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

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Check prices for these dates

In two weeks
Sep 18 - Sep 20
In two months
Oct 30 - Nov 1
In three months
Nov 27 - Nov 29
In four months
Dec 25 - Dec 27

Our top choices for Gloucester vacation homes

A marina with boats docked at the pier, reflecting the sunset sky.

1. Cripple Cove Apartment in historic home across from harbour in Gloucester, MA

Cripple Cove Apartment in historic home across from harbour in Gloucester, MA
East Gloucester
9.6 out of 10, Exceptional, (37 reviews)
"Linda was so kind and what a fun little home she opened up to us! "
United States
Hillary M.
The price is ￥32,042
￥71,582 total
includes taxes & fees
Sep 3 - Sep 4
Cripple Cove Apartment in historic home across from harbour in Gloucester, MA
A staircase with wooden steps leading to a room with a wooden ceiling.

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

Oceanside Village Home~Private Fenced Yard~Reserved Parking
Gloucester
9.6 out of 10, Exceptional, (14 reviews)
"The home was warm and inviting upon our arrival. We loved the home. Rachel responds immediately with any questions. Cape Ann is beautiful and convenient to Boston. We loved our visit and felt at home! "
United States
Melenia s.
The price is ￥21,677
￥63,659 total
includes taxes & fees
Sep 9 - Sep 10
Oceanside Village Home~Private Fenced Yard~Reserved Parking
A living room with a sectional sofa, a wooden coffee table, and a ceiling fan.

3. Cozy two bedroom house in the heart of Gloucester

Cozy two bedroom house in the heart of Gloucester
Gloucester
9.4 out of 10, Exceptional, (19 reviews)
"For our one night stay it was perfect, Clean and comfortable, plenty of basic's, bedding, towels and kitchen supply's."
United States
CHARLES
The price is ￥31,958
￥66,398 total
includes taxes & fees
Sep 21 - Sep 22
Cozy two bedroom house in the heart of Gloucester
A modern kitchen with white cabinets, a granite countertop, a built-in oven, and a stainless steel sink.

4. The Essex of Gloucester

The Essex of Gloucester
Gloucester
10.0 out of 10, Exceptional, (12 reviews)
"Very clean and perfect place to stay while we were in a wedding at the Beauport! The host checked in often and made us feel very welcomed and at home"
United States
Katie B.
The price is ￥42,936
￥54,939 total
includes taxes & fees
Sep 29 - Sep 30
The Essex of Gloucester
A spacious living room with a large window, a sofa, a coffee table, a chair, and a TV mounted on the wall.

5. 3BR/2 BA Harborside Home · Fenced Backyard+Grill · Ocean Views

3BR/2 BA Harborside Home · Fenced Backyard+Grill · Ocean Views
East Gloucester
9.8 out of 10, Exceptional, (49 reviews)
"Beautiful, wonderfully well stocked home with everything anyone would need! And not just starter supplies either! They even have beach necessities in a shed out back! Quality and quantity amazing in everything! Beautiful views, comfortable rocking chairs on front porch. Everything was great!!"
United States
Michele V.
The price is ￥36,250
￥92,253 total
includes taxes & fees
Sep 22 - Sep 23
3BR/2 BA Harborside Home · Fenced Backyard+Grill · Ocean Views
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

Classic Coastal Family Home | Walk to Sea;King Bed
Gloucester
10.0 out of 10, Exceptional, (4 reviews)
"Property was excellent, beautifully decorated with good taste, location was beautiful, everyone enjoyed the weekend stay. Rooms were clean, beds were comfortable."
United States
Maarij K.
The price is ￥42,103
￥143,929 total
includes taxes & fees
Sep 9 - Sep 10
Classic Coastal Family Home | Walk to Sea;King Bed
A wooden staircase with a railing leading to a covered deck area.

