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Holiday Rentals in Rockport

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169 rentals in Rockport.
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Artist's Studio turned Guest House Sleeps up to 3, holiday rental in Rockport
Artist's Studio turned Guest House Sleeps up to 3, holiday rental in Rockport
Artist's Studio turned Guest House Sleeps up to 3, holiday rental in Rockport

Artist's Studio turned Guest House Sleeps up to 3

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
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'We can't wait to return to Four Winds', holiday rental in Rockport
'We can't wait to return to Four Winds', holiday rental in Rockport
'We can't wait to return to Four Winds', holiday rental in Rockport

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

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Enchanting Harbor Views - Historic Bradley Wharf Bearskin Neck, holiday rental in Rockport
Enchanting Harbor Views - Historic Bradley Wharf Bearskin Neck, holiday rental in Rockport
Enchanting Harbor Views - Historic Bradley Wharf Bearskin Neck, holiday rental in Rockport

Enchanting Harbor Views - Historic Bradley Wharf Bearskin Neck

Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
More info
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Come home to Rockport!, holiday rental in Rockport
Come home to Rockport!, holiday rental in Rockport
Come home to Rockport!, holiday rental in Rockport

Come home to Rockport!

Holiday Rental House
1 bedroom
2 bathrooms
Sleeps 3
Match: Sleeps
More info
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"Absolutely lovely. The cottage, the beach, the town, the owners.", holiday rental in Rockport
"Absolutely lovely. The cottage, the beach, the town, the owners.", holiday rental in Rockport
"Absolutely lovely. The cottage, the beach, the town, the owners.", holiday rental in Rockport

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

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
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Featured on HGTV's Beach Hunters, holiday rental in Rockport
Featured on HGTV's Beach Hunters, holiday rental in Rockport
Featured on HGTV's Beach Hunters, holiday rental in Rockport

Featured on HGTV's Beach Hunters

Holiday Rental House
5 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Newly Renovated, Luxury Downtown Location. Walk To Everything. Two Paking Spaces, holiday rental in Rockport
Newly Renovated, Luxury Downtown Location. Walk To Everything. Two Paking Spaces, holiday rental in Rockport
Newly Renovated, Luxury Downtown Location. Walk To Everything. Two Paking Spaces, holiday rental in Rockport

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

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 3
Match: Sleeps
More info
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Old Garden Beach, holiday rental in Rockport
Old Garden Beach, holiday rental in Rockport
Old Garden Beach, holiday rental in Rockport

Old Garden Beach

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Periwinkle Cottage #1 - OPEN ALL YEAR, walk to everything, parking, wifi, quiet, holiday rental in Rockport
Periwinkle Cottage #1 - OPEN ALL YEAR, walk to everything, parking, wifi, quiet, holiday rental in Rockport
Periwinkle Cottage #1 - OPEN ALL YEAR, walk to everything, parking, wifi, quiet, holiday rental in Rockport

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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Fantastic ocean views and only steps to Long and Cape Hedge Beaches

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Holbrook House: Charming Rockport Village Cottage, Walk To Everything!, holiday rental in Rockport
Holbrook House: Charming Rockport Village Cottage, Walk To Everything!, holiday rental in Rockport
Holbrook House: Charming Rockport Village Cottage, Walk To Everything!, holiday rental in Rockport

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

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Perfect Rockport Vacation Destination, holiday rental in Rockport
Perfect Rockport Vacation Destination, holiday rental in Rockport
Perfect Rockport Vacation Destination, holiday rental in Rockport

Perfect Rockport Vacation Destination

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 3
Match: Sleeps
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Spectacular, luxury waterfront property directly overlooking Sandy Bay., holiday rental in Rockport
Spectacular, luxury waterfront property directly overlooking Sandy Bay., holiday rental in Rockport
Spectacular, luxury waterfront property directly overlooking Sandy Bay., holiday rental in Rockport

Spectacular, luxury waterfront property directly overlooking Sandy Bay.

Holiday Rental House
5 bedrooms
6 bathrooms
Sleeps 12
Match: Sleeps
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Amazing Twin Light Sea Views from Vintage Stonewalled Cottage at Rocky Shores!, holiday rental in Rockport
Amazing Twin Light Sea Views from Vintage Stonewalled Cottage at Rocky Shores!, holiday rental in Rockport
Amazing Twin Light Sea Views from Vintage Stonewalled Cottage at Rocky Shores!, holiday rental in Rockport

Amazing Twin Light Sea Views from Vintage Stonewalled Cottage at Rocky Shores!

