Gloucester Holiday Homes from €275: Search Top 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 holiday homes

A kitchen with wooden cabinets, a central island with bar stools, a built-in bookshelf, and a view through glass doors.

1. Beach Life Bliss - steps to the beach

Gloucester

rick b.

includes taxes & fees

20 Oct - 21 Oct

A modern kitchen with white cabinets, a granite countertop, a built-in oven, and a stainless steel sink.

2. The Essex of Gloucester

Gloucester

Katie B.

includes taxes & fees

12 Nov - 13 Nov

A residential property with a well-maintained lawn, a stone retaining wall, and a wooden deck.

3. 3BR Harborside Home • Gloucester+Rockport • Ocean View

East Gloucester

Valerie N.

A staircase with wooden steps leading to a room with a wooden ceiling.

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

Gloucester

Karen T.

includes taxes & fees

2 Nov - 3 Nov

A bedroom with a bed, bedside tables, a desk, and a bench.

5. Oceanview Home/Walk to Lanes Cove and Plum Cove beach I Sleeps 6

Gloucester

Sara G.

includes taxes & fees

26 Oct - 27 Oct

A two-story house with a wrap-around porch, a curved driveway, and a view of a large body of water.

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

Gloucester

Maarij K.

includes taxes & fees

14 Oct - 15 Oct

A spacious living room with a large TV, comfortable seating, and large windows offering a view of the outdoors.

7. Stay at Little River

Gloucester

includes taxes & fees

15 Oct - 16 Oct

A waterfront property with a dock, a small house with a balcony, and a larger house with a garage.

8. Stay at Rocky Neck

Rocky Neck

Joy B.

A beach with people sunbathing and swimming, a rocky outcrop in the foreground, and a small island in the background.

9. Bell Buoy

Rockport

"The property is nicely located but in need of updates. A lot of the lamps are plug in vs light switch and there were some flickering lights behind the TV. One lamp was missing a light bulb. No outlet in the bathroom for a hair dryer. The second bathroom is missing a door handle making it hard to open and close. We were unable to reach the ceiling fan chain without having to get on the bed, The Air Conditioner wasn't working on he first floor which made it a bit stuff but with open windows at...

Amy

includes taxes & fees

8 Nov - 9 Nov

A coastal town with a marina filled with boats, surrounded by residential buildings and a large green area.

10. Newly Renovated 2BR Rockport Home w/ parking Steps to Back Beach+Bearskin Neck!

Rockport

Bridget H.

includes taxes & fees

2 Nov - 3 Nov

A wooden deck with wicker furniture and a white chair, overlooking a beach with a rocky shoreline and a clear blue sky.

11. Oceanfront 4 BR/2 Bath Long Beach Vacation Home - Grill, Outdoor shower, AC

Rockport

Emmy D.

includes taxes & fees

18 Oct - 19 Oct

A spacious living room with a high ceiling, wooden beams, a sofa, a blue armchair, a coffee table, and a dining area with a table and chairs.

12. Historic Renovation, Walk to Front Beach and Shopping

Rockport

Dan K.

includes taxes & fees

4 Nov - 5 Nov

A stone fire pit surrounded by Adirondack chairs in a landscaped area with a stone wall and a large tree.

13. Home w/firepit l Walk to Bearskin Neck+Beach

Rockport

Juliet S.

A large, two-story house with a steeply pitched roof, surrounded by lush greenery and a view of the sea.

14. Experience Classic New England-walk to beach&shops

Rockport

Danielle L.

includes taxes & fees

8 Nov - 9 Nov

A beach with a sunset, rocky shoreline, and calm waters.

15. Singing Beach Passes|Outdoor fireplace|Wraparound Deck|King Bed

Manchester-by-the-Sea

Colorado B.

A spacious living area with a large TV, a kitchen, and a dining area.

16. Family Friendly 2BR Home · Walk to Beach + Downtown Rockport · KING Bed

Rockport

Kelley S.

includes taxes & fees

31 Oct - 1 Nov

A modern kitchen with a large island, white cabinets, and a view of a garden through a sliding glass door.

17. Historic Marblehead Nautical Home • Minutes to Salem

Marblehead Historic District

Kevin H.

includes taxes & fees

19 Oct - 20 Oct

A beach with a wooden fence, sand, and the ocean.

18. Baby Love Shack: walk to Beach, Eateries, Dancing, Arcades, Shows

Salisbury Beach

"I booked a last minute stay for some time at the ocean. The booking/check in process was so easy with very detailed instructions sent the day of my arrival. The place was exactly as pictured, a well-appointed, clean cottage, with everything I needed. The host also left a welcome gift that was thoughtful and useful. I walked the few blocks to the ocean everyday, multiple times a day to walk for hours on the beaches. I got food from a nice little Italian restaurant (Capri) just a block away. The...

Maura

includes taxes & fees

14 Oct - 15 Oct

A comfy queen bed - the perfect size for snuggling!

19. Love Shack: Walk to Beach, Carousel, Restaurants, & Dancing

Salisbury Beach

includes taxes & fees

21 Oct - 22 Oct

A room with a large window overlooking a wooden deck with white railings and a lighthouse in the distance.

20. The Sunset Lighthouse Marblehead - Exclusive Waterfront 3brm/2.5bath Home

Marblehead

Katherine B.

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Top Gloucester Hotel Reviews

DoubleTree by Hilton Boston North Shore

10/10 Excellent

"Nice property with onsite bar."

