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Orleans Vacation Rentals

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336 rentals in Orleans.
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Charming Post & Beam Near State Park and Pond, vacation rental in Orleans
Charming Post & Beam Near State Park and Pond, vacation rental in Orleans
Charming Post & Beam Near State Park and Pond, vacation rental in Orleans

Charming Post & Beam Near State Park and Pond

Rental Home
1 bedroom
2 bathrooms
Sleeps 3
Match: Sleeps
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East Orleans - walk to Nauset Beach, vacation rental in Orleans
East Orleans - walk to Nauset Beach, vacation rental in Orleans
East Orleans - walk to Nauset Beach, vacation rental in Orleans

East Orleans - walk to Nauset Beach

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Stunning Property with Private Heated Pool, Walk to Ocean Beaches, Sleeps 12, vacation rental in Orleans
Stunning Property with Private Heated Pool, Walk to Ocean Beaches, Sleeps 12, vacation rental in Orleans
Stunning Property with Private Heated Pool, Walk to Ocean Beaches, Sleeps 12, vacation rental in Orleans

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

Rental Home
4 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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Highly Rated Cottage in Orleans, Cape Cod, vacation rental in Orleans
Highly Rated Cottage in Orleans, Cape Cod, vacation rental in Orleans
Highly Rated Cottage in Orleans, Cape Cod, vacation rental in Orleans

Highly Rated Cottage in Orleans, Cape Cod

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Luxury 7 BR, 4 BA w/ Unique 60 foot Private Pool, .4 Miles to Beach, vacation rental in Orleans
Luxury 7 BR, 4 BA w/ Unique 60 foot Private Pool, .4 Miles to Beach, vacation rental in Orleans
Luxury 7 BR, 4 BA w/ Unique 60 foot Private Pool, .4 Miles to Beach, vacation rental in Orleans

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

Rental Home
7 bedrooms
4 bathrooms
Sleeps 21
Match: Sleeps
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Walk to Crystal Lake; private Pickleball/Tennis Court; Basketball Hoop, vacation rental in Orleans
Walk to Crystal Lake; private Pickleball/Tennis Court; Basketball Hoop, vacation rental in Orleans
Walk to Crystal Lake; private Pickleball/Tennis Court; Basketball Hoop, vacation rental in Orleans

Walk to Crystal Lake; private Pickleball/Tennis Court; Basketball Hoop

Rental Home
5 bedrooms
5 bathrooms
Sleeps 10
Match: Sleeps
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5 BR/4 bath w/heated pool .2 miles to Nauset Beach, vacation rental in Orleans
5 BR/4 bath w/heated pool .2 miles to Nauset Beach, vacation rental in Orleans
5 BR/4 bath w/heated pool .2 miles to Nauset Beach, vacation rental in Orleans

5 BR/4 bath w/heated pool .2 miles to Nauset Beach

Rental Home
5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Quaint Cape Near Beaches And Centrally Located, vacation rental in Orleans
Quaint Cape Near Beaches And Centrally Located, vacation rental in Orleans
Quaint Cape Near Beaches And Centrally Located, vacation rental in Orleans

Quaint Cape Near Beaches And Centrally Located

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Pristine Cottage in Orleans: AC, outdoor shower+ firepit, walk to Bakers Pond, vacation rental in Orleans
Pristine Cottage in Orleans: AC, outdoor shower+ firepit, walk to Bakers Pond, vacation rental in Orleans
Pristine Cottage in Orleans: AC, outdoor shower+ firepit, walk to Bakers Pond, vacation rental in Orleans

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

Rental Home
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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#504: Fully updated, walk to Rock Harbor, 2 min drive to downtown, central A/C!, vacation rental in Orleans
#504: Fully updated, walk to Rock Harbor, 2 min drive to downtown, central A/C!, vacation rental in Orleans
#504: Fully updated, walk to Rock Harbor, 2 min drive to downtown, central A/C!, vacation rental in Orleans

#504: Fully updated, walk to Rock Harbor, 2 min drive to downtown, central A/C!

Rental Home
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Large, Charming Cape Cod Home Close To Orleans And Chatham Beaches, vacation rental in Orleans
Large, Charming Cape Cod Home Close To Orleans And Chatham Beaches, vacation rental in Orleans
Large, Charming Cape Cod Home Close To Orleans And Chatham Beaches, vacation rental in Orleans

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

Rental Home
5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Luxury 8 Bedroom Home  w/ Pool - 4 minutes to the beach!, vacation rental in Orleans
Luxury 8 Bedroom Home  w/ Pool - 4 minutes to the beach!, vacation rental in Orleans
Luxury 8 Bedroom Home  w/ Pool - 4 minutes to the beach!, vacation rental in Orleans

Luxury 8 Bedroom Home w/ Pool - 4 minutes to the beach!

Rental Home
8 bedrooms
9 bathrooms
Sleeps 20
Match: Sleeps
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Stunning Ocean Front Luxury Home on Nauset Beach with A/C &  WiFi, vacation rental in Orleans
Stunning Ocean Front Luxury Home on Nauset Beach with A/C &  WiFi, vacation rental in Orleans
Stunning Ocean Front Luxury Home on Nauset Beach with A/C &  WiFi, vacation rental in Orleans

Stunning Ocean Front Luxury Home on Nauset Beach with A/C & WiFi

Rental Home
6 bedrooms
6 bathrooms
Sleeps 16
Match: Sleeps
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Booking now Summer 2021!

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Your perfect Cape Cod Getaway!  Fully renovated cottage minutes from the beach!, vacation rental in Orleans
Your perfect Cape Cod Getaway!  Fully renovated cottage minutes from the beach!, vacation rental in Orleans
Your perfect Cape Cod Getaway!  Fully renovated cottage minutes from the beach!, vacation rental in Orleans

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

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Charming Restored Cottage near Nauset Beach: The Summer House: walk to ice cream, vacation rental in Orleans
Charming Restored Cottage near Nauset Beach: The Summer House: walk to ice cream, vacation rental in Orleans
Charming Restored Cottage near Nauset Beach: The Summer House: walk to ice cream, vacation rental in Orleans

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

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Central air, 2 miles to Nauset Beach, HUGE yard in quiet neighborhood, vacation rental in Orleans
Central air, 2 miles to Nauset Beach, HUGE yard in quiet neighborhood, vacation rental in Orleans
Central air, 2 miles to Nauset Beach, HUGE yard in quiet neighborhood, vacation rental in Orleans

Central air, 2 miles to Nauset Beach, HUGE yard in quiet neighborhood

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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#515: Private beach just 10 feet from Crystal Lake! Brand new renovation!, vacation rental in Orleans
#515: Private beach just 10 feet from Crystal Lake! Brand new renovation!, vacation rental in Orleans
#515: Private beach just 10 feet from Crystal Lake! Brand new renovation!, vacation rental in Orleans

#515: Private beach just 10 feet from Crystal Lake! Brand new renovation!

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Rock Harbor Retreat - ***Accepting RESERVATIONS for SUMMER 2023***, vacation rental in Orleans
Rock Harbor Retreat - ***Accepting RESERVATIONS for SUMMER 2023***, vacation rental in Orleans
Rock Harbor Retreat - ***Accepting RESERVATIONS for SUMMER 2023***, vacation rental in Orleans

Rock Harbor Retreat - ***Accepting RESERVATIONS for SUMMER 2023***

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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CHARMING WATERFRONT LAKE HOUSE ON SPRING FED PILGRIM LAKE, vacation rental in Orleans
CHARMING WATERFRONT LAKE HOUSE ON SPRING FED PILGRIM LAKE, vacation rental in Orleans
CHARMING WATERFRONT LAKE HOUSE ON SPRING FED PILGRIM LAKE, vacation rental in Orleans

CHARMING WATERFRONT LAKE HOUSE ON SPRING FED PILGRIM LAKE

Rental Home
2 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Summer Breeze Cottage only 2 Miles to Nauset Beach; 5 Bedroom w/ EV Charging, vacation rental in Orleans
Summer Breeze Cottage only 2 Miles to Nauset Beach; 5 Bedroom w/ EV Charging, vacation rental in Orleans
Summer Breeze Cottage only 2 Miles to Nauset Beach; 5 Bedroom w/ EV Charging, vacation rental in Orleans

Summer Breeze Cottage only 2 Miles to Nauset Beach; 5 Bedroom w/ EV Charging

Rental Home
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Salty Dog Cottage In East Orleans With Access To Town Cove, vacation rental in Orleans
Salty Dog Cottage In East Orleans With Access To Town Cove, vacation rental in Orleans
Salty Dog Cottage In East Orleans With Access To Town Cove, vacation rental in Orleans

Salty Dog Cottage In East Orleans With Access To Town Cove

Rental Home
5 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Family home, 2 mi to Nauset Beach, sleep 8+, perfect for 2 families, vacation rental in Orleans
Family home, 2 mi to Nauset Beach, sleep 8+, perfect for 2 families, vacation rental in Orleans
Family home, 2 mi to Nauset Beach, sleep 8+, perfect for 2 families, vacation rental in Orleans

Family home, 2 mi to Nauset Beach, sleep 8+, perfect for 2 families

Rental Home
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
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Skaket Beach - 4 BR/3 BA - Post and Beam Walk to Skaket, vacation rental in Orleans
Skaket Beach - 4 BR/3 BA - Post and Beam Walk to Skaket, vacation rental in Orleans
Skaket Beach - 4 BR/3 BA - Post and Beam Walk to Skaket, vacation rental in Orleans

Skaket Beach - 4 BR/3 BA - Post and Beam Walk to Skaket

Rental Home
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Walk to Skaket Beach, vacation rental in Orleans
Walk to Skaket Beach, vacation rental in Orleans
Walk to Skaket Beach, vacation rental in Orleans

Walk to Skaket Beach

Rental Home
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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#526: Luxury waterfront, private sunbathing beach. 9-seat movie theater - GAME R, vacation rental in Orleans
#526: Luxury waterfront, private sunbathing beach. 9-seat movie theater - GAME R, vacation rental in Orleans
#526: Luxury waterfront, private sunbathing beach. 9-seat movie theater - GAME R, vacation rental in Orleans

#526: Luxury waterfront, private sunbathing beach. 9-seat movie theater - GAME R

Rental Home
6 bedrooms
5 bathrooms
Sleeps 14
Match: Sleeps
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#502: COMPLETELY Renovated, Walk to Water & Preservation Land!, vacation rental in Orleans
#502: COMPLETELY Renovated, Walk to Water & Preservation Land!, vacation rental in Orleans
#502: COMPLETELY Renovated, Walk to Water & Preservation Land!, vacation rental in Orleans

#502: COMPLETELY Renovated, Walk to Water & Preservation Land!

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Your perch to the Cape's best ocean view with private Nauset access for 8!, vacation rental in Orleans
Your perch to the Cape's best ocean view with private Nauset access for 8!, vacation rental in Orleans
Your perch to the Cape's best ocean view with private Nauset access for 8!, vacation rental in Orleans

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

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Quaint & Immaculate on Town Cove in East Orleans, vacation rental in Orleans
Quaint & Immaculate on Town Cove in East Orleans, vacation rental in Orleans
Quaint & Immaculate on Town Cove in East Orleans, vacation rental in Orleans

Quaint & Immaculate on Town Cove in East Orleans

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Updated Cottage with Heated Pool, Close To Nauset Beach; 040-O, vacation rental in Orleans
Updated Cottage with Heated Pool, Close To Nauset Beach; 040-O, vacation rental in Orleans
Updated Cottage with Heated Pool, Close To Nauset Beach; 040-O, vacation rental in Orleans

Updated Cottage with Heated Pool, Close To Nauset Beach; 040-O

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Nautical Cottage on Pleasant Bay: Go sailing, live simply, dream extravagantly, vacation rental in Orleans
Nautical Cottage on Pleasant Bay: Go sailing, live simply, dream extravagantly, vacation rental in Orleans
Nautical Cottage on Pleasant Bay: Go sailing, live simply, dream extravagantly, vacation rental in Orleans

Nautical Cottage on Pleasant Bay: Go sailing, live simply, dream extravagantly

Rental Home
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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#519: Private beach access, Screened in dining, Wrap around porch! Dog friendly!, vacation rental in Orleans
#519: Private beach access, Screened in dining, Wrap around porch! Dog friendly!, vacation rental in Orleans
#519: Private beach access, Screened in dining, Wrap around porch! Dog friendly!, vacation rental in Orleans

#519: Private beach access, Screened in dining, Wrap around porch! Dog friendly!

Rental Home
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Spacious Orleans Apartment With Private Beach Access, vacation rental in Orleans
Spacious Orleans Apartment With Private Beach Access, vacation rental in Orleans
Spacious Orleans Apartment With Private Beach Access, vacation rental in Orleans

Spacious Orleans Apartment With Private Beach Access

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Central AC, Spacious, 5-level, beautiful home, near lakes and beach, vacation rental in Orleans
Central AC, Spacious, 5-level, beautiful home, near lakes and beach, vacation rental in Orleans
Central AC, Spacious, 5-level, beautiful home, near lakes and beach, vacation rental in Orleans

Central AC, Spacious, 5-level, beautiful home, near lakes and beach

Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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#527: Deeded Beach Access, Walk to Water, Large Deck, Private Location!, vacation rental in Orleans
#527: Deeded Beach Access, Walk to Water, Large Deck, Private Location!, vacation rental in Orleans
#527: Deeded Beach Access, Walk to Water, Large Deck, Private Location!, vacation rental in Orleans

#527: Deeded Beach Access, Walk to Water, Large Deck, Private Location!

Rental Home
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Charming Cottage w/ Deck - Walk to Skaket Beach!, vacation rental in Orleans
Charming Cottage w/ Deck - Walk to Skaket Beach!, vacation rental in Orleans
Charming Cottage w/ Deck - Walk to Skaket Beach!, vacation rental in Orleans

Charming Cottage w/ Deck - Walk to Skaket Beach!

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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41 Pochet Rd 18558, vacation rental in Orleans
41 Pochet Rd 18558, vacation rental in Orleans
41 Pochet Rd 18558, vacation rental in Orleans

41 Pochet Rd 18558

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Enchanting Waterfront Summer Escape on Pleasant Bay, vacation rental in Orleans
Enchanting Waterfront Summer Escape on Pleasant Bay, vacation rental in Orleans
Enchanting Waterfront Summer Escape on Pleasant Bay, vacation rental in Orleans

Enchanting Waterfront Summer Escape on Pleasant Bay

Rental Home
4 bedrooms
5 bathrooms
Sleeps 7
Match: Sleeps
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Comfy Cape Cod studio, five minute walk to beach - great weekend getaway!, vacation rental in Orleans
Comfy Cape Cod studio, five minute walk to beach - great weekend getaway!, vacation rental in Orleans
Comfy Cape Cod studio, five minute walk to beach - great weekend getaway!, vacation rental in Orleans

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

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
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#529: Gorgeous Home w/ Water Views, Brand New Construction, Near Nauset Beach!, vacation rental in Orleans
#529: Gorgeous Home w/ Water Views, Brand New Construction, Near Nauset Beach!, vacation rental in Orleans
#529: Gorgeous Home w/ Water Views, Brand New Construction, Near Nauset Beach!, vacation rental in Orleans

#529: Gorgeous Home w/ Water Views, Brand New Construction, Near Nauset Beach!

Rental Home
4 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Delightfully Located Home Near Scenic Pah Wah Pond, vacation rental in Orleans
Delightfully Located Home Near Scenic Pah Wah Pond, vacation rental in Orleans
Delightfully Located Home Near Scenic Pah Wah Pond, vacation rental in Orleans

Delightfully Located Home Near Scenic Pah Wah Pond

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Romantic Orleans Waterfront Cottage!, vacation rental in Orleans
Romantic Orleans Waterfront Cottage!, vacation rental in Orleans
Romantic Orleans Waterfront Cottage!, vacation rental in Orleans

Romantic Orleans Waterfront Cottage!

