Location

Dates

Guests

Vacation rentals in Gloucester, Massachusetts, United States

Calder 2

3 bedrooms·1 bath

Gloucester • Massachusetts

Calder 1

2 bedrooms·1 bath

Gloucester • Massachusetts

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 totaal voor 7 nachten

8–15 nov 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 totaal voor 3 nachten

12–15 nov 2026

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 totaal voor 3 nachten

8–11 nov 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 totaal voor 3 nachten

8–11 nov 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 totaal voor 3 nachten

8–11 nov 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 totaal voor 3 nachten

8–11 nov 2026

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)

$ 702,64 USD totaal voor 3 nachten

8–11 nov 2026

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 totaal voor 3 nachten

28 feb – 3 mrt 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 totaal voor 3 nachten

8–11 nov 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(36 reviews)

$ 755,05 USD totaal voor 3 nachten

15–18 nov 2026

Second Bedroom through door in back of rv

Turnkey furnished luxury RV getaway in New England

2 bedrooms·1½ baths

Danvers • Massachusetts

$ 4.500,00 USD $ 2.250,00 USD totaal voor 90 nachten

1 mei – 30 jul 2027

Private Beach view

Coastal Charm: Lobster Château

2 bedrooms·2 baths

Swampscott • Massachusetts

$ 1.367,96 USD totaal voor 3 nachten

14–17 nov 2026

New flooring (2022)

Vaulted Ceiling

Oceanfront Penthouse Salisbury

5 bedrooms·2 baths

Salisbury • Massachusetts

5(182 reviews)

$ 1.137,00 USD totaal voor 3 nachten

8–11 nov 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 totaal voor 3 nachten

1–4 jan 2027

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)

$ 2.513,25 USD totaal voor 7 nachten

3–10 jun 2027

Your view from the house

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

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 totaal voor 7 nachten

28 mei – 4 jun 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 totaal voor 7 nachten

4–11 jun 2027

Private kitchen

Spectacular Oceanfront 1 Bedroom Unit in Winthrop

1 bedroom·1 bath

Winthrop • Massachusetts

$ 1.070,00 USD totaal voor 3 nachten

23–26 nov 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

$ 296,27 USD totaal voor 3 nachten

8–11 nov 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

$ 353,39 USD totaal voor 3 nachten

8–11 nov 2026

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

$ 284,32 USD totaal voor 3 nachten

8–11 nov 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

$ 370,80 USD totaal voor 3 nachten

8–11 nov 2026