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Cape Ann Luxury Holiday Homes

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Bedrooms

Bathrooms

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5 km
377 rentals in Cape Ann.
Dog Friendly Home in Rockport- Less Than 1/2 Mile Walk to Beaches & Shops!, holiday rental in Cape Ann
Dog Friendly Home in Rockport- Less Than 1/2 Mile Walk to Beaches & Shops!, holiday rental in Cape Ann
Dog Friendly Home in Rockport- Less Than 1/2 Mile Walk to Beaches & Shops!, holiday rental in Cape Ann

Dog Friendly Home in Rockport- Less Than 1/2 Mile Walk to Beaches & Shops!

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Oceanview Kingsize South End Studio NO FINAL CLEANING FEE, holiday rental in Cape Ann
Oceanview Kingsize South End Studio NO FINAL CLEANING FEE, holiday rental in Cape Ann
Oceanview Kingsize South End Studio NO FINAL CLEANING FEE, holiday rental in Cape Ann

Oceanview Kingsize South End Studio NO FINAL CLEANING FEE

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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4 Bedroom LUX House/with Pool Next Door, holiday rental in Cape Ann
4 Bedroom LUX House/with Pool Next Door, holiday rental in Cape Ann
4 Bedroom LUX House/with Pool Next Door, holiday rental in Cape Ann

4 Bedroom LUX House/with Pool Next Door

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Elegant Italian Villa On The Scenic Coast of New England, holiday rental in Cape Ann
Elegant Italian Villa On The Scenic Coast of New England, holiday rental in Cape Ann
Elegant Italian Villa On The Scenic Coast of New England, holiday rental in Cape Ann

Elegant Italian Villa On The Scenic Coast of New England

Holiday Rental House
10 bedrooms
6 bathrooms
Sleeps 18
Match: Sleeps
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Perfect Rockport Downtown Vacation Destination, holiday rental in Cape Ann
Perfect Rockport Downtown Vacation Destination, holiday rental in Cape Ann
Perfect Rockport Downtown Vacation Destination, holiday rental in Cape Ann

Perfect Rockport Downtown Vacation Destination

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Modern Downtown Penthouse Apartment Overlooking Front Beach, holiday rental in Cape Ann
Modern Downtown Penthouse Apartment Overlooking Front Beach, holiday rental in Cape Ann
Modern Downtown Penthouse Apartment Overlooking Front Beach, holiday rental in Cape Ann

Modern Downtown Penthouse Apartment Overlooking Front Beach

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Ocean views just steps to Back Beach, Front Beach, and downtown Rockport, holiday rental in Cape Ann
Ocean views just steps to Back Beach, Front Beach, and downtown Rockport, holiday rental in Cape Ann
Ocean views just steps to Back Beach, Front Beach, and downtown Rockport, holiday rental in Cape Ann

Ocean views just steps to Back Beach, Front Beach, and downtown Rockport

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Charming 3 bdrm Apartment in Heart of Rockport-Bearskin Neck-Walk to Beach -WiFi, holiday rental in Cape Ann
Charming 3 bdrm Apartment in Heart of Rockport-Bearskin Neck-Walk to Beach -WiFi, holiday rental in Cape Ann
Charming 3 bdrm Apartment in Heart of Rockport-Bearskin Neck-Walk to Beach -WiFi, holiday rental in Cape Ann

Charming 3 bdrm Apartment in Heart of Rockport-Bearskin Neck-Walk to Beach -WiFi

Condo/Apartment
3 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Experience Rockport charm, walk to the beach ,restaurants & Shalin Liu Center, holiday rental in Cape Ann
Experience Rockport charm, walk to the beach ,restaurants & Shalin Liu Center, holiday rental in Cape Ann
Experience Rockport charm, walk to the beach ,restaurants & Shalin Liu Center, holiday rental in Cape Ann

Experience Rockport charm, walk to the beach ,restaurants & Shalin Liu Center

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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End of an Era: limited days between now and January 15th - Then POOF!, holiday rental in Cape Ann
End of an Era: limited days between now and January 15th - Then POOF!, holiday rental in Cape Ann
End of an Era: limited days between now and January 15th - Then POOF!, holiday rental in Cape Ann

End of an Era: limited days between now and January 15th - Then POOF!

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Too many guests for Thanksgiving? Consider our cozy spacious family home!, holiday rental in Cape Ann
Too many guests for Thanksgiving? Consider our cozy spacious family home!, holiday rental in Cape Ann
Too many guests for Thanksgiving? Consider our cozy spacious family home!, holiday rental in Cape Ann

Too many guests for Thanksgiving? Consider our cozy spacious family home!

