Waterfront holiday rentals in Gloucester

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Popular amenities for Gloucester waterfront rentals

Waterfront apartment accommodation

Top Guest favourite
Apartment in Salem
5 out of 5 average rating, 123 reviews

2-Bedroom Ocean View Walk to Beach and Downtown

AdamRating, 5 stars4 days ago
Amazing location, close to Salem, beautiful views right from the living room window! We brought our bikes and were able to ride everywhere, didn’t move the car all weekend! This home will exceeded our expectations. So much care has went into this home and it really shows. Exquisitely decorated, and well stocked. The owners (and their pups) are all very nice. We would recommend this home over and over again!
Guest favourite
Apartment in Winthrop
4.93 out of 5 average rating, 138 reviews

Newly Renovated Ocean View 2 Bdrm Apt

KellyRating, 5 stars2 weeks ago
Beautiful accommodations and views. Easy access to the city. The host was very responsive. The extra coffee was also a plus 😁 Would definitely stay again!
Superhost
Apartment in Lynn
4.89 out of 5 average rating, 115 reviews

Spacious 2B Entire Home near Boston, Salem& Encore

RebeccaRating, 5 stars2 days ago
We enjoyed our stay!!! The place was great and my son commented on how comfortable the beds were . The street is a little noisy but they provided sound machines that helped drown it out .20 min drive to Salem and 30-45min drive to Boston depending on traffic . Lots of restaurants and coffee nearby .
Guest favourite
Apartment in Beverly
4.93 out of 5 average rating, 107 reviews

Enjoy Stunning Sunrises&Sunsets Ocean Views 33

JackieRating, 5 stars4 days ago
Susan was an amazing host! Her property was immaculate. She was extremely helpful when we needed a last minute adjustment to accommodate a family member. All around great experience.
Guest favourite
Apartment in Salem
4.98 out of 5 average rating, 169 reviews

Mariam’s On Becket

AmyRating, 5 stars6 months ago
Perfect location! Very homey. As listed. Great communication w host.
Top Guest favourite
Apartment in Rockport
4.92 out of 5 average rating, 143 reviews

Old Harbor

CeciliaRating, 5 stars2 months ago
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!
Top Guest favourite
Apartment in Winthrop
4.96 out of 5 average rating, 241 reviews

Oceanfront Pool. Close to Boston. Free Parking.

MichaelRating, 5 stars2 weeks ago
We loved their place and the location right on the beach and in the sea wall . Got great pics of waves hitting the seawall. Close to alll Boston and Salem locations . Had a great time apt was beautiful and Carol and John left fridge for us fully stocked with milk juice drinks and food . Couldn’t ask for more . We thoroughly enjoyed the hot tub Grest place to stay
Guest favourite
Apartment in Arlington
4.98 out of 5 average rating, 194 reviews

Lakeside apartment, patio, hot tub, outside shower

ParkerRating, 5 stars1 month ago
We had the best time in Arlington this past week! We came for the Boston marathon. The place was beautiful and the location was perfect. It was close to Boston but far enough out for the peace and quiet. Doug and Hope were the most exceptional hosts. They were accommodating and very responsive. They went above and beyond to make our stay and everything we needed as easy as possible. They were so great and we hope to come back in the future!!

Waterfront house rentals

Guest favourite
Home in Rockport
4.94 out of 5 average rating, 54 reviews

Charming waterfront home. Patio, Shops & Dining

LyndaRating, 5 stars1 week ago
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.
Guest favourite
Home in Salem
4.95 out of 5 average rating, 153 reviews

Quaint Little New Hampshire Lake House Getaway!

KevinRating, 5 stars2 weeks ago
We really enjiyed our stay and would recommend to anybody else.
Superhost
Home in Merrimack
4.86 out of 5 average rating, 107 reviews

Pond-Front Passive Solar Architectural House

SarahRating, 5 stars1 week ago
Stayed for a weekend, was absolutely beautiful! The frequent beaver visits was quite the highlight & all amenities were exactly as described!
Top Guest favourite
Home in Gloucester
5 out of 5 average rating, 11 reviews

Lovely home by the sea!