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
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Perfect apartment for a single or couple., holiday rental in Rockport
Perfect apartment for a single or couple., holiday rental in Rockport
Perfect apartment for a single or couple., holiday rental in Rockport

Perfect apartment for a single or couple.

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Modern Downtown Penthouse Apartment Overlooking Front Beach, holiday rental in Rockport
Modern Downtown Penthouse Apartment Overlooking Front Beach, holiday rental in Rockport
Modern Downtown Penthouse Apartment Overlooking Front Beach, holiday rental in Rockport

Modern Downtown Penthouse Apartment Overlooking Front Beach

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Brand new! Beautiful home in quiet neighborhood near Old Garden Beach., holiday rental in Rockport
Brand new! Beautiful home in quiet neighborhood near Old Garden Beach., holiday rental in Rockport
Brand new! Beautiful home in quiet neighborhood near Old Garden Beach., holiday rental in Rockport

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

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
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Waterfront House onThe Old Harbor Spectacular Views, holiday rental in Rockport
Waterfront House onThe Old Harbor Spectacular Views, holiday rental in Rockport
Waterfront House onThe Old Harbor Spectacular Views, holiday rental in Rockport

Waterfront House onThe Old Harbor Spectacular Views

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Luxury Home in the Heart of Rockport, holiday rental in Rockport
Luxury Home in the Heart of Rockport, holiday rental in Rockport
Luxury Home in the Heart of Rockport, holiday rental in Rockport

Luxury Home in the Heart of Rockport

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
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Gladview Rockport Apt #gladview#thacher, holiday rental in Rockport
Gladview Rockport Apt #gladview#thacher, holiday rental in Rockport
Gladview Rockport Apt #gladview#thacher, holiday rental in Rockport

Gladview Rockport Apt #gladview#thacher

Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
More info
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Charming 3 bdrm Apartment in Heart of Rockport-Bearskin Neck-Walk to Beach -WiFi, holiday rental in Rockport
Charming 3 bdrm Apartment in Heart of Rockport-Bearskin Neck-Walk to Beach -WiFi, holiday rental in Rockport
Charming 3 bdrm Apartment in Heart of Rockport-Bearskin Neck-Walk to Beach -WiFi, holiday rental in Rockport

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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Picturesque Rockport Queen Anne Cottage, holiday rental in Rockport
Picturesque Rockport Queen Anne Cottage, holiday rental in Rockport
Picturesque Rockport Queen Anne Cottage, holiday rental in Rockport

Picturesque Rockport Queen Anne Cottage

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
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Pet Friendly Rockport Getaway - Walk to town and beach!, holiday rental in Rockport
Pet Friendly Rockport Getaway - Walk to town and beach!, holiday rental in Rockport
Pet Friendly Rockport Getaway - Walk to town and beach!, holiday rental in Rockport

Pet Friendly Rockport Getaway - Walk to town and beach!

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
More info
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Spacious, Comfortable Family Home with Gorgeous Gardens near Ocean and Downtown, holiday rental in Rockport
Spacious, Comfortable Family Home with Gorgeous Gardens near Ocean and Downtown, holiday rental in Rockport
Spacious, Comfortable Family Home with Gorgeous Gardens near Ocean and Downtown, holiday rental in Rockport

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

Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
More info
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Beautiful Rockport, Steps to Front Beach, Restaurants, Shopping, holiday rental in Rockport
Beautiful Rockport, Steps to Front Beach, Restaurants, Shopping, holiday rental in Rockport
Beautiful Rockport, Steps to Front Beach, Restaurants, Shopping, holiday rental in Rockport

Beautiful Rockport, Steps to Front Beach, Restaurants, Shopping

Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Explore Cape Ann Next Year!July 4th week still available; Spring & Fall, holiday rental in Rockport
Explore Cape Ann Next Year!July 4th week still available; Spring & Fall, holiday rental in Rockport
Explore Cape Ann Next Year!July 4th week still available; Spring & Fall, holiday rental in Rockport

Explore Cape Ann Next Year!July 4th week still available; Spring & Fall

Condo/Apartment
3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
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Charming year round cottage - Pet Friendly with Wi-Fi, holiday rental in Rockport
Charming year round cottage - Pet Friendly with Wi-Fi, holiday rental in Rockport
Charming year round cottage - Pet Friendly with Wi-Fi, holiday rental in Rockport

Charming year round cottage - Pet Friendly with Wi-Fi

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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You will love our location and will return for our hospitality!, holiday rental in Rockport
You will love our location and will return for our hospitality!, holiday rental in Rockport
You will love our location and will return for our hospitality!, holiday rental in Rockport

You will love our location and will return for our hospitality!