Ocean House Hotel at Bass Rocks

8/10 Good

"This hotel is fine. The location with the view is lovely. The only disappointment was with the listing photos on Hotels.com. The large building in the first photo makes it seem like this is the hotel. It's not. It's a beautiful building that houses the lobby and maybe staff rooms? Or, maybe it has higher price point rooms that I didn't see on the listing. The actual hotel is a 2-tiered strip hotel that looks like it dates back to the 50s when that was the norm. The room was nice, and the view was lovely. I'm usually really good about going elsewhere than Hotels.com to research hotels and see what they actually look like, the location, etc. I didn't do that this time. Hotels.com puts some misleading photos on their site to make the hotel look better and not what they look like in real life."

The Cove At Salem

10/10 Excellent

"The facility appears to be new and exceptionally clean. The rooms a large with comfortable furniture. The bathrooms are well equipped and clean. You get a combination code for your room which is nice. No need to keep track of a key. There is plenty of parking for now but more rooms are being built. Cell phone service (at least Verizon) is TERRIBLE around the hotel. They have WIFI that works fairly well in the evening, but I found that when the staff is in the office, WIFI performance degrades a great deal. I don't know what they are doing to sap the bandwidth. For television, they provide Roku boxes on TVs. You can use your home account to access whatever streaming service that is supported by Roku. Just make sure you delete the quick access link which is supposed to delete your personal streaming accounts. If you're looking at going into Salem for the museums, etc., it is about a 20 minute walk. The sidewalks are very uneven, so the walk could be troublesome for those with walkers and canes. For restaurants and stores, that 20 minute walk is necessary. There is a breakfast place with 4 or 5 tables that you can reach within 10 minutes by walking. The staff pointed out they have something called "Skipper" for transportation and provided a phone number. They really should have mentioned the need to set up an account with Skipper before trying to arrange a ride. A map of the area should also be provided at the hotel. Some are free at the attractions."

Find out more about Gloucester

Gloucester Holiday Homes information

Number of reviews	317
Accommodation	521 Holiday Homes
Lowest Price	€275
Highest Price	€1,098

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Check prices for these dates

Our top choices for Gloucester holiday homes

1. Beach Life Bliss - steps to the beach

2. The Essex of Gloucester

3. 3BR Harborside Home • Gloucester+Rockport • Ocean View

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

5. Oceanview Home/Walk to Lanes Cove and Plum Cove beach I Sleeps 6

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

7. Stay at Little River

8. Stay at Rocky Neck

9. Bell Buoy

10. Newly Renovated 2BR Rockport Home w/ parking Steps to Back Beach+Bearskin Neck!

11. Oceanfront 4 BR/2 Bath Long Beach Vacation Home - Grill, Outdoor shower, AC

12. Historic Renovation, Walk to Front Beach and Shopping

13. Home w/firepit l Walk to Bearskin Neck+Beach

14. Experience Classic New England-walk to beach&shops

15. Singing Beach Passes|Outdoor fireplace|Wraparound Deck|King Bed

16. Family Friendly 2BR Home · Walk to Beach + Downtown Rockport · KING Bed

17. Historic Marblehead Nautical Home • Minutes to Salem

18. Baby Love Shack: walk to Beach, Eateries, Dancing, Arcades, Shows

19. Love Shack: Walk to Beach, Carousel, Restaurants, & Dancing

20. The Sunset Lighthouse Marblehead - Exclusive Waterfront 3brm/2.5bath Home

Find holiday rentals that suit your style

Top Gloucester Hotel Reviews

DoubleTree by Hilton Boston North Shore

Lakeside Inn

Ashworth by the Sea

Quality Inn Boston - Revere

Ocean House Hotel at Bass Rocks

The Highliner Hotel

Motel 6 Danvers, MA - Boston North

Sea Lion Motel and Cottages

The Cove At Salem

Find out more about Gloucester

Gloucester Holiday Homes information

Holiday Homes in Gloucester

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Gloucester holiday homes

1. Beach Life Bliss - steps to the beach

2. The Essex of Gloucester

3. 3BR Harborside Home • Gloucester+Rockport • Ocean View

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

5. Oceanview Home/Walk to Lanes Cove and Plum Cove beach I Sleeps 6

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

7. Stay at Little River

8. Stay at Rocky Neck

9. Bell Buoy

10. Newly Renovated 2BR Rockport Home w/ parking Steps to Back Beach+Bearskin Neck!

11. Oceanfront 4 BR/2 Bath Long Beach Vacation Home - Grill, Outdoor shower, AC

12. Historic Renovation, Walk to Front Beach and Shopping

13. Home w/firepit l Walk to Bearskin Neck+Beach

14. Experience Classic New England-walk to beach&shops

15. Singing Beach Passes|Outdoor fireplace|Wraparound Deck|King Bed

16. Family Friendly 2BR Home · Walk to Beach + Downtown Rockport · KING Bed

17. Historic Marblehead Nautical Home • Minutes to Salem

18. Baby Love Shack: walk to Beach, Eateries, Dancing, Arcades, Shows

19. Love Shack: Walk to Beach, Carousel, Restaurants, & Dancing

20. The Sunset Lighthouse Marblehead - Exclusive Waterfront 3brm/2.5bath Home

Find holiday rentals that suit your style

Top Gloucester Hotel Reviews

DoubleTree by Hilton Boston North Shore

Find out more about Gloucester

Gloucester Holiday Homes information