Holiday Rental House
5 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Luxury 1900's romantic retreat steps from the beach - King Suite!, holiday rental in Cape Ann
Luxury 1900's romantic retreat steps from the beach - King Suite!, holiday rental in Cape Ann
Luxury 1900's romantic retreat steps from the beach - King Suite!, holiday rental in Cape Ann

Luxury 1900's romantic retreat steps from the beach - King Suite!

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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A tranquil ocean retreat steps from the water's edge, holiday rental in Cape Ann
A tranquil ocean retreat steps from the water's edge, holiday rental in Cape Ann
A tranquil ocean retreat steps from the water's edge, holiday rental in Cape Ann

A tranquil ocean retreat steps from the water's edge

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
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NEW 1BR with Private Deck + Ocean Views· Private Parking · King Bed, holiday rental in Cape Ann
NEW 1BR with Private Deck + Ocean Views· Private Parking · King Bed, holiday rental in Cape Ann
NEW 1BR with Private Deck + Ocean Views· Private Parking · King Bed, holiday rental in Cape Ann

NEW 1BR with Private Deck + Ocean Views· Private Parking · King Bed

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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3BR/2 BA Harborside Home · Fenced Backyard+Grill · Ocean Views, holiday rental in Cape Ann
3BR/2 BA Harborside Home · Fenced Backyard+Grill · Ocean Views, holiday rental in Cape Ann
3BR/2 BA Harborside Home · Fenced Backyard+Grill · Ocean Views, holiday rental in Cape Ann

3BR/2 BA Harborside Home · Fenced Backyard+Grill · Ocean Views

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Charming, Modern 3 BR Home near Good Harbor Beach (Gloucester), holiday rental in Cape Ann
Charming, Modern 3 BR Home near Good Harbor Beach (Gloucester), holiday rental in Cape Ann
Charming, Modern 3 BR Home near Good Harbor Beach (Gloucester), holiday rental in Cape Ann

Charming, Modern 3 BR Home near Good Harbor Beach (Gloucester)

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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First Period Colonial Lodging in Gloucester MA, holiday rental in Cape Ann
First Period Colonial Lodging in Gloucester MA, holiday rental in Cape Ann
First Period Colonial Lodging in Gloucester MA, holiday rental in Cape Ann

First Period Colonial Lodging in Gloucester MA

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Oceanfront 4 BR/2 Bath Long Beach Vacation Home - Grill, Outdoor shower, AC, holiday rental in Cape Ann
Oceanfront 4 BR/2 Bath Long Beach Vacation Home - Grill, Outdoor shower, AC, holiday rental in Cape Ann
Oceanfront 4 BR/2 Bath Long Beach Vacation Home - Grill, Outdoor shower, AC, holiday rental in Cape Ann

Oceanfront 4 BR/2 Bath Long Beach Vacation Home - Grill, Outdoor shower, AC

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Coastal retreat steps to the beach with smart TVs, desk, grill, children's items, holiday rental in Cape Ann
Coastal retreat steps to the beach with smart TVs, desk, grill, children's items, holiday rental in Cape Ann
Coastal retreat steps to the beach with smart TVs, desk, grill, children's items, holiday rental in Cape Ann

Coastal retreat steps to the beach with smart TVs, desk, grill, children's items

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Thanksgiving getaway special: 5% rebate at checkin for your 3+night escape!, holiday rental in Cape Ann
Thanksgiving getaway special: 5% rebate at checkin for your 3+night escape!, holiday rental in Cape Ann
Thanksgiving getaway special: 5% rebate at checkin for your 3+night escape!, holiday rental in Cape Ann

Thanksgiving getaway special: 5% rebate at checkin for your 3+night escape!

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Majestic summer rental, holiday rental in Cape Ann
Majestic summer rental, holiday rental in Cape Ann
Majestic summer rental, holiday rental in Cape Ann

Majestic summer rental

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Beach Life Bliss - steps to the beach, holiday rental in Cape Ann
Beach Life Bliss - steps to the beach, holiday rental in Cape Ann
Beach Life Bliss - steps to the beach, holiday rental in Cape Ann

Beach Life Bliss - steps to the beach

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Lovely Rockport Apartment, Walk to Beaches!, holiday rental in Cape Ann
Lovely Rockport Apartment, Walk to Beaches!, holiday rental in Cape Ann
Lovely Rockport Apartment, Walk to Beaches!, holiday rental in Cape Ann

Lovely Rockport Apartment, Walk to Beaches!

Condo/Apartment
3 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Artist's Studio turned Guest House Sleeps up to 3, holiday rental in Cape Ann
Artist's Studio turned Guest House Sleeps up to 3, holiday rental in Cape Ann
Artist's Studio turned Guest House Sleeps up to 3, holiday rental in Cape Ann

Artist's Studio turned Guest House Sleeps up to 3

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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#Weddings #Holidays #Corporate short term? Just need some “in between” place ?, holiday rental in Cape Ann
#Weddings #Holidays #Corporate short term? Just need some “in between” place ?, holiday rental in Cape Ann
#Weddings #Holidays #Corporate short term? Just need some “in between” place ?, holiday rental in Cape Ann

#Weddings #Holidays #Corporate short term? Just need some “in between” place ?

