Gloucester Chalets from CA $143

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Recommended hotels in Gloucester

Two individuals in white robes by a window overlooking a body of water with a distant shoreline.

1. Beauport Hotel Gloucester

Downtown Gloucester

Stas

CA $332 total

includes taxes & fees

Dec 7 - Dec 8

A poolside area with lounge chairs and a tiled pool.

2. The Vista

East Gloucester

Lisa

CA $319 total

includes taxes & fees

Nov 10 - Nov 11

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

3. Ocean House Hotel at Bass Rocks

East Gloucester

Christie T

CA $273 total

includes taxes & fees

Nov 8 - Nov 9

A building with a brick facade, large windows, and a staircase leading to the entrance.

4. The Hotel at Cape Ann Marina

Gloucester

Myles

CA $336 total

includes taxes & fees

Dec 7 - Dec 8

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.

5. Harborview Inn

Downtown Gloucester

Martin

CA $295 total

includes taxes & fees

Dec 7 - Dec 8

A covered porch with stone walls, wicker furniture, and a view of a house in the background.

6. Castle Manor Inn

Gloucester

Stephanie

CA $327 total

includes taxes & fees

Nov 15 - Nov 16

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

7. The Highliner Hotel

Downtown Gloucester

Matthew

CA $328 total

includes taxes & fees

Nov 8 - Nov 9

A house with a stone retaining wall, a window with an air conditioning unit, and a small tree in the yard.

8. New England Coastal Residence

Gloucester

Richard B.

CA $1,076 total

includes taxes & fees

Nov 11 - Nov 12

A residential area with houses, a road, and a body of water in the background.

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

Gloucester

Maarij K.

CA $1,236 total

includes taxes & fees

Nov 16 - Nov 17

A living room with a brown leather sofa, a flat-screen TV mounted on the wall, a dining table with chairs, and a patterned rug.

10. The Essex of Gloucester

Gloucester

Katie B.

CA $329 total

includes taxes & fees

Dec 7 - Dec 8

A two-story house with a front porch, a wooden fence, and a well-maintained lawn.

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

East Gloucester

Nina R.

CA $1,102 total

includes taxes & fees

Nov 24 - Nov 25

A building with two white doors, a bench, and hanging flower baskets.

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

Gloucester

Catherine C.

CA $284 total

includes taxes & fees

Nov 8 - Nov 9

A white house with a white picket fence, a stone pathway, and a small porch.

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

Gloucester

Karen T.

CA $574 total

includes taxes & fees

Nov 10 - Nov 11

A covered outdoor deck with a glass table and chairs, metal railings, and a staircase.

14. 3BR Oceanview Townhouse on Boulevard I Walk to downtown l Sleeps 8

Gloucester

Betty

CA $922 total

includes taxes & fees

Nov 11 - Nov 12

A house with a covered patio, a stone pathway, and a fenced backyard.

15. Rockport Inn And Suites

Rockport

James

CA $209 total

includes taxes & fees

Dec 7 - Dec 8

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.

16. The Cove at Rockport Hotel

Rockport

Wendy

CA $264 total

includes taxes & fees

Nov 17 - Nov 18

A two-story house with a porch, surrounded by lush greenery and trees.

17. The Rockport House

Rockport

Ann

CA $252 total

includes taxes & fees

Nov 8 - Nov 9

A wooden deck with outdoor seating, overlooking a body of water and a rocky shoreline.

18. Bearskin Neck Motor Lodge

Rockport

Mary Beth

CA $376 total

includes taxes & fees

Nov 8 - Nov 9

A coastal building with a garden and a rocky shoreline.

19. The Yankee Clipper Inn

Rockport

Lisa

CA $280 total

includes taxes & fees

Dec 7 - Dec 8

The entrance of The Inn at Endicott with a classic architectural design featuring white columns and a beige facade.

20. The Wylie Inn and Conference Center at Endicott College

Beverly

Berna

CA $160 total

includes taxes & fees

Nov 18 - Nov 19

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Learn more about Gloucester

America's oldest working seaport offers whale watching tours where humpback sightings are common from May through October. Wander the colourful 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

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

Top reviews in Gloucester

Beauport Hotel Gloucester

Downtown Gloucester

10/10 Excellent

Stas

The Vista

East Gloucester

10/10 Excellent

Terry

Ocean House Hotel at Bass Rocks

East Gloucester

10/10 Excellent

We really enjoyed our one night stay in Gloucester at Bass Rocks. Upon arrival we were warmly welcomed and encouraged to enjoy freshly baked cookies and a cup of coffee in their cozy and scenic seating area as we planned our visit. It was difficult to choose where to eat and there were many local restaurants nearby. Afterwards, there were DVD's to borrow, a wonderfully heated pool and a large hot tub to soak in, as well as a gas fire pit area to relax around. It was lovely to have an ocean...

C.R.

Castle Manor Inn

Gloucester

10/10 Excellent

tekawisarihtha

The Hotel at Cape Ann Marina

Gloucester

10/10 Excellent

Brian

Harbor Light Inn

Marblehead Historic District

10/10 Excellent

Giovanna

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

Where do I even begin? My family of 4 fell in love with this spectacular 21 apartment style room boutique hotel! We immediately noticed how clean it smelt and how spotless & bright everything was! The level of cleanliness at The Courier Hotel far exceeded all hotels we've ever been in! All the staff was so helpful and friendly, it was like I was catching up with old friends even though we just met. Everything we needed was already there in the room. We didn't need to pack dishes, paper towels or...

Deanna