Gloucester Holiday Rentals, Massachusetts: Private House Rentals

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

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Our top choices for Gloucester hotels

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

A large hotel with multiple floors and a beach view.

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

A bar area with a long counter, multiple bar stools, and a variety of bottles and glasses.

1. Beauport Hotel Gloucester

Downtown Gloucester

Patricia

5.798.139 ₫

6.476.521 ₫ total

includes taxes & fees

2 Nov - 3 Nov

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

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 rooftop pool area with lounge chairs and a view of the ocean.

A wooden boardwalk leading to a beach with a clear sky.

2. Ocean House Hotel at Bass Rocks

East Gloucester

Michelle

3.808.560 ₫

4.889.861 ₫ total

includes taxes & fees

9 Nov - 10 Nov

A coastal beach scene with a large house on a rocky outcrop, a sandy beach with people, and a clear blue sky.

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 motel named Vista with a signboard indicating amenities like efficiencies, HBO, Wi-Fi, and off-season rates.

3. The Vista

East Gloucester

Lisa

4.889.997 ₫

5.462.049 ₫ total

includes taxes & fees

3 Nov - 4 Nov

A restaurant with large windows overlooking a marina.

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

A spacious indoor area with large windows, a yellow sofa, patterned ottoman, and a blue coffee table.

A marina with boats docked, outdoor seating with umbrellas, and a view of the water.

4. The Hotel at Cape Ann Marina

Gloucester

Myles

5.562.695 ₫

6.213.660 ₫ total

includes taxes & fees

11 Nov - 12 Nov

A coastal hotel with a rocky shoreline, multiple buildings, and a view of the ocean.

A pool area with lounge chairs, a sign for Atlantis Oceanfront Inn, and a view of the ocean.

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".

5. Atlantis Oceanfront Inn

East Gloucester

Daniel

5.847.298 ₫

6.531.380 ₫ total

includes taxes & fees

26 Oct - 27 Oct

A small stone building with a red door, surrounded by trees and a picnic table.

A parking area with a signpost indicating directions to 'Seal Lion' and 'Olde Town'.

A rectangular swimming pool with a white fence and lounge chairs.

A hotel room with a large bed, two bedside tables with lamps, a small desk, a chair, a mirror, and a window with curtains.

6. Sea Lion Motel and Cottages

East Gloucester

Scott

4.476.029 ₫

4.999.699 ₫ total

includes taxes & fees

21 Oct - 22 Oct

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

A corner room with two wicker chairs, a small wooden chest, and a window with a view of greenery.

A wooden-paneled room with a staircase, a chair, and a table.

A large, two-story house with a wrap-around porch and a stone foundation.

7. Castle Manor Inn

Gloucester

Barb

4.170.469 ₫

5.525.418 ₫ total

includes taxes & fees

8 Nov - 9 Nov

A modern apartment with a dining area, kitchen, living room, and a large window.

A two-story house with a covered patio area featuring outdoor seating and a stone wall.

A modern kitchen with a round dining table, wicker chairs, and a white countertop.

A modern kitchen with white cabinets, stainless steel appliances, and a large window.

8. Long Beach Suites

East Gloucester

Kim

3.185.483 ₫

8.615.709 ₫ total

includes taxes & fees

16 Nov - 17 Nov

A covered outdoor seating area with blue umbrellas, wicker chairs, and a view of the waterfront.

A window with a view of a street, a flag, and flowers.

A dining area with a table set for six, surrounded by blue upholstered chairs.

A cozy room with a view of the sea, featuring two armchairs, a round table, and a large window with curtains.

9. Harborview Inn

Downtown Gloucester

Martin

4.889.997 ₫

5.462.049 ₫ total

includes taxes & fees

5 Nov - 6 Nov

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

A modern living room with a white sofa, a zebra-patterned rug, and a large framed picture on the wall.

A long, narrow hallway with dark walls and wooden flooring.

A modern living room with a sofa, a small table, a zebra-patterned rug, and a staircase.

10. The Highliner Hotel

Downtown Gloucester

Matthew

4.465.162 ₫

9.033.817 ₫ total

includes taxes & fees

12 Nov - 13 Nov

A modern house with a large patio area featuring outdoor furniture and a fire pit.

A spacious living room with exposed wooden beams, a fireplace, and modern lighting fixtures.

