
Gloucester vacation rentals
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Top-rated vacation rentals in Gloucester
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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!
This place was perfect for the 1 night stay that I needed while in the area for an event. Exactly as described and had everything I needed. Lucas was a great host and provided plenty of instructions & information beforehand with multiple reminders as my stay approached. I would stay here again.

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
We had an amazing stay for a girls weekend away! The house was clean and Elizabeth was responsive when we had questions. The location is perfect being a quick walk from the beach and the town.

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
My friends and I really enjoyed the house. It was VERY clean and it was in a great location. Easy walk to the beach and a couple of fun bar/restaurants. Parking for 5 cars. Only thing for renters to be aware of is the photos make the house appear a lot bigger than it is. The living room is small and the room with the twin beds is very small. However, the deck is large and attractive! Great house for a sunny day!!!

Aerie, 2 king beds, large space, AC, 2 beaches!
My son was graduating from Landmark High School. He is a boarding student so we needed a place close by. There was room for his extended family. The kids loved the games and activities.

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
This place was the perfect choice for our girls trip. Walkable to downtown Salem and many restaurants so no need for us to rent a car. The host was always responsive and the space was very clean. The home is spacious and so pretty. Looking forward to booking again!

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
We absolutely adored our stay. The house and grounds were immaculate and beautiful. The house had all the amenities plus a sweet little beach just a few steps away. We had fun exploring Gloucester and it was an easy drive to Boston for our events.

Walk To Everything
this house was peaceful. it was clean and quiet. The town has a lot to do. the nearby beaches were beautiful. Highly recommend this property for a pleasant and peaceful getaway.

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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