Vacation homes Gloucester
Gloucester
2 guests

Adults:

2

Children:

0

Child’s age:

Gloucester

Oct 30 - Oct 31 ·
2 guests

Vacation homes in Gloucester

Gloucester
2 guests

Adults:

2

Children:

0

Child’s age:

Over 70 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

Vacation Homes in Gloucester

5. The Buoys

6. Gloucester Harbor Hideaway

7. Point Radio Cottage

Vacation Homes in Gloucester,Massachusetts with Private Pool

8. Beau

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

10. Spacious 2Nd Floor Suite

Ocean Breeze-8Min Walk To Beach Ocean Breeze-8Min Walk To Beach

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

The spacious 81 m² Ocean Breeze-8Min Walk To Beach Gloucester apartment is nearly a 10-minute ride from 7 Seas Whale Watch, and enjoys a prime location in Gloucester.

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

The spacious 81 m² Ocean Breeze-8Min Walk To Beach Gloucester apartment is nearly a 10-minute ride from 7 Seas Whale Watch, and enjoys a prime location in Gloucester.

9.6
37 reviews
From US$ 116 / night
  • Beach access
A By The Bay - Stunning Seaside Apartment A By The Bay - Stunning Seaside Apartment

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 A By The Bay - Stunning Seaside Apartment Gloucester lies within a 900-metre distance of a natural paradise like the shaped Half Moon Beach, and features luggage storage. Guests can make use of Wi-Fi for both business and leisure purposes.

Guests will immerse themselves in the ultimate relaxation at this property, boasting luxurious amenities such as a sun deck and a picnic area.

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 A By The Bay - Stunning Seaside Apartment Gloucester lies within a 900-metre distance of a natural paradise like the shaped Half Moon Beach, and features luggage storage. Guests can make use of Wi-Fi for both business and leisure purposes.

Guests will immerse themselves in the ultimate relaxation at this property, boasting luxurious amenities such as a sun deck and a picnic area.

9.7
40 reviews
From US$ 224 / night
  • Beach access
Cbythesea - Ocean View Penthouse Cbythesea - Ocean View Penthouse

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

The 93 m² Cbythesea - Ocean View Penthouse Gloucester apartment offers easy access to such tourist sites as the small Pavilion Sandy Beach, located about 5 minutes' walk away.

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

The 93 m² Cbythesea - Ocean View Penthouse Gloucester apartment offers easy access to such tourist sites as the small Pavilion Sandy Beach, located about 5 minutes' walk away.

8.7
37 reviews
From US$ 190 / night

Vacation Homes in Gloucester

  • Guest favorite
Retreat Near Beaches Retreat Near Beaches

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

Retreat Near Beaches Gloucester apartment enjoys a convenient location and provides easy access to Gloucester Fishermen's Wives Memorial 2.5 km away. Guests can stay at the unique 2-room apartment with views of the garden, and with a sundeck and a picnic area available on site.

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

Retreat Near Beaches Gloucester apartment enjoys a convenient location and provides easy access to Gloucester Fishermen's Wives Memorial 2.5 km away. Guests can stay at the unique 2-room apartment with views of the garden, and with a sundeck and a picnic area available on site.

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

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 course

Situated 3.3 km from the medieval-style Hammond Castle, The Buoys Villa Gloucester offers guests to enjoy a picnic area and a golf course. This 3-bedroom holiday home accommodates 6 guests and includes bicycles and hire available 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 course

The Buoys

Situated 3.3 km from the medieval-style Hammond Castle, The Buoys Villa Gloucester offers guests to enjoy a picnic area and a golf course. This 3-bedroom holiday home accommodates 6 guests and includes bicycles and hire available for rent.

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

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 2-bedroom Gloucester Harbor Hideaway apartment lies in a prime location in Gloucester, about a 5-minute walk from Main Street. This spacious apartment offers modern facilities, such as Wi-Fi and essentials like parking for car travellers.

Guests have the opportunity to make their stay at Gloucester Harbor Hideaway apartment more exciting by participating in hiking, cycling, and fisheries.