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Romantic Summerwind Cottage,  Scenic Harbor View w/Deck!, holiday rental in Cape Ann
Romantic Summerwind Cottage,  Scenic Harbor View w/Deck!, holiday rental in Cape Ann
Romantic Summerwind Cottage,  Scenic Harbor View w/Deck!, holiday rental in Cape Ann

Romantic Summerwind Cottage, Scenic Harbor View w/Deck!

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Ocean front and 3 beaches across ,parks, short walk to historic downtown!, holiday rental in Cape Ann
Ocean front and 3 beaches across ,parks, short walk to historic downtown!, holiday rental in Cape Ann
Ocean front and 3 beaches across ,parks, short walk to historic downtown!, holiday rental in Cape Ann

Ocean front and 3 beaches across ,parks, short walk to historic downtown!

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Downtown Home near the Beach & Downtown w/Gas Grill, Washer/Dryer & Deck, holiday rental in Cape Ann
Downtown Home near the Beach & Downtown w/Gas Grill, Washer/Dryer & Deck, holiday rental in Cape Ann
Downtown Home near the Beach & Downtown w/Gas Grill, Washer/Dryer & Deck, holiday rental in Cape Ann

Downtown Home near the Beach & Downtown w/Gas Grill, Washer/Dryer & Deck

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Downtown Dahlias fully remodeled in the heart of Gloucester, holiday rental in Cape Ann
Downtown Dahlias fully remodeled in the heart of Gloucester, holiday rental in Cape Ann
Downtown Dahlias fully remodeled in the heart of Gloucester, holiday rental in Cape Ann

Downtown Dahlias fully remodeled in the heart of Gloucester

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Come home to Rockport!, holiday rental in Cape Ann
Come home to Rockport!, holiday rental in Cape Ann
Come home to Rockport!, holiday rental in Cape Ann

Come home to Rockport!

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
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Spectacular views of Thatcher Island and the Atlantic Ocean, holiday rental in Cape Ann
Spectacular views of Thatcher Island and the Atlantic Ocean, holiday rental in Cape Ann
Spectacular views of Thatcher Island and the Atlantic Ocean, holiday rental in Cape Ann

Spectacular views of Thatcher Island and the Atlantic Ocean

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Ocean Front House Long Beach Rockport, holiday rental in Cape Ann
Ocean Front House Long Beach Rockport, holiday rental in Cape Ann
Ocean Front House Long Beach Rockport, holiday rental in Cape Ann

Ocean Front House Long Beach Rockport

Holiday Rental House
5 bedrooms
1 bathroom
Sleeps 10
Match: Sleeps
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Walk to the ocean, very private. Secluded, woodsy location., holiday rental in Cape Ann
Walk to the ocean, very private. Secluded, woodsy location., holiday rental in Cape Ann
Walk to the ocean, very private. Secluded, woodsy location., holiday rental in Cape Ann

Walk to the ocean, very private. Secluded, woodsy location.

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Beach & King -  Ocean Views
Now only a 4 Day minimum!, holiday rental in Cape Ann
Beach & King -  Ocean Views
Now only a 4 Day minimum!, holiday rental in Cape Ann
Beach & King -  Ocean Views
Now only a 4 Day minimum!, holiday rental in Cape Ann

Beach & King - Ocean Views Now only a 4 Day minimum!

Holiday Rental House
8 bedrooms
5 bathrooms
Sleeps 14
Match: Sleeps
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Steps to Good Harbor Beach, 5 Bedrooms, Air Conditioning, Large Deck, Fire Pit, holiday rental in Cape Ann
Steps to Good Harbor Beach, 5 Bedrooms, Air Conditioning, Large Deck, Fire Pit, holiday rental in Cape Ann
Steps to Good Harbor Beach, 5 Bedrooms, Air Conditioning, Large Deck, Fire Pit, holiday rental in Cape Ann

Steps to Good Harbor Beach, 5 Bedrooms, Air Conditioning, Large Deck, Fire Pit

Holiday Rental House
5 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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Rustic Luxe FarmHouse a Few Miles To Crane Beach: deck &jacuzzi overlooking pond, holiday rental in Cape Ann
Rustic Luxe FarmHouse a Few Miles To Crane Beach: deck &jacuzzi overlooking pond, holiday rental in Cape Ann
Rustic Luxe FarmHouse a Few Miles To Crane Beach: deck &jacuzzi overlooking pond, holiday rental in Cape Ann

