A harbor with boats, including a 'Whale Watch' and a 'Wejack' named boat.

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Dates

November 2026

December 2026

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Recommended hotels in Gloucester

A hotel room with a large bed, a fireplace, a television, and a view of the water.

1. Beauport Hotel Gloucester

Downtown Gloucester

Stas

$209 nightly

Dec 6 - Dec 7

Total with taxes and fees

A large, white, two-story building with a balcony and a staircase leading to a lower level.

2. Ocean House Hotel at Bass Rocks

East Gloucester

Christie T

$175 nightly

Nov 8 - Nov 9

Total with taxes and fees

A modern hotel room with a large bed, a flat-screen TV, a fireplace, and a chandelier.

3. The Highliner Hotel

Downtown Gloucester

Matthew

$218 nightly

Nov 8 - Nov 9

Total with taxes and fees

A neatly made bed with a tray holding a bottle of Chandon champagne and two glasses, a large headboard, and a modern chandelier.

4. The Hotel at Cape Ann Marina

Gloucester

Myles

$215 nightly

Nov 8 - Nov 9

Total with taxes and fees

A hotel room with two beds, a balcony with a view, and a desk with a chair.

5. The Vista

East Gloucester

Lisa

$204 nightly

Nov 10 - Nov 11

Total with taxes and fees

A room with a bed, a desk, a chair, a ceiling fan, and a window with curtains.

6. Harborview Inn

Downtown Gloucester

Martin

$189 nightly

Nov 8 - Nov 9

Total with taxes and fees

A bedroom with a wooden bed, a nightstand, a large window with curtains, a TV, and a potted plant.

7. Castle Manor Inn

Gloucester

Stephanie

$229 nightly

Nov 6 - Nov 7

Total with taxes and fees

A bedroom with a bed, bedside tables, a bench, a window, a wall clock, and a painting.

8. Charming Retreat

East Gloucester

Margaret

$256 nightly

Nov 14 - Nov 15

Total with taxes and fees

A bedroom with a bed, a window with curtains, a bedside table, and a wall-mounted light.

9. The Essex of Gloucester

Gloucester

Katie B.

$212 nightly

Dec 2 - Dec 3

Total with taxes and fees

A bedroom with a bed, a chair, a desk, a macrame wall hanging, and a painting.

10. Quirky 1-bedroom apartment with AC in delightful Gloucester, near water

Gloucester

Catherine C.

$183 nightly

Nov 8 - Nov 9

Total with taxes and fees

A bedroom with a bed, a ceiling fan, a bookshelf, and a doorway leading to another room.

11. New England Coastal Residence

Gloucester

Richard B.

$693 nightly

Nov 11 - Nov 12

Total with taxes and fees

A cozy attic bedroom with wooden walls, a sloped ceiling, and a skylight. There are three beds arranged in a U-shape, a small table, and a bench.

12. Oceanside Village Home~Private Fenced Yard~Reserved Parking

Gloucester

Karen T.

$359 nightly

Nov 10 - Nov 11

Total with taxes and fees

A bedroom with a bed, a ceiling fan, a nightstand, a dresser, and a mirror.

13. Classic Coastal Family Home | Walk to Sea;King Bed

Gloucester

Maarij K.

$785 nightly

Nov 16 - Nov 17

Total with taxes and fees

A modern bathroom with a toilet, sink, and shower. There is a wooden floor and a bed with a blue blanket in the adjacent bedroom.

14. The Mariner · Walk to Beach+Rocky Neck · Fenced Backyard

East Gloucester

Nina R.

$688 nightly

Nov 24 - Nov 25

Total with taxes and fees

A bedroom with a bed, a nightstand, a window, and a door leading to a bathroom.

15. 3BR Oceanview Townhouse on Boulevard I Walk to downtown l Sleeps 8

Gloucester

Betty

$577 nightly

Nov 11 - Nov 12

Total with taxes and fees

A hotel room with a bed, a sofa, a coffee table, a TV, and a bathroom visible through an open door.

16. Rockport Inn And Suites

Rockport

James

$128 nightly

Dec 6 - Dec 7

Total with taxes and fees

A balcony with two lounge chairs and two glasses of orange juice, a small kitchenette, a flat-screen TV, and a view of the sea.

