Gloucester
2 guests

Adults:

2

Children:

0

Child’s age:

Gloucester

Sep 24 - Sep 25 ·
2 guests

Gloucester Vacation Rentals

Gloucester
2 guests

Adults:

2

Children:

0

Child’s age:

Over 65 stays assessed to highlight the standout picks

Navigation

1. Ocean Breeze-8Min Walk To Beach

2. A By The Bay - Stunning Seaside Apartment

3. Cbythesea - Ocean View Penthouse

4. Retreat Near Beaches

Cheap Vacation Rentals in Gloucester Massachusetts

5. The Buoys

6. Gloucester Harbor Hideaway

7. Point Radio Cottage

Pet Friendly Vacation Rentals Gloucester Massachusetts

8. Beau

9. 1 Mi To Beach! Family Gloucester Gem W/ Yard

10. Spacious 2Nd Floor Suite

Gloucester Luxury Vacation Rentals

Hotel Image Hotel Image

Ocean Breeze-8Min Walk To Beach

6A Starknaught Heights
2.9 km (1.8 mi) from city center
81
  • Cookware/ Kitchen utensils
  • Free parking
  • Express check-in/ -out
  • Air conditioning
  • Flat-screen TV
  • Sun terrace

To enjoy your vacation in Gloucester, stay at the spacious 81 m² Ocean Breeze-8Min Walk To Beach Gloucester apartment, which is within 3 km of Dogtown and about a 10-minute ride from the Stage Fort Park. The maximum occupancy at the 1-bedroom apartment is 4 guests.

9.6
37 reviews
~ US$116 / night

Ocean Breeze-8Min Walk To Beach

2.9 km (1.8 mi) from city center
81
  • Cookware/ Kitchen utensils
  • Free parking
  • Express check-in/ -out
  • Air conditioning
  • Flat-screen TV
  • Sun terrace

Ocean Breeze-8Min Walk To Beach

To enjoy your vacation in Gloucester, stay at the spacious 81 m² Ocean Breeze-8Min Walk To Beach Gloucester apartment, which is within 3 km of Dogtown and about a 10-minute ride from the Stage Fort Park. The maximum occupancy at the 1-bedroom apartment is 4 guests.

9.6
37 reviews
From US$ 116 / night
  • Beach access
Hotel Image Hotel Image

A By The Bay - Stunning Seaside Apartment

6 Centennial Avenue Apt A
1.1 km (0.7 mi) from city center
111
  • BBQ facilities
  • Free parking
  • VIP check-in/ -out
  • Air conditioning
  • Flat-screen TV
  • Sun terrace

The spacious 111 m² A By The Bay - Stunning Seaside Apartment Gloucester is a good choice for accommodating up to 6 guests, offering a convenient setting fairly close to the Melody Phaneuf Paintings. The 2-bedroom apartment with a sunbathing terrace is located only 500 metres from the Gloucester Fishermen's Wives Memorial.

Access to an ice rink helps guests maintain their bodies.

9.7
40 reviews
~ US$224 / night

A By The Bay - Stunning Seaside Apartment

1.1 km (0.7 mi) from city center
111
  • BBQ facilities
  • Free parking
  • VIP check-in/ -out
  • Air conditioning
  • Flat-screen TV
  • Sun terrace

A By The Bay - Stunning Seaside Apartment

The spacious 111 m² A By The Bay - Stunning Seaside Apartment Gloucester is a good choice for accommodating up to 6 guests, offering a convenient setting fairly close to the Melody Phaneuf Paintings. The 2-bedroom apartment with a sunbathing terrace is located only 500 metres from the Gloucester Fishermen's Wives Memorial.

Access to an ice rink helps guests maintain their bodies.

9.7
40 reviews
From US$ 224 / night
  • Beach access
Hotel Image Hotel Image

Cbythesea - Ocean View Penthouse

6 Centennial Avenue
1.1 km (0.7 mi) from city center
93
  • Cookware/ Kitchen utensils
  • Free parking
  • VIP check-in/ -out
  • Air conditioning
  • Flat-screen TV
  • Sun terrace

Featuring a prime location a 5-minute walk from the small Pavilion Sandy Beach, the spacious Cbythesea - Ocean View Penthouse Gloucester apartment accommodates up to 4 guests. Wi-Fi is provided for both business and leisure activities.

To keep up with sports routine, access to an ice rink is provided.

