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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CbytheSea - Ocean View Penthouse

Gloucester

Situated in Gloucester, the recently renovated CbytheSea - Ocean View Penthouse features accommodation 600 metres from Pavilion Beach and 27 km from Peabody Essex Museum.

D
David
From
United Kingdom
Lovely light and airy feel to the appt. - great location by the seafront and easy walk into town. Had all the facilities you need and nice touch was the coffees, snacks and wine welcome pack
Scored out of 10, guest rating 9.5
Exceptional - What previous guests thought, 40 reviews
Price from
US$548.90
1 night, 2 adults

Ocean Breeze-8min Walk to Beach

Gloucester

Situated in Gloucester, 700 metres from Good Harbor Beach and 30 km from Peabody Essex Museum, Ocean Breeze-8min Walk to Beach offers a garden and air conditioning.

F
Francis
From
Ireland
I had a one night visit to Gloucester to visit family . I was delighted with the property. Well located , the apartment is spotless clean & has great amenities. Beautifully decorated.
Scored out of 10, guest rating 9.5
Exceptional - What previous guests thought, 39 reviews
Price from
US$249
1 night, 2 adults

Retreat near Beaches

Gloucester

1.4 km from Good Harbor Beach, Retreat near Beaches is a recently renovated property set in Gloucester and offers air-conditioned rooms with free WiFi and private parking.

M
Mary
From
Australia
You need a car for this location. Charming apartment well appointed. Very clean and comfortable.
Scored out of 10, guest rating 9.0
Superb - What previous guests thought, 62 reviews
Price from
US$149
1 night, 2 adults

Spacious 2nd floor Suite

Gloucester

Offering city views, Spacious 2nd floor Suite is an accommodation situated in Gloucester, 26 km from Peabody Essex Museum and 26 km from The House of the Seven Gables.

H
Hélène
From
France
Very good localisation and great host, we had a great time there!
Scored out of 10, guest rating 7.6
Good - What previous guests thought, 8 reviews
Price from
US$173
1 night, 2 adults

Sally Webster Inn

Rockport (Near Gloucester)

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.

A
ASHLIE
From
Australia
Very cosy and stylish. Great breakfast. The nicest duvet! I loved my stay at this B&B!.
Scored out of 10, guest rating 8.4
Very good - What previous guests thought, 109 reviews
Price from
US$203
1 night, 2 adults

The Beverly

Beverly (Near Gloucester)

Situated in Beverly, 8.1 km from Peabody Essex Museum, The Beverly features accommodation with free WiFi and free private parking.

W
Williams
From
United States
Was exactly what my son and I needed as we visited Gordon College. Clean and a great value for the money!
Scored out of 10, guest rating 7.9
Good - What previous guests thought, 606 reviews
Price from
US$119.70
1 night, 2 adults

An authentic, rustic luxurious little single family home in Old Town. All yours.

Marblehead (Near Gloucester)

Located in Marblehead, 1.6 km from Gas House Beach and 6.2 km from Peabody Essex Museum, An authentic, rustic luxurious little single family home in Old Town. All yours.

V
Vitalina
From
United States
The place is beautiful, great location! Everything was perfect
Scored out of 10, guest rating 10.0
Exceptional - What previous guests thought, 23 reviews
Price from
US$222.60
1 night, 2 adults

NEW! Family-Friendly Getaway -1 Mi to Dtwn Salem w Roof Deck & Tiki Bar

Salem (Near Gloucester)

Featuring air-conditioned accommodation with a patio, NEW! Family-Friendly Getaway -1 Mi to Dtwn Salem w Roof Deck & Tiki Bar is set in Salem.

Scored out of 10, guest rating 9.0
Superb - What previous guests thought, 30 reviews
Price from
US$380.25
1 night, 2 adults

Daniels House Inn

Salem (Near Gloucester)

Located in Salem, within 1.6 km of Dead Horse Beach and 300 metres of The House of the Seven Gables, Daniels House Inn provides accommodation with a garden and free WiFi as well as free private...

R
Rebecca
From
Australia
The History in the building in unreal and is very well preserved. we stayed in “The Great Room” and it was absolutely beautiful and 1 of the oldest rooms in the house. Vijay was so lovely and even though we came in off season, he still made time to show us parts of the house that the guests wouldn’t have access too due to it being in its most original form from the 1600’s. We fell in love with the property, the town and the people. We are super lucky to have seen the town and are even more excited to come back and see it in full swing in the month of October.
Scored out of 10, guest rating 9.2
Superb - What previous guests thought, 58 reviews
Price from
US$306.90
1 night, 2 adults

Silsbee's by Daniels House

Salem (Near Gloucester)

Situated in Salem, within 1.5 km of Dead Horse Beach and 300 metres of The House of the Seven Gables, Silsbee's by Daniels House features accommodation with a garden and as well as free private...

R
Rhoda
From
United Kingdom
The property was so unique in its character and history. Location was very good as it’s very central to everything but still nice and quiet. Patrick was very accommodating and helpful.
Scored out of 10, guest rating 8.7
Fabulous - What previous guests thought, 23 reviews
Price from
US$320.85
1 night, 2 adults
All holiday rentals in Gloucester

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

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

  • Sally Webster Inn

    Rockport
    Free cancellation options available
    Scored out of 10, guest rating 8.4
    Very good - What previous guests thought, 109 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$266.96 per night
  • 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.

  • Ocean Front Cottage - Long Beach

    Rockport
    Free cancellation options available
    Scored out of 10, guest rating 9.0
    Superb - What previous guests thought, 7 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.

  • High Street Hideaway

    Rockport
    Free cancellation options available
    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.

  • Made for Beach Other

    Rockport
    Free cancellation options available
    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.

  • Vintage Rockport Escape

    Rockport
    Free cancellation options available
    Scored out of 10, guest rating 8.4
    Very good - What previous guests thought, 21 reviews

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

  • Lantana House

    Rockport
    Free cancellation options available
    Scored out of 10, guest rating 9.2
    Superb - What previous guests thought, 67 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.

  • 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

Enjoy breakfast in Gloucester and nearby

  • Willow Cove

    Rockport
    Breakfast options
    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.

  • Pine House

    Rockport
    Breakfast options

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

  • Scored out of 10, guest rating 6.8
    Pleasant - 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.

  • Seafarer Inn

    Rockport
    Breakfast options
    Scored out of 10, guest rating 9.4
    Superb - What previous guests thought, 81 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.

  • 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.

  • Great Marsh House

    Essex
    Breakfast options
    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.

Highly rated holiday rentals in Gloucester and nearby

  • Scored out of 10, guest rating 9.7
    Exceptional - What previous guests thought, 30 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

FAQ about holiday rentals in Gloucester

Holiday rentals that guests love in Gloucester

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  • Avg. price/night: US$492.06
    Scored out of 10, guest rating 9.0
    Superb - What previous guests thought, 62 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
  • 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