Holiday rentals in Gloucester

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Popular amenities for Gloucester holiday rentals

Stay near Gloucester's top sights

Wingaersheek Beach66 locals recommend
Crane Beach124 locals recommend
Good Harbor Beach118 locals recommend
Halibut Point State Park115 locals recommend
Rockport Music-Shalin Liu Performance Center77 locals recommend
Cape Ann Museum69 locals recommend

Other great holiday rentals in Gloucester

Guest favourite
Home in Hampton
4.9 out of 5 average rating, 79 reviews

Lux Getaway! Perfect for Groups 8+ppl

AhmedRating, 5 stars5 months ago
Josh and Tracy are very nice and friendly and their place is amazing! I highly recommend their place to anyone visiting the area!
Guest favourite
Home in Hampton Beach
4.94 out of 5 average rating, 105 reviews

Pearls on Perkins, Beautiful Condo!

ValerieRating, 5 stars7 months ago
We had an amazing time, perfect unit, location was just WOW and Karen was so kind and helpful. Will be back for sure!!
Top guest favourite
Home in Seabrook Beach
5 out of 5 average rating, 10 reviews

Peaceful sunset retreat (bottom floor)

AmandaRating, 5 stars7 months ago
A lovely setting with beautiful marsh views. Close to good seafood restaurants & beach. Responsive friendly hosts. We had a great time!
Top guest favourite
Home in Sandown
4.94 out of 5 average rating, 16 reviews

Sunrise Beach Escape

DebraRating, 5 starstoday
This was the perfect location for our family to spend spring break together! The teenagers loved the games and hot tub, and the adults loved sitting on the patio and chit chatting. The beds were all comfortable, and the window air-conditioning units let each room pick their comfortable temperature. There is plenty of space in the kitchen, and the house had a ton of items available! They provided sufficient paper towels, toilet paper, and dishwasher soap (which so many do not) We all enjoyed the pinball enough that we definitely had to get an extra few rolls of quarters for our 5 night trip. We also all don't do well with the Melaluca brand products that the house uses, so we got our own soaps. There are so many great spaces on the property, and we would have spent even more time outdoors if the weather was warmer, but there was SO much to do inside! We all kept commenting how perfect it was for our group of 6 adults, 2 teens, and 2 tweens.
Top guest favourite
Home in Hull
4.95 out of 5 average rating, 21 reviews

Every room a water view updated kitchen & bath

JohnRating, 5 stars3 months ago
Excellent experience. Easy check in and the place was perfect, she even had some snacks waiting for us upon arrival. Easy walk to the ferry into Boston, and easy parking. It was winter, but there were plenty of outdoor activities so we'd love to come back during the summer. Older house but so charming and great location. Overall great communication before, during, and after; she even offered to ship a shoe my niece left behind to us. Would love to come back and would absolutely recommend to anyone looking for a great place in Hull.
Superhost
Flat in Brighton
4.84 out of 5 average rating, 31 reviews

The Curie-Perfect for Monthly Stays

XuemeiRating, 5 stars6 days ago
This apartment is a great find! The location is perfect, not far from Boston, near every colleges for those who come visiting! This apartment building is indeed very new, built in 2021; but also blended in with history, the leasing office/lobby was converted from an old day chapel, pristine, elegant. Very unique Airbnb experience indeed. The small town is full of vibe with various kinds of cuisines, very good for families, young or old. Melissa, the host is super, giving us very detailed information and instructions from parking to checking in, every tiny details she thoughtfully considered. We couldn’t be happier to stay in this apartment. Highly recommended!
Guest favourite
Cottage in Newburyport
4.99 out of 5 average rating, 165 reviews

True North Cottage*Ocean side of Boat Basin!*

ErikRating, 5 stars6 months ago
Located just a short walk to the beach this charming cottage offered the perfect blend of comfort and convenience for my whole family. The spacious cottage was clean and very well designed with everything we needed for a relaxing stay, including a fully equipped kitchen and cozy living area with modern amenities. The hosts, Elia and Rob, were incredibly welcoming and accommodating and we hope to visit again soon. I would highly recommend True North Cottage to anyone looking for a peaceful getaway near the beach and scenic, downtown Newburyport.
Guest favourite
Guest suite in Rockport
4.97 out of 5 average rating, 111 reviews

8 Bells by the Sea - Private Suite-On the Beach!

AlisonRating, 5 stars7 months ago
My stay at 8 Bells by the Sea was peaceful, fun, and unique. It was a delight living mere feet from the water and feeling so connected to the tides. Robin was very helpful before and during the trip, providing me with recommendations and advice about the area. The apartment is located on a small street, filled with adorable beachy stores, restaurants, art galleries, jewelry shops, and more. The room is charmingly decorated in aquatic tones of blue and green, with thoughtful art and trinkets. There are many windows which look out onto a beautiful view of the water. The bathroom is large and was very clean. I appreciated and utilized the small refrigerator and freezer, as well as the silverware and glassware. My favorite part was mudlarking right outside the room on the beach when the tide was low. I found many pieces of ceramics, and enjoyed hanging out with the ducks and watching other birds. Highly recommend 8 Bells by the Sea for those who enjoy a cute small town by the water.

Quick stats about holiday 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

Destinations to explore

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  5. Gloucester