8 Best Vacation Rentals In Gloucester, Massachusetts - Updated 2024

Jaclyn
Jaclyn 
Updated
| 4 min read

Gloucester, Massachusetts is the oldest seaport and working art colony in North America. There are a lot of things you can do when staying in this coastal city. Bring your family or your friends to go whale watching, sailing, kayaking, and fishing. Explore the lighthouses, museums and historical places. See the Gloucester Fisherman’s Memorial at the Gloucester Harbor. Visit the Rocky Neck Art Colony’s Studios and Gallery and check out the works of dozens of painters, photographers, potters, jewelry makers, and textile designers. Feast on fresh seafood at Gloucester House. This is a coastal city, after all. Fresh seafood is a must. And visit the Hammond Castle, with its organ with 8,200 pipes and a 30,000-gallon swimming pool that switches from fresh to saltwater with a lever. Stay at a vacation rental in Gloucester, Massachusetts, and continue to revel in the charming appeal of the city.

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 February 04, 2024.

1. Pet-friendly vacation home with panoramic harbor views (from USD 408)

This private vacation rental in Gloucester, Massachusetts offers panoramic views of the harbor and is less than a mile away to the beach. It’s very pet-friendly since the owners have three Labradors that run around the property freely. This two-bedroom apartment is on the second floor of the owner’s house and each bedroom has their own bathrooms. The full kitchen is complete with a stove, microwave, coffee maker, and toaster. There is also an open-plan dining and living area with cable TV, WiFi, sofa, and a breakfast bar with four stool chairs.

Stayed at this property?

1.44 km (0.9 mi) from Good Harbor Beach
209 reviews   Wifi Available
Apartment 6 Guests 2 Bedrooms 2 Bathrooms

Accommodates: 6
Minimum Nights: 2
Refund Policy : 100% refund if you cancel at least 14 days before check-in.

Top guest reviews
Amenities & Room:
was private comfortable place with a view
Our two grandsons aged 6 and 3 loved the freedom to climb the boulders in the yard and LOVED the three dogs
And a toenail in the living room
Well equipped with just about everything one would need
The view of the harbor cannot be beat
Host:
She even shipped us back some clothes we accidentally left behind
Dot Rebecca and pups could not have been more welcoming
Dot and Rebecca were awesome hosts
It was really nice to have the dogs (Stella Dash and Chester all cute as heck)
This property was exceptionally charming comfortable relaxing and Rebecca and Dot were so fun and helpful and wonderfully informative about the area and things to do
Location:
The location is a little bit of heaven and our visit was perfect
great view Close to everything for day trips dining and beaches
If you like quilts you will be be in quilting heaven as Dot makes amazing quilts and pot holders some of which are for sale
Five of us comfortably at Rebecca's home over the long Columbus Day weekend for the annual Cape Ann Plein Air Competition
Their garden was at the end of the season
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2. Private getaway near the beach (from USD 175)

This private fully updated getaway can sleep up to seven people and is a few minutes’ walk away from Good Harbor Beach. The kitchen has new appliances. The living room has WiFi and a flat-screen TV. There’s also an outdoor shower for those times when you just came from the beach and need to wash off before heading inside the house. And there’s also a new deck with a gas grill.

Stayed at this property?

779 meters (0.5 ft) from Good Harbor Beach
149 reviews   Wifi Available
House 7 Guests 3 Bedrooms 3 Bathrooms

Accommodates: 7
Minimum Nights: 2
Refund Policy : 100% refund if you cancel at least 14 days before check-in.

Top guest reviews
Amenities & Room:
There was plenty of room and the cottage was equipped with everything you might need
The bedrooms have window AC units
I think for the size of the property
It was cozy and clean and felt like home
The living space is a bit small with limited seating for dining and TV viewing but we ate most meals outside and spent most days at the beach
Cleanliness:
The Sandpiper cottage was exactly as described
The owners were very easy to contact and very responsive
Host:
and the beach was very dog friendly off season
This made the living area very warm
The hosts are wonderful and meet all your needs Thanks again for helping make some great memories for our family
They had everything they needed Being able to walk to Good Harbor Beach was super
great location love the outdoor shower
Location:
It is a "Home Away" from home
Although the temperatures were well below normal and not ideal beach weather
The perfect place to relax eat lobster
It is not lakeside or
It is probably a 15 min walk to the Good Harbor beach Very convenient to Rockport and other great sites
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3. Bright, sunny home in Gloucester (from USD 506)

This recently updated sunny home is just minutes away from Good Harbor and Long Beach, New England’s most beautiful beaches. The home has three bedrooms, two with queen-sized beds and one with two single beds, good for six people. It comes with a newly renovated kitchen and even the outdoor grill area has been renovated.

