
Gloucester vacation rentals
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Top-rated vacation rentals in Gloucester
Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.
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Popular amenities for Gloucester vacation rentals
Gloucester beach vacation rentals

The Crows Nest | Near Shops & Beaches
We had such a wonderful stay at the Crows Nest! We used Carl & Julie's beautiful home as a "home base" during our adventures through Salem and greater Boston and it was such a wonderful place to come back to. Everything was easy to find, the place was very clean and accommodated myself and my friends perfectly! Rockport is also very cute with a generous beach. Cannot recommend enough!

Long Beach Suites: Steps Away From Surf!
A hidden gem. Typically the pictures are better than any unit is in person, but it was the opposite for this sweet unit. It was even better in person. So close to the beach, with views from the balcony. We will be back!

Old Harbor
We stayed at Sarah's lovely place for three days in April. We had a great time! The location is perfect, very near shops and restaurants, and also walking distance to the performance center. We didn't get to enjoy the deck because of the weather, unfortunately. Parking is a tight squeeze, but we managed without problems. The downstairs bedroom and half bathroom are small, but they work fine. The view is amazing, and we definitely recommend it!

waterview guest suite
Dominique is a great host, and stands out from others in the Gloucester area with her kindness and openness. She welcomed us even though we arrived later than the check in time, guided us to the unit, and made sure that we felt right at home. Her friendliness to our family and our pet is something we really value and appreciate. If you need a cozy riverside apartment within 10 minutes of the lovely cafes and shops of Downtown Gloucester or 15 minutes from picturesque Bearskin Neck in Rockport, this should be at the top of your list!

Life of Reilly at Back Beach
Our third time staying here and although the weather was lousy, it was nice to have such a great cottage to hunker down in when needed

Gloucester Private Contemporary 4 bedrooms
Beautiful spacious home, tucked away by in quiet cove. The home was clean, comfortable and the kitchen was well stocked. Communication with the host was very easy and pleasant.

House with Pool, 4 Houses from Harbor, Fort Sewall
Didn't want to leave!!! The house was beautiful and I loved the beachy style. It was tastefully decorated. The furnishings were so comfy. I felt right at home. The pool was perfect. I hope to visit again in the future! Thank you for everything!

Plum Cove Cottage with king suite!
I spent 3 weeks at Christine’s fabulous cottage while working in the area. I felt a pang of sadness as I closed the door for the last time…this comfortable, charming little retreat had become home! It is airy and bright, the full kitchen is well-appointed and functional, the bathroom is clean and well-designed, and the sleeping loft is cozy and breezy at the same time! Christine is a responsive and pleasant host, check-in is easy. I will be back!
Gloucester house rentals

Beach House on a Private Beach!
Oh my goodness. This place was a DREAM. Such a beautiful home with a view you can’t top. My husband and I stayed with our children and two friends for an east coast summer getaway and we could not have found a better place. Awesome setup, view, and Gaby could not have been more helpful. We would love to stay here again.

Hillside
Amazing place to stay! Beautiful decor with high-quality furnishings & housewares. Ocean views were truly fabulous. Early morning coffee on the deck watching fishing boats go out was so peaceful. Kitchen well stocked with every spice you'd need from Whole Foods. Teas too. Has whatever you'll need- can't say enough- just bring clothes & groceries. You won't be disappointed. Easy to see why this is top rated!! Regarding the lay out: there are around 15 stairs from the basement level which has a nice entry way & laundry room. Main floor has a bedroom with queen bed. The bathroom on main level is walk in shower perfect if traveling with elderly. Upper floor has primary bedroom with King and amazing views as pictured. Also room with 2 twins and full bath. Perfect place. Would rent again if in the area!

Hillside Ocean View 2BR with Private Beach Access
Great location to getaway. Short walk to two different beaches as well as parking pass for great neck beach. Lots of room for two people to spread out. Lots of games to play. Living room was very comfortable, kitchen well stocked. Easy check-in and checkout

Plum Perch: Professionally Cleaned, Close to Beach
Great spot, within a 5 minute walk to the beach. Plenty of space to spread out, though we barely even used the basement, which has an additional bedroom, bathroom, and living room (and the laundry). Our son loved the loft bedroom upstairs. The beds were comfortable, and everything was clean. Would stay again!

Aerie, 2 king beds, large space, AC, 2 beaches!
This was the perfect home to host us as we got ready for my sister's wedding in Gloucester. It was close enough to all of the activities we had planned, and large enough to host a large bridal party as we got ready. I loved that Patrick sent clear and informative instructions before our arrival. That made check-in a breeze. The driveway was a bit treacherous, but that's no ones fault! We didn't get to spend much time at the house, since most of our stay was spent running around. It was a beautiful home, in a very quiet neighborhood. Luckily, we didn't need to reach out to Patrick at all during our stay since everything went smoothly, and again he covered everything ahead of time. He provided everything we needed to follow his check-out instructions efficiently. It was a bit expensive for just a couple of nights, but it was a very spacious and accommodating home.

Stagehill Beach House
We stayed at Katie’s home over a weekend to celebrate my sisters upcoming marriage. Ever person spent the weekend gushing about how adorable this place was. It was full of charm and we LOVED it. We had a bonfire, walked to the beach, and loved having an outdoor space to hang out. Katie was wonderful and responsive! She was so kind and flexible. This was truly one of the best Airbnb experiences I’ve ever had.

Brivera by the Sea, a Beautiful Plum Island Escape
Great house, awesome location, everything was perfect and communication was great.

