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Holiday Apartments in Orleans

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

Charming Post & Beam Near State Park and Pond

Holiday Rental House
1 bedroom
2 bathrooms
Sleeps 3
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
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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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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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Luxury 7 BR, 4 BA w/ Unique 60 foot Private Pool, .4 Miles to Beach, holiday rental in Orleans
Luxury 7 BR, 4 BA w/ Unique 60 foot Private Pool, .4 Miles to Beach, holiday rental in Orleans
Luxury 7 BR, 4 BA w/ Unique 60 foot Private Pool, .4 Miles to Beach, holiday rental in Orleans

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

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

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

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

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

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

Quaint Cape Near Beaches And Centrally Located

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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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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#504: Fully updated, walk to Rock Harbor, 2 min drive to downtown, central A/C!, holiday rental in Orleans
#504: Fully updated, walk to Rock Harbor, 2 min drive to downtown, central A/C!, holiday rental in Orleans
#504: Fully updated, walk to Rock Harbor, 2 min drive to downtown, central A/C!, holiday rental in Orleans

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

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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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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Luxury 8 Bedroom Home  w/ Pool - 4 minutes to the beach!, holiday rental in Orleans
Luxury 8 Bedroom Home  w/ Pool - 4 minutes to the beach!, holiday rental in Orleans
Luxury 8 Bedroom Home  w/ Pool - 4 minutes to the beach!, holiday rental in Orleans

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

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

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

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

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

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

Holiday Rental House
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, 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
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Central air, 2 miles to Nauset Beach, HUGE yard in quiet neighborhood, holiday rental in Orleans
Central air, 2 miles to Nauset Beach, HUGE yard in quiet neighborhood, holiday rental in Orleans
Central air, 2 miles to Nauset Beach, HUGE yard in quiet neighborhood, holiday rental in Orleans

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

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

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

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

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

Holiday Rental House
3 bedrooms
3 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
More info
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Summer Breeze Cottage only 2 Miles to Nauset Beach; 5 Bedroom w/ EV Charging, holiday rental in Orleans
Summer Breeze Cottage only 2 Miles to Nauset Beach; 5 Bedroom w/ EV Charging, holiday rental in Orleans
Summer Breeze Cottage only 2 Miles to Nauset Beach; 5 Bedroom w/ EV Charging, holiday rental in Orleans

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

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
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Salty Dog Cottage In East Orleans With Access To Town Cove, holiday rental in Orleans
Salty Dog Cottage In East Orleans With Access To Town Cove, holiday rental in Orleans
Salty Dog Cottage In East Orleans With Access To Town Cove, holiday rental in Orleans

Salty Dog Cottage In East Orleans With Access To Town Cove

Holiday Rental House
5 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
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Family home, 2 mi to Nauset Beach, sleep 8+, perfect for 2 families, holiday rental in Orleans
Family home, 2 mi to Nauset Beach, sleep 8+, perfect for 2 families, holiday rental in Orleans
Family home, 2 mi to Nauset Beach, sleep 8+, perfect for 2 families, holiday rental in Orleans

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

Holiday Rental House
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, holiday rental in Orleans
Skaket Beach - 4 BR/3 BA - Post and Beam Walk to Skaket, holiday rental in Orleans
Skaket Beach - 4 BR/3 BA - Post and Beam Walk to Skaket, holiday rental in Orleans

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

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
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Walk to Skaket Beach, holiday rental in Orleans
Walk to Skaket Beach, holiday rental in Orleans
Walk to Skaket Beach, holiday rental in Orleans

Walk to Skaket Beach

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

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

Holiday Rental House
6 bedrooms
5 bathrooms
Sleeps 14
Match: Sleeps
More info
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#502: COMPLETELY Renovated, Walk to Water & Preservation Land!, holiday rental in Orleans
#502: COMPLETELY Renovated, Walk to Water & Preservation Land!, holiday rental in Orleans
#502: COMPLETELY Renovated, Walk to Water & Preservation Land!, holiday rental in Orleans

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

Holiday Rental House
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!, 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
More info
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Quaint & Immaculate on Town Cove in East Orleans, holiday rental in Orleans
Quaint & Immaculate on Town Cove in East Orleans, holiday rental in Orleans
Quaint & Immaculate on Town Cove in East Orleans, holiday rental in Orleans

Quaint & Immaculate on Town Cove in East Orleans

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Updated Cottage with Heated Pool, Close To Nauset Beach; 040-O, holiday rental in Orleans
Updated Cottage with Heated Pool, Close To Nauset Beach; 040-O, holiday rental in Orleans
Updated Cottage with Heated Pool, Close To Nauset Beach; 040-O, holiday rental in Orleans

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

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Nautical Cottage on Pleasant Bay: Go sailing, live simply, dream extravagantly, holiday rental in Orleans
Nautical Cottage on Pleasant Bay: Go sailing, live simply, dream extravagantly, holiday rental in Orleans
Nautical Cottage on Pleasant Bay: Go sailing, live simply, dream extravagantly, holiday rental in Orleans