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
More info
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Tranquil VIEWS - HEART OF HISTORICAL ROCKPORT  with Reserved Parking, holiday rental in Rockport
Tranquil VIEWS - HEART OF HISTORICAL ROCKPORT  with Reserved Parking, holiday rental in Rockport
Tranquil VIEWS - HEART OF HISTORICAL ROCKPORT  with Reserved Parking, holiday rental in Rockport

Tranquil VIEWS - HEART OF HISTORICAL ROCKPORT with Reserved Parking

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Quaint getaway w/ a full kitchen & lush yard - close to the beach & downtown, holiday rental in Rockport
Quaint getaway w/ a full kitchen & lush yard - close to the beach & downtown, holiday rental in Rockport
Quaint getaway w/ a full kitchen & lush yard - close to the beach & downtown, holiday rental in Rockport

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

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Rockport, MA 3 BR 2017 Old Garden Beach Home With Gorgeous Views And Hot Tub, holiday rental in Rockport
Rockport, MA 3 BR 2017 Old Garden Beach Home With Gorgeous Views And Hot Tub, holiday rental in Rockport
Rockport, MA 3 BR 2017 Old Garden Beach Home With Gorgeous Views And Hot Tub, holiday rental in Rockport

Rockport, MA 3 BR 2017 Old Garden Beach Home With Gorgeous Views And Hot Tub

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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Walk Over The Foot Bridge And Onto Long Beach!, holiday rental in Rockport
Walk Over The Foot Bridge And Onto Long Beach!, holiday rental in Rockport
Walk Over The Foot Bridge And Onto Long Beach!, holiday rental in Rockport

Walk Over The Foot Bridge And Onto Long Beach!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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� Book now for Fall & Winter & 2023, or inquire about sooner options�, holiday rental in Rockport
� Book now for Fall & Winter & 2023, or inquire about sooner options�, holiday rental in Rockport
� Book now for Fall & Winter & 2023, or inquire about sooner options�, holiday rental in Rockport

� Book now for Fall & Winter & 2023, or inquire about sooner options�

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
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Peaceful Cottage Retreat, holiday rental in Rockport
Peaceful Cottage Retreat, holiday rental in Rockport
Peaceful Cottage Retreat, holiday rental in Rockport

Peaceful Cottage Retreat

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Ocean views just steps to Back Beach, Front Beach, and downtown Rockport

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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STUNNING OCEAN VIEWS FROM OUR 2 BEDROOM COTTAGE, holiday rental in Rockport
STUNNING OCEAN VIEWS FROM OUR 2 BEDROOM COTTAGE, holiday rental in Rockport
STUNNING OCEAN VIEWS FROM OUR 2 BEDROOM COTTAGE, holiday rental in Rockport

STUNNING OCEAN VIEWS FROM OUR 2 BEDROOM COTTAGE

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Private Pet Friendly hideaway near the beach and town center., holiday rental in Rockport
Private Pet Friendly hideaway near the beach and town center., holiday rental in Rockport
Private Pet Friendly hideaway near the beach and town center., holiday rental in Rockport

Private Pet Friendly hideaway near the beach and town center.

