
Waterfront vacation rentals in Gloucester
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Top-rated waterfront rentals in Gloucester
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Popular amenities for Gloucester waterfront rentals
Waterfront apartment rentals

Mary's By The Sea
Ideal location walking distance to shops and restaurants. Unit provided everything we needed for our stay very much recommend this apartment to anyone planning to travel to Rockport

Harborside Oasis | Harbor View | Heart of Downtown
This is a beautiful apartment located in the heart of Rockport. Will definitely come back here if possible for another trip!

Newly Renovated Ocean View 2 Bdrm Apt
Our first trip to the Boston area couldn’t have been better! This Airbnb was absolutely perfect for our family of four. The bedroom I stayed in had its own balcony with a beautiful ocean view—ideal for peaceful summer mornings or warm, relaxing nights. The open-concept living room and kitchen gave us plenty of space to unwind after a day of exploring. But what really sets this place apart are two unbeatable features: first, you won’t find easier access to public transportation—there’s a bus stop just a 30-second walk away that takes you right into Boston. Second, the hosts, Milan and Anna, were some of the kindest and most helpful we’ve ever met. Their local tips made our stay even better. Great amenities, smartTV, updated shower, dishwasher, laundry, grill available to use, etc. Right next to the house is a beautiful walkway that stretches down the beachfront of Winthrop. We’re already talking about coming back as the Boston area is second to none!

Enjoy Stunning Sunrises&Sunsets Ocean Views 33
Everything was perfect , felt right at home the beds were the most comfortable I’ve ever slept on ! Shower was wonderful /great water pressure.

Amazing Ocean View In-Law Apt.
I needed a special place for a special weekend. I didn't want to propose in a loud, busy Boston location. I wanted private, quiet and intimate. Thats what the photos felt like and I'm happy to say that was the exact experience. April is a perfect time with sunny weather in the 50's. We had a pleasant conversation with Susan in the shared driveway on our way to dinner. She recommended Seaport Grill, specifically the Chilean Sea Bass. It did not disappoint. Plus the Hammond Castle. It was an unforgettable weekend. She said Yes!

Ocean view studio with hot tub & access to Boston
This place is a perfect Nahant beach get-away. We were there for a wedding over the weekend, and were so lucky to find Elyse's place! Elyse is a wonderful host, and she communicated everything in such a detailed manner that finding the place/checking in was a breeze. It poured rain all weekend, but the cozy, clean unit that is decorated beautifully and is so conveniently located to everything made us feel at home. The unit has everything you need - even a lovely deck overlooking Boston Harbor. Elyse was gracious enough to offer to turn on the hot tub for us while we were arriving, and she had great local recommendations. While we did not get to use the hot tub or go to the beach because of the rain, we hope to return and take full advantage of how special this place is again!

4 Bed 2.5 Bath Water view Downtown with Parking
Great place to stay. Super accommodating and friendly to do business with.

Oceanfront Pool. Close to Boston. Free Parking.
This was a perfect location for a long weekend getaway! Proximity to public transportation makes this place an awesome option for Boston travels, the ocean is absolutely gorgeous! I ran the Boston marathon on my visit and the hot tub was incredible for recovery! The bed is so comfortable and even though we didn’t cook anything, we easily could have! Having a washer and dryer in the unit available meant that I don’t have piles of laundry to do when I get home!
Waterfront house rentals

2 Bedroom Beach Bungalow, Steps from the Beach!
Out of the Airbnbs I’ve stayed at, this one has been my favorite! Sharon was very accommodating, left the best personal touches, and was so friendly and welcoming. Highly recommend this place for you & your loved ones

Beach House on a Private Beach!
Great house! Great beach! Great hosts!!!

Views over Lobster Cove! Book spring weekends
Property was just as pictured, which I find extremely important. This spot is off the beaten path and quiet with a nice little walking bridge for a stroll. Close enough by car, to all the attractions of Glouchester when your ready to get out and about.

WATERFRONT-15 min to BOS/3BdRm/2BA
Super responsive hosts and a great place to stay!

Quaint Little New Hampshire Lake House Getaway!
James was an excellent host for my family and me. We thoroughly enjoyed the place and its beautiful surroundings.

*Ocean View* Charming beach house
House was spacious in a quiet neighborhood. The beach is a short walk away. There was some mold in the bottom of the shower which was the only downside, but it did not detract from the overall stay. Would stay here again!