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 2-bedroom Gloucester Harbor Hideaway apartment lies in a prime location in Gloucester, about a 5-minute walk from Main Street. This spacious apartment offers modern facilities, such as Wi-Fi and essentials like parking for car travellers.

Guests have the opportunity to make their stay at Gloucester Harbor Hideaway apartment more exciting by participating in hiking, cycling, and fisheries.

9.4
5 reviews
From US$ 558 / night

Vacation Homes in Gloucester,Massachusetts with Private Pool

Point Radio Cottage Point Radio Cottage

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

The Cultural Center at Rocky Neck lies nearly 25 minutes' walk from the spacious 149 m² Point Radio Cottage Gloucester, while the shaped Half Moon Beach is a mere 1.1 km away.

Make your stay at the accommodation more exciting by joining in windsurfing, snorkelling, and diving.

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

The Cultural Center at Rocky Neck lies nearly 25 minutes' walk from the spacious 149 m² Point Radio Cottage Gloucester, while the shaped Half Moon Beach is a mere 1.1 km away.

Make your stay at the accommodation more exciting by joining in windsurfing, snorkelling, and diving.

9.3
3 reviews
From US$ 256 / night
Beau Beau

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 2-bedroom Beau Villa Gloucester offers easy access to such tourist spots as Community Church at East Gloucester, located just a 5-minute walk away.

Snorkelling, snow skiing, and mini golf are offered in the vicinity of the Gloucester property.

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 2-bedroom Beau Villa Gloucester offers easy access to such tourist spots as Community Church at East Gloucester, located just a 5-minute walk away.

Snorkelling, snow skiing, and mini golf are offered in the vicinity of the Gloucester property.

7.7
3 reviews
From US$ 221 / night
1 Mi To Beach! Family Gloucester Gem W/ Yard 1 Mi To Beach! Family Gloucester Gem W/ Yard

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

The 2-bedroom 1 Mi To Beach! Family Gloucester Gem W/ Yard villa accommodates up to 6 guests and is within 3 km of significant historical sites such as the medieval-style Hammond 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

The 2-bedroom 1 Mi To Beach! Family Gloucester Gem W/ Yard villa accommodates up to 6 guests and is within 3 km of significant historical sites such as the medieval-style Hammond Castle.

10
2 reviews
From US$ 445 / night

Luxury Vacation Homes in Gloucester

Spacious 2Nd Floor Suite Spacious 2Nd Floor Suite

Spacious 2Nd Floor Suite

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

The 2-bedroom Spacious 2Nd Floor Suite Gloucester offers a prime location nearly 5 minutes' walk from Rogers Street. The maximum occupancy at this 149 m² apartment is 4 guests.

8.3
11 reviews
~ US$173 / night

Spacious 2Nd Floor Suite

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

Spacious 2Nd Floor Suite

The 2-bedroom Spacious 2Nd Floor Suite Gloucester offers a prime location nearly 5 minutes' walk from Rogers Street. The maximum occupancy at this 149 m² apartment is 4 guests.

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

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

The 3-bedroom Stay At Rocky Neck Gloucester villa accommodates up to 7 guests and offers proximity to Maritime Gloucester, located just a 5-minute 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

The 3-bedroom Stay At Rocky Neck Gloucester villa accommodates up to 7 guests and offers proximity to Maritime Gloucester, located just a 5-minute walk away.

10
4 reviews
From US$ 518 / night
Bianca Bianca

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

The 2-bedroom Bianca Villa Gloucester is located within 5 minutes' walk of Rogers Street and provides guests with a patio and a golf course to ensure a memorable stay. At this Gloucester holiday home, located in the vicinity of 7 Seas Whale Watch, guests can enjoy cycling and fisheries.

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

The 2-bedroom Bianca Villa Gloucester is located within 5 minutes' walk of Rogers Street and provides guests with a patio and a golf course to ensure a memorable stay. At this Gloucester holiday home, located in the vicinity of 7 Seas Whale Watch, guests can enjoy cycling and fisheries.

