Gloucester vacation rentals

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Popular amenities for Gloucester vacation rentals

Stay near Gloucester's top sights

Wingaersheek Beach33 locals recommend
Crane Beach124 locals recommend
Halibut Point State Park35 locals recommend

Gloucester beach vacation rentals

Top guest favorite
A charming yellow house is surrounded by lush greenery, with a large wrap-around porch featuring ample seating. A white picket fence borders the property, while a tall tree provides shade. The house showcases a traditional design and is bathed in natural light.
Apartment in Rockport
4.97 out of 5 average rating, 108 reviews

The Crows Nest | Near Shops & Beaches

HayleyRating, 5 stars6 months ago
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!
Superhost
An open-concept living area is highlighted by a modern kitchen featuring a large island with seating for four. A spacious seating area with a blue couch complements the dining space, while a sliding door leads to an outdoor patio. Ample lighting enhances the contemporary design.
Apartment in Rockport
4.84 out of 5 average rating, 95 reviews

Long Beach Suites: Steps Away From Surf!

JennaRating, 5 stars1 month ago
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!
Top guest favorite
A two-story apartment building is seen along the waterfront, showcasing large bay windows and a spacious deck. A small boat is docked in front, with the calm water reflecting the structure. Nearby buildings feature a mix of materials and architectural styles.
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!
Superhost
A serene sunset over the Mill River is captured, with vibrant orange and purple hues reflected on the water's surface. Silhouettes of trees frame the scene, while boats are anchored nearby, contributing to the tranquil waterfront atmosphere.
Guest suite in Gloucester
4.82 out of 5 average rating, 57 reviews

waterview guest suite

AndrewRating, 5 stars5 months ago
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!
Guest favorite
The cottage's exterior features a white façade with large windows, framed by greenery. A spacious deck with planters holds colorful flowers, while a barbecue grill is positioned nearby. A manicured lawn provides an inviting outdoor space, complemented by a peaceful neighborhood ambiance.
Cottage in Rockport
4.91 out of 5 average rating, 104 reviews

Life of Reilly at Back Beach

NormanRating, 5 stars2 weeks ago
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
Guest favorite
A contemporary house is set amidst lush greenery and vibrant flowers, showcasing a large yard. The exterior features large windows and a wraparound balcony on the upper level, while the surrounding garden is filled with various blooming plants.
Home in Gloucester
4.83 out of 5 average rating, 190 reviews

Gloucester Private Contemporary 4 bedrooms

AimeeRating, 5 stars1 week ago
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.
Top guest favorite
The inviting backyard features a clear pool reflecting a serene atmosphere. A patio with seating is visible near the pool. The house, with large windows, provides a bright indoor space that overlooks the outdoor area, surrounded by lush greenery and charming landscaping.
Cottage in Lakeside Marblehead
4.98 out of 5 average rating, 118 reviews

House with Pool, 4 Houses from Harbor, Fort Sewall

KimRating, 5 stars4 days ago
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!
Superhost
A quaint stone cottage is surrounded by lush greenery and colorful flowers, with a well-maintained garden featuring clusters of purple blooms. The cottage's rustic charm is complemented by a sloped lawn and mature trees, creating a serene outdoor atmosphere.
Guesthouse in Gloucester
4.91 out of 5 average rating, 93 reviews

Plum Cove Cottage with king suite!

MilesRating, 5 stars2 weeks ago
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

Guest favorite
The living room features a light and airy design, with large windows providing ocean views. A comfortable sectional sofa and two armchairs are positioned around a rustic wooden coffee table. Bright decor elements and a ceiling fan enhance the inviting space.
Home in Annisquam
4.96 out of 5 average rating, 28 reviews

Beach House on a Private Beach!

ToriRating, 5 starstoday
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.
Top guest favorite
A well-lit bedroom features large windows with scenic water views. A spacious bed is dressed in soft linens, accompanied by a cozy throw. A small seating area includes two chairs and a lamp, enhancing the relaxing atmosphere of the room.
Home in Ipswich
4.97 out of 5 average rating, 105 reviews

Hillside

PamelaRating, 5 stars3 weeks ago
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!
Guest favorite
A coastal view is captured, featuring distant houses and the ocean merging into the horizon. Power lines stretch across the scene, while lush green foliage adds a natural frame to the image. The clear sky complements the tranquil atmosphere.
Home in Ipswich
4.89 out of 5 average rating, 109 reviews

Hillside Ocean View 2BR with Private Beach Access

NancyRating, 5 stars1 week ago
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
Top guest favorite
A bright living area features a cozy seating arrangement with a brown sofa and a patterned rug. A large television sits beside a white brick fireplace with decorative elements. Natural light fills the space through expansive windows, while a dining table with soft chairs is visible in the foreground.
Home in Plum Island
5 out of 5 average rating, 119 reviews

Plum Perch: Professionally Cleaned, Close to Beach

ChrisRating, 5 stars1 week ago
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!
Guest favorite
Aerial view of the spacious home reveals a wraparound deck with multiple seating areas, including shaded tables beneath umbrellas. The exterior features a light yellow façade complemented by large windows, surrounded by greenery that enhances the property's serene, secluded ambiance.
Home in Gloucester
4.92 out of 5 average rating, 105 reviews

Aerie, 2 king beds, large space, AC, 2 beaches!

