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Holiday Rentals in Orleans

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Bedrooms

Bathrooms

Amenities

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Property type

Distinctive Features

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5 km
439 rentals in Orleans.
Large, Charming Cape Cod Home Close To Orleans And Chatham Beaches, holiday rental in Orleans
Large, Charming Cape Cod Home Close To Orleans And Chatham Beaches, holiday rental in Orleans
Large, Charming Cape Cod Home Close To Orleans And Chatham Beaches, holiday rental in Orleans

Large, Charming Cape Cod Home Close To Orleans And Chatham Beaches

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Large Heated Pool & Hot Tub - 5 Minutes from Nauset Beach, holiday rental in Orleans
Large Heated Pool & Hot Tub - 5 Minutes from Nauset Beach, holiday rental in Orleans
Large Heated Pool & Hot Tub - 5 Minutes from Nauset Beach, holiday rental in Orleans

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

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Luxury 7 BR, 4 BA w/ Unique 60 ft Pool, .4 Miles to Beach, holiday rental in Orleans
Luxury 7 BR, 4 BA w/ Unique 60 ft Pool, .4 Miles to Beach, holiday rental in Orleans
Luxury 7 BR, 4 BA w/ Unique 60 ft Pool, .4 Miles to Beach, holiday rental in Orleans

Luxury 7 BR, 4 BA w/ Unique 60 ft Pool, .4 Miles to Beach

Holiday Rental House
7 bedrooms
4 bathrooms
Sleeps 21
Match: Sleeps
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Beautiful home in Orleans. Park, Beach, Lake & Ocean.  Telsa charge, holiday rental in Orleans
Beautiful home in Orleans. Park, Beach, Lake & Ocean.  Telsa charge, holiday rental in Orleans
Beautiful home in Orleans. Park, Beach, Lake & Ocean.  Telsa charge, holiday rental in Orleans

Beautiful home in Orleans. Park, Beach, Lake & Ocean. Telsa charge

Holiday Rental House
7 bedrooms
5 bathrooms
Sleeps 26
Match: Sleeps
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Amazing location!  Quiet, picturesque neighborhood!, holiday rental in Orleans
Amazing location!  Quiet, picturesque neighborhood!, holiday rental in Orleans
Amazing location!  Quiet, picturesque neighborhood!, holiday rental in Orleans

Amazing location! Quiet, picturesque neighborhood!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Lakefront retreat w/ deck, dock, sandy beach, 3 watercraft, <6 mins to 2 beaches, holiday rental in Orleans
Lakefront retreat w/ deck, dock, sandy beach, 3 watercraft, <6 mins to 2 beaches, holiday rental in Orleans
Lakefront retreat w/ deck, dock, sandy beach, 3 watercraft, <6 mins to 2 beaches, holiday rental in Orleans

Lakefront retreat w/ deck, dock, sandy beach, 3 watercraft, <6 mins to 2 beaches

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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4 Doane Terrace, holiday rental in Orleans
4 Doane Terrace, holiday rental in Orleans
4 Doane Terrace, holiday rental in Orleans

4 Doane Terrace

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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5 bedrooms ocean view estate overlooking cape cod bay, holiday rental in Orleans
5 bedrooms ocean view estate overlooking cape cod bay, holiday rental in Orleans
5 bedrooms ocean view estate overlooking cape cod bay, holiday rental in Orleans

5 bedrooms ocean view estate overlooking cape cod bay

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Rock Harbor Retreat - OWNER'S SPECIAL RATE --Sept. 4 to 7 & 10 to 13, holiday rental in Orleans
Rock Harbor Retreat - OWNER'S SPECIAL RATE --Sept. 4 to 7 & 10 to 13, holiday rental in Orleans
Rock Harbor Retreat - OWNER'S SPECIAL RATE --Sept. 4 to 7 & 10 to 13, holiday rental in Orleans

Rock Harbor Retreat - OWNER'S SPECIAL RATE --Sept. 4 to 7 & 10 to 13

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Come enjoy Orleans and Chatham, holiday rental in Orleans
Come enjoy Orleans and Chatham, holiday rental in Orleans
Come enjoy Orleans and Chatham, holiday rental in Orleans

Come enjoy Orleans and Chatham

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Nauset Heights, Walk to Beaches, Pristine Interior: 004-OA, holiday rental in Orleans
Nauset Heights, Walk to Beaches, Pristine Interior: 004-OA, holiday rental in Orleans
Nauset Heights, Walk to Beaches, Pristine Interior: 004-OA, holiday rental in Orleans

Nauset Heights, Walk to Beaches, Pristine Interior: 004-OA

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Short bike trail <1mile to Skaket Beach Cape Home with Hot-tub and Gas Fireplace, holiday rental in Orleans
Short bike trail <1mile to Skaket Beach Cape Home with Hot-tub and Gas Fireplace, holiday rental in Orleans
Short bike trail <1mile to Skaket Beach Cape Home with Hot-tub and Gas Fireplace, holiday rental in Orleans