Stayed at this property?

545 meters (0.4 ft) from Good Harbor Beach
46 reviews   Wifi Available
House 8 Guests 3 Bedrooms 2 Bathrooms

Accommodates: 8
Minimum Nights: 4
Refund Policy : 100% refund if you cancel at least 30 days before check-in.

Top guest reviews
Amenities & Room:
The downstairs is like its own little studio apartment with games and a family room
We spent most of our time around the island in the kitchen
It was spotless and very evident that the owners take great care of it
If you like staying in a comfortable home
Everything you need Short walk to the beach and to ice cream stand
Cleanliness:
We loved the decor and the House was very clean Great backyard and deck
The beds were super comfy and the decor is beachy and perfect
Host:
We particularly loved the back deck and the outdoor shower
This home was perfect in all respects : comfort location well stocked and beautiful outdoor eating area and garden
Maureen was helpful and responsive Hope to be back next summer
She was very accommodating and has all the stuff you would need for a beach getaway (wagon chairs etc)
This home is very nice and is very convenient to whale watching excursions
Location:
and we enjoyed barbecuing fish bought from Connolly's fish market
A lot of great memories were made
Great location Very comfortable house
The main living area was perfect for my elderly parents with bathroom
insanely good (half price lobster roll Tuesday also ) Convenient to shops in Gloucester and Rockport
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4. Cozy studio with harbor views (from USD 215)

This scenic vacation rental in Gloucester, Massachusetts is the perfect studio for couples or solo travelers. There are three rooms in this house. The bedroom/living room has a queen-sized bed, two chairs at the foot, and a door that opens up to the balcony. The second room is the kitchen/dining room. The kitchen is equipped with basic appliances, stove, microwave, toaster, and kettle and also has room for a two-chair dining table. The third is the bathroom. Outside on the patio, there is outdoor furniture and an outdoor grill on the patio.

Stayed at this property?

1.57 km (1.0 mi) from Good Harbor Beach
101 reviews   Wifi Available
studio 2 Guests 1 Bedroom 1 Bathroom

Accommodates: 2
Minimum Nights: 3
Refund Policy : 100% refund if you cancel at least 30 days before check-in.

Top guest reviews
Amenities & Room:
The bedroom is comfortable with a view of boats in the harbor
- that was fun and easy to do
The view over the inner harbor from the bedroom/deck was all I needed
The bed was very comfortable too
The kitchen has the necessary utensils for cooking
Cleanliness:
The rooms are tastefully decorated
The apartment was very clean
smells and "feel" of seaport towns
The accommodations were clean and well equipped
It is indeed clean peaceful well stocked and beautifully decorated
Host:
Linda was very helpful when we first arrived giving us plenty of information & a printed sheet that had some of her favorite spots & resturants
addressed questions very quickly and was so so sweet
Linda and her husband were very nice and accommodating
well maintained and comfortable
Secondly these are about two of the nicest most helpful folks you'll ever meet
Location:
The location is close to downtown Gloucester and grocery stores and restaurants
The location is perfect as it is close to shops supermarkets
It is a great centuralized location to take day trips to surronding areas in the Cape Ann area
There are lovely beaches nearby and beautiful drives
it was a good space in which to "hang out "
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5. Romantic beach house best for couples (from USD 65)

Are you looking to have a romantic getaway with your partner? This might be the one for you! It’s got an open plan dining, living room, and kitchen. The entrance to the bedroom is just across the kitchen. The living room also opens up to a patio. After dinner, go on walks by the beach with your partner. The kitchen is fully equipped with the stove, microwave, Keurig coffee maker, kettle, and toaster.

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
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6. Charming hideaway with nature views

This secluded two-bedroom vacation rental in Gloucester, Massachusetts, is perfect for those who want to stay close to nature but relate more to the park. Ravenswood Park, with lots of hiking and walking trails, is just nearby. This cabin can accommodate up to three people and has been completely updated. The kitchen has a blender, stove, and microwave. The living room has cable TV with HBO, central A/C, and WiFi.

