Cape Ann Vacation Rentals
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340 rentals in Cape Ann.
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Good Harbor Beach House
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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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
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Sunset Views, Waterfront Property, Dock - Sleeps 12
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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Romantic “Summerwind Cottage” - Scenic Harbor View w/Large Deck
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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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
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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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."
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 7
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Beautiful Oceanfront Home in Estate Setting, Gloucester WINTER RENTAL AVAILABLE
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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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
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 5
Match: Sleeps
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Featured on HGTV's Beach Hunters
Holiday Rental House
5 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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A tranquil ocean retreat steps from the water's edge
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Perfect Good Harbor Beach vacation home for large and/or extended family getaway
Holiday Rental House
5 bedrooms
6 bathrooms
Sleeps 16
Match: Sleeps
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Nature Lover's Paradise: cozy couples/families, near beaches, nature walks
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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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!
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
Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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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.
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
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 3
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Enchanting Harbor Views - Historic Bradley Wharf Bearskin Neck
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
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Newly Renovated, Luxury Downtown Location. Walk To Everything. Two Paking Spaces
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 3
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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.
Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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Cape Ann, Annisquam panoramic ocean views from every room.
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 11
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'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
Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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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
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 9
Match: Sleeps
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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
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.
Holiday Rental House
6 bedrooms
5 bathrooms
Sleeps 14
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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
Holiday Rental House
6 bedrooms
6 bathrooms
Sleeps 12
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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
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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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
Holiday Rental House
6 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Charming year round cottage - Pet Friendly with Wi-Fi
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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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.
Holiday Rental House
9 bedrooms
5 bathrooms
Sleeps 9
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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
Holiday Rental House
8 bedrooms
7 bathrooms
Sleeps 13
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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
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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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.
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
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Fabulous fully furnished vacation home between Good Harbor Beach and Long Beach!
Condo/Apartment
3 bedrooms
3 bathrooms
Sleeps 10
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Showing results 1-50 of 340
Frequently Asked Questions about Cape Ann
- Yes, here are some popular vacation rentals in Cape Ann that have a pool:
- GLORIOUS OCEAN VIEWS FROM LOBLOLLY COVE - DECK - SEASIDE PATH TO BEACH AND TOWN
- GULLY POINT AT THE SEAWARD EXUDES CLASSIC COASTAL CHARM
- LOVER'S COVE AT THE SEAWARD WITH OCEAN VIEWS & SEASIDE PATH TO BEACH &TOWN
- Yes, here are some popular vacation rentals in Cape Ann that have internet access:
- GLORIOUS OCEAN VIEWS FROM LOBLOLLY COVE - DECK - SEASIDE PATH TO BEACH AND TOWN
- GULLY POINT AT THE SEAWARD EXUDES CLASSIC COASTAL CHARM
- LOVER'S COVE AT THE SEAWARD WITH OCEAN VIEWS & SEASIDE PATH TO BEACH &TOWN
- The best pet friendly rentals in Cape Ann are:
- GLORIOUS OCEAN VIEWS FROM LOBLOLLY COVE - DECK - SEASIDE PATH TO BEACH AND TOWN
- GULLY POINT AT THE SEAWARD EXUDES CLASSIC COASTAL CHARM
- LOVER'S COVE AT THE SEAWARD WITH OCEAN VIEWS & SEASIDE PATH TO BEACH &TOWN
- Some of the most popular kid friendly rentals in Cape Ann are:
- GLORIOUS OCEAN VIEWS FROM LOBLOLLY COVE - DECK - SEASIDE PATH TO BEACH AND TOWN
- GULLY POINT AT THE SEAWARD EXUDES CLASSIC COASTAL CHARM
- LOVER'S COVE AT THE SEAWARD WITH OCEAN VIEWS & SEASIDE PATH TO BEACH &TOWN