TiffanyRating, 5 stars1 month ago
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.
Top guest favorite
A fire pit is surrounded by colorful adirondack chairs in a grassy area, with bright yellow flowers adding a pop of color. The view in the background includes a landscape of greenery leading to the water, suggesting a peaceful outdoor space for gatherings.
Home in Ipswich
4.98 out of 5 average rating, 196 reviews

Stagehill Beach House

EmilyRating, 5 stars1 month ago
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.
Guest favorite
The exterior of the house showcases a spacious design with a light-colored facade and large windows. A spiral staircase leads to an upper deck, offering additional outdoor space. Natural grasses and shrubs surround the property, enhancing the connection to the beach environment.
Home in Plum Island
4.91 out of 5 average rating, 158 reviews

Brivera by the Sea, a Beautiful Plum Island Escape

JoshuaRating, 5 stars5 days ago
Great house, awesome location, everything was perfect and communication was great.
Top guest favorite
Home in Rockport
4.97 out of 5 average rating, 330 reviews

Charming Toe-Hold, A Short Walk to Town and Beach

MichaelRating, 5 stars2 weeks ago
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

Top guest favorite
The charming cottage exterior features a welcoming porch with two rocking chairs and lush greenery surrounding it. The light-colored facade is complemented by dark windows and a pitched roof, creating a cozy, inviting appearance. A manicured lawn enhances the overall setting.
Home in Gloucester
5 out of 5 average rating, 12 reviews

Chic Coastal Retreat

SandyRating, 5 stars2 weeks ago
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 ❤️
Top guest favorite
A modern living area features vaulted ceilings and wooden accents, creating an open atmosphere. A large flat-screen television is mounted on a white media console. Comfortable seating is provided on a dark sectional sofa, complemented by natural light from skylights and windows.
Home in Plum Island
4.99 out of 5 average rating, 140 reviews

“Salty Girl” Plum Island, MA

LeighaRating, 5 stars2 days ago
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!
Guest favorite
Two white rocking chairs sit invitingly along a stone walkway, facing a calm harbor. Reflections of colorful buildings and boats can be seen on the water's surface, framed by a vibrant sky during sunset.
Home in Rockport
4.94 out of 5 average rating, 54 reviews

Charming waterfront home. Patio, Shops & Dining

LyndaRating, 5 stars5 days 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.
Top guest favorite
Home in Salem
4.95 out of 5 average rating, 125 reviews

Beautiful historical house in Salem

AmandaRating, 5 stars1 week ago
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.
Guest favorite
A quaint beach cottage is surrounded by a lush garden, featuring blooming flowers and greenery. Stone steps lead to the entrance, which is framed by white railing. Two individuals are seen tending to the garden, adding to the inviting atmosphere of the property.
Home in Annisquam
5 out of 5 average rating, 28 reviews

Annisquam Getaway - Water View+Walk To The Beach

MatthewRating, 5 stars1 week ago
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.
Top guest favorite
A charming two-story home is presented, featuring a white exterior with dark shutters. A stone pathway leads to the entrance, bordered by lush greenery and colorful flowers. The front yard exhibits a natural landscape, inviting guests to explore the property further.
Home in Gloucester
4.97 out of 5 average rating, 95 reviews

Charming Year Round Home, Plum Cove Cottage

JaneRating, 5 stars6 months ago
Super cute cottage right next to Plum Cove. Very cozy and plenty of amenities.
Top guest favorite
A spacious living area showcases a modern leather sofa facing a wall-mounted television. Natural light filters through large windows, creating a bright atmosphere. A dining table with light-colored chairs is positioned nearby, with a decorative plant placed in the center.
Home in Lakeside Marblehead
4.98 out of 5 average rating, 121 reviews

Walk To Everything

LauraRating, 5 stars1 week ago
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!
Guest favorite
An open living space features a modern kitchen with white cabinetry and stainless-steel appliances, including a dishwasher. A spiral staircase leads to the upper level. A cozy seating area with a sofa and decorative plants is visible, enhancing the home's bright and welcoming ambiance.
Home in Gloucester
4.94 out of 5 average rating, 36 reviews

Townhouse #3 in Downtown with Parking

JamieRating, 5 stars1 week ago
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.

Destinations to explore

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  4. Essex County
  5. Gloucester