8.7
37 reviews
~ US$190 / night

Cbythesea - Ocean View Penthouse

1.1 km (0.7 mi) from city center
93
  • Cookware/ Kitchen utensils
  • Free parking
  • VIP check-in/ -out
  • Air conditioning
  • Flat-screen TV
  • Sun terrace

Cbythesea - Ocean View Penthouse

Featuring a prime location a 5-minute walk from the small Pavilion Sandy Beach, the spacious Cbythesea - Ocean View Penthouse Gloucester apartment accommodates up to 4 guests. Wi-Fi is provided for both business and leisure activities.

To keep up with sports routine, access to an ice rink is provided.

8.7
37 reviews
From US$ 190 / night

Cheap Vacation Rentals in Gloucester Massachusetts

  • Guest favorite
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Retreat Near Beaches

8 Calder Street 2Nd Floor
1.6 km (1.0 mi) from city center
  • BBQ facilities
  • Free parking
  • Express check-in/ -out
  • Air conditioning
  • Flat-screen TV
  • Sun terrace

Staying at the unique Retreat Near Beaches Gloucester apartment, guests can relax on a terrace 25 minutes' walk from the Eastern Point Lighthouse. This apartment is situated 6 km from Rockport train station and in close proximity to Beach & Moorland Roads bus station.

9
66 reviews
~ US$357 / night

Retreat Near Beaches

1.6 km (1.0 mi) from city center
  • BBQ facilities
  • Free parking
  • Express check-in/ -out
  • Air conditioning
  • Flat-screen TV
  • Sun terrace

Retreat Near Beaches

Staying at the unique Retreat Near Beaches Gloucester apartment, guests can relax on a terrace 25 minutes' walk from the Eastern Point Lighthouse. This apartment is situated 6 km from Rockport train station and in close proximity to Beach & Moorland Roads bus station.

9
66 reviews
From US$ 357 / night
  • Beach access
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The Buoys

9 Stuart Road
1.9 km (1.2 mi) from city center
93
  • BBQ facilities
  • Free parking
  • VIP check-in/ -out
  • Air conditioning
  • Flat-screen TV
  • Golf centre

The Buoys Villa Gloucester is within 500 metres of Gloucester Cinema, which includes cars for rent.

9.4
12 reviews
~ US$430 / night

The Buoys

1.9 km (1.2 mi) from city center
93
  • BBQ facilities
  • Free parking
  • VIP check-in/ -out
  • Air conditioning
  • Flat-screen TV
  • Golf centre

The Buoys

The Buoys Villa Gloucester is within 500 metres of Gloucester Cinema, which includes cars for rent.

9.4
12 reviews
From US$ 430 / night
  • Top location
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Gloucester Harbor Hideaway

52 Main Street 2Nd Floor
0.5 km (0.3 mi) from city center
84
  • Cookware/ Kitchen utensils
  • Free parking
  • Air conditioning
  • Ironing facilities
  • Tea and coffee facilities
  • Heating

The 84 m² Gloucester Harbor Hideaway apartment is located 2.4 km from the Eastern Point Lighthouse and about a 25-minute walk from the Small Niles Sandy Beach. The spacious apartment boasts an ice rink, perfect for guests who enjoy staying active.

Engaging in activities like hiking, cycling, and fishing can add an exciting touch to guests' stay.

9.4
5 reviews
~ US$558 / night

Gloucester Harbor Hideaway

0.5 km (0.3 mi) from city center
84
  • Cookware/ Kitchen utensils
  • Free parking
  • Air conditioning
  • Ironing facilities
  • Tea and coffee facilities
  • Heating

Gloucester Harbor Hideaway

The 84 m² Gloucester Harbor Hideaway apartment is located 2.4 km from the Eastern Point Lighthouse and about a 25-minute walk from the Small Niles Sandy Beach. The spacious apartment boasts an ice rink, perfect for guests who enjoy staying active.

Engaging in activities like hiking, cycling, and fishing can add an exciting touch to guests' stay.

9.4
5 reviews
From US$ 558 / night

Pet Friendly Vacation Rentals Gloucester Massachusetts

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Point Radio Cottage

160 Western Avenue
2.5 km (1.5 mi) from city center
149
  • BBQ facilities
  • Free parking
  • Flat-screen TV
  • Tea and coffee facilities
  • Heating
  • Garden area

To enjoy your vacation in Gloucester, stay at the spacious Point Radio Cottage Gloucester, which is just 1.8 km from the historic 8-ft bronze statue "Fishermen's Memorial Monument" and about 25 minutes' walk from the Eastern Point Lighthouse. To keep up with a sport routine, horseback riding, cycling, and fishing are offered, along with an ice rink.