7. 3BR Oceanview Townhouse on Boulevard I Walk to downtown l Sleeps 8

3BR Oceanview Townhouse on Boulevard I Walk to downtown l Sleeps 8
Gloucester
10.0 out of 10, Exceptional, (17 reviews)
"Rachel was very responsive and attentive, excellent host. The house was in a great location, clean, and very comfortable. Would stay there again should the need arise."
United States
Betty
The price is ￥43,651
￥94,929 total
includes taxes & fees
Sep 3 - Sep 4
3BR Oceanview Townhouse on Boulevard I Walk to downtown l Sleeps 8
A kitchen with wooden cabinets, a central island with bar stools, a built-in bookshelf, and a view through glass doors.

8. Beach Life Bliss - steps to the beach

Beach Life Bliss - steps to the beach
Gloucester
9.8 out of 10, Exceptional, (54 reviews)
"A wonderful place to stay!"
United States
rich k.
The price is ￥52,411
￥96,919 total
includes taxes & fees
Sep 9 - Sep 10
Beach Life Bliss - steps to the beach
A bedroom with a bed, bedside tables, a desk, and a bench.

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

Oceanview Home/Walk to Lanes Cove and Plum Cove beach I Sleeps 6
Gloucester
10.0 out of 10, Exceptional, (1 review)
"We loved our stay. The property is beautiful with wonderful views. Convenient to get most places."
United States
Sara G.
Oceanview Home/Walk to Lanes Cove and Plum Cove beach I Sleeps 6
A living room with a fireplace, sofas, a TV, and wooden beams on the ceiling.

10. Stay at Good Harbor Beach

Stay at Good Harbor Beach
East Gloucester
10.0 out of 10, Exceptional, (1 review)
"House was incredible and great for a group. Super nice house with everything we needed. Walked to the beach , cooked great meals, Allie was super helpful and accommodating. Would love to come back."
United States
hawley s.
The price is ￥258,860
￥419,965 total
includes taxes & fees
Sep 21 - Sep 22
Stay at Good Harbor Beach
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.

11. Historic Renovation, Walk to Front Beach and Shopping

Historic Renovation, Walk to Front Beach and Shopping
Rockport
9.8 out of 10, Exceptional, (9 reviews)
"This house worked well for our family with seven people of all ages and really enjoyed our first trip to the Rockport/Gloucester area. Hopefully we'll get a chance to return and would highly recommend the area and property."
United States
Dan K.
The price is ￥38,222
￥99,808 total
includes taxes & fees
Sep 7 - Sep 8
Historic Renovation, Walk to Front Beach and Shopping
A coastal town with a marina filled with boats, surrounded by residential buildings and a large green area.

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

Newly Renovated 2BR Rockport Home w/ parking Steps to Back Beach+Bearskin Neck!
Rockport
10.0 out of 10, Exceptional, (44 reviews)
"Great stay. Will stay again for sure!"
United States
Maryanne H.
The price is ￥41,715
￥89,610 total
includes taxes & fees
Sep 17 - Sep 18
Newly Renovated 2BR Rockport Home w/ parking Steps to Back Beach+Bearskin Neck!
A spacious living area with a large TV, a kitchen, and a dining area.

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

Family Friendly 2BR Home · Walk to Beach + Downtown Rockport · KING Bed
Rockport
9.8 out of 10, Exceptional, (19 reviews)
"Absolutely loved this home!!! We didn’t want to leave and tried for another night , but unfortunately wasn’t able to stay because it was booked with someone else already! The location was close to down town and everyone here was as absolutely welcoming! Would love to stay again!"
United States
Angela G.
The price is ￥38,072
￥84,651 total
includes taxes & fees
Sep 27 - Sep 28
Family Friendly 2BR Home · Walk to Beach + Downtown Rockport · KING Bed
A wooden deck with wicker furniture and a white chair, overlooking a beach with a rocky shoreline and a clear blue sky.

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

Oceanfront 4 BR/2 Bath Long Beach Vacation Home - Grill, Outdoor shower, AC
Rockport
10.0 out of 10, Exceptional, (38 reviews)
"Great spot right on Long Beach! Has great views of the ocean right on the water. We definitely stay there again pet friendly."
United States
Emmy D.
Oceanfront 4 BR/2 Bath Long Beach Vacation Home - Grill, Outdoor shower, AC
A beach with a wooden fence, sand, and the ocean.

