A beach with a lifeguard tower, waves, and a large house with a tower on a rocky shore.

Find Hotels with a Pool in Gloucester, MA

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Gloucester Hotels with a Pool

This weekend
6 Nov - 8 Nov
Next weekend
13 Nov - 15 Nov

Our top choices for Gloucester hotels with a pool

A poolside area with lounge chairs and umbrellas, a pool, and a view of the sea.

1. Beauport Hotel Gloucester

Beauport Hotel Gloucester
3.5 star property
Downtown Gloucester
9.6 out of 10, Exceptional, (1,006 reviews)
"Great location, cool vibe, comfortable facilities."
Canada
Stas
The price is AED 782
AED 873 total
includes taxes & fees
4 Nov - 5 Nov
Beauport Hotel Gloucester
A two-story building with a sign reading 'Harborview Inn.' There are two umbrellas in front of the building, and a rope barrier with flowers.

2. Harborview Inn

Harborview Inn
3.5 star property
Downtown Gloucester
9.6 out of 10, Exceptional, (343 reviews)
"Great location! Staff excellent. Great vale."
United States
Martin
The price is AED 694
AED 775 total
includes taxes & fees
6 Nov - 7 Nov
Harborview Inn
A poolside area with lounge chairs and a tiled pool.

3. The Vista

The Vista
2.5 star property
East Gloucester
9.4 out of 10, Exceptional, (459 reviews)
"Very friendly staff Rooms were very clean Beautiful area to visit"
United States
Lisa
The price is AED 664
AED 742 total
includes taxes & fees
10 Nov - 11 Nov
The Vista
A modern hotel room with a large bed, a flat-screen TV, a fireplace, and a chandelier.

4. The Highliner Hotel

The Highliner Hotel
3.5 star property
Downtown Gloucester
9.0 out of 10, Wonderful, (24 reviews)
"Great stay"
United States
Matthew
The price is AED 494
AED 859 total
includes taxes & fees
8 Nov - 9 Nov
The Highliner Hotel
A rooftop pool area with lounge chairs and a view of the ocean.

5. Ocean House Hotel at Bass Rocks

Ocean House Hotel at Bass Rocks
4.0 star property
East Gloucester
9.0 out of 10, Wonderful, (885 reviews)
"It was a lovely hotel perfectly situated by the sea."
United States
Christie T
The price is AED 560
AED 716 total
includes taxes & fees
4 Nov - 5 Nov
Ocean House Hotel at Bass Rocks
A covered porch with stone walls, wicker furniture, and a view of a house in the background.

6. Castle Manor Inn

Castle Manor Inn
2.5 star property
Gloucester
8.6 out of 10, Excellent, (1,000 reviews)
"Staff was really friendly, bed was super comfortable, breakfast was delicious!"
United States
Stephanie
The price is AED 599
AED 792 total
includes taxes & fees
4 Dec - 5 Dec
Castle Manor Inn
A restaurant with large windows overlooking a marina.

7. The Hotel at Cape Ann Marina

The Hotel at Cape Ann Marina
3.5 star property
Gloucester
8.4 out of 10, Very good, (829 reviews)
"I had a great stay!"
United States
Myles
The price is AED 790
AED 882 total
includes taxes & fees
5 Nov - 6 Nov
The Hotel at Cape Ann Marina
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties

Choose what matters most at hotels with a pool in Gloucester

Breakfast included
Hot tub

Top Gloucester Hotel Reviews

Lakeside Inn

Lakeside Inn

8/10 Good
"My only complaint was the band at the bar Saturday night I can hear them all the way from my room but luckily they play well otherwise great experience here"
Sandra 2-night trip
Posted 2 hours ago
Lakeside Inn

Frequently asked questions

What are some accommodations with pools in Gloucester?
Ocean House Hotel at Bass Rocks: Features free self parking, a seasonal outdoor pool, and complimentary bicycles. The Vista: Offers continental, an outdoor pool, and free self parking.
What is there to see and do in Gloucester?
Surround yourself with nature at Half Moon Beach and Stage Fort Park. During your stay, check out sights such as Capt Bill & Sons Whale Watch, Cape Ann Museum, and Maritime Gloucester. Visitors to Gloucester speak highly of the natural attractions, including the beautiful ocean views.
When is the best time to book a hotel with a pool in Gloucester?
Taking into account the local weather in Gloucester can help you maximize your time at the pool during your trip. The hottest months are usually July and August with an average temp of 66°F, while the coldest months are January and February with an average of 34°F. The snowiest months in Gloucester are January, February, December, and March, with each month seeing an average of 6 inches of snowfall.
What's the best way to travel around Gloucester?
Knowing the transportation options in Gloucester can help you enjoy the area beyond your hotel pool. To venture out into the surrounding area, hop aboard a train at Gloucester Station or West Gloucester Station. Gloucester might not have many public transit choices so consider renting a car to explore more.

Explore a world of travel with Expedia