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Cape Ann Vacation Rentals

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340 rentals in Cape Ann.
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Good Harbor Beach House, vacation rental in Cape Ann
Good Harbor Beach House, vacation rental in Cape Ann
Good Harbor Beach House, vacation rental in Cape Ann

Good Harbor Beach House

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
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Artist's Studio turned Guest House Sleeps up to 3, vacation rental in Cape Ann
Artist's Studio turned Guest House Sleeps up to 3, vacation rental in Cape Ann
Artist's Studio turned Guest House Sleeps up to 3, vacation rental in Cape Ann

Artist's Studio turned Guest House Sleeps up to 3

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 3
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WaterViews Overlooking Gloucester Inner Harbor /Sunroom/ Deck /Walk to Town/ AC, vacation rental in Cape Ann
WaterViews Overlooking Gloucester Inner Harbor /Sunroom/ Deck /Walk to Town/ AC, vacation rental in Cape Ann
WaterViews Overlooking Gloucester Inner Harbor /Sunroom/ Deck /Walk to Town/ AC, vacation rental in Cape Ann

WaterViews Overlooking Gloucester Inner Harbor /Sunroom/ Deck /Walk to Town/ AC

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
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Sunset Views, Waterfront Property, Dock - Sleeps 12, vacation rental in Cape Ann
Sunset Views, Waterfront Property, Dock - Sleeps 12, vacation rental in Cape Ann
Sunset Views, Waterfront Property, Dock - Sleeps 12, vacation rental in Cape Ann

Sunset Views, Waterfront Property, Dock - Sleeps 12

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 12
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Romantic “Summerwind Cottage” - Scenic Harbor View w/Large Deck, vacation rental in Cape Ann
Romantic “Summerwind Cottage” - Scenic Harbor View w/Large Deck, vacation rental in Cape Ann
Romantic “Summerwind Cottage” - Scenic Harbor View w/Large Deck, vacation rental in Cape Ann

Romantic “Summerwind Cottage” - Scenic Harbor View w/Large Deck

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
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Good Harbor Beach House - Walk to Shops, vacation rental in Cape Ann
Good Harbor Beach House - Walk to Shops, vacation rental in Cape Ann
Good Harbor Beach House - Walk to Shops, vacation rental in Cape Ann

Good Harbor Beach House - Walk to Shops

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 7
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4 Bedroom LUX House/with Pool Next Door, vacation rental in Cape Ann
4 Bedroom LUX House/with Pool Next Door, vacation rental in Cape Ann
4 Bedroom LUX House/with Pool Next Door, vacation rental in Cape Ann

4 Bedroom LUX House/with Pool Next Door

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 6
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Newly Renovated!! Beautiful 3 bed home...steps from beach!, vacation rental in Cape Ann
Newly Renovated!! Beautiful 3 bed home...steps from beach!, vacation rental in Cape Ann
Newly Renovated!! Beautiful 3 bed home...steps from beach!, vacation rental in Cape Ann

Newly Renovated!! Beautiful 3 bed home...steps from beach!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
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"Absolutely lovely. The cottage, the beach, the town, the owners.", vacation rental in Cape Ann
"Absolutely lovely. The cottage, the beach, the town, the owners.", vacation rental in Cape Ann
"Absolutely lovely. The cottage, the beach, the town, the owners.", vacation rental in Cape Ann

"Absolutely lovely. The cottage, the beach, the town, the owners."

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 7
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Beautiful Oceanfront Home in Estate Setting, Gloucester WINTER RENTAL AVAILABLE, vacation rental in Cape Ann
Beautiful Oceanfront Home in Estate Setting, Gloucester WINTER RENTAL AVAILABLE, vacation rental in Cape Ann
Beautiful Oceanfront Home in Estate Setting, Gloucester WINTER RENTAL AVAILABLE, vacation rental in Cape Ann

