Gloucester Luxury Vacation Rentals
Ocean Breeze-8Min Walk To Beach
- 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.
Ocean Breeze-8Min Walk To Beach
- 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.
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Beach access
A By The Bay - Stunning Seaside Apartment
- 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.
A By The Bay - Stunning Seaside Apartment
- 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.
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Beach access
Cbythesea - Ocean View Penthouse
- 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.
Cbythesea - Ocean View Penthouse
- 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.
Cheap Vacation Rentals in Gloucester Massachusetts
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Guest favorite
Retreat Near Beaches
- 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.
Retreat Near Beaches
- 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.
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Beach access
The Buoys
- 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.
The Buoys
- 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.
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Top location
Gloucester Harbor Hideaway
- 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.
Gloucester Harbor Hideaway
- 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.
Pet Friendly Vacation Rentals Gloucester Massachusetts
Point Radio Cottage
- 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.
Point Radio Cottage
- 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.
Beau
- 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.
Beau
- 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.
1 Mi To Beach! Family Gloucester Gem W/ Yard
- 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.
1 Mi To Beach! Family Gloucester Gem W/ Yard
- 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.
Gloucester Vacation Rentals Oceanfront
Spacious 2Nd Floor Suite
- 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.
Spacious 2Nd Floor Suite
- 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.
Stay At Rocky Neck
- 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.
Stay At Rocky Neck
- 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.
Bianca
- 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.
Bianca
- 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.
Gloucester Vacation Rentals with Private Pool
Gloucester Coastal Gem
- 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.
Gloucester Coastal Gem
- 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.
Walk To Good Harbor Ocean Views Open All Year
- 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.
Walk To Good Harbor Ocean Views Open All Year
- 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.
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Great deal
Stay At Smith Cove
- 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.
Stay At Smith Cove
- 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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
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.
Visit during lunch hours for special menu items and to avoid long wait times for dinner service.