Rustic Luxe FarmHouse a Few Miles To Crane Beach: deck &jacuzzi overlooking pond

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
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✩1 min to Front Beach✩Cute Studio✩Prime location, holiday rental in Cape Ann
✩1 min to Front Beach✩Cute Studio✩Prime location, holiday rental in Cape Ann
✩1 min to Front Beach✩Cute Studio✩Prime location, holiday rental in Cape Ann

✩1 min to Front Beach✩Cute Studio✩Prime location

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Open concept, 2-level apartment with scenic view, holiday rental in Cape Ann
Open concept, 2-level apartment with scenic view, holiday rental in Cape Ann
Open concept, 2-level apartment with scenic view, holiday rental in Cape Ann

Open concept, 2-level apartment with scenic view

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Mill Pond Cottage: Historic Gloucester charm with modern comforts., holiday rental in Cape Ann
Mill Pond Cottage: Historic Gloucester charm with modern comforts., holiday rental in Cape Ann
Mill Pond Cottage: Historic Gloucester charm with modern comforts., holiday rental in Cape Ann

Mill Pond Cottage: Historic Gloucester charm with modern comforts.

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Modern Cottage, Private Island, Unparalleled beauty, holiday rental in Cape Ann
Modern Cottage, Private Island, Unparalleled beauty, holiday rental in Cape Ann
Modern Cottage, Private Island, Unparalleled beauty, holiday rental in Cape Ann

Modern Cottage, Private Island, Unparalleled beauty

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Good Harbor Beach Apt.- 6/10 mile, holiday rental in Cape Ann
Good Harbor Beach Apt.- 6/10 mile, holiday rental in Cape Ann
Good Harbor Beach Apt.- 6/10 mile, holiday rental in Cape Ann

Good Harbor Beach Apt.- 6/10 mile

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Cozy summer house near the beach, holiday rental in Cape Ann
Cozy summer house near the beach, holiday rental in Cape Ann
Cozy summer house near the beach, holiday rental in Cape Ann

Cozy summer house near the beach

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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Dot's Place: A sunny escape in the heart of Rockport., holiday rental in Cape Ann
Dot's Place: A sunny escape in the heart of Rockport., holiday rental in Cape Ann
Dot's Place: A sunny escape in the heart of Rockport., holiday rental in Cape Ann

Dot's Place: A sunny escape in the heart of Rockport.

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Charming Coastal Cottage, Steps to Ocean & Rockport Village!, holiday rental in Cape Ann
Charming Coastal Cottage, Steps to Ocean & Rockport Village!, holiday rental in Cape Ann
Charming Coastal Cottage, Steps to Ocean & Rockport Village!, holiday rental in Cape Ann

Charming Coastal Cottage, Steps to Ocean & Rockport Village!

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Sea Glass House - Tranquil Retreat or Base for Adventure, holiday rental in Cape Ann
Sea Glass House - Tranquil Retreat or Base for Adventure, holiday rental in Cape Ann
Sea Glass House - Tranquil Retreat or Base for Adventure, holiday rental in Cape Ann

Sea Glass House - Tranquil Retreat or Base for Adventure

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps
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Ocean Breeze / 8-Minute Walk to Beach, holiday rental in Cape Ann
Ocean Breeze / 8-Minute Walk to Beach, holiday rental in Cape Ann
Ocean Breeze / 8-Minute Walk to Beach, holiday rental in Cape Ann

Ocean Breeze / 8-Minute Walk to Beach

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Folly Cove Cottage: Picturesque home near lovely and scenic Folly Cove., holiday rental in Cape Ann
Folly Cove Cottage: Picturesque home near lovely and scenic Folly Cove., holiday rental in Cape Ann
Folly Cove Cottage: Picturesque home near lovely and scenic Folly Cove., holiday rental in Cape Ann

Folly Cove Cottage: Picturesque home near lovely and scenic Folly Cove.

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Location location…min from Good Harbor Beach, holiday rental in Cape Ann
Location location…min from Good Harbor Beach, holiday rental in Cape Ann
Location location…min from Good Harbor Beach, holiday rental in Cape Ann

Location location…min from Good Harbor Beach

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Location Location Location walk to all the favorite Rockport  attractions, holiday rental in Cape Ann
Location Location Location walk to all the favorite Rockport  attractions, holiday rental in Cape Ann
Location Location Location walk to all the favorite Rockport  attractions, holiday rental in Cape Ann

Location Location Location walk to all the favorite Rockport attractions

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Seaside Village of Lanesville - North Gloucester, MA, holiday rental in Cape Ann
Seaside Village of Lanesville - North Gloucester, MA, holiday rental in Cape Ann
Seaside Village of Lanesville - North Gloucester, MA, holiday rental in Cape Ann

Seaside Village of Lanesville - North Gloucester, MA

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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