9.3
3 reviews
~ US$256 / night

Point Radio Cottage

2.5 km (1.5 mi) from city center
149
  • BBQ facilities
  • Free parking
  • Flat-screen TV
  • Tea and coffee facilities
  • Heating
  • Garden area

Point Radio Cottage

To enjoy your vacation in Gloucester, stay at the spacious Point Radio Cottage Gloucester, which is just 1.8 km from the historic 8-ft bronze statue "Fishermen's Memorial Monument" and about 25 minutes' walk from the Eastern Point Lighthouse. To keep up with a sport routine, horseback riding, cycling, and fishing are offered, along with an ice rink.

9.3
3 reviews
From US$ 256 / night
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Beau

72 Mt Pleasant Ave
1.5 km (0.9 mi) from city center
101
  • BBQ facilities
  • Free parking
  • Air conditioning
  • Tea and coffee facilities
  • Skiing

The 3-bedroom Beau'S Beach House Gloucester villa, located around 5 minutes' walk from Community Church at East Gloucester, can host up to 6 guests. The accommodation features opportunities for windsurfing, snorkelling, and snow skiing in the area, 4.5 km from the medieval - style Hammond Castle.

7.7
3 reviews
~ US$221 / night

Beau

1.5 km (0.9 mi) from city center
101
  • BBQ facilities
  • Free parking
  • Air conditioning
  • Tea and coffee facilities
  • Skiing

Beau

The 3-bedroom Beau'S Beach House Gloucester villa, located around 5 minutes' walk from Community Church at East Gloucester, can host up to 6 guests. The accommodation features opportunities for windsurfing, snorkelling, and snow skiing in the area, 4.5 km from the medieval - style Hammond Castle.

7.7
3 reviews
From US$ 221 / night
Hotel Image Hotel Image

1 Mi To Beach! Family Gloucester Gem W/ Yard

22 Edgewood Rd
2.3 km (1.4 mi) from city center
128
  • Cookware/ Kitchen utensils
  • Free parking
  • Express check-in/ -out
  • Ironing facilities
  • Sun loungers

Welcoming a maximum of 6 guests, the 2-bedroom 1 Mi To Beach! Family Gloucester Gem W/ Yard villa enjoys a convenient location approximately 3 km from iconic historical sites such as Hammond Medieval Castle.

10
2 reviews
~ US$445 / night

1 Mi To Beach! Family Gloucester Gem W/ Yard

2.3 km (1.4 mi) from city center
128
  • Cookware/ Kitchen utensils
  • Free parking
  • Express check-in/ -out
  • Ironing facilities
  • Sun loungers

1 Mi To Beach! Family Gloucester Gem W/ Yard

Welcoming a maximum of 6 guests, the 2-bedroom 1 Mi To Beach! Family Gloucester Gem W/ Yard villa enjoys a convenient location approximately 3 km from iconic historical sites such as Hammond Medieval Castle.

10
2 reviews
From US$ 445 / night

Gloucester Vacation Rentals Oceanfront

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Spacious 2Nd Floor Suite

7 Alpine Court 2
0.7 km (0.5 mi) from city center
149
  • Cookware/ Kitchen utensils
  • Flat-screen TV
  • Ironing facilities
  • Tea and coffee facilities

To enjoy your vacation in Gloucester, stay at Spacious 2Nd Floor Suite Gloucester, which is about 20 minutes' walk from the Maritime Gloucester and 1.5 km from the historic 8-ft bronze statue "Fishermen's Memorial Monument". The apartment is situated within a 6-km distance of Rockport train station and right around the corner from Washington & Grove Streets bus station.

To keep up with sports routine, access to an ice rink is provided.

8.3
11 reviews
~ US$173 / night

Spacious 2Nd Floor Suite

0.7 km (0.5 mi) from city center
149
  • Cookware/ Kitchen utensils
  • Flat-screen TV
  • Ironing facilities
  • Tea and coffee facilities

Spacious 2Nd Floor Suite

To enjoy your vacation in Gloucester, stay at Spacious 2Nd Floor Suite Gloucester, which is about 20 minutes' walk from the Maritime Gloucester and 1.5 km from the historic 8-ft bronze statue "Fishermen's Memorial Monument". The apartment is situated within a 6-km distance of Rockport train station and right around the corner from Washington & Grove Streets bus station.

