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Vacation rentals in Gloucester, Massachusetts, United States

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 gesamt für 7 Nächte

7.–14. Sept. 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/ Nacht(zzgl. Gebühren & Steuern)

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 gesamt für 3 Nächte

7.–10. Sept. 2026

Bedroom 1 -Queen Bed

The Waterline

2 bedrooms·1 bath

Rockport • Massachusetts

1.143,95 $ USD gesamt für 3 Nächte

31. Okt. – 3. Nov. 2026

Kostenlose Stornierung

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 gesamt für 3 Nächte

7.–10. Sept. 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 gesamt für 3 Nächte

3.–6. Nov. 2026

Kostenlose Stornierung

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 gesamt für 3 Nächte

17.–20. Okt. 2026

Kostenlose Stornierung

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/ Nacht(zzgl. Gebühren & Steuern)

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 gesamt für 3 Nächte

7.–10. Sept. 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/ Nacht(zzgl. Gebühren & Steuern)

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 gesamt für 3 Nächte

9.–12. Sept. 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(4 reviews)

905,59 $ USD gesamt für 3 Nächte

8.–11. Sept. 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 gesamt für 3 Nächte

8.–11. Sept. 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 gesamt für 3 Nächte

8.–11. Sept. 2026

Private Beach view

Coastal Charm: Lobster Château

2 bedrooms·2 baths

Swampscott • Massachusetts

1.190,43 $ USD gesamt für 3 Nächte

7.–10. Sept. 2026

New flooring (2022)

Vaulted Ceiling

Oceanfront Penthouse Salisbury

5 bedrooms·2 baths

Salisbury • Massachusetts

5(182 reviews)

1.965,00 $ USD gesamt für 3 Nächte

10.–13. Sept. 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 gesamt für 3 Nächte

7.–10. Sept. 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/ Nacht(zzgl. Gebühren & Steuern)

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/ Nacht(zzgl. Gebühren & Steuern)

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 gesamt für 7 Nächte

11.–18. Sept. 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

$77 – $276/ Nacht(zzgl. Gebühren & Steuern)

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 gesamt für 3 Nächte

19.–22. Sept. 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

326,82 $ USD gesamt für 3 Nächte

7.–10. Sept. 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 gesamt für 3 Nächte

7.–10. Sept. 2026