House vacation rentals in Gloucester

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Popular amenities for Gloucester house rentals

House rentals with free parking

Guest favorite
Home in Gloucester
4.9 out of 5 average rating, 20 reviews

2 bedroom in heart of Gloucester

MichelleRating, 5 stars7 months ago
Our family had an amazing time. Very nice and clean inside. The bed was so comfortable. Felt very homey. Enjoyed the backyard as well. Close to the train. We went to Salem for Halloween. All in all a great experience! Thank you Michael for all your help! Would definitely come back!
Guest favorite
Home in Rockport
5 out of 5 average rating, 38 reviews

Eden Cove

KimRating, 5 stars1 month ago
The views this home offers are beautiful. It is a nice neighborhood for walking a dog. The home has everything you would need. The host is very responsive.
Top guest favorite
Home in Rockport
5 out of 5 average rating, 10 reviews

Whale Cove Waterview

SusanRating, 5 stars7 months ago
Beautiful place just a one minute ride to the Rockport Golf Club where my daughter was getting married. We had plenty of room for all six of us. A nice big kitchen with a very large center island so we could share many meals and prepare food and platters for the wedding. The living room has a lovely gas fireplace and we had many cozy evenings there as we destressed from all the wedding festivities. We spent quite a lot of time outdoors, walking down to the ocean and sitting on the deck, watching the stars. October is a lovely time to visit Rockport. Less traffic, pretty autumn colors, no big crowds at restaurants so short wait for tables. If we needed to come back for another event, I would choose this home again. *for those with back issues- all of the beds were cozy but not supportive and very soft.
Top guest favorite
Home in Gloucester
5 out of 5 average rating, 10 reviews

Waterfront 4 bed/2 bath-Stunning Annisquam Sunsets

RaghavRating, 5 stars1 day ago
Had a great stay in Gloucester with a large group of friends and families from college. The house is as described with plenty of living and sleeping space for large groups. The screened porch is perfect for hanging out and eating in. The backyard is right on the water with plenty of outdoor games, a grill, fire pit, and paddle boards and a kayak to get on the water. Extremely family friendly with fun board games, life vests of all sizes, beach toys and floats etc. Location is great too, close to beaches, grocery stores and downtown Gloucester. Was the perfect space for a long weekend, and located very conveniently to Boston to accommodate families flying in from far away.
Superhost
Home in Gloucester
4.88 out of 5 average rating, 34 reviews

Cheerful 3-bedroom home with easy access to beach

PaytonRating, 5 stars7 months ago
Had a nice time, house was close to a lot. Great location and kept us close to friends and family. We will be back. Would recommend this home to anyone looking to stay in Gloucester
Top guest favorite
Home in Rockport
5 out of 5 average rating, 45 reviews

New South End Home Quiet Lane To Old Garden Beach

JeffreyRating, 5 stars3 weeks ago
Wonderful stay. Wide open spaces downstairs and great bedrooms upstairs. Super clean with lots of amenities. Judy was super helpful and responsive. Highly recommend this space if you are staying anywhere near Rockport. Do not hesitate with this wonderful home and host. We would 100% stay again.
Top guest favorite
Home in Salem
5 out of 5 average rating, 14 reviews

Cottage-style home in Salem

MishondaRating, 5 stars7 months ago
Beautiful home and well located to explore. Rewan is an amazing host! Truly exceptional
Top guest favorite
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.

House rentals with a pool

Superhost
Home in Gloucester
4.73 out of 5 average rating, 15 reviews

Mansion in Gloucester with Pool

MaryRating, 5 stars6 months ago
My family and I were fortunate enough to spend the thanksgiving holiday here. It was the perfect space for a group gathering. Would highly recommend!
Guest favorite
Home in North Andover
4.94 out of 5 average rating, 157 reviews

Nana-tucket Inn

AdamRating, 5 stars2 weeks ago
The Nana-Tucket Inn is an absolutely gorgeous and pristine property with everything a family could need! It was perfect for our family while we were visiting New England. It was a great space for family time and our teenagers had plenty to do. Nancy and Joe are the perfect hosts! They are kind and extremely helpful while they maintain the beautiful property. They are not intrusive at all but are there if you need anything. During our stay, a huge storm blew through Massachusetts with extremely strong winds and tons of rain. Nancy and Joe had the mess made by the storm was cleaned up immediately by a professional crew the next morning so that we did not miss a single moment of the property amenities! Nancy also made us a blueberry crumble cake that was delicious and so kind. We thoroughly enjoyed our stay and we cannot wait to return during our next New England trip.
Top guest favorite
Home in Newton
5 out of 5 average rating, 18 reviews

Villa with private Pool in Boston's Elite Enclave

BrandonRating, 5 stars3 weeks ago
We stayed for a graduation for our son and the house comfortable accommodated our entire family including parents/ in-laws. There was a creek in the back, pool, Firepit. We had fun playing pool (billiards) and darts. Nice Kitchen with new appliances. The 3 bedrooms are nice in size and we never felt cramped accommodating us all. The host communicated very quickly and was sooo nice. We unfortunately won’t be in Boston in near future however if we did and needed the space we would book again.
Top guest favorite
Home in Hampton
5 out of 5 average rating, 43 reviews

Sleeps 10, Indoor Pool, Hot Tub, Pups Ok

DeniseRating, 5 stars3 days ago
We enjoyed our stay so much! The house was perfect for our vacation. Plenty of room that everyone had their own space. The house is beautifully decorated, made you feel right at home. Comfortable seating found throughout inside and outside area. