10 Best Airbnb Vacation Rentals In Gloucester, Massachusetts - Updated 2024

Stephen
Stephen 
Updated
| 5 min read

Perched on the scenic Cape Ann, Gloucester is a beautiful vibrant coastal city in Massachusetts that boasts a wide variety of exciting options. Although it is popular for fishing and other water activities, it also serves as a hub for glitzy nightlife, contemporary art, business, and fashion. In addition, it has a plethora of mind-blowing and blood-twisting attractions such as museums, pristine beaches, and gorgeous parks. It is also blessed with exciting culinary cultures and a wide range of beautiful, luxurious vacation rentals. If you’re looking for nice accommodation, read on to know more about best Airbnb vacation rentals in Gloucester, Massachusetts.

We handpicked these listings carefully, considering (wherever possible) Superhost status, recent guest reviews, location, accommodation type, prices, availability of dates, decor, and amenities. The image galleries get refreshed with the latest updates regularly. They were last updated on April 09, 2024.

1. Colorful studio best for couples (from USD 150)

Are you a couple looking for a quiet, romantic place to stay away from the chaos of the city? Check out this hidden located close to the beach and just a walking distance to downtown. It is a cozy studio that features warm, eye-catching interior décor and can accommodate up to three guests. It features a sumptuous living room with cozy lighting and a comfy sofa. Next, is the bedroom area that comes with a comfy double bed and clean bedding. There are a fully equipped kitchen and a Euro-style bathroom with toiletries. Other features include a deck and a private garden, among others.

Stayed at this property?
Gloucester, Massachusetts, United States
1.86 km (1.2 mi) from Good Harbor Beach
91 reviews   Wifi Available
ENTIRE RENTAL UNIT 2 Beds 3 Guests 0 Bedrooms 1 Bathroom

Accommodates: 3

Top guest reviews
Amenities & Room:
the space is charming and comfortable with a beautiful outdoor garden for dining and relaxing
and though it's small it was quite comfortable
the apartment is very well equipped with many thoughtful touches and richard was a genial host
this is a fun comfortable eclectic space
Cleanliness:
place was clean and lots eclectic decorations
it was a very nice clean and convieniently located
the space is clean and in a great location
excellent funky decor and every nook and cranny was very clean
it's clean and cozy as described with a lot of quirky design features
Host:
richard is a class act and a great host
richard was a gracious and knowledgable host
such an awesome place and richard is a fantastic host
so peaceful and quiet neighbors were friendly and didn't make any noise
richard is a genuinely kind host and a great conversationalist
Location:
the location was wonderful
he recommended several great restaurants and nearby sites in walking distance
this is a unique eclectic place to be sure but that suited us just fine
Read more reviews

2. Romantic hideaway with beach views (from USD 65)

Discover this hidden gem tucked away in a quiet secluded area near a private beach. It is a gorgeous one-bedroom vacation rental with a bungalow taste on it and is suitable for a couple. From the tranquil turquoise waters to the romantic sunsets, there’s always something romantic about this place. It has a divine interior which is carefully designed. The kitchen is spacious and well-equipped with high-quality appliances, granite countertops, and a fridge. The living area is furnished with cozy sofas, a TV, a table, and a door leading to the deck. There are comfy beds, Wi-Fi, laptop-friendly workspace, free parking, and a bathroom.

Stayed at this property?
Gloucester, Massachusetts, United States
8.2 km (5.1 mi) from Good Harbor Beach
374 reviews   Superhost Wifi Available
Entire guest suite 1 Bed 2 Guests 1 Bedroom 1 Bathroom

Accommodates: 2

Top guest reviews
Amenities & Room:
i enjoyed having my morning coffee and breakfast with a view and the sunsets were incredible
the view from the living room is amazing
the bed was like sleeping on a cloud
the deck facing the dunes is great for breakfast and cocktails
the unit is super cozy and has an incredible view
Cleanliness:
the place was tidy and clean
the apartment itself was very clean
everything was very clean and there were little goodies everywhere
the cottage was meticulously clean tastefully decorated and the personal touches they left throughout were so appreciated
the space was comfortable and clean
Host:
the owners are incredibly nice and helpful
the accommodations were very nice the hosts were gracious and thoughtful and the beach was perfect
thanks to our hosts this stay was exceptional
great hosts quick responses the best view
gwen and terry are outstanding hosts and made sure that i had everything i needed
Location:
great location with amazing scenery
splash landing was a great location for a weekend get away
such a great location we had a refreshing time
what a beautiful location and a lovely space by the sea
the location on a this calm peaceful beach was perfect
Read more reviews

3. Seaside apartment with modern amenities (from USD 228)

Oozing with seaside charm and rewarding tranquility, this is a stylish one-bedroom apartment, a vacationer’s dream destination, situated just a walking distance from the beach. Deep your feet in the pristine waters as you enjoy a stroll on the beach. Its interior is spacious, bright, and tastefully decorated. It has a cozy queen bed with clean, warm linen and pillows. The kitchen is well-appointed with modern appliances and a fridge. Free Wi-Fi and a flat-screen TV are there to offer entertainment. Also, there’s a super clean bathroom with essential toiletries. Other features include a hairdryer, hangers, and a fire extinguisher.

