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Cape Ann Holiday Rentals

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145 rentals in Cape Ann.
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Directly on Long Beach Rockport MA, holiday rental in Cape Ann

Directly on Long Beach Rockport MA

4 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
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Enchanting Harbor Views - Historic Bradley Wharf Bearskin Neck, holiday rental in Cape Ann

Enchanting Harbor Views - Historic Bradley Wharf Bearskin Neck

1 bedroom
1 bathroom
Sleeps 4
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Good Harbor Beach House, holiday rental in Cape Ann

Good Harbor Beach House

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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On the Cove - Beautiful Apartment Right on Lanes Cove, holiday rental in Cape Ann

On the Cove - Beautiful Apartment Right on Lanes Cove

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Willow House - Garden Setting, Ocean View, Steps to Rocky Neck!, holiday rental in Cape Ann

Willow House - Garden Setting, Ocean View, Steps to Rocky Neck!

1 bedroom
1 bathroom
Sleeps 4
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Quality Accommodations in Quiet Seaside Village, holiday rental in Cape Ann

Quality Accommodations in Quiet Seaside Village

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Newly Renovated!! Beautiful 3 bed home...steps from beach!, holiday rental in Cape Ann

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

3 bedrooms
2 bathrooms
Sleeps 8
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Beautiful Oceanfront Home in Estate Setting in Gloucester, holiday rental in Cape Ann

Beautiful Oceanfront Home in Estate Setting in Gloucester

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

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

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Featured on HGTV's Beach Hunters, holiday rental in Cape Ann

Featured on HGTV's Beach Hunters

5 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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BRAND NEW3 Bedroom On Lobster Cove, Direct Waterfront, Views And Access, w/kayak, holiday rental in Cape Ann

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

3 bedrooms
2 bathrooms
Sleeps 6
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Perfect Good Harbor Beach vacation home for large and/or extended family getaway, holiday rental in Cape Ann

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

5 bedrooms
6 bathrooms
Sleeps 16
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

4 bedrooms
2 bathrooms
Sleeps 6
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Walk Over The Foot Bridge And Onto Long Beach!, holiday rental in Cape Ann

Walk Over The Foot Bridge And Onto Long Beach!

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Renovated Water Front 2BR - amazing View - Walk to Beach, Shps, Restaurant Train, holiday rental in Cape Ann

Renovated Water Front 2BR - amazing View - Walk to Beach, Shps, Restaurant Train

2 bedrooms
2 bathrooms
Sleeps 5
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Perfect apartment for a single or couple., holiday rental in Cape Ann

Perfect apartment for a single or couple.

0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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Luxury Home in the Heart of Rockport, holiday rental in Cape Ann

Luxury Home in the Heart of Rockport

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Gloucester/Annisquam Getaway: Beach-Biking-Nature Walks-Kayaking, holiday rental in Cape Ann

Gloucester/Annisquam Getaway: Beach-Biking-Nature Walks-Kayaking

3 bedrooms
1 bathroom
Sleeps 6
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Long Beach-Gloucester-1 minute walk to Beach Lovely setting & big yard. Sleeps 6, holiday rental in Cape Ann

Long Beach-Gloucester-1 minute walk to Beach Lovely setting & big yard. Sleeps 6

3 bedrooms
2 bathrooms
Sleeps 6
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Walk to Good Harbor Beach, pet friendly, family beach home, holiday rental in Cape Ann

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

3 bedrooms
2 bathrooms
Sleeps 8
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Gladview Rockport Apt #gladview#thacher, holiday rental in Cape Ann

Gladview Rockport Apt #gladview#thacher

1 bedroom
1 bathroom
Sleeps 2
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Romantic SUMMERWIND COTTAGE- Scenic Harbor View, holiday rental in Cape Ann

Romantic SUMMERWIND COTTAGE- Scenic Harbor View

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Renovated Historic Seaside House on Magnolia Point, Gloucester – Walk to Beach, holiday rental in Cape Ann

Renovated Historic Seaside House on Magnolia Point, Gloucester – Walk to Beach

5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Newly Renovated One Bedroom Cottage - Walk to Long Beach/Good Harbor Beach, holiday rental in Cape Ann

Newly Renovated One Bedroom Cottage - Walk to Long Beach/Good Harbor Beach

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Charming year round cottage - Pet Friendly with Wi-Fi, holiday rental in Cape Ann

Charming year round cottage - Pet Friendly with Wi-Fi

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Picturesque Rockport Queen Anne Cottage, holiday rental in Cape Ann

Picturesque Rockport Queen Anne Cottage

3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Breezy home w/patio -dogs OK, walk to beach, harbor & restaurants, holiday rental in Cape Ann

Breezy home w/patio -dogs OK, walk to beach, harbor & restaurants

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Walk to downtown Gloucester & Pavilion Beach!, holiday rental in Cape Ann

Walk to downtown Gloucester & Pavilion Beach!