Charming Toe-Hold, A Short Walk to Town and Beach
Fantastic spot! Incredibly clean, homey, and has everything you need. Her backyard was a gem to get some needed R&R. Highly recommend!
Beach house rentals in Gloucester

Chic Coastal Retreat
I had a horrible experience with a house in Rockport and feel that Katherine was a Blessing sent from God to me. She was so generous, flexible and gracious. I have enjoyed all my conversations with her. Her home is 10+. Best place I have been to in Gloucester/Rockport Big Thank you to Katherine for your kindness ❤️

“Salty Girl” Plum Island, MA
Another wonderful stay at the Salty Girl! This was our second stay and was just as great as the first. Erin is very responsive and accommodating. Perfect for our little family with a toddler. We hope to be back again!

Charming waterfront home. Patio, Shops & Dining
I can’t thank you enough for letting me stay in this beautiful location. I’ve been going through chemo treatment and trying to find beautiful places in between treatment to enjoy. This place was a fav. Which I sort of want to keep to myself. I didn’t have a lot of energy to do a lot but it was exactly what I needed. Parked my car and left it behind. Watched the tide, walked around a beautiful place with my dog. I couldn’t ask for more.

Beautiful historical house in Salem
My family and I had a great stay at this Broad Street residence. The house was beautifully decorated, and had everything we needed. It was very easy to cook meals as the kitchen contained all of the essential items. There was no washer and dryer, but we stayed for a short time, so it was no issue. This is also clear in the description. The beds were comfortable, bedding was very clean, and the bathrooms were spotless. This location is perfect. We could walk to several historic sites as well as some of the main streets (shopping/dining). This is close to Essex street, the Pickering House, the Witch House, and it was one block over from beautiful Chestnut Street. We took a trip to Gloucester. We stopped at Stage Fort Park to have a picnic after whale watching with 7 Seas. I highly recommend visiting this town to whale watch. It was an experience of a lifetime. We saw several whales up close.

Annisquam Getaway - Water View+Walk To The Beach
A fantastic experience. The house was very clean and a great place to relax. We vacationed with our young family and there was plenty to do at the house. The house is set up great with games, books, and supplies. The house and backyard are better than the pictures. I would book again. The beach is a little bit away, but it is a beautiful walk and a great beach. Tom was a great host.

Charming Year Round Home, Plum Cove Cottage
Super cute cottage right next to Plum Cove. Very cozy and plenty of amenities.

Walk To Everything
I was in Marblehead for my niece’s wedding and this house was the perfect spot and size for my family to stay in. The house was incredibly clean and tidy. The host was quick to return any of my messages before we arrived. While I didn’t need to reach out to them during my stay, but I knew I could reach out to them with questions and that they would be quick to respond. Lots of shops and restaurants within walking distance. Thank you for letting us stay!

Townhouse #3 in Downtown with Parking
Peter's spot is walking distance to many restaurants and little shops. The pictures are accurate- and the place is just as cute as it looks in the photos ! Very comfortable sleeping arrangements and great shower. Was nice to have the washer and dryer to do a quick load of laundry. I would definitely recommend this spot to others !
Quick stats about vacation rentals in Gloucester
Total rentals
590 properties
Total number of reviews
25K reviews
Family-friendly rentals
380 properties are a good fit for families
Pet-friendly rentals
160 properties allow pets
Rentals with a pool
10 properties have a pool
Rentals with dedicated workspaces
270 properties have a dedicated workspace
Frequently Asked Questions
Where should I stay in Gloucester?
Make yourself at home in Gloucester by choosing from our most frequently booked neighborhoods. We have over 330 vacation rentals in Annisquam, over 250 vacation rentals in Riverview, and over 250 vacation rentals in West Gloucester.
Are there vacation rentals with a dedicated workspace in Gloucester?
Yes! Work meets play with ease at over 270 vacation rentals in Gloucester featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly vacation rentals in Gloucester?
Four-legged friends are welcome in Gloucester. Choose from more than 160 vacation rentals for guests traveling with pets.
Are there Gloucester vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 10 vacation homes with pools in Gloucester, available on Airbnb. Make a splash and soak up the sun in style!
How much does it cost to stay in cottage rentals in Gloucester?
Experience the best of Gloucester with our cottage rentals, starting at about $100 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do house rentals in Gloucester have a gym?
Absolutely! We offer over 10 house rentals with a gym in Gloucester. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Gloucester have self check-in?
Absolutely! We offer over 100 house rentals with self check-in in Gloucester. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Gloucester have a bbq area?
Absolutely! We offer over 110 house rentals with a bbq area in Gloucester. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly house rentals in Gloucester?
Gloucester has more than 250 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
What are the most popular amenities for House Rentals in Gloucester?
Enhance your stay in our House Rentals with the most popular amenities: over 110 homes with a bbq area, over 10 homes with a gym, over 100 homes with self check-in, and more. Indulge in the ultimate retreat, tailored to your preferences.
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- Hampton Beach
- Ogunquit Beach
- Wells Beach
- Boston Common
- Revere Beach
- Fenway Park
- TD Garden
- Harvard University
- Lynn Beach
- Duxbury Beach
- York Harbor Beach
- North Hampton Beach
- New England Aquarium
- Long Beach
- Freedom Trail
- Faneuil Hall Marketplace
- Crane Beach
- Long Sands Beach
- Prudential Center
- Canobie Lake Park
- Good Harbor Beach
- MIT Museum
- Rye North Beach
- Bear Brook State Park