Beautiful Oceanfront Home in Estate Setting, Gloucester WINTER RENTAL AVAILABLE

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 9
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Periwinkle Cottage #1 - OPEN ALL YEAR, walk to everything, parking, wifi, quiet, vacation rental in Cape Ann
Periwinkle Cottage #1 - OPEN ALL YEAR, walk to everything, parking, wifi, quiet, vacation rental in Cape Ann
Periwinkle Cottage #1 - OPEN ALL YEAR, walk to everything, parking, wifi, quiet, vacation rental in Cape Ann

Periwinkle Cottage #1 - OPEN ALL YEAR, walk to everything, parking, wifi, quiet

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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4 Bedroom Cottage With Singing Beach Access, vacation rental in Cape Ann
4 Bedroom Cottage With Singing Beach Access, vacation rental in Cape Ann
4 Bedroom Cottage With Singing Beach Access, vacation rental in Cape Ann

4 Bedroom Cottage With Singing Beach Access

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 5
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Featured on HGTV's Beach Hunters, vacation rental in Cape Ann
Featured on HGTV's Beach Hunters, vacation rental in Cape Ann
Featured on HGTV's Beach Hunters, vacation rental in Cape Ann

Featured on HGTV's Beach Hunters

Holiday Rental House
5 bedrooms
2 bathrooms
Sleeps 9
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A tranquil ocean retreat steps from the water's edge, vacation rental in Cape Ann
A tranquil ocean retreat steps from the water's edge, vacation rental in Cape Ann
A tranquil ocean retreat steps from the water's edge, vacation rental in Cape Ann

A tranquil ocean retreat steps from the water's edge

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
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Perfect Good Harbor Beach vacation home for large and/or extended family getaway, vacation rental in Cape Ann
Perfect Good Harbor Beach vacation home for large and/or extended family getaway, vacation rental in Cape Ann
Perfect Good Harbor Beach vacation home for large and/or extended family getaway, vacation rental in Cape Ann

Perfect Good Harbor Beach vacation home for large and/or extended family getaway

Holiday Rental House
5 bedrooms
6 bathrooms
Sleeps 16
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Nature Lover's Paradise: cozy couples/families, near beaches, nature walks, vacation rental in Cape Ann
Nature Lover's Paradise: cozy couples/families, near beaches, nature walks, vacation rental in Cape Ann
Nature Lover's Paradise: cozy couples/families, near beaches, nature walks, vacation rental in Cape Ann

Nature Lover's Paradise: cozy couples/families, near beaches, nature walks

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
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Gloucester/Annisquam Getaway: Beach-Biking-Nature Walks Mins Away, vacation rental in Cape Ann
Gloucester/Annisquam Getaway: Beach-Biking-Nature Walks Mins Away, vacation rental in Cape Ann
Gloucester/Annisquam Getaway: Beach-Biking-Nature Walks Mins Away, vacation rental in Cape Ann

Gloucester/Annisquam Getaway: Beach-Biking-Nature Walks Mins Away

Condo/Apartment
3 bedrooms
1 bathroom
Sleeps 6
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Sunset Studio "PLUS" - Scenic Harbor View!, vacation rental in Cape Ann
Sunset Studio "PLUS" - Scenic Harbor View!, vacation rental in Cape Ann
Sunset Studio "PLUS" - Scenic Harbor View!, vacation rental in Cape Ann

Sunset Studio "PLUS" - Scenic Harbor View!

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Steps to Good Harbor Beach, 5 Bedrooms, Air Conditioning, Large Deck, Fire Pit, vacation rental in Cape Ann
Steps to Good Harbor Beach, 5 Bedrooms, Air Conditioning, Large Deck, Fire Pit, vacation rental in Cape Ann
Steps to Good Harbor Beach, 5 Bedrooms, Air Conditioning, Large Deck, Fire Pit, vacation rental in Cape Ann

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

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 12
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2 Bedroom Waterfront Unit, Vacation or Short Term Rental, vacation rental in Cape Ann
2 Bedroom Waterfront Unit, Vacation or Short Term Rental, vacation rental in Cape Ann
2 Bedroom Waterfront Unit, Vacation or Short Term Rental, vacation rental in Cape Ann

2 Bedroom Waterfront Unit, Vacation or Short Term Rental

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Spectacular, luxury waterfront property directly overlooking Sandy Bay., vacation rental in Cape Ann
Spectacular, luxury waterfront property directly overlooking Sandy Bay., vacation rental in Cape Ann
Spectacular, luxury waterfront property directly overlooking Sandy Bay., vacation rental in Cape Ann

Spectacular, luxury waterfront property directly overlooking Sandy Bay.