Stayed at this property?
Gloucester, Massachusetts, United States
8.23 km (5.2 mi) from Good Harbor Beach
254 reviews   Superhost Wifi Available
Entire guest suite 1 Bed 2 Guests 1 Bedroom 1 Bathroom

Accommodates: 2

Top guest reviews
Amenities & Room:
the amenities were fantastic from comfortable beach chairs umbrellas to fishing rods
the cottage is very comfortable and has everything you need
the room was just as described but even more lovely than we imagined
our room was absolutely amazing
Cleanliness:
very clean and comfortable
it was very clean very quaint and well-decorated
their place was beautiful and clean
squish inn is impeccably clean cozy and welcoming
it was sparkling clean and a perfect location for us
Host:
great hosts and great people
they are kind and thoughtful hosts
genuinely kind host who wants to make sure you have the perfect stay
hosts were attentive and provided nice extra touches
awesome place and awesome hosts amazing beach
Location:
a great location
for starters the location is absolutely amazing
the location is wonderful - safe beautiful easy to access
the location and beach were great we really enjoyed our time
a beautiful room a few steps away from a long and quiet private beach
Read more reviews

4. Beautiful one-bedroom cottage (from USD 225)

Enjoy romantic sunsets from this gorgeous one-bedroom cottage located a walking distance from Lighthouse Beach, Cambridge Beach, and the Market Restaurant. Filled with a romantic atmosphere, this eclectic cottage can comfortably accommodate three people. There’s a lovely seating area downstairs furnished with nice sofas, a table, and a flat-screen TV. Above it, is a charming bedroom with a queen-size bed and cathedral ceilings. Next, there’s a well-appointed kitchen and a backyard patio where you can relax with a glass of wine. Temperatures are regulated by heating floors and air conditioning. Wi-Fi, free parking, a laptop-friendly workspace, and a bathroom are provided.

Stayed at this property?
Gloucester, Massachusetts, United States
5.3 km (3.3 mi) from Good Harbor Beach
217 reviews   Wifi Available
Entire guesthouse 1 Bed 3 Guests 1 Bedroom 1 Bathroom

Accommodates: 3

Top guest reviews
Amenities & Room:
the cottage is very quaint and comfortable
doug has done a fantastic job renovating the cottage into a cozy retreat in annisquam
the bunny cottage was absolutely cozy clean and delightful
Cleanliness:
the space was clean and comfortable with great touches
doug’s place was so charming and clean
they absolutely loved it they said it was impeccably clean and loved the personal touches
the cottage was clean and exactly like the picture
this place is great doug keeps it super clean and is very approachable for any questions
Host:
dough was a wonderful host
adorable small space with a cozy feel and very hospitable owners
doug was an amazing host his travel book is extremely useful
thank you for hosting us if ever we are back to massachusetts this is where we will land
awesome hosts will revisit next time i visit family in the area
Location:
great location a tiny house with a lot of magic
such a cute place in a very peaceful setting
it was a great and peaceful location with everything we needed
great place to spend a few nights in gloucester area
this is a wonderful place to kick back and relax
Read more reviews

5. Lovely getaway near the ocean (from USD 200)

Nestled in a tranquil, lush green neighborhood, this is a nice three-bedroom vacation rental that invites you to come and experience the romantic, coastal vibe. It is located a stone-throw away from major social joints such as breweries, shopping centers, and Hammond Castle. The living area is furnished with comfy sofas and a flat-screen TV to keep you entertained. The kitchen is fully equipped with high-quality appliances and top-class utensils. Each bedroom comes with a comfy bed, clean linen, and storage areas. There’s a lovely deck to relax with a glass of wine and enjoy the fresh breeze. There are two bathrooms, Wi-Fi, and free parking.

Stayed at this property?
Gloucester, Massachusetts, United States
2.66 km (1.7 mi) from Good Harbor Beach
137 reviews   Superhost Wifi Available
ENTIRE HOME 5 Beds 8 Guests 3 Bedrooms 2 Bathrooms

Accommodates: 8

Top guest reviews
Amenities & Room:
we found the house very comfortable and cozy
Cleanliness:
the house was simple and clean
clean home and nicely furnished
house was clean & welcoming & convenient
place is clean and centrally located
Location:
beautiful house in a great location
beautiful house in a nice location
our stay was great good location and excellent tips for things to do nearby
amazing place to stay good location and host left excellent tips for things near by
tiffany's place is an adorable house within walking distance to downtown gloucester including a nearby ice cream shop
Read more reviews

6. Spacious apartment near the beach (from USD 99)

Located about 15 minutes from downtown Gloucester and just a walking distance from Wingaersheek beach, this is a spacious, cozy one-bedroom apartment with a glamorous interior. It comes with a nice dining area and a well-equipped, spacious kitchen with lovely countertops, a fridge, and top-class appliances. The living area is air and tastefully furnished with a cushy sofa, a table, and a TV. In the bedroom, there’s a queen-sized bed, clean bedding, and storage spaces. There’s air conditioning throughout and free parking for guests on the premises. Also, this apartment is just within a touching distance of beautiful restaurants, and a vibrant shopping center.

Stayed at this property?
Gloucester, Massachusetts, United States
6.99 km (4.4 mi) from Good Harbor Beach
163 reviews   Wifi Available
ENTIRE RENTAL UNIT 1 Bed 3 Guests 1 Bedroom 1 Bathroom

Accommodates: 3

Top guest reviews
Amenities & Room:
comfy bed good ac helped in muggy weather
this space has so much room we loved having our own entrance and all of the rooms were large
Cleanliness:
very clean and spacious
a very great place very clean the bed is very comfortable
quiet clean and spacious very easy to find
beautiful spacious and very clean private space in west gloucester
the apartment was super clean and well equipped for our little family
Host:
the hosts were very kind
our hosts were quick to respond and very helpful with our questions
hosts are incredibly kind and offer great suggestions for fun things to do
we really enjoyed staying here and the hosts were very kind
rachel is very responsive to messages and very helpful with local info
Location:
nice secluded area close to town
great location in a nice quiet location that is just a quick few minutes' drive to town
awesome space super close to downtown and very spacious
really close to beaches and downtown but also a nice quiet getaway
a nice and quiet place at walking distance from a park (walk/run)
Read more reviews
Weekly discount: 15% off

7. Awesome studio for a couple

Situated in a quiet, peaceful area away from the hustle and bustle of the city, this is a romantic studio with a wonderful outdoor space with grill facilities where you can enjoy a barbeque or hold a party. It has a spacious interior that has a gorgeous fireplace. The seating area is furnished with cushy sofas, a table, and a flat-screen to keep you entertained. Next to it is a nice dining area and a door leading to the outdoor space. Its sleeping area has a comfy queen bed for a great night’s sleep. Other features are a bathroom and free on-street parking.

Stayed at this property?
Gloucester, Massachusetts, United States
3.47 km (2.2 mi) from Good Harbor Beach
86 reviews   Wifi Available
ENTIRE RENTAL UNIT 2 Beds 3 Guests 0 Bedrooms 1 Bathroom

Accommodates: 3

Top guest reviews
Amenities & Room:
loved having access to the washer and dryer with detergent a kitchen table high top and bar
Cleanliness:
place was clean and spacious highly recommend
Host:
kelly and bobby are wonderful hosts and super accommodating
each of the hosts’ recommendations in downtown gloucester were excellent
Location:
really cool space and close to the beach
secure accommodation in a quiet neighborhood
great location with great hosts
kelly and bobby’s place was great for our night away to gloucester
Read more reviews

8. Gorgeous bungalow-style apartment

Nestled in a nice, picturesque neighborhood in Gloucester, this is a lovely two-bedroom apartment that is within a walking distance from MBTA commuter rail. Outside, it has a beautiful area with a grill and a firepit. Its interior is bright, spacious, and intricately decorated. It comes with a well-equipped kitchen with modern appliances and top quality utensils. The living area is airy and furnished with nice, cozy sofas, a table, and a flat-screen TV. The bedrooms are beautiful and come with large comfy beds, clean linen, and storage areas. There’s air conditioning throughout, free on-street parking, and a bathroom with necessary toiletries.

