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

Hotels with Swimming Pool in Gloucester, Massachusetts

  • 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 Swimming Pool

Tonight
Oct 7 - Oct 8
Tomorrow
Oct 8 - Oct 9
This weekend
Oct 9 - Oct 11
Next weekend
Oct 16 - Oct 18

Our top choices for Gloucester hotels with a pool

A rooftop pool area with lounge chairs and a view of the ocean.
A spacious living room with a large bed, a sofa, and a chair. There is a chessboard on a table, and a view of the ocean through the windows.
A large, white, two-story building with a balcony and a staircase leading to a lower level.
A wooden boardwalk leading to a beach with a clear sky.

1. Ocean House Hotel at Bass Rocks

Ocean House Hotel at Bass Rocks
East Gloucester
  • Seasonal heated pool meets Atlantic views at this beachside retreat by the water.
P9,241
P11,864 total
includes taxes & fees
Nov 1 - Nov 2
Ocean House Hotel at Bass Rocks
A poolside area with lounge chairs and a tiled pool.
A hotel room with a large bed, a chair, a desk, and a view of a golf course through an open door.
A coastal beach scene with a large house on a rocky outcrop, a sandy beach with people, and a clear blue sky.
A hotel with a swimming pool, multiple guest rooms, and a red barn-like structure.

2. The Vista

The Vista
East Gloucester
  • Dive into serenity at this oceanfront hotel with a sparkling pool and beautiful beach views nearby.
P11,865
P13,253 total
includes taxes & fees
Nov 3 - Nov 4
The Vista
A pool area with lounge chairs, a sign for Atlantis Oceanfront Inn, and a view of the ocean.
A beach with a wooden boardwalk leading to the water, houses in the background, and people relaxing on the sand.
A hotel room with two beds, a desk, and a chair. There is a large window with a view of the ocean and a balcony.
A breakfast table with a view of the ocean and a sign reading "ATLANTIS".

3. Atlantis Oceanfront Inn

Atlantis Oceanfront Inn
East Gloucester
  • Discover oceanfront serenity at this Cape Ann retreat, where the outdoor pool offers a refreshing escape with stunning sea views.
P17,915
P20,011 total
includes taxes & fees
Oct 14 - Oct 15
Atlantis Oceanfront Inn
A rectangular swimming pool with a white fence and lounge chairs.
A wooden deck with a red door and a window, surrounded by white railings and outdoor furniture.
A hotel room with a bed, a desk, two chairs, and two framed pictures on the walls.
A parking area with a signpost indicating directions to 'Seal Lion' and 'Olde Town'.

4. Sea Lion Motel and Cottages

Sea Lion Motel and Cottages
East Gloucester
  • Float in the sparkling outdoor pool with serene garden views at this quiet Gloucester motel just steps from Good Harbor Beach.
P10,837
P12,105 total
includes taxes & fees
Oct 14 - Oct 15
Sea Lion Motel and Cottages
An indoor swimming pool with wooden beams, lounge chairs, and large windows.
A house with a covered patio, a stone pathway, and a fenced backyard.
A harbor with boats docked near a red building with an American flag.
A spacious living room with exposed wooden beams, a fireplace, and modern lighting fixtures.

5. Rockport Inn And Suites

Rockport Inn And Suites
Rockport
  • Splash into vacation mode at this clean, well-maintained indoor pool with year-round access and welcoming vibes.
P8,418
P9,403 total
includes taxes & fees
Nov 2 - Nov 3
Rockport Inn And Suites
A pool with white lounge chairs and a view of the ocean.
A hotel room with a large window, a bed with white linens, and a wooden headboard.
A room with a large window overlooking the ocean, two patterned armchairs, and a small table with a book.
A covered porch with white columns, a row of black rocking chairs, and a view of the ocean.

6. Emerson Inn

Emerson Inn
Rockport
  • Scenic seasonal pool awaits at historic Georgian hotel, with terrace views and beachfront dining at Emerson Inn.
P16,725
P18,683 total
includes taxes & fees
Nov 3 - Nov 4
Emerson Inn
Indoor pool
An outdoor patio with wicker furniture and a fire pit.
A hotel lobby with a blue sofa, green armchairs, and a patterned rug.
A modern reception area with a white desk, two computer monitors, a blue sofa, and a green chair.

7. Best Western Plus North Shore Hotel

Best Western Plus North Shore Hotel
Danvers
  • Dive into refreshing swims year-round in this remodeled hotel's indoor aquatic sanctuary after exploring New England attractions.
P8,342
P9,318 total
includes taxes & fees
Nov 4 - Nov 5
Best Western Plus North Shore Hotel
An indoor swimming pool with a blue ceiling, clear pool tiles, and lounge chairs along the side.
A modern restaurant with wooden flooring, bar seating, and a patterned wall.
A modern bathroom with a glass-enclosed shower, a freestanding bathtub, and a large vanity with a mirror.
A modern hotel room with a large bed, a bedside table with a lamp, a round coffee table, and a view of the city through the window.

