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Cape Ann Vacation Rentals

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Bedrooms

Bathrooms

Amenities

Suitability

Property type

Distinctive Features

Distance from

5 km
359 rentals in Cape Ann.
Coastal, Cute & Cozy|Close to Everything, vacation rental in Cape Ann
Coastal, Cute & Cozy|Close to Everything, vacation rental in Cape Ann
Coastal, Cute & Cozy|Close to Everything, vacation rental in Cape Ann

Coastal, Cute & Cozy|Close to Everything

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Dog Friendly Home - Less Than 1/2 Mile Walk or Drive to Beaches & Shops!, vacation rental in Cape Ann
Dog Friendly Home - Less Than 1/2 Mile Walk or Drive to Beaches & Shops!, vacation rental in Cape Ann
Dog Friendly Home - Less Than 1/2 Mile Walk or Drive to Beaches & Shops!, vacation rental in Cape Ann

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

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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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
Match: Sleeps
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Oceanview Kingsize South End Studio (NO FINAL CLEANING FEE), vacation rental in Cape Ann
Oceanview Kingsize South End Studio (NO FINAL CLEANING FEE), vacation rental in Cape Ann
Oceanview Kingsize South End Studio (NO FINAL CLEANING FEE), vacation 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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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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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
Match: Sleeps
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Elegant Italian Villa On The Scenic Coast of New England, vacation rental in Cape Ann
Elegant Italian Villa On The Scenic Coast of New England, vacation rental in Cape Ann
Elegant Italian Villa On The Scenic Coast of New England, vacation 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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Steps to Downtown Gloucester & A/C throughout the house, vacation rental in Cape Ann
Steps to Downtown Gloucester & A/C throughout the house, vacation rental in Cape Ann
Steps to Downtown Gloucester & A/C throughout the house, vacation rental in Cape Ann

Steps to Downtown Gloucester & A/C throughout the house

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Discover Your Perfect Cape Ann Getaway - A Charming Bayview Retreat, vacation rental in Cape Ann
Discover Your Perfect Cape Ann Getaway - A Charming Bayview Retreat, vacation rental in Cape Ann
Discover Your Perfect Cape Ann Getaway - A Charming Bayview Retreat, vacation rental in Cape Ann

Discover Your Perfect Cape Ann Getaway - A Charming Bayview Retreat

Condo/Apartment
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Perfect Rockport Downtown Vacation Destination, vacation rental in Cape Ann
Perfect Rockport Downtown Vacation Destination, vacation rental in Cape Ann
Perfect Rockport Downtown Vacation Destination, vacation rental in Cape Ann

Perfect Rockport Downtown Vacation Destination

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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SEASIDE GARDENS AFFORDABLE GUEST ROOM(S)  IN VILLAGE BY BEACH, WALK EVERYWHERE!, vacation rental in Cape Ann
SEASIDE GARDENS AFFORDABLE GUEST ROOM(S)  IN VILLAGE BY BEACH, WALK EVERYWHERE!, vacation rental in Cape Ann
SEASIDE GARDENS AFFORDABLE GUEST ROOM(S)  IN VILLAGE BY BEACH, WALK EVERYWHERE!, vacation rental in Cape Ann

SEASIDE GARDENS AFFORDABLE GUEST ROOM(S) IN VILLAGE BY BEACH, WALK EVERYWHERE!

Private Room
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Payment Protection
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
Match: Sleeps
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Enjoy the ambiance of a New England Seaside Getaway, without the crowds!, vacation rental in Cape Ann
Enjoy the ambiance of a New England Seaside Getaway, without the crowds!, vacation rental in Cape Ann
Enjoy the ambiance of a New England Seaside Getaway, without the crowds!, vacation rental in Cape Ann

Enjoy the ambiance of a New England Seaside Getaway, without the crowds!

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
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Gladview Rockport Apt #gladview#thacher, vacation rental in Cape Ann
Gladview Rockport Apt #gladview#thacher, vacation rental in Cape Ann
Gladview Rockport Apt #gladview#thacher, vacation rental in Cape Ann

Gladview Rockport Apt #gladview#thacher

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Quaint getaway with full kitchen and lush yard - close to the beach and downtown, vacation rental in Cape Ann
Quaint getaway with full kitchen and lush yard - close to the beach and downtown, vacation rental in Cape Ann
Quaint getaway with full kitchen and lush yard - close to the beach and downtown, vacation rental in Cape Ann

Quaint getaway with full kitchen and lush yard - close to the beach and downtown

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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"Rockport Sail Loft: 2 Bed/1 Bath Oceanfront Haven, vacation rental in Cape Ann
"Rockport Sail Loft: 2 Bed/1 Bath Oceanfront Haven, vacation rental in Cape Ann
"Rockport Sail Loft: 2 Bed/1 Bath Oceanfront Haven, vacation rental in Cape Ann

"Rockport Sail Loft: 2 Bed/1 Bath Oceanfront Haven

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Dog-Friendly, Waterfront Home with High-Speed WiFi, W/D, & Two Decks, vacation rental in Cape Ann
Dog-Friendly, Waterfront Home with High-Speed WiFi, W/D, & Two Decks, vacation rental in Cape Ann
Dog-Friendly, Waterfront Home with High-Speed WiFi, W/D, & Two Decks, vacation rental in Cape Ann