Short bike trail <1mile to Skaket Beach Cape Home with Hot-tub and Gas Fireplace

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Orleans Beach Bungalow, holiday rental in Orleans
Orleans Beach Bungalow, holiday rental in Orleans
Orleans Beach Bungalow, holiday rental in Orleans

Orleans Beach Bungalow

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Stunning Property with Private Heated Pool, Walk to Ocean Beaches, Sleeps 12, holiday rental in Orleans
Stunning Property with Private Heated Pool, Walk to Ocean Beaches, Sleeps 12, holiday rental in Orleans
Stunning Property with Private Heated Pool, Walk to Ocean Beaches, Sleeps 12, holiday rental in Orleans

Stunning Property with Private Heated Pool, Walk to Ocean Beaches, Sleeps 12

Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 12
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 4
Match: Sleeps
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South Orleans Hideaway, holiday rental in Orleans
South Orleans Hideaway, holiday rental in Orleans
South Orleans Hideaway, holiday rental in Orleans

South Orleans Hideaway

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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East Orleans - walk to Nauset Beach, holiday rental in Orleans
East Orleans - walk to Nauset Beach, holiday rental in Orleans
East Orleans - walk to Nauset Beach, holiday rental in Orleans

East Orleans - walk to Nauset Beach

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Pristine Cottage in Orleans: AC, outdoor shower+ firepit, walk to Bakers Pond, holiday rental in Orleans
Pristine Cottage in Orleans: AC, outdoor shower+ firepit, walk to Bakers Pond, holiday rental in Orleans
Pristine Cottage in Orleans: AC, outdoor shower+ firepit, walk to Bakers Pond, holiday rental in Orleans

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

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
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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Skaket Dream 2/10 mile to the Beach!, holiday rental in Orleans
Skaket Dream 2/10 mile to the Beach!, holiday rental in Orleans
Skaket Dream 2/10 mile to the Beach!, holiday rental in Orleans

Skaket Dream 2/10 mile to the Beach!

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Fantastic Home by Eldridge Park!, holiday rental in Orleans
Fantastic Home by Eldridge Park!, holiday rental in Orleans
Fantastic Home by Eldridge Park!, holiday rental in Orleans

Fantastic Home by Eldridge Park!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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CHARMING WATERFRONT LAKE HOUSE ON SPRING FED PILGRIM LAKE, holiday rental in Orleans
CHARMING WATERFRONT LAKE HOUSE ON SPRING FED PILGRIM LAKE, holiday rental in Orleans
CHARMING WATERFRONT LAKE HOUSE ON SPRING FED PILGRIM LAKE, holiday rental in Orleans

CHARMING WATERFRONT LAKE HOUSE ON SPRING FED PILGRIM LAKE

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 8
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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Your perch to the Cape's best ocean view with private Nauset access for 8!, holiday rental in Orleans
Your perch to the Cape's best ocean view with private Nauset access for 8!, holiday rental in Orleans
Your perch to the Cape's best ocean view with private Nauset access for 8!, holiday rental in Orleans

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

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Rock Harbor Hideaway, holiday rental in Orleans
Rock Harbor Hideaway, holiday rental in Orleans
Rock Harbor Hideaway, holiday rental in Orleans

Rock Harbor Hideaway

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Renovated 1820’s Historic Cape House, holiday rental in Orleans
Renovated 1820’s Historic Cape House, holiday rental in Orleans
Renovated 1820’s Historic Cape House, holiday rental in Orleans

Renovated 1820’s Historic Cape House

Holiday Rental House
5 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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Comfy Studio Cottage, Walk to Beach & Dining - 300 Yards to Nauset Beach, holiday rental in Orleans
Comfy Studio Cottage, Walk to Beach & Dining - 300 Yards to Nauset Beach, holiday rental in Orleans
Comfy Studio Cottage, Walk to Beach & Dining - 300 Yards to Nauset Beach, holiday rental in Orleans

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

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
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Comfy Cape Cod studio, 5-minute walk to beach - great weekend getaway, holiday rental in Orleans
Comfy Cape Cod studio, 5-minute walk to beach - great weekend getaway, holiday rental in Orleans
Comfy Cape Cod studio, 5-minute walk to beach - great weekend getaway, holiday rental in Orleans

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

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
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Peaceful Cape Cod Condo 7 minutes to great Nauset Beach!, holiday rental in Orleans
Peaceful Cape Cod Condo 7 minutes to great Nauset Beach!, holiday rental in Orleans
Peaceful Cape Cod Condo 7 minutes to great Nauset Beach!, holiday rental in Orleans

Peaceful Cape Cod Condo 7 minutes to great Nauset Beach!

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Cozy apartment in a quiet wooded neighborhood, just 2 miles from Nauset Beach., holiday rental in Orleans
Cozy apartment in a quiet wooded neighborhood, just 2 miles from Nauset Beach., holiday rental in Orleans
Cozy apartment in a quiet wooded neighborhood, just 2 miles from Nauset Beach., holiday rental in Orleans

Cozy apartment in a quiet wooded neighborhood, just 2 miles from Nauset Beach.