To keep up with sports routine, access to an ice rink is provided.

8.3
11 reviews
From US$ 173 / night
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Stay At Rocky Neck

21 Horton Street
1.0 km (0.6 mi) from city center
112
  • Cookware/ Kitchen utensils
  • Free parking
  • Air conditioning
  • Ironing facilities
  • Tea and coffee facilities
  • Patio

Up to 7 guests can stay at the 3-bedroom Stay At Rocky Neck Gloucester villa and enjoy the Elynn Kroger Gallery, located just 6 minutes' walk away.

10
4 reviews
~ US$518 / night

Stay At Rocky Neck

1.0 km (0.6 mi) from city center
112
  • Cookware/ Kitchen utensils
  • Free parking
  • Air conditioning
  • Ironing facilities
  • Tea and coffee facilities
  • Patio

Stay At Rocky Neck

Up to 7 guests can stay at the 3-bedroom Stay At Rocky Neck Gloucester villa and enjoy the Elynn Kroger Gallery, located just 6 minutes' walk away.

10
4 reviews
From US$ 518 / night
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Bianca

1 Exchange St
0.6 km (0.4 mi) from city center
88
  • Cookware/ Kitchen utensils
  • Free parking
  • Air conditioning
  • Tea and coffee facilities
  • Heating
  • Patio

Bianca Villa Gloucester, located about 5 minutes' walk from the Rogers Street, can host up to 4 guests. This accommodation features opportunities for cycling and fishing in the area, just 1.6 km from the Cape Ann Whale Watch.

9
6 reviews
~ US$285 / night

Bianca

0.6 km (0.4 mi) from city center
88
  • Cookware/ Kitchen utensils
  • Free parking
  • Air conditioning
  • Tea and coffee facilities
  • Heating
  • Patio

Bianca

Bianca Villa Gloucester, located about 5 minutes' walk from the Rogers Street, can host up to 4 guests. This accommodation features opportunities for cycling and fishing in the area, just 1.6 km from the Cape Ann Whale Watch.

9
6 reviews
From US$ 285 / night

Gloucester Vacation Rentals with Private Pool

Hotel Image Hotel Image

Gloucester Coastal Gem

27 Haskell St
1.5 km (0.9 mi) from city center
118
  • BBQ facilities
  • Free parking
  • Air conditioning
  • Ironing facilities
  • Tea and coffee facilities
  • Garden area

The 3-bedroom Gloucester Coastal Gem villa is located nearly 25 minutes' walk from The Cultural Center at Rocky Neck and provides hiking, cycling, and fishing for active guests.

9.8
13 reviews
~ US$666 / night

Gloucester Coastal Gem

1.5 km (0.9 mi) from city center
118
  • BBQ facilities
  • Free parking
  • Air conditioning
  • Ironing facilities
  • Tea and coffee facilities
  • Garden area

Gloucester Coastal Gem

The 3-bedroom Gloucester Coastal Gem villa is located nearly 25 minutes' walk from The Cultural Center at Rocky Neck and provides hiking, cycling, and fishing for active guests.

9.8
13 reviews
From US$ 666 / night
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Walk To Good Harbor Ocean Views Open All Year

Beachcroft Road 6
2.7 km (1.7 mi) from city center
119
  • Cookware/ Kitchen utensils
  • Free parking
  • Air conditioning
  • Ironing facilities
  • Tea and coffee facilities
  • Garden area

Located 4.1 km from the Bearskin Neck, the 3-bedroom Walk To Good Harbor Ocean Views Open All Year Gloucester villa provides access to various tourist attractions in the vicinity.

9
1 reviews
~ US$439 / night

Walk To Good Harbor Ocean Views Open All Year

2.7 km (1.7 mi) from city center
119
  • Cookware/ Kitchen utensils
  • Free parking
  • Air conditioning
  • Ironing facilities
  • Tea and coffee facilities
  • Garden area

Walk To Good Harbor Ocean Views Open All Year

Located 4.1 km from the Bearskin Neck, the 3-bedroom Walk To Good Harbor Ocean Views Open All Year Gloucester villa provides access to various tourist attractions in the vicinity.

9
1 reviews
From US$ 439 / night
  • Great deal
Hotel Image Hotel Image

Stay At Smith Cove

73 Rocky Neck Avenue
1.1 km (0.7 mi) from city center
158
  • Cookware/ Kitchen utensils
  • Free parking
  • Air conditioning
  • Ironing facilities
  • Golf centre
  • Patio

The 2-bedroom Stay At Smith Cove Gloucester villa, located only a 6-minute walk from the Rocky Neck Park, can host up to 7 guests. This accommodation features opportunities for fishing in the area, around 6 km from the Stage Fort Park.