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Quaint getaway w/ a full kitchen & lush yard - close to the beach & downtown, holiday rental in Cape Ann

Quaint getaway w/ a full kitchen & lush yard - close to the beach & downtown

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Ocean Front- 2 BR House-Directly on the ocean ! Book now !, holiday rental in Cape Ann

Ocean Front- 2 BR House-Directly on the ocean ! Book now !

2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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Ocean Front Cottage on Scenic Long Beach, holiday rental in Cape Ann

Ocean Front Cottage on Scenic Long Beach

4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Modern beach home w/ deck, central AC, & free WiFi, steps from the ocean, holiday rental in Cape Ann

Modern beach home w/ deck, central AC, & free WiFi, steps from the ocean

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Quaint Ocean View Apartment exudes Classic Coastal Charm, holiday rental in Cape Ann

Quaint Ocean View Apartment exudes Classic Coastal Charm

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Charming Studio Cottage On Quiet Lane, holiday rental in Cape Ann

Charming Studio Cottage On Quiet Lane

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Create a Memorable Family Vacation Here!, holiday rental in Cape Ann

Create a Memorable Family Vacation Here!

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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STUNNING OCEAN VIEWS FROM OUR 2 BEDROOM COTTAGE, holiday rental in Cape Ann

STUNNING OCEAN VIEWS FROM OUR 2 BEDROOM COTTAGE

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Tranquil VIEWS - HEART OF HISTORICAL ROCKPORT  with Reserved Parking, holiday rental in Cape Ann

Tranquil VIEWS - HEART OF HISTORICAL ROCKPORT with Reserved Parking

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Fabulous fully furnished vacation home between Good Harbor Beach and Long Beach!, holiday rental in Cape Ann

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

3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Beautiful Rockport, Steps to Front Beach, Restaurants, Shopping, holiday rental in Cape Ann

Beautiful Rockport, Steps to Front Beach, Restaurants, Shopping

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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New listing! Dog-friendly apartment in a prime location - walk to town beaches!, holiday rental in Cape Ann

New listing! Dog-friendly apartment in a prime location - walk to town beaches!

1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Private hideaway near the beach and town center., holiday rental in Cape Ann

Private hideaway near the beach and town center.

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Quaint Seaside Village Ground floor Studio Steps  From Beach WITH PARKING, holiday rental in Cape Ann

Quaint Seaside Village Ground floor Studio Steps From Beach WITH PARKING

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Beautiful vacation home across street from 2 beaches, holiday rental in Cape Ann

Beautiful vacation home across street from 2 beaches

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Beach Bungalow: The perfect getaway to two of Rockport's finest beaches!, holiday rental in Cape Ann

Beach Bungalow: The perfect getaway to two of Rockport's finest beaches!

2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Cedar Ledge Annisquam: Ocean views & traditional New England charm., holiday rental in Cape Ann

Cedar Ledge Annisquam: Ocean views & traditional New England charm.

6 bedrooms
2 bathrooms
Sleeps 14
Match: Sleeps
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Beach &  King Street Inn / Beach House Rental, holiday rental in Cape Ann

Beach & King Street Inn / Beach House Rental

6 bedrooms
5 bathrooms
Sleeps 14
Match: Sleeps
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The View: A classic New England cottage with panoramic ocean views., holiday rental in Cape Ann

The View: A classic New England cottage with panoramic ocean views.

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Stunning SUNSET STUDIO w/Scenic Harbor View, holiday rental in Cape Ann

Stunning SUNSET STUDIO w/Scenic Harbor View

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Stunning classic family home that has central AC & outdoor patio w/ kitchen & TV, holiday rental in Cape Ann

Stunning classic family home that has central AC & outdoor patio w/ kitchen & TV

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Admire ocean views from the deck of this gorgeous, family-friendly getaway, holiday rental in Cape Ann

Admire ocean views from the deck of this gorgeous, family-friendly getaway

3 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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