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 Commons and about a 10-minute ride from Stage Fort Park. The 1-bedroom apartment can hold up to 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 Commons and about a 10-minute ride from Stage Fort Park. The 1-bedroom apartment can hold up to 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
To enjoy your vacation in Gloucester, stay at the spacious 111 m² A By The Bay - Stunning Seaside Apartment Gloucester, which is only 50 metres from Melody Phaneuf Paintings and around a 10-minute ride from The Cultural Center at Rocky Neck. The 2-bedroom apartment is situated only a few steps from Gloucester Fishermen's Wives Memorial and offers a sunbathing terrace and a picnic area.
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
To enjoy your vacation in Gloucester, stay at the spacious 111 m² A By The Bay - Stunning Seaside Apartment Gloucester, which is only 50 metres from Melody Phaneuf Paintings and around a 10-minute ride from The Cultural Center at Rocky Neck. The 2-bedroom apartment is situated only a few steps from Gloucester Fishermen's Wives Memorial and offers a sunbathing terrace and a picnic area.
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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. This apartment is situated 7 km from Rockport train station and just steps from Western & Centennial Avenues bus station.
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. This apartment is situated 7 km from Rockport train station and just steps from Western & Centennial Avenues bus station.
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
The unique Retreat Near Beaches Gloucester apartment is located 2.4 km from Eastern Point Lighthouse and 25 minutes' walk from the historic 8-ft bronze statue "Fishermen's Memorial Monument". This apartment provides guests with garden views and luggage storage.
Thanks to luxuries such as a sun deck and a picnic area, the ultimate relaxation experience is ensured.
Retreat Near Beaches
- BBQ facilities
- Free parking
- Express check-in/ -out
- Air conditioning
- Flat-screen TV
- Sun terrace
Retreat Near Beaches
The unique Retreat Near Beaches Gloucester apartment is located 2.4 km from Eastern Point Lighthouse and 25 minutes' walk from the historic 8-ft bronze statue "Fishermen's Memorial Monument". This apartment provides guests with garden views and luggage storage.
Thanks to luxuries such as a sun deck and a picnic area, the ultimate relaxation experience is ensured.
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Beach access
The Buoys
- BBQ facilities
- Free parking
- VIP check-in/ -out
- Air conditioning
- Flat-screen TV
- Golf centre
Suitable for 6 guests, The Buoys Villa Gloucester offers a location within 500 metres of Gloucester Cinema and features a picnic area and a golf course. Located a 10-minute drive from Cape Ann Historical Museum, the 3-bedroom villa provides Wi-Fi and a car park.
The Buoys
- BBQ facilities
- Free parking
- VIP check-in/ -out
- Air conditioning
- Flat-screen TV
- Golf centre
The Buoys
Suitable for 6 guests, The Buoys Villa Gloucester offers a location within 500 metres of Gloucester Cinema and features a picnic area and a golf course. Located a 10-minute drive from Cape Ann Historical Museum, the 3-bedroom villa provides Wi-Fi and a car park.
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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 Eastern Point Lighthouse and about a 25-minute walk from the Small Niles Sandy Beach. Wi-Fi and parking are also available at the spacious apartment.
For a more exciting experience, guests can take part in hiking, cycling, and fisheries during their 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 Eastern Point Lighthouse and about a 25-minute walk from the Small Niles Sandy Beach. Wi-Fi and parking are also available at the spacious apartment.
For a more exciting experience, guests can take part in hiking, cycling, and fisheries during their 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 1-bedroom 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 Eastern Point Lighthouse. This 149 m² apartment is situated approximately 10 minutes' drive from Rockport train station and within reach of Western Avenue & Stillington Drive bus station.
If you're drawn to sports, windsurfing, snorkelling, and diving available at the apartment are sure to delight.
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 1-bedroom 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 Eastern Point Lighthouse. This 149 m² apartment is situated approximately 10 minutes' drive from Rockport train station and within reach of Western Avenue & Stillington Drive bus station.
If you're drawn to sports, windsurfing, snorkelling, and diving available at the apartment are sure to delight.
Beau
- BBQ facilities
- Free parking
- Air conditioning
- Tea and coffee facilities
- Skiing
The 2-bedroom Beau Villa Gloucester, located around 5 minutes' walk from Community Church at East Gloucester, can host up to 6 guests. This accommodation features opportunities for windsurfing, snorkelling, and snow skiing in the area, 4.5 km from Hammond Medieval Castle.