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

An indoor swimming pool with wooden beams, lounge chairs, and large windows.

11. Rockport Inn And Suites

Rockport

Marci

3.469.569 ₫

3.875.508 ₫ total

includes taxes & fees

8 Nov - 9 Nov

A covered outdoor deck with wicker furniture, a view of the sea, and houses in the background.

A coastal view with a stone bench, clear sky, and a distant church.

A spacious dining area with a view of the sea, white furniture, and two exit signs.

A bay window with a bench, white railings, and a view of the sea.

12. The Cove at Rockport Hotel

Rockport

Justin

4.587.516 ₫

5.124.255 ₫ total

includes taxes & fees

2 Nov - 3 Nov

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

A covered porch with a table and chairs, surrounded by trees and a white fence.

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

A modern living room with a grey sofa, a round coffee table, and a TV mounted on the wall.

13. The Rockport House

Rockport

Erin

3.405.533 ₫

4.526.485 ₫ total

includes taxes & fees

25 Oct - 26 Oct

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

A residential house with a stone pathway leading to the front door, surrounded by lush greenery and flowering plants.

A coastal scene with a sandy beach, fishing equipment, and houses in the background.

14. Addison Choate Inn

Rockport

Nicholas

5.332.425 ₫

5.956.482 ₫ total

includes taxes & fees

1 Nov - 2 Nov

A sign for the Sally Webster Collection by Addison Choate, mounted on a building with a window and greenery in the foreground.

A waterfront property with a prominent building featuring large windows and a balcony, situated next to a stone wall and a body of water.

A living room with a fireplace, two leather armchairs, a blue sofa, and a coffee table.

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

15. Sally Webster Inn

Rockport

Cara

4.254.297 ₫

4.752.049 ₫ total

includes taxes & fees

1 Nov - 2 Nov

A coastal building with a garden and a rocky shoreline.

A room with a large window overlooking the sea, two armchairs, a small round table, and a wooden cabinet.

A dining area with tables and chairs, large windows, and a view of the water.

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

16. The Yankee Clipper Inn

Rockport

Anthony

5.151.314 ₫

5.754.017 ₫ total

includes taxes & fees

16 Nov - 17 Nov

A covered porch with white columns, a row of black rocking 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 coastal landscape with rocky terrain, a clear view of the sea, and a distant shoreline with buildings.

17. Emerson Inn

Rockport

Keith

6.898.672 ₫

7.706.016 ₫ total

includes taxes & fees

3 Nov - 4 Nov

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

An outdoor patio with wooden tables and chairs, a pergola, and a view of the water and hills.

A view from inside a room with large windows overlooking a street. There are potted plants on the windowsill and outside.

A coastal building with a balcony, large rocks in the foreground, and a clear sky.

18. Bearskin Neck Motor Lodge

Rockport

Mary Beth

6.214.320 ₫

6.941.395 ₫ total

includes taxes & fees

1 Nov - 2 Nov

A coastal scene with a sandy beach, rocky outcrops, and a lighthouse in the distance.

A hotel lobby with a sofa, armchairs, a coffee table, a TV, and a dining area with chairs and tables.

A gym with treadmills, elliptical machines, and weight equipment.

A bar area with a flat-screen TV, bar stools, a counter with various bottles, and a coffee machine.

19. The Wylie Inn and Conference Center at Endicott College

Beverly

Berna

2.724.427 ₫

3.043.185 ₫ total

includes taxes & fees

16 Nov - 17 Nov

An aerial view of a town with a prominent church, residential houses, and a large green arrow pointing downwards.

A dining area with a wooden table, chairs, and a ceiling fan.

A spacious living room with hardwood floors, a grey sofa, and a blue armchair. A kitchen with white cabinets and a refrigerator is visible in the background.

A balcony with a table set for two, featuring a bottle of wine and glasses. A chair with a towel draped over it is visible.

20. Eagle House Motel

Rockport

Glen

5.308.065 ₫

5.929.238 ₫ total

includes taxes & fees

8 Nov - 9 Nov

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Where to stay in Gloucester

Find the best Gloucester areas for the activities you enjoy most.Learn more about Gloucester

A lighthouse, a white building with a red roof, and a stone walkway leading to the water.

A lighthouse on a rocky shore with a white building and red roof in the background.