Holiday Rental House
5 bedrooms
6 bathrooms
Sleeps 12
Match: Sleeps
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BRAND NEW3 Bedroom On Lobster Cove, Direct Waterfront, Views And Access, w/kayak, vacation rental in Cape Ann
BRAND NEW3 Bedroom On Lobster Cove, Direct Waterfront, Views And Access, w/kayak, vacation rental in Cape Ann
BRAND NEW3 Bedroom On Lobster Cove, Direct Waterfront, Views And Access, w/kayak, vacation rental in Cape Ann

BRAND NEW3 Bedroom On Lobster Cove, Direct Waterfront, Views And Access, w/kayak

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 3
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Enchanting Harbor Views - Historic Bradley Wharf Bearskin Neck, vacation rental in Cape Ann
Enchanting Harbor Views - Historic Bradley Wharf Bearskin Neck, vacation rental in Cape Ann
Enchanting Harbor Views - Historic Bradley Wharf Bearskin Neck, vacation rental in Cape Ann

Enchanting Harbor Views - Historic Bradley Wharf Bearskin Neck

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Newly Renovated, Luxury Downtown Location. Walk To Everything. Two Paking Spaces, vacation rental in Cape Ann
Newly Renovated, Luxury Downtown Location. Walk To Everything. Two Paking Spaces, vacation rental in Cape Ann
Newly Renovated, Luxury Downtown Location. Walk To Everything. Two Paking Spaces, vacation rental in Cape Ann

Newly Renovated, Luxury Downtown Location. Walk To Everything. Two Paking Spaces

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 3
Match: Sleeps
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Prime Gloucester Property Overlooking Inner Harbor, vacation rental in Cape Ann
Prime Gloucester Property Overlooking Inner Harbor, vacation rental in Cape Ann
Prime Gloucester Property Overlooking Inner Harbor, vacation rental in Cape Ann

Prime Gloucester Property Overlooking Inner Harbor

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Perfect apartment for a single or couple., vacation rental in Cape Ann
Perfect apartment for a single or couple., vacation rental in Cape Ann
Perfect apartment for a single or couple., vacation rental in Cape Ann

Perfect apartment for a single or couple.

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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Cape Ann, Annisquam panoramic ocean views from every room., vacation rental in Cape Ann
Cape Ann, Annisquam panoramic ocean views from every room., vacation rental in Cape Ann
Cape Ann, Annisquam panoramic ocean views from every room., vacation rental in Cape Ann

Cape Ann, Annisquam panoramic ocean views from every room.

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 11
Match: Sleeps
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'We can't wait to return to Four Winds', vacation rental in Cape Ann
'We can't wait to return to Four Winds', vacation rental in Cape Ann
'We can't wait to return to Four Winds', vacation rental in Cape Ann

'We can't wait to return to Four Winds'

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Fantastic Ocean Views-2 Min Walk to Long & Cape Hedge Beaches -Text *******-1486, vacation rental in Cape Ann
Fantastic Ocean Views-2 Min Walk to Long & Cape Hedge Beaches -Text *******-1486, vacation rental in Cape Ann
Fantastic Ocean Views-2 Min Walk to Long & Cape Hedge Beaches -Text *******-1486, vacation rental in Cape Ann

Fantastic Ocean Views-2 Min Walk to Long & Cape Hedge Beaches -Text *******-1486

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Old Garden Beach, vacation rental in Cape Ann
Old Garden Beach, vacation rental in Cape Ann
Old Garden Beach, vacation rental in Cape Ann