Beau
- BBQ facilities
- Free parking
- Air conditioning
- Tea and coffee facilities
- Skiing
Beau
The 2-bedroom Beau Villa Gloucester, located around 5 minutes' walk from Community Church at East Gloucester, can host up to 6 guests. This accommodation features opportunities for windsurfing, snorkelling, and snow skiing in the area, 4.5 km from 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
Welcoming a maximum of 6 guests, the 2-bedroom 1 Mi To Beach! Family Gloucester Gem W/ Yard villa enjoys a prime location approximately 3 km from iconic historical sites such as the medieval-style Hammond Castle. Located around 10 minutes' drive from the Small Niles Sandy Beach, the accommodation provides Wi-Fi and parking.
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 prime location approximately 3 km from iconic historical sites such as the medieval-style Hammond Castle. Located around 10 minutes' drive from the Small Niles Sandy Beach, the accommodation provides Wi-Fi and parking.
Gloucester Vacation Rentals Oceanfront
Spacious 2Nd Floor Suite
- Cookware/ Kitchen utensils
- Flat-screen TV
- Ironing facilities
- Tea and coffee facilities
The 149 m² Spacious 2Nd Floor Suite Gloucester is located approximately 6 km from Rockport train station and approximately a 5-minute walk from Rogers Street. This 2-bedroom apartment features Wi-Fi, along with parking for guests travelling by car.
Spacious 2Nd Floor Suite
- Cookware/ Kitchen utensils
- Flat-screen TV
- Ironing facilities
- Tea and coffee facilities
Spacious 2Nd Floor Suite
The 149 m² Spacious 2Nd Floor Suite Gloucester is located approximately 6 km from Rockport train station and approximately a 5-minute walk from Rogers Street. This 2-bedroom apartment features Wi-Fi, along with parking for guests travelling by car.
Stay At Rocky Neck
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Ironing facilities
- Tea and coffee facilities
- Patio
The 3-bedroom Stay At Rocky Neck Gloucester villa is situated merely 6 minutes' walk from Elynn Kroger Gallery, featuring such comforts as Wi-Fi and a private parking lot.
Stay At Rocky Neck
- 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 is situated merely 6 minutes' walk from Elynn Kroger Gallery, featuring such comforts as Wi-Fi and a private parking lot.
Bianca
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Tea and coffee facilities
- Heating
- Patio
Located around 5 minutes' walk from Gloucester Center, the 2-bedroom Bianca Villa Gloucester offers cycling and fisheries to diversify guests' leisure. This accommodation boasts a patio and a golf course, while Cape Ann Whale Watch is just 1.6 km away.
Bianca
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Tea and coffee facilities
- Heating
- Patio
Bianca
Located around 5 minutes' walk from Gloucester Center, the 2-bedroom Bianca Villa Gloucester offers cycling and fisheries to diversify guests' leisure. This accommodation boasts a patio and a golf course, while Cape Ann Whale Watch is just 1.6 km away.
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 windsurfing, snorkelling, and fisheries for active guests. Providing guests with Wi-Fi and a car park, this Gloucester holiday home is 2.9 km from the shaped Half Moon Beach.
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 windsurfing, snorkelling, and fisheries for active guests. Providing guests with Wi-Fi and a car park, this Gloucester holiday home is 2.9 km from the shaped Half Moon Beach.
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 Bearskin Neck Cape, the 3-bedroom Walk To Good Harbor, Ocean Views, Open All Year! Gloucester villa provides access to various tourist attractions in the vicinity. With a maximum capacity of 6 guests, this accommodation offers a car park.
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 Bearskin Neck Cape, the 3-bedroom Walk To Good Harbor, Ocean Views, Open All Year! Gloucester villa provides access to various tourist attractions in the vicinity. With a maximum capacity of 6 guests, this accommodation offers a car park.
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Great deal
Stay At Smith Cove
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Ironing facilities
- Golf centre
- Patio
At the 2-bedroom Stay At Smith Cove Gloucester villa, guests can enjoy fisheries as well as a location approximately a 5-minute walk from The Cultural Center at Rocky Neck.
Stay At Smith Cove
- Cookware/ Kitchen utensils
- Free parking
- Air conditioning
- Ironing facilities
- Golf centre
- Patio
Stay At Smith Cove
At the 2-bedroom Stay At Smith Cove Gloucester villa, guests can enjoy fisheries as well as a location approximately a 5-minute walk from The Cultural Center at Rocky Neck.
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.