Location

Dates

Guests

Vacation rentals in Rockport, Massachusetts, United States

Anchor's Away @ The Sail Loft!

Living room with dining table

Comfortable chair

View out windows to White Wharf

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

2 bedrooms·1 bath

Rockport • Massachusetts

4.87(143 reviews)

$1,160.10 USD total for 3 nights

Sep 7 – 10, 2026

Bedroom 1 -Queen Bed

The Waterline

2 bedrooms·1 bath

Rockport • Massachusetts

$1,143.95 USD total for 3 nights

Oct 31 – Nov 3, 2026

Free cancellation

Living Room: Bright space with nautical charm, leather couch, and dining for four! Perfect for relaxing!

Living Room: Relax in style with plush seating, vintage decor, and warm natural light!

Views of Bearskin neck and peeks of the Harbor from windows

Living Room: Sunlight dances through windows, inviting relaxation in stylish comfort and charm!

Bedroom 1 -Queen Bed

The Waterline

2 bedrooms·1 bath

Rockport • Massachusetts

5(17 reviews)

$892.98 USD total for 3 nights

Sep 7 – 10, 2026

Sunny 1st floor unit with views

Smart TV in living room for streaming

Leather arm chairs

The Orca

2 bedrooms·1 bath

Rockport • Massachusetts

$1,000.58 USD total for 3 nights

Nov 3 – 6, 2026

Free cancellation

Sunny 1st floor unit with views

Smart TV in living room for streaming

Leather arm chairs

The Orca

2 bedrooms·1 bath

Rockport • Massachusetts

5(9 reviews)

$975.58 USD total for 3 nights

Oct 17 – 20, 2026

Free cancellation

Living room with Plenty of Sunlight

Bedroom 1 with Queen bed

Open Beam Ceilings- Sail Hooks still in Posts for mending sails!

The Captain's Quarters

2 bedrooms·1 bath

Rockport • Massachusetts

4.82(150 reviews)

$151 – $329/ night(excl. fees & taxes)

Living Room: Timber beams and natural light create a vibrant space for relaxation and fun!

Living Room: Bright and airy space with unique decor, perfect for relaxation and coastal views!

Living Room: Timber beams and a blend of vintage charm invite relaxation and great conversations!

Bedroom: Charming retreat illuminated by natural light with rustic beams and delightful decor!

Bar style eating counter overlooking Bearskin beck

The Captain's Quarters

2 bedrooms·1 bath

Rockport • Massachusetts

5(10 reviews)

$822.36 USD total for 3 nights

Sep 7 – 10, 2026

The Crow's Nest

The Crow's Nest

The Crow's Nest

The Crow's Nest

The Crow's Nest

The Crow's Nest

1 bedroom·1 bath

Rockport • Massachusetts

$285/ night(excl. fees & taxes)

Charming Loft Kitchen: Enjoy culinary adventures in a sunlit space with rustic beams and modern flair!

The Crow's Nest

The Crow's Nest

The Crow's Nest

The Crow's Nest

The Crow's Nest

1 bedroom·1 bath

Rockport • Massachusetts

5(5 reviews)

$793.61 USD total for 3 nights

Sep 9 – 12, 2026

our place from the beach

twin beds, back left

House front from yard

Beach Bridge

3 bedrooms·1 bath

Gloucester • Massachusetts

$4,235.00 USD total for 7 nights

Sep 7 – 14, 2026

Bright, Spacious Bedroom

Bright and spacious room, comfy bed.