Old Garden Beach

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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*PREMIUM PROPERTY* - Private 2-Acre Retreat (MODERN 4 Bedrooms) **See Video Tour, vacation rental in Cape Ann
*PREMIUM PROPERTY* - Private 2-Acre Retreat (MODERN 4 Bedrooms) **See Video Tour, vacation rental in Cape Ann
*PREMIUM PROPERTY* - Private 2-Acre Retreat (MODERN 4 Bedrooms) **See Video Tour, vacation rental in Cape Ann

*PREMIUM PROPERTY* - Private 2-Acre Retreat (MODERN 4 Bedrooms) **See Video Tour

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 9
Match: Sleeps
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Modern Downtown Penthouse Apartment Overlooking Front Beach, vacation rental in Cape Ann
Modern Downtown Penthouse Apartment Overlooking Front Beach, vacation rental in Cape Ann
Modern Downtown Penthouse Apartment Overlooking Front Beach, vacation 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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Perfect Rockport Vacation Destination, vacation rental in Cape Ann
Perfect Rockport Vacation Destination, vacation rental in Cape Ann
Perfect Rockport Vacation Destination, vacation rental in Cape Ann

Perfect Rockport Vacation Destination

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 3
Match: Sleeps
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Beach & King Beach House stunning ocean views and short walk to town., vacation rental in Cape Ann
Beach & King Beach House stunning ocean views and short walk to town., vacation rental in Cape Ann
Beach & King Beach House stunning ocean views and short walk to town., vacation rental in Cape Ann

Beach & King Beach House stunning ocean views and short walk to town.

Holiday Rental House
6 bedrooms
5 bathrooms
Sleeps 14
Match: Sleeps
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Charming, Modern 3 BR Home near Good Harbor Beach (Gloucester), vacation rental in Cape Ann
Charming, Modern 3 BR Home near Good Harbor Beach (Gloucester), vacation rental in Cape Ann
Charming, Modern 3 BR Home near Good Harbor Beach (Gloucester), vacation rental in Cape Ann

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

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 3
Match: Sleeps
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Spacious Estate, min. to Beach, pool - options, vacation rental in Cape Ann
Spacious Estate, min. to Beach, pool - options, vacation rental in Cape Ann
Spacious Estate, min. to Beach, pool - options, vacation rental in Cape Ann

Spacious Estate, min. to Beach, pool - options

Holiday Rental House
6 bedrooms
6 bathrooms
Sleeps 12
Match: Sleeps
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Spacious, Comfortable Family Home with Gorgeous Gardens near Ocean and Downtown, vacation rental in Cape Ann
Spacious, Comfortable Family Home with Gorgeous Gardens near Ocean and Downtown, vacation rental in Cape Ann
Spacious, Comfortable Family Home with Gorgeous Gardens near Ocean and Downtown, vacation rental in Cape Ann

Spacious, Comfortable Family Home with Gorgeous Gardens near Ocean and Downtown

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
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Walk to Good Harbor Beach, pet friendly, family beach home, vacation rental in Cape Ann
Walk to Good Harbor Beach, pet friendly, family beach home, vacation rental in Cape Ann
Walk to Good Harbor Beach, pet friendly, family beach home, vacation rental in Cape Ann

Walk to Good Harbor Beach, pet friendly, family beach home

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Picturesque Rockport Queen Anne Cottage, vacation rental in Cape Ann
Picturesque Rockport Queen Anne Cottage, vacation rental in Cape Ann
Picturesque Rockport Queen Anne Cottage, vacation rental in Cape Ann

Picturesque Rockport Queen Anne Cottage

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Wingaersheek, Private & Public Beach, Luxury Home, Ext'd Family View Annisquam, vacation rental in Cape Ann
Wingaersheek, Private & Public Beach, Luxury Home, Ext'd Family View Annisquam, vacation rental in Cape Ann
Wingaersheek, Private & Public Beach, Luxury Home, Ext'd Family View Annisquam, vacation rental in Cape Ann