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Rock Harbor Beach Haven, holiday rental in Orleans
Rock Harbor Beach Haven, holiday rental in Orleans
Rock Harbor Beach Haven, holiday rental in Orleans

Rock Harbor Beach Haven

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Hensons Cove - Updated 2 Bedroom Near Water and Nature Trails, holiday rental in Orleans
Hensons Cove - Updated 2 Bedroom Near Water and Nature Trails, holiday rental in Orleans
Hensons Cove - Updated 2 Bedroom Near Water and Nature Trails, holiday rental in Orleans

Hensons Cove - Updated 2 Bedroom Near Water and Nature Trails

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Walk to the beach at Little Pleasant Bay from this newly decorated cottage!, holiday rental in Orleans
Walk to the beach at Little Pleasant Bay from this newly decorated cottage!, holiday rental in Orleans
Walk to the beach at Little Pleasant Bay from this newly decorated cottage!, holiday rental in Orleans

Walk to the beach at Little Pleasant Bay from this newly decorated cottage!

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Cozy Cottage Overlooking Rock Harbor Creek, holiday rental in Orleans
Cozy Cottage Overlooking Rock Harbor Creek, holiday rental in Orleans
Cozy Cottage Overlooking Rock Harbor Creek, holiday rental in Orleans

Cozy Cottage Overlooking Rock Harbor Creek

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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East Orleans Waterview Getaway, holiday rental in Orleans
East Orleans Waterview Getaway, holiday rental in Orleans
East Orleans Waterview Getaway, holiday rental in Orleans

East Orleans Waterview Getaway

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Central location! Bungalow for 2 + Garden & BBQ, holiday rental in Orleans
Central location! Bungalow for 2 + Garden & BBQ, holiday rental in Orleans
Central location! Bungalow for 2 + Garden & BBQ, holiday rental in Orleans

Central location! Bungalow for 2 + Garden & BBQ

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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3/10 mi to Mill Pond and Nauset Inlet, holiday rental in Orleans
3/10 mi to Mill Pond and Nauset Inlet, holiday rental in Orleans
3/10 mi to Mill Pond and Nauset Inlet, holiday rental in Orleans

3/10 mi to Mill Pond and Nauset Inlet

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Bakers Pond Hideaway, holiday rental in Orleans
Bakers Pond Hideaway, holiday rental in Orleans
Bakers Pond Hideaway, holiday rental in Orleans

Bakers Pond Hideaway

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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2 mins from Nauset Beach!, holiday rental in Orleans
2 mins from Nauset Beach!, holiday rental in Orleans
2 mins from Nauset Beach!, holiday rental in Orleans

2 mins from Nauset Beach!

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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1 min drive to Rock Harbor 2 min to Town!, holiday rental in Orleans
1 min drive to Rock Harbor 2 min to Town!, holiday rental in Orleans
1 min drive to Rock Harbor 2 min to Town!, holiday rental in Orleans

1 min drive to Rock Harbor 2 min to Town!

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Orleans Cottage with Water Views, holiday rental in Orleans
Orleans Cottage with Water Views, holiday rental in Orleans
Orleans Cottage with Water Views, holiday rental in Orleans

Orleans Cottage with Water Views

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Lakefront Townhouse Condo in Cape Cod, MA, holiday rental in Orleans
Lakefront Townhouse Condo in Cape Cod, MA, holiday rental in Orleans
Lakefront Townhouse Condo in Cape Cod, MA, holiday rental in Orleans

Lakefront Townhouse Condo in Cape Cod, MA

Condo/Apartment
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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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

Cabin Holiday Rental
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Cozy Cottage Near Rock Harbor, holiday rental in Orleans
Cozy Cottage Near Rock Harbor, holiday rental in Orleans
Cozy Cottage Near Rock Harbor, holiday rental in Orleans

Cozy Cottage Near Rock Harbor

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
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Charming Restored Cottage near Nauset Beach: The Summer House: walk to ice cream, holiday rental in Orleans
Charming Restored Cottage near Nauset Beach: The Summer House: walk to ice cream, holiday rental in Orleans
Charming Restored Cottage near Nauset Beach: The Summer House: walk to ice cream, holiday rental in Orleans

Charming Restored Cottage near Nauset Beach: The Summer House: walk to ice cream

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Near Asa's Landing and Town Cove, holiday rental in Orleans
Near Asa's Landing and Town Cove, holiday rental in Orleans
Near Asa's Landing and Town Cove, holiday rental in Orleans

Near Asa's Landing and Town Cove

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Walk to Nauset from this Cozy Cottage!, holiday rental in Orleans
Walk to Nauset from this Cozy Cottage!, holiday rental in Orleans
Walk to Nauset from this Cozy Cottage!, holiday rental in Orleans

Walk to Nauset from this Cozy Cottage!

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
More info
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Luxury Waterfront Home With Heated Pool, holiday rental in Orleans
Luxury Waterfront Home With Heated Pool, holiday rental in Orleans
Luxury Waterfront Home With Heated Pool, holiday rental in Orleans

Luxury Waterfront Home With Heated Pool

Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
More info
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Showing results 1-50 of 439
Frequently Asked Questions about Orleans