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

Baby Love Shack: walk to Beach, Eateries, Dancing, Arcades, Shows
Salisbury Beach
10.0 out of 10, Exceptional, (3 reviews)
"Clean, quiet & quaint! Perfect for a couple’s get away!"
United States
Shannon S.
The price is ￥20,295
￥70,503 total
includes taxes & fees
Sep 7 - Sep 8
Baby Love Shack: walk to Beach, Eateries, Dancing, Arcades, Shows
A modern kitchen with a large island, white cabinets, and a view of a garden through a sliding glass door.

16. 2BR Historic Marblehead Home+Minutes to Beach

2BR Historic Marblehead Home+Minutes to Beach
Marblehead Historic District
10.0 out of 10, Exceptional, (25 reviews)
"We enjoyed our stay at this property. It is in a great location. Easy to walk to restaurants and stores in Marblehead. It was nice to not have to spend more time in our car after driving from Georgia. Property had everything we needed to live comfortably during our stay."
United States
Kevin H.
The price is ￥36,250
￥79,580 total
includes taxes & fees
Sep 20 - Sep 21
2BR Historic Marblehead Home+Minutes to Beach
A beach with people sunbathing and swimming, a rocky outcrop in the foreground, and a small island in the background.

17. Bell Buoy

Bell Buoy
3.5 star property
Rockport
6.0 out of 10, (1 review)
"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...
United States
Amy
The price is ￥49,245
￥91,653 total
includes taxes & fees
Sep 28 - Sep 29
Bell Buoy
A large, two-story house with a steeply pitched roof, surrounded by lush greenery and a view of the sea.

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

Experience Classic New England-walk to beach&shops
Rockport
10.0 out of 10, Exceptional, (1 review)
"Property was extremely clean. Comfortably fit my group of 8 adults. The deck hot tub was the biggest hot tub I have ever seen. Such a great place! Victor was extremely nice and responsive. "
United States
Danielle L.
The price is ￥68,634
￥167,573 total
includes taxes & fees
Sep 8 - Sep 9
Experience Classic New England-walk to beach&shops
A room with a large window overlooking a wooden deck with white railings and a lighthouse in the distance.

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

The Sunset Lighthouse Marblehead - Exclusive Waterfront 3brm/2.5bath Home
Marblehead
9.8 out of 10, Exceptional, (22 reviews)
"The property was lovely and well kept! And the location was amazing! Very nice and quiet neighborhood - definitely recommend "
United States
Katherine B.
The price is ￥43,143
￥102,273 total
includes taxes & fees
Sep 8 - Sep 9
The Sunset Lighthouse Marblehead - Exclusive Waterfront 3brm/2.5bath Home
A spacious kitchen with a dining area, a balcony, and a sign reading "BEACH HOUSE".

20. Plovers Nest: Stay in the Heart of Newburyport for Yankee Homecoming!

Plovers Nest: Stay in the Heart of Newburyport for Yankee Homecoming!
Newburyport
9.8 out of 10, Exceptional, (88 reviews)
"Perfect for a two person stay to relax and enjoy the local activities!"
United States
Tom B.
The price is ￥33,965
￥78,942 total
includes taxes & fees
Sep 10 - Sep 11
Plovers Nest: Stay in the Heart of Newburyport for Yankee Homecoming!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Gloucester Hotel Reviews

Atlantis Oceanfront Inn

Atlantis Oceanfront Inn

10/10 Excellent
"The Atlantis Oceanfront Inn was definitely a great choice for our stay. We were in the area to take our son to college. The ocean view was spectacular. The property was absolutely spotless. The rooms were comfortable and had everything we needed. Staff were very friendly and helpful. We were impressed - including my husband, who is very particular. Would definitely stay there again!"
Amanda 3-night trip
Posted 3 hours ago
Atlantis Oceanfront Inn

Find out more about Gloucester

Gloucester Vacation Homes information

Number of reviews
419
Accommodation
516 Vacation Homes
Lowest Price
￥54,939
Highest Price
￥419,965