9
6 reviews
From US$ 285 / night

Cheap Vacation Homes in Gloucester,Massachusetts

Gloucester Coastal Gem Gloucester Coastal Gem

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 around a 10-minute ride from Gloucester Fishermen's Wives Memorial and allows guests to enjoy windsurfing, snorkelling, and diving.

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 around a 10-minute ride from Gloucester Fishermen's Wives Memorial and allows guests to enjoy windsurfing, snorkelling, and diving.

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

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

The 3-bedroom Walk To Good Harbor, Ocean Views, Open All Year! Gloucester villa offers proximity to nearby tourist spots, such as Cape Ann Whale Watch, situated nearly 25 minutes' walk away.

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

The 3-bedroom Walk To Good Harbor, Ocean Views, Open All Year! Gloucester villa offers proximity to nearby tourist spots, such as Cape Ann Whale Watch, situated nearly 25 minutes' walk away.

9
1 reviews
From US$ 439 / night
Stay At Smith Cove Stay At Smith Cove

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 course
  • Patio

The 2-bedroom Stay At Smith Cove Gloucester villa hosts up to 7 guests and provides proximity to The Cultural Center at Rocky Neck, situated only 5 minutes' walk away. This Gloucester holiday home features opportunities for fisheries in the area, 3.6 km from the gaff rigged knockabout Adventure Schooner.

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 course
  • Patio

Stay At Smith Cove

The 2-bedroom Stay At Smith Cove Gloucester villa hosts up to 7 guests and provides proximity to The Cultural Center at Rocky Neck, situated only 5 minutes' walk away. This Gloucester holiday home features opportunities for fisheries in the area, 3.6 km from the gaff rigged knockabout Adventure Schooner.

10
1 reviews

Pet Friendly Vacation Homes in Gloucester

Stay At The Neck Stay At The Neck

Stay At The Neck

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

Situated about 5 minutes' walk from The Cultural Center at Rocky Neck, the 3-bedroom Stay At The Neck Gloucester villa entices guests with fisheries in the area. Providing guests with Wi-Fi and private parking, the property is 3.9 km from the medieval - style Hammond Castle.

10
1 reviews

Stay At The Neck

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

Stay At The Neck

Situated about 5 minutes' walk from The Cultural Center at Rocky Neck, the 3-bedroom Stay At The Neck Gloucester villa entices guests with fisheries in the area. Providing guests with Wi-Fi and private parking, the property is 3.9 km from the medieval - style Hammond Castle.

10
1 reviews
  • Great deal
Airstream & Ocean View: Unique Gloucester Getaway Airstream & Ocean View: Unique Gloucester Getaway

Airstream & Ocean View: Unique Gloucester Getaway

7 Whale Rocks Rd
5.8 km (3.6 mi) from city center
74
  • Cookware/ Kitchen utensils
  • Free parking
  • 24-hour reception
  • Flat-screen TV
  • Ironing facilities
  • Sun loungers

The 2-bedroom Airstream & Ocean View: Unique Gloucester Getaway villa hosts up to 4 guests and is nestled approximately a 10-minute ride from natural sites such as the scenic Wingaersheek Beach.

Added amenities at Airstream & Ocean View: Unique Gloucester Getaway villa include canyoning and hiking for sport lovers.

10
1 reviews

Airstream & Ocean View: Unique Gloucester Getaway

5.8 km (3.6 mi) from city center
74
  • Cookware/ Kitchen utensils
  • Free parking
  • 24-hour reception
  • Flat-screen TV
  • Ironing facilities
  • Sun loungers

Airstream & Ocean View: Unique Gloucester Getaway

The 2-bedroom Airstream & Ocean View: Unique Gloucester Getaway villa hosts up to 4 guests and is nestled approximately a 10-minute ride from natural sites such as the scenic Wingaersheek Beach.

Added amenities at Airstream & Ocean View: Unique Gloucester Getaway villa include canyoning and hiking for sport lovers.

10
1 reviews

Are you in a hurry?

Here is a quick list of hotels 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$

Location