DawnRating, 5 stars3 weeks ago
Thank you for sharing your beautiful, well appointed home as a gentle landing place for a busy graduation weekend. It was a wonderful relaxing environment to celebrate with family.
Guest favourite
Home in Derry
4.92 out of 5 average rating, 470 reviews

Little Lake House, the Bungalow

NickRating, 5 stars1 month ago
We had a great stay and with the rain the cabin was a cozy environment with plenty to do to occupy our time. Also it was close to some great restaurants and a winery with mini golf for the kids and adults only a 15 minute drive. Great location
Superhost
Home in Gloucester
4.86 out of 5 average rating, 50 reviews

Oceanfront 4BR Newly Renovated Modern Home

CatherineRating, 5 stars1 month ago
We so enjoyed hosting our retreat here -- beautiful location, amazing views, and updated and lovely interior. Communication with Rachel, our host, could not have been easier; she was incredibly responsive (often within the hour!), accommodating, and instructions for the house were clear and easy to follow. We'd book again!
Guest favourite
Home in Durham
4.95 out of 5 average rating, 150 reviews

Newly Renovated | Farm Stay | Near Portsmouth!

LisaRating, 5 stars4 days ago
Beautiful home, incredible convenience of being able to walk down a trail to the market and cafe for everything you could possibly need (and then some!) and such picturesque surroundings -- including trails on their property along with Wagon Hill Farm across the street. This property is perfection!
Top Guest favourite
Home in Gloucester
4.98 out of 5 average rating, 82 reviews

Overlook Gloucester's Inner Harbor, Walk to Town

LisaRating, 5 stars5 months ago
Look no further for a central spot to enjoy everything Gloucester has to offer! Cozy home with the quintessential fishing port views. Short walk to shops, restaurants and many historical sites to enjoy. This home is perfect for families to gather and feel comfortable, safe and comfortable. Excellent value for location, amenities, walkable, and quiet!!! Beautiful home. Our family had our best Christmas Holiday ever. Kathy is an exceptional host.

Waterfront condo accommodation

Guest favourite
Condo in Kittery
4.98 out of 5 average rating, 172 reviews

Badgers Island Condo-Sweeping Portsmouth Views #3

AlexRating, 5 stars6 days ago
We loved our stay here, perfect location and a clean and comfortable stay! Lots to do in Portsmouth and the surrounding area and especially lots of great places nearby to eat. Convenient to have 2 parking spots and to be right next to a great restaurant! Well hope to be back in the future!
Superhost
Condo in Salisbury
4.84 out of 5 average rating, 114 reviews

Beachfront | Panoramic Views | "Oceanfront Oasis"

TroyRating, 5 stars2 months ago
Had a wonderful stay. Great location right on the beach. Condo was very nice and well equipped.. Sean was a great host. Would definitely stay there again.
Superhost
Condo in Hampton Beach
4.82 out of 5 average rating, 238 reviews

2 minutes walk to Beach parking and Wi-Fi

AaliyahRating, 5 stars1 week ago
We spent a few nights and had an amazing time right by the beach very peaceful it was great will definitely stay again
Top Guest favourite
Condo in Hampton Beach
4.98 out of 5 average rating, 155 reviews

Beachfront Getaway

SamanthaRating, 5 stars9 months ago
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!!
Guest favourite
Condo in Hampton Beach
4.94 out of 5 average rating, 112 reviews

Summer bliss in our oceanfront 2BR condo awaits!

DavidRating, 5 stars2 months ago
Excellent condo, clean and felt like we were at home. I would stay here again in a minute. Highly recommended. Thank you Jose.
Top Guest favourite
Condo in Hampton Beach
4.97 out of 5 average rating, 272 reviews

Oceanfront Retreat

ShannonRating, 5 stars2 weeks ago
Diane’s condo was a wonderful choice! Her place is clean and spacious and she left very clear helpful instructions for an easy stay. It comes with everything you need and anything you’d want to do in walking distance, highly recommend this spot!
Guest favourite
Condo in Hampton Beach
4.95 out of 5 average rating, 159 reviews

Sunrise In Bed~Couples Retreat

ReneeRating, 5 stars1 month ago
I enjoyed my stay. The location is great - just beyond the main beach traffic but close enough to enjoy all the shops/restaurants. Loved being able to see the ocean from bed and watching the sunrise from the apartment/balcony.
Guest favourite
Condo in Hampton Beach
4.94 out of 5 average rating, 127 reviews

Oceanfront, private balcony, panoramic view Ocean

AnnRating, 5 stars3 weeks ago
The place was described and looked like the pictures. Nice location place was spotless,Even in the hallways and lobbies.Husband loved the snacks.(he’s a junk food junkie.) Nicely decorated and had everything we needed. We have been going to Hampton for a quick 3-4 day getaways for 35 + years and I would highly recommend this place.

Quick stats about waterfront rentals in Gloucester

  • Total rentals

    160 properties

  • Nightly prices starting at

    $133 NZD 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

Destinations to explore

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  2. United States
  3. Massachusetts
  4. Essex County
  5. Gloucester
  6. Waterfront rentals