Cape Ann sunset (up the road at Plum Cove)

Quirky, Bright, Spacious Private Room Near Water

1 bedroom·1 bath

Gloucester • Massachusetts

5(15 reviews)

$159 – $209/ night(excl. fees & taxes)

Living room - sectional couch

Bedroom with airconditioner

Well appointed and comfortable

Beams on ceiling

The Sailor's Retreat

1 bedroom·1 bath

Marblehead • Massachusetts

5(4 reviews)

$905.59 USD total for 3 nights

Sep 8 – 11, 2026

Living room with Open Beam ceiling

The most comfortable chair

Large Smart TV & Wifi

Sea Bird Suite

1 bedroom·1 bath

Marblehead • Massachusetts

4.87(39 reviews)

$732.88 USD total for 3 nights

Sep 8 – 11, 2026

Comfortable leather couch and two captains chairs

Barn Doors open to Bedroom

Lots of Sunlight. Great views of beautiful back yard

Eat In Kitchen dining table

Yachtsman Suite

1 bedroom·1 bath

Marblehead • Massachusetts

4.89(35 reviews)

$732.88 USD total for 3 nights

Sep 8 – 11, 2026

New flooring (2022)

Vaulted Ceiling

Oceanfront Penthouse Salisbury

5 bedrooms·2 baths

Salisbury • Massachusetts

5(182 reviews)

$1,965.00 USD total for 3 nights

Sep 10 – 13, 2026

Sea La Vie - Multifamily Home image 1

Sea La Vie - Multifamily Home image 39

Sea La Vie - Multifamily Home image 2

Sea La Vie - Multifamily Home image 17

Sea La Vie - Multifamily Home image 8

Sea La Vie - Multifamily Home

5 bedrooms·2 baths

Salisbury • Massachusetts

5(10 reviews)

$2,401.55 USD total for 3 nights

Sep 7 – 10, 2026

Fully equipped Kitchen

Welcome to Salisbury Sea Breeze

Sea Breeze Guest Home

Sea Breeze Guest Home

2 bedrooms·1 bath

Salisbury • Massachusetts

5(9 reviews)

$300/ night(excl. fees & taxes)

Bright and comfortable living room featuring a new queen sleeper sofa, wall-mounted TV, and air conditioning—perfect for relaxing after a beach day or enjoying a cozy evening at your Salisbury Beach getaway.

Welcome to Salisbury Sea Breeze

View of the Kitchen Area

Salisbury Sea Breeze Guest Home

2 bedrooms·1 bath

Salisbury • Massachusetts

5(1 review)

$300 – $315/ night(excl. fees & taxes)

Salisbury Sea Breeze Vacation Homes , Ocean Front (On the BEACH)

Your view from the house

Fully Equipped Kitchen

Ocean Side - Master BDR (King size bed)

New Master Bathroom

Salisbury Sea Breeze Vacation Home

3 bedrooms·3 baths

Salisbury • Massachusetts

5(2 reviews)

$4,321.53 USD total for 7 nights

Sep 11 – 18, 2026

Private Beach view

Coastal Charm: Lobster Château

2 bedrooms·2 baths

Swampscott • Massachusetts

$1,190.43 USD total for 3 nights

Sep 7 – 10, 2026

Twin XL Bed|Boston|RM 1

Twin XL Bed|Boston|RM 1

Twin XL Bed|Boston|RM 1

Twin XL Bed|Boston|RM 1

Twin XL Bed|Boston|RM 1

Twin XL Bed|Boston|RM 1

1 bedroom·1 bath

Stoneham • Massachusetts

$405.18 USD total for 3 nights

Sep 19 – 22, 2026

Bedroom on the second floor with a queen bed

Front view of the home

Walk to the kitchen

Wide kitchen shot

Queen Bed |Boston|RM 2

1 bedroom·2 baths

Stoneham • Massachusetts

$76 – $276/ night(excl. fees & taxes)

Queen Bed |Boston|RM 3

Queen Bed |Boston|RM 3

Queen Bed |Boston|RM 3

Queen Bed |Boston|RM 3

Queen Bed |Boston|RM 3

Queen Bed |Boston|RM 3

1 bedroom·1 bath

Stoneham • Massachusetts

$326.82 USD total for 3 nights

Sep 7 – 10, 2026

Enchanting Hidden Door Escape

4 bedrooms·2 baths

Stoneham • Massachusetts

$1,533.50 USD total for 3 nights

Sep 7 – 10, 2026