10
1 reviews

Stay At Smith Cove

1.1 km (0.7 mi) from city center
158
  • Cookware/ Kitchen utensils
  • Free parking
  • Air conditioning
  • Ironing facilities
  • Golf centre
  • Patio

Stay At Smith Cove

The 2-bedroom Stay At Smith Cove Gloucester villa, located only a 6-minute walk from the Rocky Neck Park, can host up to 7 guests. This accommodation features opportunities for fishing in the area, around 6 km from the Stage Fort Park.

10
1 reviews

Are you in a hurry?

Here is a quick list of Vacation Rentals in Gloucester, selected based on their rating

Name of hotel Accommodation Rating Price, $
Ocean Breeze-8Min Walk To Beach

9.6 / 10

(37 Reviews)

From 116$
A By The Bay - Stunning Seaside Apartment

9.7 / 10

(40 Reviews)

From 224$
Cbythesea - Ocean View Penthouse

8.7 / 10

(37 Reviews)

From 190$
Retreat Near Beaches

9.0 / 10

(66 Reviews)

From 357$
The Buoys

9.4 / 10

(12 Reviews)

From 430$

Frequently Asked Questions

Which vacation rentals in Gloucester are best for beach access?

Point Radio Cottage and Ocean Breeze offer easy walking distance to popular beaches like Pavilion Beach. Both rentals provide unique sea views and spacious outdoor areas for relaxation.

Tip:

Try to visit Pavilion Beach before 10am for the best family-friendly atmosphere and fewer crowds.

What are some Gloucester rentals ideal for families?

Consider staying at 1 Mi To Beach! Family Gloucester Gem or Point Radio Cottage. They both offer ample space and are located near kid-friendly attractions.

Tip:

Book directly with the proprietors for possible discounts on extended stays or package deals for families.

Which Gloucester vacation rentals offer views?

Cbythesea - Ocean View Penthouse and A By The Bay - Stunning Seaside Apartment both provide fantastic ocean views. They also have balconies perfect for morning coffee.

Tip:

Opt for sunset hours to enjoy panoramic views while spotting passing boats along the coastline.

Are there vacation rentals in Gloucester that allow pets?

Point Radio Cottage and The Buoys are pet-friendly and welcome dogs. Enjoy your vacation without leaving your furry friends at home.

Tip:

Contact property owners directly to confirm pet policies and inquire about any associated fees.

Where can I find Gloucester rentals with kitchens?

Beau and Point Radio Cottage feature fully equipped kitchens for home-cooked meals. This amenity is convenient for families and those wanting to save on dining costs.

Tip:

Purchase local ingredients at nearby grocery stores to enhance your cooking experience while enjoying the regional flavors.

What are the best rental options for outdoor activities in Gloucester?

Stay At Rocky Neck and Gloucester Coastal Gem both offer easy access to outdoor adventures like cycling and fishing. Both locations are near popular outdoor landmarks.

Tip:

Plan outdoor activities early in the day when temperatures are cooler and wildlife is more active.

Which vacation rentals in Gloucester are suitable for a romantic getaway?

Consider Gloucester Harbor Hideaway or Retreat Near Beaches for a cozy retreat. These properties offer intimate settings and scenic views for couples.

Tip:

Book a stay during the off-season for lower rates and a quieter atmosphere to enjoy each other's company.

What seasonal events can I expect during my visit to Gloucester?

In summer, enjoy the Gloucester Fishermen's Festival, celebrating the city's fishing heritage. Autumn brings the Gloucester's Art Week, showcasing local artists.

Tip:

Plan to attend these events for a true taste of local culture, and check schedules for additional activities happening during your stay.

How can I navigate Gloucester and find local attractions?

Gloucester is walkable, but consider renting a bike or using local buses for farther destinations. Key bus stops are near major attractions like the Peabody Essex Museum.

Tip:

Download a city map app to help navigate the bike paths and frequently used public transport routes.

Where can I find the best local seafood in Gloucester?

Try Cape Ann Seafood or The Lobster Pool for fresh seafood experiences in Gloucester. They both offer local catches and stunning views.

Tip:

Visit during lunch hours for special menu items and to avoid long wait times for dinner service.

Location