Stayed at this property?
Gloucester, Massachusetts, United States
3.37 km (2.1 mi) from Good Harbor Beach
13 reviews  
Entire house 2 Beds 2 Bedrooms 1 Bathroom
Top guest reviews
Amenities & Room:
lisa and bob's place was great the furniture was very comfortable and the house was cozy without being cramped
the beds are very comfortable and are a warm welcome after a fun-filled day
this house is cozy quaint and serene
Cleanliness:
very clean and comfortable house
the frig was spotless decorations are attractive and not overwhelming
Host:
the hosts were very responsive and checked in to make sure that things were going well
they were totally attentive and committed to serving us and making our stay just perfect
Location:
it's in a great location
wonderful town to walk around and explore
it's located in the perfect place to enjoy this part of new england
this is a wonderful place to come for a restful visit
super close to boston and salem which was excellent
Read more reviews

9. Splendid, airy beach studio

Very appealing from a distance, this is a breathtaking one-bedroom beach studio that acts as a small paradise for honeymooners and love birds looking to enjoy a peaceful, romantic alone time. Situated near downtown Gloucester and important social amenities, this place ensures guests enjoy a wonderful stay. It comes with a spacious living area with a sofa, a TV, and a table. The cooking area is well-equipped to ensure you enjoy your cooking. There’s a large, comfy bed in the sleeping area with clean bedding. Its bathroom comes with a bathtub, a hairdryer, and toiletries. Free high-speed Wi-Fi is also accessible.

Stayed at this property?
Gloucester, Massachusetts, United States
685 meters (0.5 ft) from Good Harbor Beach
303 reviews  
Entire apartment 1 Bed 1 Bedroom 1 Bathroom
Top guest reviews
Amenities & Room:
she made a delightful breakfast treat which was enjoyed with fresh coffee and milk each morning
we didn’t miss having a full kitchen but an electric tea kettle would have been useful
the bathroom was bigger than expected and the beach chairs and umbrella were very useful
the studio was terrific it was open with a mini bed for our daughter
it was so charming and cozy
Cleanliness:
the linens were clean and the bathroom sink/toilet/shower seemed clean but everything else was filthy
everything was clean neat and colorful
super clean great parking and very nice
her apartment is particularly clean and well-appointed
felt very safe in terms of covid as everything was very clean 10/10 would recommend staying here
Host:
barbara was a wonderful host
barbara was a good host
barbara is a wonderful host
barbara was a great host
she responded so quickly when we accidentally locked ourselves out she was super responsive
Location:
great space within walking distance a beautiful beach
the location was quiet and restful with a lovely walk to the beach
nice walk in the neighborhood and an easy 15 minute walk to the beach
great location close to beach where we ended our weekend
outstanding accommodation & great location
Read more reviews

10. Tastefully furnished one-bedroom apartment

Are you a pet lover looking for a wonderful apartment where you can live with your dog in Gloucester? Perched on the harbor side of East Main Street in East Gloucester, this beautiful one-bedroom apartment is exactly what you’re seeking. Its bedroom is furnished with a comfy queen bed with warm, clean bedding, and storage spaces. The kitchen is well-appointed with the best kitchen appliances, a sink, and a fridge. In the living room, there’s a TV, comfy sofas, a table, a nice dining area next to it. There are Wi-Fi and air conditioning throughout, heating, a bathroom, and free parking.

Stayed at this property?
Gloucester, Massachusetts, United States
1.75 km (1.1 mi) from Good Harbor Beach
86 reviews  
Entire guesthouse 1 Bed 1 Bedroom 1 Bathroom
Top guest reviews
Amenities & Room:
i had the luxury of enjoying a new gas heater and new windows
the cottage is cozy and adorable
the upstairs a/c works very well since the upstairs is small and cools off quickly
the main heating in the living room looked like a storage heater
the cottage was comfortable even with what some would consider a small bathroom
Cleanliness:
very clean and very well maintained
it was clean and very comfortable
the house is very clean and cheery
the house was quaint clean and comfortable with everything we needed
comfortable living room space downstairs and comfortable bedroom upstairs with clean linens comfortable bed and plenty of towels
Host:
ken was a great host and his suggestions were perfect
he was kind and communicative
ken was super friendly and a wonderful host
ken was a great host and respectful of our privacy
ken was a great host with great information
Location:
ken's place is located in a great area of glosta close to many great /walkable spots
easy to get to and close to downtown gloucester
close to area attractions and beaches
centrally located and easy walk or bike-ride to downtown restaurants galleries beaches
it is cute and cozy and in a great location between the beach and downtown
Read more reviews

Enjoy world-class accommodation in Gloucester, Massachusetts

Gloucester is a vibrant city and a place of many possibilities that’s it’s always flowing with tourists seeking fun, entertainment, and adventure. In order to enjoy a wonderful time during your vacation, you also need wonderful accommodation. With Airbnb vacation rentals, you’ll be able to enjoy the time of your life.

Any must-sees we missed? Tell us about them in the comments section or write a post here to help out fellow travelers!
Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.

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Stephen is an avid content writer with a passion for adventure. He enjoys traveling and has visited several countries around the world. So far, South Africa stands out as his most exciting...Read more

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