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Near Orleans Center with water views and a heated Pool! 039-O; sleeps 24, vacation rental in Orleans
Near Orleans Center with water views and a heated Pool! 039-O; sleeps 24, vacation rental in Orleans
Near Orleans Center with water views and a heated Pool! 039-O; sleeps 24, vacation rental in Orleans

Near Orleans Center with water views and a heated Pool! 039-O; sleeps 24

Rental Home
10 bedrooms
11 bathrooms
Sleeps 24
Match: Sleeps
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#505: Walk to Nauset Beach! Private yard & large private patio!, vacation rental in Orleans
#505: Walk to Nauset Beach! Private yard & large private patio!, vacation rental in Orleans
#505: Walk to Nauset Beach! Private yard & large private patio!, vacation rental in Orleans

#505: Walk to Nauset Beach! Private yard & large private patio!

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Orleans Oasis on Pleasant Bay, estate with 2 homes & heated pool; 137-O, vacation rental in Orleans
Orleans Oasis on Pleasant Bay, estate with 2 homes & heated pool; 137-O, vacation rental in Orleans
Orleans Oasis on Pleasant Bay, estate with 2 homes & heated pool; 137-O, vacation rental in Orleans

Orleans Oasis on Pleasant Bay, estate with 2 homes & heated pool; 137-O

Rental Home
6 bedrooms
7 bathrooms
Sleeps 14
Match: Sleeps
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Waterfront E Orleans! Panoramic views, Dock, Central heating, kayaks, go to the, vacation rental in Orleans
Waterfront E Orleans! Panoramic views, Dock, Central heating, kayaks, go to the, vacation rental in Orleans
Waterfront E Orleans! Panoramic views, Dock, Central heating, kayaks, go to the, vacation rental in Orleans

Waterfront E Orleans! Panoramic views, Dock, Central heating, kayaks, go to the

Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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SPACIOUS 5 BR SOUTH ORLEANS HOME NEAR BEACHES, GOLF & MORE IN BEAUTIFUL CAPE COD, vacation rental in Orleans
SPACIOUS 5 BR SOUTH ORLEANS HOME NEAR BEACHES, GOLF & MORE IN BEAUTIFUL CAPE COD, vacation rental in Orleans
SPACIOUS 5 BR SOUTH ORLEANS HOME NEAR BEACHES, GOLF & MORE IN BEAUTIFUL CAPE COD, vacation rental in Orleans

SPACIOUS 5 BR SOUTH ORLEANS HOME NEAR BEACHES, GOLF & MORE IN BEAUTIFUL CAPE COD

Rental Home
5 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Charming Family-Friendly Home On Beach Rd.  Close To Nauset Beach & Village Ctr., vacation rental in Orleans
Charming Family-Friendly Home On Beach Rd.  Close To Nauset Beach & Village Ctr., vacation rental in Orleans
Charming Family-Friendly Home On Beach Rd.  Close To Nauset Beach & Village Ctr., vacation rental in Orleans

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

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Discounted Beach Home: June 18-July 8, vacation rental in Orleans
Discounted Beach Home: June 18-July 8, vacation rental in Orleans
Discounted Beach Home: June 18-July 8, vacation rental in Orleans

Discounted Beach Home: June 18-July 8

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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#530: Amazing Nauset Heights Location, Steps to Nauset Beach, Large Private Yard, vacation rental in Orleans
#530: Amazing Nauset Heights Location, Steps to Nauset Beach, Large Private Yard, vacation rental in Orleans
#530: Amazing Nauset Heights Location, Steps to Nauset Beach, Large Private Yard, vacation rental in Orleans

#530: Amazing Nauset Heights Location, Steps to Nauset Beach, Large Private Yard

Rental Home
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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