17. The Cove at Rockport Hotel

Rockport

Wendy

$158 nightly

Nov 17 - Nov 18

Total with taxes and fees

A hotel room with a large bed, a TV, a desk with a computer, and a window with curtains.

18. The Rockport House

Rockport

Ann

$179 nightly

Nov 8 - Nov 9

Total with taxes and fees

A hotel room with a large bed, a desk, a chair, a wardrobe, and a patterned rug.

19. The Wylie Inn and Conference Center at Endicott College

Beverly

Berna

$106 nightly

Nov 18 - Nov 19

Total with taxes and fees

A bedroom with a large bed, wicker chairs, a glass table, and a view of the sea.

20. The Yankee Clipper Inn

Rockport

Lisa

$189 nightly

Nov 9 - Nov 10

Total with taxes and fees

View all properties

Learn more about Gloucester

America's oldest working seaport offers whale watching tours where humpback sightings are common from May through October. Wander the colorful harborfront where fishermen unload their catch, then sample the freshest lobster rolls at family-owned seafood shacks along Rocky Neck.

See all hotels in Gloucester

Top reviews in Gloucester

Beauport Hotel Gloucester

Downtown Gloucester

10/10 Excellent

Kim

A cozy living room with a sofa, armchair, and a coffee maker on a table.

Addison Choate Inn

Rockport

10/10 Excellent

Craig

A hotel room with two beds, a small table with a chair, a TV, and a view of the sea through the window.

Bearskin Neck Motor Lodge

Rockport

10/10 Excellent

Mary Beth

The Vista

East Gloucester

10/10 Excellent

I wasn't expecting much when I booked with Vista, but as soon as I got there I was impressed. The staff was friendly and made you feel welcome and took the time to explain everything you needed to know while staying there. Our room was a little dated, but it was spacious, and very clean! I love to travel and I have to say it was one of the cleanest places I've stayed at. When I booked I was concerned about the view I would be getting based off of others reviews...but I was pleasantly surprised...

morgan

The Rockport House

Rockport

10/10 Excellent

We had an amazing stay at the Rockport House. My wife and I had a beautiful, clean king room on the third floor, with a very comfortable bed with plenty of pillows, and an immaculate bathroom. The house was a quick walk to all the fun of Bearskin Neck and the incredibly cute hub of Rockport. Such a great autumnal New England stay! Check-in was so very easy, with seamless communication between us and the owners. I highly recommend! It felt like an old school bed and breakfast. Thank you...

Tony

Harbor Light Inn

Marblehead Historic District

10/10 Excellent

Alison

A hotel room with a large bed, yellow curtains, patterned wallpaper, and two bedside lamps.

Sally Webster Inn

Rockport

10/10 Excellent

Mary

A hotel room with a large window, a bed, a white sink, a mirror, and a potted plant.

The Courier Hotel

Downtown Salem

10/10 Excellent

Joshua

A bedroom with a bed, a bedside lamp, a fireplace, and a seating area with chairs.

Briar Barn Inn

Rowley

10/10 Excellent

Great staff, beautiful aesthetic and charming. We happened upon the Briar Barn looking for a quaint place to sleep for the night. This place was beyond our expectations and we are already planning another visit, with friends, to stay and see the sights of the area. We are New Yorkers and were so impressed by they service, the cleanliness, the vibe, the amenities and the space. We will come back and recommend to others.

Anonymous traveler

Ocean House Hotel at Bass Rocks

East Gloucester

10/10 Excellent

Norwich

A bedroom with a bed, a nightstand, a lamp, a window with blinds, a coat rack, and a bathroom with a glass door.

The Cabot Lodge

Beverly

10/10 Excellent

Bruce

A bunk bed with a pirate-themed design, including skull and crossbones pillows, and a wooden headboard.

The Cove At Salem

Salem

10/10 Excellent

Emily

A living room with a fireplace, a sofa, a dining table with chairs, and a television.

Compass Rose Inn

Newburyport

10/10 Excellent

Darren

The Wylie Inn and Conference Center at Endicott College

Beverly

10/10 Excellent

The room was clean and comfortable. The staff friendly and helpful. There were two things I really liked. The first was that there is a quiet time between 11:00 pm and 7:00 am. We've all stayed in hotels where there is a loud party going on in the room next door. The second was the ability to cast from your personal device to the TV, so you have access to every streaming service you pay for.. a very nice feature. I would definitely stay again.

Nicole