The 10 best holiday rentals in Gloucester, USA | Booking.com
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Holiday Rentals in Gloucester

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The best holiday rentals in Gloucester

Check out our pick of great holiday rentals in Gloucester

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Most booked holiday rentals in Gloucester and surroundings in the past month

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Enjoy breakfast in Gloucester and nearby

  • Scored out of 10, guest rating 9.0
    Superb - What previous guests thought, 4 reviews

    Situated in Gloucester, Good Harbor Haven features a restaurant, 400 metres from Good Harbor Beach and 30 km from Peabody Essex Museum.

  • Located 31 km from Peabody Essex Museum and 31 km from The House of the Seven Gables, Inviting Rockport Rental with Deck Walk to Beach! provides accommodation situated in Rockport.

  • Scored out of 10, guest rating 9.0
    Superb - What previous guests thought, 6 reviews

    Ocean Front Cottage - Long Beach is a beachfront property located in Rockport, 80 metres from Long Beach Rockport and 31 km from Peabody Essex Museum.

  • Scored out of 10, guest rating 8.8
    Fabulous - What previous guests thought, 5 reviews

    Featuring accommodation with a patio, High Street Hideaway is located in Rockport.

  • Scored out of 10, guest rating 4.7
    Disappointing - What previous guests thought, 3 reviews

    Located in Rockport in the Massachusetts region, Made for Beach Other has a patio.

  • Scored out of 10, guest rating 7.9
    Good - What previous guests thought, 11 reviews

    Located in Rockport, 33 km from Peabody Essex Museum and 33 km from The House of the Seven Gables, Lovely Rockport Apartment, Walk to Beaches! offers a garden and air conditioning.

  • Scored out of 10, guest rating 8.3
    Very good - What previous guests thought, 20 reviews

    Featuring air-conditioned accommodation with a patio, Vintage Rockport Escape is located in Rockport.

  • Lantana House

    Rockport
    Breakfast options
    Scored out of 10, guest rating 9.2
    Superb - What previous guests thought, 68 reviews

    Set in Rockport, within 200 metres of Front Beach and 33 km of Peabody Essex Museum, Lantana House offers accommodation with a shared lounge as well as free private parking for guests who drive.

Highly rated holiday rentals in Gloucester and nearby

  • Scored out of 10, guest rating 9.6
    Exceptional - What previous guests thought, 29 reviews

    Offering sea views, Beach & King Street Inn is an accommodation set in Rockport, a few steps from Front Beach and 33 km from Peabody Essex Museum.

    From US$385.37 per night

  • Sally Webster Inn

    Rockport
    8.0+ review score
    Scored out of 10, guest rating 8.4
    Very good - What previous guests thought, 114 reviews

    Located in Rockport, less than 1 km from Front Beach, Sally Webster Inn provides accommodation with a garden, free WiFi, a housekeeping service, and private check-in and check-out.

    From US$318.35 per night

  • Willow Cove

    Rockport
    8.0+ review score
    Scored out of 10, guest rating 8.4
    Very good - What previous guests thought, 5 reviews

    Located in Rockport, 1 km from Front Beach and 34 km from Peabody Essex Museum, Willow Cove offers air conditioning. The The House of the Seven Gables is within 34 km of the holiday home.

  • Seafarer Inn

    Rockport
    8.0+ review score
    Scored out of 10, guest rating 9.4
    Superb - What previous guests thought, 86 reviews

    Seafarer Inn is located in Rockport, within 35 km of Peabody Essex Museum and 35 km of The House of the Seven Gables. Each accommodation at the 3-star capsule hotel has sea views and free WiFi.

  • Great Marsh House

    Essex
    8.0+ review score
    Scored out of 10, guest rating 9.2
    Superb - What previous guests thought, 5 reviews

    Set in Essex, 21 km from Peabody Essex Museum and 21 km from The House of the Seven Gables, Great Marsh House offers air conditioning. The holiday home is 47 km from Cambridge College.

These holiday rentals in Gloucester and nearby have options with free cancellation

  • Olde New House

    Rockport
    Free cancellation options available
    Scored out of 10, guest rating 7.0
    Good - What previous guests thought, 4 reviews

    Located in Rockport, 400 metres from Front Beach and 33 km from Peabody Essex Museum, Olde New House provides a restaurant.

    From US$415.50 per night

  • Pine House

    Rockport
    Free cancellation options available

    Situated in Rockport, 400 metres from Back Beach and 34 km from Peabody Essex Museum, Pine House features a restaurant and sea views.

  • Rustic Rockport Cottage

    Rockport
    Free cancellation options available
    Scored out of 10, guest rating 7.3
    Good - What previous guests thought, 9 reviews

    Located in Rockport, 700 metres from Back Beach and 34 km from Peabody Essex Museum, Rustic Rockport Cottage provides a restaurant and sea views. The property has garden views.

  • Andrews Point Ocean Home

    Rockport
    Free cancellation options available
    Scored out of 10, guest rating 8.0
    Very good - What previous guests thought, 1 review

    Andrews Point Ocean Home is set in Rockport, 36 km from Peabody Essex Museum, 37 km from The House of the Seven Gables, and 36 km from Salem Witch Museum.

FAQ about holiday rentals in Gloucester

Holiday rentals that guests love in Gloucester

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  • Retreat near Beaches

    Holiday Rental in Gloucester
    Scored out of 10, guest rating 9.0
    Superb - What previous guests thought, 61 reviews
    Ideal set-up and generally well-stocked, including often forgotten items like toothbrush and razor. Clean and comfortable. Easy check-in. I liked having a bench in the bedroom. It was a handy place for our luggage. I also appreciated the lights, including lamps for reading and under-cabinet lights in the kitchen. And throw blankets to wrap up in when watching TV. Mirrors. These things set it above many vacation rentals.
    Guest review by
    Peterson
    Family with young children

  • Stay at Niles Beach

    Holiday Rental in Gloucester
    Scored out of 10, guest rating 10.0
    Exceptional - What previous guests thought, 5 reviews
    Our stay at this Gloucester gem was nothing short of magical! From the cozy interiors to the breathtaking ocean views, every detail was perfection. The hosts' hospitality made us feel right at home, and the proximity to local attractions added an extra layer of convenience. If you're looking for a picturesque retreat, this vacation home is an absolute dream. Can't wait to come back and create more unforgettable memories!
    Guest review by
    Courtney Mozingo
    Family with young children