Beach access, walking distance to downtown!
We had a wonderful stay at Hampton Beach. The house is right across the street from the beach and has a great view from the top floor. The house is cute and comfy and Larissa was very helpful and responsive in communication. The house is also within walking distance of many shops, restaurants, ice cream places, etc. Just of note, the house is right next to the street and parking lot so it's a great location if you are walking to the beach but not super quiet if you want to sit outside at the house. There is also only one parking space that goes with the house so when it is busy can be difficult to park a second car. That didn't effect our stay, though, and we really enjoyed the house and location.

Little Lake House, the Bungalow
One of the best places l've ever stayed! The lake view is absolutely amazing-so peaceful and beautiful. The whole vibe is just perfect for a relaxing weekend. I wish everyone could experience this place at least once. It's truly a hidden gem, with the best views and the best atmosphere. Highly recommend for anyone looking to unwind and enjoy nature.
Waterfront condo rentals

Beachfront | Panoramic Views | "Oceanfront Oasis"
An amazing beachfront getaway! The property was clean, well-maintained, and offered breathtaking views of the ocean. Waking up to the sound of waves and enjoying sunsets from the patio was a dream. The host was responsive and made everything seamless. Perfect for a relaxing stay—can’t wait to come back!

2 minutes walk to Beach parking and Wi-Fi
Our stay was great! Weather was dreary and chilly, but Diana's place was cozy and spacious, just right for two girls out for a fun weekend. Appreciated the coffee and coffee maker, and ice in the freezer. Diana was very responsive and proactive when I was having trouble with the internet. (weather and user related, not her fault at all) There were plenty of extra blankets and pillows, towels (though we brought our own) and most anything we could have anticipated needing before we could get to a store for staples. It was nice and quiet, but then again, Rainy April weekend. Can't wait to come back when the weather is warmer! Definitely would be back again.

Beachfront Getaway
This is a way to truly get away. The studio was gorgeous, the bed was incredibly comfortable and having the ocean right outside was amazing. We only booked for a weekend, but I wish we had booked for a week - so amazing!! Everything was perfect!!

Summer bliss in our oceanfront 2BR condo awaits!
Really enjoyed our stay here. The condo was clean and the electronic fireplace made us felt at home and comfortable. I especially loved the small touches with the books and games tucked away above the tv waiting to be found. Also we got a nice surprise on NYE with some fireworks on the beach. The hardest thing to figure out was where the trash room was but José sent a picture which helped a lot.

Beachfront Summer Fun
Diane was great to communicate with and made evrything super easy for our stay!

Boston Harbor View!Free Parking!North End 3 bed
We stayed Thursday night through Sunday 4-2-25 thru 4-6-25. Almost everything was in walking distance. We tried a new restaurant every night, eating mostly Italian. We weren't to far from Quincy Market, we had brunch almost every day and did shopping. It is right across the street from the wharf and we had a beautiful view from the living room. We went to go and see the Red Sox game for opening day. Couldn't have asked for better weather and a wonderful place to stay. Any questions we had were answered quickly and they game us great recommendations for restaurants. We will definitely be going back again, rating was 5 stars! Anne Duran

Sunrise In Bed~Couples Retreat
Clean and comfortable. The Sunrise view from the bed was beautiful. It was low season and the noise from the road was noticeable in the daytime but quiet in the morning and evening. Not many restaurants open at this time but I expected this. I recommend this accommodation for a relaxing stay. Great location and beach walkability. The hosts were very responsive. It was a perfect 2 nights for me.

Oceanfront, private balcony, panoramic view Ocean
Beautiful view of the ocean. Steps the beach! Very clean. Hosts were very communicative & friendly.
Quick stats about waterfront rentals in Gloucester
Total rentals
160 properties
Nightly prices starting at
ﺩ.ﺇ294 before taxes and fees
Total number of reviews
7.8K reviews
Family-friendly rentals
100 properties are a good fit for families
Pet-friendly rentals
40 properties allow pets
Rentals with a pool
10 properties have a pool
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- Hampton Beach
- Wells Beach
- Boston Common
- TD Garden
- Fenway Park
- Harvard University
- North Hampton Beach
- Ogunquit Playhouse
- Long Beach
- New England Aquarium
- Faneuil Hall Marketplace
- Long Sands Beach
- Freedom Trail
- Prudential Center
- Symphony Hall
- Boston Public Library
- Crane Beach
- Rye North Beach
- Aaronap Cellars
- John Hancock Tower
- Boston Children's Museum
- Quincy Market
- Pavilion Beach
- Wentworth by the Sea Country Club