor fireplace, holiday rental in Orleans
Classic Cape Cod home near beaches with yard, patio & outdoor fireplace, holiday rental in Orleans
Classic Cape Cod home near beaches with yard, patio & outdoor fireplace, holiday rental in Orleans

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

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Spacious Home with Sprawling Yard!, holiday rental in Orleans
Spacious Home with Sprawling Yard!, holiday rental in Orleans
Spacious Home with Sprawling Yard!, holiday rental in Orleans

Spacious Home with Sprawling Yard!

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Beautifully Remodeled Classic Beach Home on Cape Cod Rail Trail, holiday rental in Orleans
Beautifully Remodeled Classic Beach Home on Cape Cod Rail Trail, holiday rental in Orleans
Beautifully Remodeled Classic Beach Home on Cape Cod Rail Trail, holiday rental in Orleans

Beautifully Remodeled Classic Beach Home on Cape Cod Rail Trail

Holiday Rental House
5 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Crystal Lake Haven | 3 Bed, 2.5 Bath, holiday rental in Orleans
Crystal Lake Haven | 3 Bed, 2.5 Bath, holiday rental in Orleans
Crystal Lake Haven | 3 Bed, 2.5 Bath, holiday rental in Orleans

Crystal Lake Haven | 3 Bed, 2.5 Bath

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Near Mill Pond & Nauset Inlet | 3 Bed, 2 Bath, holiday rental in Orleans
Near Mill Pond & Nauset Inlet | 3 Bed, 2 Bath, holiday rental in Orleans
Near Mill Pond & Nauset Inlet | 3 Bed, 2 Bath, holiday rental in Orleans

Near Mill Pond & Nauset Inlet | 3 Bed, 2 Bath

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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West-facing pure waterfront home in Orleans, overlooking Arey's Pond, holiday rental in Orleans
West-facing pure waterfront home in Orleans, overlooking Arey's Pond, holiday rental in Orleans
West-facing pure waterfront home in Orleans, overlooking Arey's Pond, holiday rental in Orleans

West-facing pure waterfront home in Orleans, overlooking Arey's Pond

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Reconstructed History, holiday rental in Orleans
Reconstructed History, holiday rental in Orleans
Reconstructed History, holiday rental in Orleans

Reconstructed History

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Steps to Skaket Beach!, holiday rental in Orleans
Steps to Skaket Beach!, holiday rental in Orleans
Steps to Skaket Beach!, holiday rental in Orleans

Steps to Skaket Beach!

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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