8. Salem Waterfront Hotel & Suites

Salem Waterfront Hotel & Suites
Salem
  • Discover the refreshing sanctuary of Salem's indoor pool retreat, where serene swimming meets maritime charm.
P20,653
P23,070 total
includes taxes & fees
Nov 2 - Nov 3
Salem Waterfront Hotel & Suites
A swimming pool with a swan float, a white fence, and a building in the background.
A spacious living room with a staircase, a sofa set, and a large window.
A bar area with wooden ceiling beams, hanging pendant lights, and a bar stocked with various bottles. There are six wooden bar stools with cushioned seats.
A large, white, two-story building with a cylindrical tower, surrounded by well-maintained gardens and outdoor seating.

9. Briar Barn Inn

Briar Barn Inn
Rowley
  • Seasonal splashes and spa indulgences await at this New England hotel's outdoor pool retreat.
P10,757
P13,418 total
includes taxes & fees
Nov 1 - Nov 2
Briar Barn Inn
A backyard with a swimming pool, lounge chairs, and umbrellas.
A bar area with a wine rack, bottles, and glasses. There are three people seated at the bar.
A modern bathroom with a large mirror, two sinks, a shower, and wicker chairs.
A dining area with tables set for four, large windows, and a television mounted on the wall.

10. Harbor Light Inn

Harbor Light Inn
Marblehead Historic District
  • Dive into this harbor-side pool retreat with plush loungers and colonial charm, all steps from Marblehead's treasures.
P14,548
P16,251 total
includes taxes & fees
Nov 2 - Nov 3
Harbor Light Inn
View all properties

Choose what matters most at hotels with a pool in Gloucester

Breakfast included
Hot tub
4 stars
Spa
5 stars

Top Gloucester Hotel Reviews

Holiday Inn Hotel & Suites Boston - Peabody by IHG

Holiday Inn Hotel & Suites Boston - Peabody by IHG

10/10 Excellent
"Love the hotel, staff was friendly and room was clean"
Daniel 2-night trip
Posted 11 hours ago
Holiday Inn Hotel & Suites Boston - Peabody by IHG
Motel 6 Danvers, MA - Boston North

Motel 6 Danvers, MA - Boston North

10/10 Excellent
"Excellent"
katherine 1-night trip
Posted 12 hours ago
Motel 6 Danvers, MA - Boston North
Ashworth by the Sea

Ashworth by the Sea

10/10 Excellent
"We always stay at the Ashworth on our visits to Hampton Beach. Friendly staff, clean rooms, bikes and perfect location. Highly recommend."
Melissa 1-night trip
Posted 19 hours ago
Ashworth by the Sea
DoubleTree by Hilton Boston North Shore

DoubleTree by Hilton Boston North Shore

10/10 Excellent
"Clean room and good location"
Jim 3-night trip
Posted 22 hours ago
DoubleTree by Hilton Boston North Shore
Extended Stay America Suites Boston Peabody

Extended Stay America Suites Boston Peabody

8/10 Good
"The gentleman at the desk was quick with checkin. He was friendly and welcoming, very quick to act when we requested items for our room. He was also very helpful when I had laundry issues. The lobby and hallways were very clean as was the elevator. Our room was wheelchair accessible right from the door. In this room the bed was lower and medium firm, rollin shower with a shower chair, lower counters and grab bars in bathroom with good turning radius. The room also had a kitchenette that isnt accessible as it is a galley style. You also need to order everything at the desk ie coffee maker, dishes, cookware. That was inconvenient but definitely not a big deal and I understand it is to control loss. The only real downer was this room faced the interstate so a lot of road noise all night long. We would definitely stay again."
norma 1-night trip
Posted 1 day ago
Extended Stay America Suites Boston Peabody
Sea Lion Motel and Cottages

Sea Lion Motel and Cottages

10/10 Excellent
"The staff was extremely helpful and accomodating. They made arrangements for a late check in which was effortless and well explained. They even turned our lights on so our room was ready. The property is quaint and well kept. Rooms were clean and spacious. Great location. Easily accessible to the train and town. Would definitely stay again!"
Meghan 3-night trip
Posted 2 days ago
Sea Lion Motel and Cottages
The Vista

The Vista

8/10 Good
"Very friendly staff Rooms were very clean Beautiful area to visit"
Lisa 2-night trip
Posted 4 days ago
The Vista
Ocean House Hotel at Bass Rocks

Ocean House Hotel at Bass Rocks

10/10 Excellent
"The location of this hotel was incredible. Overlooking the ocean, with a large balcony, and a lovely walkway along the ocean. The room was large and clean and comfortable with a couch and seating area. The bathroom was small but adequate. We walked to the hotel next door for a nice breakfast. The pool area was inviting but too cool to enjoy when we went. We'd definitely go back."
Donna M 2-night trip
Posted 8 days ago
Ocean House Hotel at Bass Rocks

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