Wingaersheek, Private & Public Beach, Luxury Home, Ext'd Family View Annisquam

Holiday Rental House
6 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Charming year round cottage - Pet Friendly with Wi-Fi, vacation rental in Cape Ann
Charming year round cottage - Pet Friendly with Wi-Fi, vacation rental in Cape Ann
Charming year round cottage - Pet Friendly with Wi-Fi, vacation rental in Cape Ann

Charming year round cottage - Pet Friendly with Wi-Fi

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
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Good Harbor Beachfront at the Footbridge, vacation rental in Cape Ann
Good Harbor Beachfront at the Footbridge, vacation rental in Cape Ann
Good Harbor Beachfront at the Footbridge, vacation rental in Cape Ann

Good Harbor Beachfront at the Footbridge

Holiday Rental House
6 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Spacious Home, 9BR/5BA, Pool, Walk to beach and town., vacation rental in Cape Ann
Spacious Home, 9BR/5BA, Pool, Walk to beach and town., vacation rental in Cape Ann
Spacious Home, 9BR/5BA, Pool, Walk to beach and town., vacation rental in Cape Ann

Spacious Home, 9BR/5BA, Pool, Walk to beach and town.

Holiday Rental House
9 bedrooms
5 bathrooms
Sleeps 9
Match: Sleeps
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Waterfront Home with Spectacular Viewsof the Annisquam River, vacation rental in Cape Ann
Waterfront Home with Spectacular Viewsof the Annisquam River, vacation rental in Cape Ann
Waterfront Home with Spectacular Viewsof the Annisquam River, vacation rental in Cape Ann

Waterfront Home with Spectacular Viewsof the Annisquam River

Holiday Rental House
6 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Historic Estate with Sweeping, Ocean Views, Beautiful Gardens, and Private Beach, vacation rental in Cape Ann
Historic Estate with Sweeping, Ocean Views, Beautiful Gardens, and Private Beach, vacation rental in Cape Ann
Historic Estate with Sweeping, Ocean Views, Beautiful Gardens, and Private Beach, vacation rental in Cape Ann

Historic Estate with Sweeping, Ocean Views, Beautiful Gardens, and Private Beach

Holiday Rental House
8 bedrooms
7 bathrooms
Sleeps 13
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Come home to Rockport!, vacation rental in Cape Ann
Come home to Rockport!, vacation rental in Cape Ann
Come home to Rockport!, vacation rental in Cape Ann

Come home to Rockport!

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Waterfront House onThe Old Harbor Spectacular Views, vacation rental in Cape Ann
Waterfront House onThe Old Harbor Spectacular Views, vacation rental in Cape Ann
Waterfront House onThe Old Harbor Spectacular Views, vacation rental in Cape Ann

Waterfront House onThe Old Harbor Spectacular Views

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Wingaersheek, Private & Public Beach, Beautiful Luxury Home, Ext'd Family, vacation rental in Cape Ann
Wingaersheek, Private & Public Beach, Beautiful Luxury Home, Ext'd Family, vacation rental in Cape Ann
Wingaersheek, Private & Public Beach, Beautiful Luxury Home, Ext'd Family, vacation rental in Cape Ann

Wingaersheek, Private & Public Beach, Beautiful Luxury Home, Ext'd Family

Holiday Rental House
6 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
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Brand new! Beautiful home in quiet neighborhood near Old Garden Beach., vacation rental in Cape Ann
Brand new! Beautiful home in quiet neighborhood near Old Garden Beach., vacation rental in Cape Ann
Brand new! Beautiful home in quiet neighborhood near Old Garden Beach., vacation rental in Cape Ann

Brand new! Beautiful home in quiet neighborhood near Old Garden Beach.

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Fabulous fully furnished vacation home between Good Harbor Beach and Long Beach!, vacation rental in Cape Ann
Fabulous fully furnished vacation home between Good Harbor Beach and Long Beach!, vacation rental in Cape Ann
Fabulous fully furnished vacation home between Good Harbor Beach and Long Beach!, vacation rental in Cape Ann

Fabulous fully furnished vacation home between Good Harbor Beach and Long Beach!

Condo/Apartment
3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Frequently Asked Questions about Cape Ann