East Gloucester

If you're spending some time in East Gloucester, Good Harbor Beach and Niles Beach are top sights worth seeing.

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A statue of a man with a wheel, surrounded by a stone base with an inscription, in a public square with houses and cars in the background.

Downtown Gloucester

While visiting Downtown Gloucester, you might make a stop by sights like Cape Ann Museum and Maritime Gloucester.

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A lighthouse on a rocky shore with a wooden walkway leading to it.

Rocky Neck

While Rocky Neck isn't home to many top sights, Rocky Neck Art Colony and Maritime Gloucester are some notable places to visit nearby.

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A coastal landscape with a lighthouse, rocky shoreline, and a beach.

A lighthouse on rocky shore with clear blue water and a wooden pier.

A lighthouse on a rocky outcrop by the sea, with waves gently lapping at the shore.

Annisquam

Though Annisquam may not have many top sights, you can venture to the surrounding area to see attractions like Wingaersheek Beach and Plum Cove Beach.

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A garden with purple flowers and a foggy coastline.

Magnolia

You'll enjoy the beaches and restaurants in Magnolia. You might want to make time for a stop at Gray Beach or Massachusetts Bay.

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Stay near popular Gloucester attractions

A beach sign with footprints and a message to keep the beach clean.

Good Harbor Beach

9.2/10 (191 reviews)

Stroll along Good Harbour Beach's pristine white sands, walking to Salt Island at low tide. Reserve summer parking in advance to enjoy this Atlantic gem with its gentle surf and family-friendly atmosphere.

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Hammond Castle

9.4/10 (86 reviews)

Explore this 1920s medieval-style castle built by inventor John Hays Hammond Jr. on Massachusetts' coast. Wander through grand halls filled with Roman and Renaissance artefacts while enjoying dramatic ocean views.

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A sandy beach with a row of houses in the background.

Wingaersheek Beach

9.4/10 (83 reviews)

This pristine beach captivates with white sands, clear shallow waters, and dramatic rock formations. Visit at low tide to explore expansive sandbars and discover hidden tide pools teeming with marine life.

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A coastal town with rocky shores, a prominent church, and a clear blue sky.

Stage Fort Park

9.2/10 (71 reviews)

After visiting Stage Fort Park, make a plan to see the other sights and activities in Gloucester. Wander through the beautiful beaches and seaside in this family-friendly area.

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A bustling harbor with a red building, a maritime heritage center sign, and a crowd of people.

Maritime Gloucester

9.4/10 (63 reviews)

Maritime Gloucester showcases the oldest operating marine railway in the US alongside interactive exhibits of local marine life. Explore the historic Dory Shop or sail the harbour aboard the traditional Schooner Ardelle.

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A museum exhibit with a large wooden boat and a painting titled 'Out o' Gloucester'.

Cape Ann Museum

9.0/10 (23 reviews)

You can spend an afternoon exploring the galleries in Cape Ann Museum in Gloucester. Wander through the beautiful beaches and seaside in this family-friendly area.

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A beach with clear water, sandy shore, and green foliage.

Half Moon Beach

9.0/10 (45 reviews)

This crescent-shaped cove offers calm waters and golden sand within historic Stage Fort Park. Explore the rocky cliffs for picturesque views of Gloucester Harbour while enjoying the tranquil atmosphere.

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Plum Cove Beach

8.0/10 (2 reviews)

If a restful holiday is part of your travel plans, Plum Cove Beach might be the perfect place to visit during your trip to Gloucester. While you're in the area, stroll along the seaside.

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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 Gloucester Hotel Reviews

Beauport Hotel Gloucester

10/10 Excellent

"This hotel was excellent. It is right on the water so the views were amazing. There is a bar off the lobby where you could enjoy a cocktail and relax. The restaurant was very good. The hotel provided transportation to and from the train station for our visit to Salem."

Ashworth by the Sea

10/10 Excellent

"Clean room, nice staff"

Holiday Inn Hotel & Suites Boston - Peabody by IHG

10/10 Excellent

"The hotel was very clean and our room was really quiet. Location was good - we were going to Salem and it was easy to get to and from. Traffic was a bear but that’s not the hotel’s fault !"

Comfort Inn & Suites Logan International Airport

10/10 Excellent

"Nice airport hotel. Enjoyed the weight room"

Extended Stay America Suites Boston Peabody

8/10 Good

"It’s a bit out of the way n terms of being tucked away but staff were great even checking in at 11.30pm! Grounds looked clean, the free grab and go breakfast is awful but expected… would stay there again definitely."

Sea Lion Motel and Cottages

10/10 Excellent

"Very cozy, clean room. Had everything we needed. Great staff and premise all around."

DoubleTree by Hilton Boston North Shore

10/10 Excellent

"The staff was excellent and the place was great"

Ocean House Hotel at Bass Rocks

10/10 Excellent

"This was the perfect place to stay. Fantastic views, beautiful rooms and friendly staff. Highly recommend."

Motel 6 Danvers, MA - Boston North

8/10 Good

"Great 1 nighter"

More cheap stays in Gloucester

Red Roof Inn PLUS+ Boston - Logan

920 Broadway Saugus MA

2.243.189 ₫

2.505.541 ₫ total

15 Nov - 16 Nov

includes taxes & fees

The Northshore Hotel - Boston/Danvers

219 Newbury St. Danvers MA

2.561.427 ₫

2.861.113 ₫ total

2 Nov - 3 Nov

includes taxes & fees

Lakeside Inn

595 North Ave Wakefield MA

2.810.584 ₫

3.139.423 ₫ total

8 Nov - 9 Nov

includes taxes & fees

Best Western Plus North Shore Hotel

50 Dayton St Danvers MA

3.164.785 ₫

3.535.065 ₫ total

16 Nov - 17 Nov

includes taxes & fees

Comfort Inn & Suites Logan International Airport

85 American Legion Hwy Revere MA

3.840.847 ₫

4.445.465 ₫ total

16 Nov - 17 Nov

includes taxes & fees

9/10 Wonderful! (2,427 reviews)

Motel 6 Danvers, MA - Boston North

65 Newbury Street/US Route 1 North Danvers MA

4.010.056 ₫

4.479.233 ₫ total

20 Oct - 21 Oct

includes taxes & fees

5.6/10 (1,000 reviews)

Hotels in Gloucester with star rating

Frequently asked questions

What's the seasonal weather like in Gloucester?

The hottest months are usually July and August, with an average temperature of 19°C, while the coldest months are January and February, with an average of 1°C. The snowiest months in Gloucester are January, February, December and March, with each month seeing an average of 14 cm of snowfall.

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Find hotels in Gloucester, MA from 2.505.541 ₫

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Gloucester

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Gloucester hotels

1. Beauport Hotel Gloucester

2. Ocean House Hotel at Bass Rocks

3. The Vista

4. The Hotel at Cape Ann Marina

5. Atlantis Oceanfront Inn

6. Sea Lion Motel and Cottages

7. Castle Manor Inn

8. Long Beach Suites

9. Harborview Inn

10. The Highliner Hotel

11. Rockport Inn And Suites

12. The Cove at Rockport Hotel

13. The Rockport House

14. Addison Choate Inn

15. Sally Webster Inn

16. The Yankee Clipper Inn

17. Emerson Inn

18. Bearskin Neck Motor Lodge

19. The Wylie Inn and Conference Center at Endicott College

20. Eagle House Motel

Where to stay in Gloucester

East Gloucester

Downtown Gloucester

Rocky Neck

Annisquam

Magnolia

Stay near popular Gloucester attractions

Good Harbor Beach

Hammond Castle

Wingaersheek Beach

Stage Fort Park

Maritime Gloucester

Cape Ann Museum

Half Moon Beach

Plum Cove Beach

Learn more about Gloucester

Top Gloucester Hotel Reviews

Beauport Hotel Gloucester

Ashworth by the Sea

Holiday Inn Hotel & Suites Boston - Peabody by IHG

Comfort Inn & Suites Logan International Airport

Extended Stay America Suites Boston Peabody

Sea Lion Motel and Cottages

DoubleTree by Hilton Boston North Shore

Ocean House Hotel at Bass Rocks

Motel 6 Danvers, MA - Boston North

More cheap stays in Gloucester

Red Roof Inn PLUS+ Boston - Logan

The Northshore Hotel - Boston/Danvers

Lakeside Inn

Best Western Plus North Shore Hotel

Comfort Inn & Suites Logan International Airport

Motel 6 Danvers, MA - Boston North

Hotels in Gloucester with star rating

Frequently asked questions

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