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Cape Ann Vacation Rentals

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Bedrooms

Bathrooms

Amenities

Suitability

Property type

Distinctive Features

Distance from

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

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

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Good Harbor Beach House - walk to beach, close to restaurants and shopping!, vacation rental in Cape Ann
Good Harbor Beach House - walk to beach, close to restaurants and shopping!, vacation rental in Cape Ann
Good Harbor Beach House - walk to beach, close to restaurants and shopping!, vacation rental in Cape Ann

Good Harbor Beach House - walk to beach, close to restaurants and shopping!

Rental Home
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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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

Rental Home
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

Rental Home
10 bedrooms
6 bathrooms
Sleeps 18
Match: Sleeps
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Single Level Home - Steps to Downtown Gloucester & A/C throughout, vacation rental in Cape Ann
Single Level Home - Steps to Downtown Gloucester & A/C throughout, vacation rental in Cape Ann
Single Level Home - Steps to Downtown Gloucester & A/C throughout, vacation rental in Cape Ann

Single Level Home - Steps to Downtown Gloucester & A/C throughout

Rental Home
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
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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

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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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

Rental Home
5 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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"Rocky Neck Hideaway" on Wonson Cove, Rocky Neck - Gloucester, vacation rental in Cape Ann
"Rocky Neck Hideaway" on Wonson Cove, Rocky Neck - Gloucester, vacation rental in Cape Ann
"Rocky Neck Hideaway" on Wonson Cove, Rocky Neck - Gloucester, vacation rental in Cape Ann

"Rocky Neck Hideaway" on Wonson Cove, Rocky Neck - Gloucester

Rental Home
2 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
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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

Rental Home
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
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Dog-Friendly, Waterfront Home with Washer and dryer & Two Decks, vacation rental in Cape Ann
Dog-Friendly, Waterfront Home with Washer and dryer & Two Decks, vacation rental in Cape Ann
Dog-Friendly, Waterfront Home with Washer and dryer & Two Decks, vacation rental in Cape Ann

Dog-Friendly, Waterfront Home with Washer and dryer & Two Decks

Rental Home
1 bedroom
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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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

Rental Home
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
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NEWLY Renovated Luxury Home, Walk To Town & Beach. 5 Bedroom, 3.5 Bath + Office., vacation rental in Cape Ann
NEWLY Renovated Luxury Home, Walk To Town & Beach. 5 Bedroom, 3.5 Bath + Office., vacation rental in Cape Ann
NEWLY Renovated Luxury Home, Walk To Town & Beach. 5 Bedroom, 3.5 Bath + Office., vacation rental in Cape Ann

NEWLY Renovated Luxury Home, Walk To Town & Beach. 5 Bedroom, 3.5 Bath + Office.

Rental Home
5 bedrooms
4 bathrooms
Sleeps 10
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

Rental Home
6 bedrooms
3 bathrooms
Sleeps 15
Match: Sleeps
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Experience Rockport charm, walk to the beach ,restaurants & Shalin Liu Center, vacation rental in Cape Ann
Experience Rockport charm, walk to the beach ,restaurants & Shalin Liu Center, vacation rental in Cape Ann
Experience Rockport charm, walk to the beach ,restaurants & Shalin Liu Center, vacation rental in Cape Ann

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

Rental Home
3 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Adorable Beach house with lots of outdoor space and steps to Long Beach!, vacation rental in Cape Ann
Adorable Beach house with lots of outdoor space and steps to Long Beach!, vacation rental in Cape Ann
Adorable Beach house with lots of outdoor space and steps to Long Beach!, vacation rental in Cape Ann

Adorable Beach house with lots of outdoor space and steps to Long Beach!

Rental Home
2 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
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2 Bd/2 Bth with  ·King bed ·2 floors · Private Parking · Downtown Rockport, vacation rental in Cape Ann
2 Bd/2 Bth with  ·King bed ·2 floors · Private Parking · Downtown Rockport, vacation rental in Cape Ann
2 Bd/2 Bth with  ·King bed ·2 floors · Private Parking · Downtown Rockport, vacation rental in Cape Ann

2 Bd/2 Bth with ·King bed ·2 floors · Private Parking · Downtown Rockport

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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End of an Era: limited days between now and January 10th - Then POOF!, vacation rental in Cape Ann
End of an Era: limited days between now and January 10th - Then POOF!, vacation rental in Cape Ann
End of an Era: limited days between now and January 10th - Then POOF!, vacation rental in Cape Ann

End of an Era: limited days between now and January 10th - Then POOF!