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Spectacular Views...Charming House with Guest House

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
More info
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Charming Pet Friendly Studio Cottage On Quiet Lane, holiday rental in Rockport
Charming Pet Friendly Studio Cottage On Quiet Lane, holiday rental in Rockport
Charming Pet Friendly Studio Cottage On Quiet Lane, holiday rental in Rockport

Charming Pet Friendly Studio Cottage On Quiet Lane

Holiday Rental House
0 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Quaint Seaside Village Ground floor Studio Steps  From Beach WITH PARKING, holiday rental in Rockport
Quaint Seaside Village Ground floor Studio Steps  From Beach WITH PARKING, holiday rental in Rockport
Quaint Seaside Village Ground floor Studio Steps  From Beach WITH PARKING, holiday rental in Rockport

Quaint Seaside Village Ground floor Studio Steps From Beach WITH PARKING

Private Room
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Payment Protection

Ocean Front Cottage on Scenic Long Beach, holiday rental in Rockport
Ocean Front Cottage on Scenic Long Beach, holiday rental in Rockport
Ocean Front Cottage on Scenic Long Beach, holiday rental in Rockport

Ocean Front Cottage on Scenic Long Beach

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
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Payment Protection

Come home to Rockport!, holiday rental in Rockport
Come home to Rockport!, holiday rental in Rockport
Come home to Rockport!, holiday rental in Rockport

Come home to Rockport!

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 5
Match: Sleeps
More info
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Peaceful and magical, full ocean view cottage at Rocky Shores by the sea., holiday rental in Rockport
Peaceful and magical, full ocean view cottage at Rocky Shores by the sea., holiday rental in Rockport
Peaceful and magical, full ocean view cottage at Rocky Shores by the sea., holiday rental in Rockport

Peaceful and magical, full ocean view cottage at Rocky Shores by the sea.

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 3
Match: Sleeps
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Ocean Front- 2 BR House-Directly on the ocean ! Book now !, holiday rental in Rockport
Ocean Front- 2 BR House-Directly on the ocean ! Book now !, holiday rental in Rockport
Ocean Front- 2 BR House-Directly on the ocean ! Book now !, holiday rental in Rockport

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

Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
More info
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New listing! Dog-friendly apartment in a prime location - walk to town beaches!, holiday rental in Rockport
New listing! Dog-friendly apartment in a prime location - walk to town beaches!, holiday rental in Rockport
New listing! Dog-friendly apartment in a prime location - walk to town beaches!, holiday rental in Rockport

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

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
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PERIWINKLE COTTAGE #2 - OPEN ALL YEAR - walk to everything, parking, wifi, quiet, holiday rental in Rockport
PERIWINKLE COTTAGE #2 - OPEN ALL YEAR - walk to everything, parking, wifi, quiet, holiday rental in Rockport
PERIWINKLE COTTAGE #2 - OPEN ALL YEAR - walk to everything, parking, wifi, quiet, holiday rental in Rockport

PERIWINKLE COTTAGE #2 - OPEN ALL YEAR - walk to everything, parking, wifi, quiet

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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The Captains Quarters,2BR Heart of Bearskin Neck, Rockport. Entire apartment, holiday rental in Rockport
The Captains Quarters,2BR Heart of Bearskin Neck, Rockport. Entire apartment, holiday rental in Rockport
The Captains Quarters,2BR Heart of Bearskin Neck, Rockport. Entire apartment, holiday rental in Rockport

The Captains Quarters,2BR Heart of Bearskin Neck, Rockport. Entire apartment

Condo/Apartment
2 bedrooms
3 bathrooms
Sleeps 4
Match: Sleeps
More info
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Quaint Ocean View Apartment exudes Classic Coastal Charm, holiday rental in Rockport
Quaint Ocean View Apartment exudes Classic Coastal Charm, holiday rental in Rockport
Quaint Ocean View Apartment exudes Classic Coastal Charm, holiday rental in Rockport

Quaint Ocean View Apartment exudes Classic Coastal Charm

Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
More info
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Family home – 40 Atlantic Ave., Rockport, MA., holiday rental in Rockport
Family home – 40 Atlantic Ave., Rockport, MA., holiday rental in Rockport
Family home – 40 Atlantic Ave., Rockport, MA., holiday rental in Rockport

Family home – 40 Atlantic Ave., Rockport, MA.

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
More info
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Sweeping, dog-friendly, waterfront home w/ a sun room, ocean views, & fireplaces, holiday rental in Rockport
Sweeping, dog-friendly, waterfront home w/ a sun room, ocean views, & fireplaces, holiday rental in Rockport
Sweeping, dog-friendly, waterfront home w/ a sun room, ocean views, & fireplaces, holiday rental in Rockport

Sweeping, dog-friendly, waterfront home w/ a sun room, ocean views, & fireplaces

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
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