10 Best Vacation Rentals In Gloucester, Massachusetts - Updated 2022


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.

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.

Prime Gloucester Property - Overlooking Harbor with Private Pool
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
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
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.

Good Harbor Beach House - Walk to Shops
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
The Sandpiper cottage was exactly as described
The owners were very easy to contact and very responsive
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
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.

Newly Renovated!! Beautiful 3 bed home...steps from 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
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
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
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.

Sunset Studio "PLUS" - Scenic Harbor View!
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
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
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
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 299)

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.

SplashLanding Private Beach Getaway in Gloucester
Gloucester, Massachusetts, United States
309 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
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
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
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.

Cottage In The Woods
Gloucester, Massachusetts, United States
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
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
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 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

Harbor View Hideaway: 1st flr furnished apartment
Gloucester, Massachusetts, United States
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
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
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
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. Secluded home with ocean views

This serene peaceful retreat house is great for those who want to get away from their troubles. This vacation rental in Gloucester, Massachusetts, is also located at the entrance of America’s oldest working colonies. Windows on all sides provide lots of air and lots of light. There is also a fully-equipped kitchen, a cozy living room, and an outdoor patio.

Willow House - Garden Setting, Ocean View, Steps to Rocky Neck!
56 reviews
Apartment 4 Guests 1 Bedroom 1 Bathroom
Top guest reviews
Amenities & Room:
The home has everything you need and was immaculate
no driving/parking hassles)
The bedroom and bath just add to your comfort with the bed having a sleep number mattress; also nice to have 2 entrances to your bathroom
The flat is fabulously equipped as well
We enjoy the light bright space and beautiful yard
And you can't beat the location
We had the most relaxing time at The Willow House to celebrate our 20th anniversary Everything was perfect and as described
Our hostess was most gracious
We couldn't have dreamed of a better experience in Gloucester and the area
Rokhaya was a communicative responsive host who gave us plenty of space and privacy while promptly helping us out whenever we had a question Highly recommend this as a place to stay when you're ...
Beautiful luminous colors inside too
We are so happy we found
Quite a selection of restaurants in the area
Willow House is a peaceful and beautiful property in an amazing location
It is easy to imagine returning here
the galleries and good restaurants
The unit is a short walk to galleries restaurants and many beautiful landscapes
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9. 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.

Fishnet Cottage
Gloucester, Massachusetts, United States
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
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
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 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
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10. Coastal retreat with harbor views

This one-bedroom vacation rental in Gloucester, Massachusetts is a perfect coastal retreat for your small family, or for you and your friends. It’s located a few minutes away on foot from Half Moon Beach and Crescent Beach. Stage Fort Park and Good Harbor Beach are also nearby. The proximity to these places lets you have easier access to whale watching and deep sea fishing. Inside the house, you’ve got a full kitchen, cable TV, WiFi, and a fireplace. The whole place can accommodate up to four people, two in the bedroom and two on the sofa bed in the living room. There is also an outdoor grill and furniture on the patio.

Inviting apartment with harbor views, fireplace, patio, & gas grill!
35 reviews
House 4 Guests 1 Bedroom 1 Bathroom
Top guest reviews
Amenities & Room:
I Would rate this stay a 4 5 Small details Coffee pot tired and Could use update Light in Living room and over bathroom sink not working Stain on couch not too appealing as it is the only seati...
We went in the spring and enjoyed the lower rates
We went in the spring and enjoyed the lower rates
The inside has everything you need and then some Loved the New England feel Has a rustic fireplace and tall windows with views views views
The shower curtain could be updated and there was a wasp nest outside the house
The apartment was very clean
The place was clean and quiet
It has a beautiful view and it was clean and relaxing
It was stained and not pleasant to look ir even to consider sleeping on it
The weather wasn't the best
Sometimes expectations fall short of the rental listing
Recommend the home owners clean the couch before the next group arrives
This rental is very nice
This rental is very nice
so we were going to cookout
A beautiful water view close to the park and walking distance to town Perfect for a couple who are interested in exploring Cape Ann and love to eat sea food
A beautiful water view close to the park and walking distance to town Perfect for a couple who are interested in exploring Cape Ann and love love to eat sea food
It has multiple stains on it
What a beautiful place Beautiful view of Gloucester Harbour Nice walk to town
These are easy fixes and would make this home a 5 star
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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?

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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