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Vacation rentals in Rockport

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

Nov 17 – 20, 2026

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)

$769.69 USD total for 3 nights

Nov 17 – 20, 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

5(11 reviews)

$723.01 USD total for 3 nights

Nov 17 – 20, 2026

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

4.83(160 reviews)

$769.69 USD total for 3 nights

Nov 21 – 24, 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(17 reviews)

$552.00 USD total for 3 nights

Nov 19 – 22, 2026

Calder 2

3 bedrooms·1 bath

Gloucester • Massachusetts

Calder 1

2 bedrooms·1 bath

Gloucester • Massachusetts

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(5 reviews)

$624.35 USD total for 3 nights

Feb 28 – Mar 3, 2027

Living room with Open Beam ceiling

The most comfortable chair

Large Smart TV & Wifi

Sea Bird Suite

1 bedroom·1 bath

Marblehead • Massachusetts

4.88(41 reviews)

$755.05 USD total for 3 nights

Nov 17 – 20, 2026

New flooring (2022)

Vaulted Ceiling

Oceanfront Penthouse Salisbury

5 bedrooms·2 baths

Salisbury • Massachusetts

5(196 reviews)

$1,137.00 USD total for 3 nights

Nov 17 – 20, 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)

$2,010.60 USD total for 3 nights

Jan 1 – 4, 2027

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)

$4,902.45 USD total for 7 nights

May 28 – Jun 4, 2027

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)

$2,731.31 USD total for 7 nights

Jun 4 – 11, 2027

Enchanting Hidden Door Escape

4 bedrooms·2 baths

Stoneham • Massachusetts

$248 – $1,418/ night(excl. fees & taxes)

Modern Three Bedroom Condo - Near Boston

Modern Three Bedroom Condo - Near Boston

Modern Three Bedroom Condo - Near Boston

Modern Three Bedroom Condo - Near Boston

Modern Three Bedroom Condo - Near Boston

Modern Three Bedroom Condo - Near Boston

3 bedrooms·1 bath

Stoneham • Massachusetts

$1,703.57 USD total for 4 nights

Feb 10 – 14, 2027

Casa Castor • Private Room 3

Casa Castor • Private Room 3

Casa Castor • Private Room 3

Casa Castor • Private Room 3

Casa Castor • Private Room 3

Casa Castor • Private Room 3

1 bedroom·1 bath

Chelsea • Massachusetts

$370.80 USD total for 3 nights

Nov 17 – 20, 2026

Casa Castor • Private Room 2

Casa Castor • Private Room 2

Casa Castor • Private Room 2

Casa Castor • Private Room 2

Casa Castor • Private Room 2

Casa Castor • Private Room 2

1 bedroom·1 bath

Chelsea • Massachusetts

$370.80 USD total for 3 nights

Nov 17 – 20, 2026

Casa Castor • Private Room 1

Casa Castor • Private Room 1

Casa Castor • Private Room 1

Casa Castor • Private Room 1

Casa Castor • Private Room 1

Casa Castor • Private Room 1

1 bedroom·1 bath

Chelsea • Massachusetts

$370.80 USD total for 3 nights

Nov 17 – 20, 2026

Casa Castor • Private Room 3

Casa Castor • Private Room 3

Casa Castor • Private Room 3

Casa Castor • Private Room 3

Casa Castor • Private Room 3

Casa Castor • Private Room 3

1 bedroom·1 bath

Chelsea • Massachusetts

$417.15 USD total for 3 nights

Nov 19 – 22, 2026

Bright, cozy bedroom with storage bed and plenty of natural light

Casa Castor • Private Room 2

Casa Castor • Private Room 2

Casa Castor • Private Room 2

Casa Castor • Private Room 2

Casa Castor • Private Room 2

1 bedroom·1 bath

Chelsea • Massachusetts

$417.15 USD total for 3 nights

Nov 19 – 22, 2026

Casa Castor • Private Room 1

Casa Castor • Private Room 1

Casa Castor • Private Room 1

Casa Castor • Private Room 1

Casa Castor • Private Room 1

Casa Castor • Private Room 1

1 bedroom·1 bath

Chelsea • Massachusetts

$417.15 USD total for 3 nights

Nov 19 – 22, 2026

Serene Suite near Logan Intl/MBTA Airport station image 17

We are located on the downstairs floor unit.

Serene Suite near Logan Intl/MBTA Airport station image 2

Serene Suite near Logan Intl/MBTA Airport station image 3

Serene Suite near Logan Intl/MBTA Airport station image 4

Serenity Suite Homes

2 bedrooms·1 bath

Boston • Massachusetts

4.89(144 reviews)

$916.48 USD $870.64 USD total for 3 nights

Feb 1 – 4, 2027