Rental Home
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

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Wonderful home sitting right between two terrific beaches!, vacation rental in Cape Ann
Wonderful home sitting right between two terrific beaches!, vacation rental in Cape Ann
Wonderful home sitting right between two terrific beaches!, vacation rental in Cape Ann

Wonderful home sitting right between two terrific beaches!

Rental Home
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

Rental Home
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

Rental Home
4 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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Luxury 1900's romantic retreat steps from the beach - King Suite!, vacation rental in Cape Ann
Luxury 1900's romantic retreat steps from the beach - King Suite!, vacation rental in Cape Ann
Luxury 1900's romantic retreat steps from the beach - King Suite!, vacation rental in Cape Ann

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

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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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
2 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
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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
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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

Rental Home
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!

Rental Home
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

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

Rental Home
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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WALK TO BEACH! Conveniently located! Booking for June & Sept 2025!, vacation rental in Cape Ann
WALK TO BEACH! Conveniently located! Booking for June & Sept 2025!, vacation rental in Cape Ann
WALK TO BEACH! Conveniently located! Booking for June & Sept 2025!, vacation rental in Cape Ann

WALK TO BEACH! Conveniently located! Booking for June & Sept 2025!

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

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

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
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)

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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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

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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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

Rental Home
4 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Grafton Estate: Ultimate Luxury With Private Beach, vacation rental in Cape Ann
Grafton Estate: Ultimate Luxury With Private Beach, vacation rental in Cape Ann
Grafton Estate: Ultimate Luxury With Private Beach, vacation rental in Cape Ann

Grafton Estate: Ultimate Luxury With Private Beach

Rental Home
8 bedrooms
7 bathrooms
Sleeps 13
Match: Sleeps
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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

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Coastal retreat steps to the beach with smart TVs, desk, grill, children's items, vacation rental in Cape Ann
Coastal retreat steps to the beach with smart TVs, desk, grill, children's items, vacation rental in Cape Ann
Coastal retreat steps to the beach with smart TVs, desk, grill, children's items, vacation rental in Cape Ann

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

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Beach dreaming??, vacation rental in Cape Ann
Beach dreaming??, vacation rental in Cape Ann
Beach dreaming??, vacation rental in Cape Ann

Beach dreaming??

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Sweeping saltmarsh & river views, birdwatching, great restaurants, cozy peace., vacation rental in Cape Ann
Sweeping saltmarsh & river views, birdwatching, great restaurants, cozy peace., vacation rental in Cape Ann
Sweeping saltmarsh & river views, birdwatching, great restaurants, cozy peace., vacation rental in Cape Ann

Sweeping saltmarsh & river views, birdwatching, great restaurants, cozy peace.

Rental Home
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Long Beach Suites: Ocean Views, Book 2025 Already!, vacation rental in Cape Ann
Long Beach Suites: Ocean Views, Book 2025 Already!, vacation rental in Cape Ann
Long Beach Suites: Ocean Views, Book 2025 Already!, vacation rental in Cape Ann

Long Beach Suites: Ocean Views, Book 2025 Already!

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Majestic summer rental, vacation rental in Cape Ann
Majestic summer rental, vacation rental in Cape Ann
Majestic summer rental, vacation rental in Cape Ann

Majestic summer rental

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Stunning Views from Beachfront House in Manchester-by-the-Sea!, vacation rental in Cape Ann
Stunning Views from Beachfront House in Manchester-by-the-Sea!, vacation rental in Cape Ann
Stunning Views from Beachfront House in Manchester-by-the-Sea!, vacation rental in Cape Ann

Stunning Views from Beachfront House in Manchester-by-the-Sea!

Rental Home
5 bedrooms
3 bathrooms
Sleeps 11
Match: Sleeps
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