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.
Top guest reviews
Amenities & Room:
was private comfortable place with a viewOur two grandsons aged 6 and 3 loved the freedom to climb the boulders in the yard and LOVED the three dogsAnd a toenail in the living roomWell equipped with just about everything one would needThe view of the harbor cannot be beatHost:
She even shipped us back some clothes we accidentally left behindDot Rebecca and pups could not have been more welcomingDot and Rebecca were awesome hostsIt 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 doRead more reviewsLocation:
The location is a little bit of heaven and our visit was perfectgreat view Close to everything for day trips dining and beachesIf you like quilts you will be be in quilting heaven as Dot makes amazing quilts and pot holders some of which are for saleFive of us comfortably at Rebecca's home over the long Columbus Day weekend for the annual Cape Ann Plein Air CompetitionTheir garden was at the end of the season
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.
Top guest reviews
Amenities & Room:
There was plenty of room and the cottage was equipped with everything you might needThe bedrooms have window AC unitsI think for the size of the propertyIt was cozy and clean and felt like homeThe 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 beachCleanliness:
The Sandpiper cottage was exactly as describedThe owners were very easy to contact and very responsiveHost:
and the beach was very dog friendly off seasonThis made the living area very warmThe hosts are wonderful and meet all your needs Thanks again for helping make some great memories for our familyThey had everything they needed Being able to walk to Good Harbor Beach was supergreat location love the outdoor showerRead more reviewsLocation:
It is a "Home Away" from homeAlthough the temperatures were well below normal and not ideal beach weatherThe perfect place to relax eat lobsterIt is not lakeside orIt is probably a 15 min walk to the Good Harbor beach Very convenient to Rockport and other great sites
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.
Top guest reviews
Amenities & Room:
The downstairs is like its own little studio apartment with games and a family roomWe spent most of our time around the island in the kitchenIt was spotless and very evident that the owners take great care of itIf you like staying in a comfortable homeEverything you need Short walk to the beach and to ice cream standCleanliness:
We loved the decor and the House was very clean Great backyard and deckThe beds were super comfy and the decor is beachy and perfectHost:
We particularly loved the back deck and the outdoor showerThis home was perfect in all respects : comfort location well stocked and beautiful outdoor eating area and gardenMaureen was helpful and responsive Hope to be back next summerShe 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 excursionsRead more reviewsLocation:
and we enjoyed barbecuing fish bought from Connolly's fish marketA lot of great memories were madeGreat location Very comfortable houseThe main living area was perfect for my elderly parents with bathroominsanely good (half price lobster roll Tuesday also ) Convenient to shops in Gloucester and Rockport
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.
Top guest reviews
Amenities & Room:
The bedroom is comfortable with a view of boats in the harbor- that was fun and easy to doThe view over the inner harbor from the bedroom/deck was all I neededThe bed was very comfortable tooThe kitchen has the necessary utensils for cookingCleanliness:
The rooms are tastefully decoratedThe apartment was very cleansmells and "feel" of seaport townsThe accommodations were clean and well equippedIt is indeed clean peaceful well stocked and beautifully decoratedHost:
Linda was very helpful when we first arrived giving us plenty of information & a printed sheet that had some of her favorite spots & resturantsaddressed questions very quickly and was so so sweetLinda and her husband were very nice and accommodatingwell maintained and comfortableSecondly these are about two of the nicest most helpful folks you'll ever meetRead more reviewsLocation:
The location is close to downtown Gloucester and grocery stores and restaurantsThe location is perfect as it is close to shops supermarketsIt is a great centuralized location to take day trips to surronding areas in the Cape Ann areaThere are lovely beaches nearby and beautiful drivesit was a good space in which to "hang out "
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.
Top guest reviews
Amenities & Room:
i enjoyed having my morning coffee and breakfast with a view and the sunsets were incrediblethe view from the living room is amazingthe bed was like sleeping on a cloudthe deck facing the dunes is great for breakfast and cocktailsthe unit is super cozy and has an incredible viewCleanliness:
the place was tidy and cleanthe apartment itself was very cleaneverything was very clean and there were little goodies everywherethe cottage was meticulously clean tastefully decorated and the personal touches they left throughout were so appreciatedthe space was comfortable and cleanHost:
the owners are incredibly nice and helpfulthe accommodations were very nice the hosts were gracious and thoughtful and the beach was perfectthanks to our hosts this stay was exceptionalgreat hosts quick responses the best viewgwen and terry are outstanding hosts and made sure that i had everything i neededRead more reviewsLocation:
great location with amazing scenerysplash landing was a great location for a weekend get awaysuch a great location we had a refreshing timewhat a beautiful location and a lovely space by the seathe location on a this calm peaceful beach was perfect
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.
Gloucester, Massachusetts, United States
6.32 km (4.0 mi) from Good Harbor BeachAccommodates: 2
Top guest reviews
Amenities & Room:
the bed and couch were super comfortable and the kitchen had all the space we neededkeith's cottage is very comfortable and thoughtfully arrangedkeith's cottage is adorable comfortable and privatewe loved the cottage it was very cozy warm and comfortable; having everything needed for a relaxing staythe cottage is neat and cozy keith was very attentive and responsiveCleanliness:
it was clean and comfortableeverything was clean and well keptplace very clean and invitingit is clean peaceful and secludedthe space was clean cozy and comfortableHost:
keith was a wonderful hosthe was an excellent hostkeith was a wonderful host and made us feel very welcomekeith has great response times and very accommodatingkeith was a very helpful hostRead more reviewsLocation:
location is amazing privacy convenience and close to everythingreally good quiet place near gloucester centerit is an excellent locationlovely location close to everything yet set away from busy roadgreat value and location
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
Gloucester, Massachusetts, United States
1.51 km (1.0 mi) from Good Harbor BeachTop guest reviews
Amenities & Room:
carol left us breakfast food and coffee which was a lovely surprisereally comfortable apartment with all the amenities of your own home -- plus morejust wonderful and amazingly comfortable beds and the heavenly deckit is well stocked and comfortable with a nice viewnice bed great living space; cable and wifi; kitchen just brimming with pots pans dishes etcCleanliness:
very clean and very accommodatingspotless comfortable and welcoming touchesthe place was very clean organized and comfythe property was very clean and stocked with everything you could possibly needthe place was very clean and well supplied with everything you would possibly needHost:
carol was an amazing hostthe hosts were very nice and accommodatinggreat place our host was very helpfulcarol and rory were excellent hostscarol and rory were amazing hostsRead more reviewsLocation:
the location is excellentthis is a great locationgreat location to stay to experience gloucester everything is only a short walk awaya special location that is quiet and convenient to all the things gloucester offersgreat location and had everything we needed
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.
Gloucester, Massachusetts, United States
2.51 km (1.6 mi) from Good Harbor BeachTop guest reviews
Amenities & Room:
there was a large fan in the bedroom which we ran both nightsthe cottage is charming and cozyfishnet cottage is charming and comfortablefishnet cottage is cozy and comfortable and convenientone of a kind cottage with plenty of room to spread outCleanliness:
if you like clean and tidy this isn’t the place for you eitherthe cottage was adorable clean and a perfect getaway for a couplethe cottage we stayed in was very clean very homey and cottage like and very relaxingthe acomodations are very clean and there is just about anything you would need thereHost:
ken was a really nice hostken was a gracious hostken was a great hostken the host definitely deserves the super host designationken is a wonderful hostRead more reviewsLocation:
location is quiet safe and close to everythingthe location was so perfecteasy walk to niles beachgreat location in east gloucestera perfect location authentic gloucester feel
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?
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