Dog-Friendly, Waterfront Home with High-Speed WiFi, W/D, & Two Decks

Condo/Apartment
0 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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The Duval House, vacation rental in Cape Ann
The Duval House, vacation rental in Cape Ann
The Duval House, vacation rental in Cape Ann

The Duval House

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 6
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
More info
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Ocean views just steps to Back Beach, Front Beach, and downtown Rockport, vacation rental in Cape Ann
Ocean views just steps to Back Beach, Front Beach, and downtown Rockport, vacation rental in Cape Ann
Ocean views just steps to Back Beach, Front Beach, and downtown Rockport, vacation 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, vacation rental in Cape Ann
Charming 3 bdrm Apartment in Heart of Rockport-Bearskin Neck-Walk to Beach -WiFi, vacation rental in Cape Ann
Charming 3 bdrm Apartment in Heart of Rockport-Bearskin Neck-Walk to Beach -WiFi, vacation 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
More info
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Newly Renovated Family Getaway, Walk to Harbor, Beach, and Downtown, vacation rental in Cape Ann
Newly Renovated Family Getaway, Walk to Harbor, Beach, and Downtown, vacation rental in Cape Ann
Newly Renovated Family Getaway, Walk to Harbor, Beach, and Downtown, vacation rental in Cape Ann

Newly Renovated Family Getaway, Walk to Harbor, Beach, and Downtown

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
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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 15
Match: Sleeps
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Luxury Downtown Renovated Carraige House. Walk To Everything. Two Paking Spaces, vacation rental in Cape Ann
Luxury Downtown Renovated Carraige House. Walk To Everything. Two Paking Spaces, vacation rental in Cape Ann
Luxury Downtown Renovated Carraige House. Walk To Everything. Two Paking Spaces, vacation rental in Cape Ann

Luxury Downtown Renovated Carraige House. Walk To Everything. Two Paking Spaces

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Beach house only steps to beautiful Long Beach!, vacation rental in Cape Ann
Beach house only steps to beautiful Long Beach!, vacation rental in Cape Ann
Beach house only steps to beautiful Long Beach!, vacation rental in Cape Ann

Beach house only steps to beautiful Long Beach!

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
More info
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NEW 2BR/2Bath · 2 floors · 2 King Beds · Private Parking · Downtown Rockport, vacation rental in Cape Ann
NEW 2BR/2Bath · 2 floors · 2 King Beds · Private Parking · Downtown Rockport, vacation rental in Cape Ann
NEW 2BR/2Bath · 2 floors · 2 King Beds · Private Parking · Downtown Rockport, vacation rental in Cape Ann

NEW 2BR/2Bath · 2 floors · 2 King Beds · Private Parking · Downtown Rockport

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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� Cancellation! -> Halloween in Rockport at TWT- Open �, vacation rental in Cape Ann
� Cancellation! -> Halloween in Rockport at TWT- Open �, vacation rental in Cape Ann
� Cancellation! -> Halloween in Rockport at TWT- Open �, vacation rental in Cape Ann

� Cancellation! -> Halloween in Rockport at TWT- Open �

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Sweet cozy house located in Pigeon Cove, vacation rental in Cape Ann
Sweet cozy house located in Pigeon Cove, vacation rental in Cape Ann
Sweet cozy house located in Pigeon Cove, vacation rental in Cape Ann

Sweet cozy house located in Pigeon Cove

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Cozy spacious home - Walk to both Good Harbor Beach and Long Beach, & Rockport, vacation rental in Cape Ann
Cozy spacious home - Walk to both Good Harbor Beach and Long Beach, & Rockport, vacation rental in Cape Ann
Cozy spacious home - Walk to both Good Harbor Beach and Long Beach, & Rockport, vacation rental in Cape Ann

Cozy spacious home - Walk to both Good Harbor Beach and Long Beach, & Rockport

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

Luxury 1900's romantic retreat steps from the beach

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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HEART OF HISTORICAL ROCKPORT  with Reserved Parking, vacation rental in Cape Ann
HEART OF HISTORICAL ROCKPORT  with Reserved Parking, vacation rental in Cape Ann
HEART OF HISTORICAL ROCKPORT  with Reserved Parking, vacation rental in Cape Ann

HEART OF HISTORICAL ROCKPORT with Reserved Parking

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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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
Match: Sleeps
More info
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Relaxing Rivers Edge Main Street Retreat, vacation rental in Cape Ann
Relaxing Rivers Edge Main Street Retreat, vacation rental in Cape Ann
Relaxing Rivers Edge Main Street Retreat, vacation rental in Cape Ann

Relaxing Rivers Edge Main Street Retreat

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Steps to Wingaersheek's Private 1.5 Mile White Dune Beach, vacation rental in Cape Ann
Steps to Wingaersheek's Private 1.5 Mile White Dune Beach, vacation rental in Cape Ann
Steps to Wingaersheek's Private 1.5 Mile White Dune Beach, vacation rental in Cape Ann

Steps to Wingaersheek's Private 1.5 Mile White Dune Beach

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Holbrook House: Charming Rockport Village Cottage, Walk To Everything!, vacation rental in Cape Ann
Holbrook House: Charming Rockport Village Cottage, Walk To Everything!, vacation rental in Cape Ann
Holbrook House: Charming Rockport Village Cottage, Walk To Everything!, vacation rental in Cape Ann

Holbrook House: Charming Rockport Village Cottage, Walk To Everything!