Stayed at this property?
Gloucester, Massachusetts, United States
6.32 km (4.0 mi) from Good Harbor Beach
145 reviews   Wifi Available
Entire cottage 1 Bed 2 Guests 1 Bedroom 1 Bathroom

Accommodates: 2

Top guest reviews
Amenities & Room:
the bed and couch were super comfortable and the kitchen had all the space we needed
keith's cottage is very comfortable and thoughtfully arranged
keith's cottage is adorable comfortable and private
we loved the cottage it was very cozy warm and comfortable; having everything needed for a relaxing stay
the cottage is neat and cozy keith was very attentive and responsive
Cleanliness:
it was clean and comfortable
everything was clean and well kept
place very clean and inviting
it is clean peaceful and secluded
the space was clean cozy and comfortable
Host:
keith was a wonderful host
he was an excellent host
keith was a wonderful host and made us feel very welcome
keith has great response times and very accommodating
keith was a very helpful host
Location:
location is amazing privacy convenience and close to everything
really good quiet place near gloucester center
it is an excellent location
lovely location close to everything yet set away from busy road
great value and location
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7. Well-furnished cottage with views of the harbor

This one-bedroom house can accommodate up to four people, with a queen-sized bed in the bedroom and a sleeper sofa in the living room. The kitchen is complete with the stove, microwave, coffee maker, Keurig coffee maker, and toaster. When you step out into the patio, you’ll get fresh views of the harbor. If you want to eat out, there are restaurants just a few minutes away

Stayed at this property?
Gloucester, Massachusetts, United States
1.51 km (1.0 mi) from Good Harbor Beach
108 reviews  
Entire apartment 2 Beds 1 Bedroom 1 Bathroom
Top guest reviews
Amenities & Room:
carol left us breakfast food and coffee which was a lovely surprise
really comfortable apartment with all the amenities of your own home -- plus more
just wonderful and amazingly comfortable beds and the heavenly deck
it is well stocked and comfortable with a nice view
nice bed great living space; cable and wifi; kitchen just brimming with pots pans dishes etc
Cleanliness:
very clean and very accommodating
spotless comfortable and welcoming touches
the place was very clean organized and comfy
the property was very clean and stocked with everything you could possibly need
the place was very clean and well supplied with everything you would possibly need
Host:
carol was an amazing host
the hosts were very nice and accommodating
great place our host was very helpful
carol and rory were excellent hosts
carol and rory were amazing hosts
Location:
the location is excellent
this is a great location
great location to stay to experience gloucester everything is only a short walk away
a special location that is quiet and convenient to all the things gloucester offers
great location and had everything we needed
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8. Cottage for two near the Artists' Colony

This small vacation rental in Gloucester, Massachusetts is perfect for artists or art enthusiast who want to be near the Artist’s Colony in Gloucester. Downtown, is still accessible by the bus. The kitchen is complete with a stove, microwave, blender, toaster, and coffee maker. There is also a TV room with lots of books and DVDs.

Stayed at this property?
Gloucester, Massachusetts, United States
2.51 km (1.6 mi) from Good Harbor Beach
135 reviews  
Entire guesthouse 2 Beds 1 Bedroom 1 Bathroom
Top guest reviews
Amenities & Room:
there was a large fan in the bedroom which we ran both nights
the cottage is charming and cozy
fishnet cottage is charming and comfortable
fishnet cottage is cozy and comfortable and convenient
one of a kind cottage with plenty of room to spread out
Cleanliness:
if you like clean and tidy this isn’t the place for you either
the cottage was adorable clean and a perfect getaway for a couple
the cottage we stayed in was very clean very homey and cottage like and very relaxing
the acomodations are very clean and there is just about anything you would need there
Host:
ken was a really nice host
ken was a gracious host
ken was a great host
ken the host definitely deserves the super host designation
ken is a wonderful host
Location:
location is quiet safe and close to everything
the location was so perfect
easy walk to niles beach
great location in east gloucester
a perfect location authentic gloucester feel
Read more reviews

Make a holiday getaway at Gloucester

It’s definitely nice to just sit back and relax even when you’re on vacation. These vacation rentals in Gloucester, Massachusetts offer that for travelers. Have you been to Gloucester, Massachusetts? Where did you stay?

Stayed at this property?
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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Jaclyn is a creative writer, screenwriter, entrepreneur, and social media marketer all at once. She cherishes her vacation and travel breaks because she gets to let her hair down and discover new...Read more

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