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

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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#519: Private beach access, Screened in dining, Wrap around porch! Dog friendly!, holiday rental in Orleans
#519: Private beach access, Screened in dining, Wrap around porch! Dog friendly!, holiday rental in Orleans
#519: Private beach access, Screened in dining, Wrap around porch! Dog friendly!, holiday rental in Orleans

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

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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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
More info
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Central AC, Spacious, 5-level, beautiful home, near lakes and beach, holiday rental in Orleans
Central AC, Spacious, 5-level, beautiful home, near lakes and beach, holiday rental in Orleans
Central AC, Spacious, 5-level, beautiful home, near lakes and beach, holiday rental in Orleans

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

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
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#527: Deeded Beach Access, Walk to Water, Large Deck, Private Location!, holiday rental in Orleans
#527: Deeded Beach Access, Walk to Water, Large Deck, Private Location!, holiday rental in Orleans
#527: Deeded Beach Access, Walk to Water, Large Deck, Private Location!, holiday rental in Orleans

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

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Charming Cottage w/ Deck - Walk to Skaket Beach!, holiday rental in Orleans
Charming Cottage w/ Deck - Walk to Skaket Beach!, holiday rental in Orleans
Charming Cottage w/ Deck - Walk to Skaket Beach!, holiday rental in Orleans

Charming Cottage w/ Deck - Walk to Skaket Beach!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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41 Pochet Rd 18558, holiday rental in Orleans
41 Pochet Rd 18558, holiday rental in Orleans
41 Pochet Rd 18558, holiday rental in Orleans

41 Pochet Rd 18558

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Enchanting Waterfront Summer Escape on Pleasant Bay, holiday rental in Orleans
Enchanting Waterfront Summer Escape on Pleasant Bay, holiday rental in Orleans
Enchanting Waterfront Summer Escape on Pleasant Bay, holiday rental in Orleans

Enchanting Waterfront Summer Escape on Pleasant Bay

Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 7
Match: Sleeps
More info
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Comfy Cape Cod studio, five minute walk to beach - great weekend getaway!, holiday rental in Orleans
Comfy Cape Cod studio, five minute walk to beach - great weekend getaway!, holiday rental in Orleans
Comfy Cape Cod studio, five minute walk to beach - great weekend getaway!, holiday 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
More info
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#529: Gorgeous Home w/ Water Views, Brand New Construction, Near Nauset Beach!, holiday rental in Orleans
#529: Gorgeous Home w/ Water Views, Brand New Construction, Near Nauset Beach!, holiday rental in Orleans
#529: Gorgeous Home w/ Water Views, Brand New Construction, Near Nauset Beach!, holiday rental in Orleans

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

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
More info
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Delightfully Located Home Near Scenic Pah Wah Pond, holiday rental in Orleans
Delightfully Located Home Near Scenic Pah Wah Pond, holiday rental in Orleans
Delightfully Located Home Near Scenic Pah Wah Pond, holiday rental in Orleans

Delightfully Located Home Near Scenic Pah Wah Pond

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Romantic Orleans Waterfront Cottage!, holiday rental in Orleans
Romantic Orleans Waterfront Cottage!, holiday rental in Orleans
Romantic Orleans Waterfront Cottage!, holiday rental in Orleans

Romantic Orleans Waterfront Cottage!

Holiday Rental House
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, holiday rental in Orleans
Near Orleans Center with water views and a heated Pool! 039-O; sleeps 24, holiday rental in Orleans
Near Orleans Center with water views and a heated Pool! 039-O; sleeps 24, holiday rental in Orleans

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

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

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

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Orleans Oasis on Pleasant Bay, estate with 2 homes & heated pool; 137-O, holiday rental in Orleans
Orleans Oasis on Pleasant Bay, estate with 2 homes & heated pool; 137-O, holiday rental in Orleans
Orleans Oasis on Pleasant Bay, estate with 2 homes & heated pool; 137-O, holiday rental in Orleans

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

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

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

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
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SPACIOUS 5 BR SOUTH ORLEANS HOME NEAR BEACHES, GOLF & MORE IN BEAUTIFUL CAPE COD, holiday rental in Orleans
SPACIOUS 5 BR SOUTH ORLEANS HOME NEAR BEACHES, GOLF & MORE IN BEAUTIFUL CAPE COD, holiday rental in Orleans
SPACIOUS 5 BR SOUTH ORLEANS HOME NEAR BEACHES, GOLF & MORE IN BEAUTIFUL CAPE COD, holiday rental in Orleans

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

Holiday Rental House
5 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
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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
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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Discounted Beach Home: June 18-July 8, holiday rental in Orleans
Discounted Beach Home: June 18-July 8, holiday rental in Orleans
Discounted Beach Home: June 18-July 8, holiday rental in Orleans

Discounted Beach Home: June 18-July 8

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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#530: Amazing Nauset Heights Location, Steps to Nauset Beach, Large Private Yard, holiday rental in Orleans
#530: Amazing Nauset Heights Location, Steps to Nauset Beach, Large Private Yard, holiday rental in Orleans
#530: Amazing Nauset Heights Location, Steps to Nauset Beach, Large Private Yard, holiday rental in Orleans

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

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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