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Classic charmer near the coast with with a firepit, outdoor shower, & beach gear, vacation rental in Cape Ann
Classic charmer near the coast with with a firepit, outdoor shower, & beach gear, vacation rental in Cape Ann
Classic charmer near the coast with with a firepit, outdoor shower, & beach gear, vacation rental in Cape Ann

Classic charmer near the coast with with a firepit, outdoor shower, & beach gear

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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NEW 1BR with Private Deck + Ocean Views · King Bed · Private Parking, vacation rental in Cape Ann
NEW 1BR with Private Deck + Ocean Views · King Bed · Private Parking, vacation rental in Cape Ann
NEW 1BR with Private Deck + Ocean Views · King Bed · Private Parking, vacation rental in Cape Ann

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

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Quaint Two-bedroom House with Ocean Views in the South End of Rockport, vacation rental in Cape Ann
Quaint Two-bedroom House with Ocean Views in the South End of Rockport, vacation rental in Cape Ann
Quaint Two-bedroom House with Ocean Views in the South End of Rockport, vacation rental in Cape Ann

Quaint Two-bedroom House with Ocean Views in the South End of Rockport

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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WALK TO BEACH! Convenient location! Beautifully updated! Sept-Dec Availability!, vacation rental in Cape Ann
WALK TO BEACH! Convenient location! Beautifully updated! Sept-Dec Availability!, vacation rental in Cape Ann
WALK TO BEACH! Convenient location! Beautifully updated! Sept-Dec Availability!, vacation rental in Cape Ann

WALK TO BEACH! Convenient location! Beautifully updated! Sept-Dec Availability!

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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NEW 3BR/2 BA Harborside Home · Backyard+Grill · Ocean Views, vacation rental in Cape Ann
NEW 3BR/2 BA Harborside Home · Backyard+Grill · Ocean Views, vacation rental in Cape Ann
NEW 3BR/2 BA Harborside Home · Backyard+Grill · Ocean Views, vacation rental in Cape Ann

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

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Stunning, Classic Home with Central AC, WiFi, Outdoor Patio, and Full Kitchen, vacation rental in Cape Ann
Stunning, Classic Home with Central AC, WiFi, Outdoor Patio, and Full Kitchen, vacation rental in Cape Ann
Stunning, Classic Home with Central AC, WiFi, Outdoor Patio, and Full Kitchen, vacation rental in Cape Ann

Stunning, Classic Home with Central AC, WiFi, Outdoor Patio, and Full Kitchen

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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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 8
Match: Sleeps
More info
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First Period Colonial Lodging in Gloucester MA, vacation rental in Cape Ann
First Period Colonial Lodging in Gloucester MA, vacation rental in Cape Ann
First Period Colonial Lodging in Gloucester MA, vacation rental in Cape Ann

First Period Colonial Lodging in Gloucester MA

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Loft on Main - DWTN, Beach, PVT Deck, Coffee Bar, vacation rental in Cape Ann
Loft on Main - DWTN, Beach, PVT Deck, Coffee Bar, vacation rental in Cape Ann
Loft on Main - DWTN, Beach, PVT Deck, Coffee Bar, vacation rental in Cape Ann

Loft on Main - DWTN, Beach, PVT Deck, Coffee Bar

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Oceanfront 4 BR/2 Bath Long Beach Vacation Home - Grill, Outdoor shower, AC, vacation rental in Cape Ann
Oceanfront 4 BR/2 Bath Long Beach Vacation Home - Grill, Outdoor shower, AC, vacation rental in Cape Ann
Oceanfront 4 BR/2 Bath Long Beach Vacation Home - Grill, Outdoor shower, AC, vacation 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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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
6 bathrooms
Sleeps 13
Match: Sleeps
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Quaint Seaside Village Ground floor Studio Steps  From Beach WITH PARKING, vacation rental in Cape Ann
Quaint Seaside Village Ground floor Studio Steps  From Beach WITH PARKING, vacation rental in Cape Ann
Quaint Seaside Village Ground floor Studio Steps  From Beach WITH PARKING, vacation rental in Cape Ann

Quaint Seaside Village Ground floor Studio Steps From Beach WITH PARKING

Private Room
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Payment Protection
Newly Renovated One Bedroom Cottage - Walk to Long Beach/Good Harbor Beach, vacation rental in Cape Ann
Newly Renovated One Bedroom Cottage - Walk to Long Beach/Good Harbor Beach, vacation rental in Cape Ann
Newly Renovated One Bedroom Cottage - Walk to Long Beach/Good Harbor Beach, vacation rental in Cape Ann

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

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Showing results 1-50 of 359
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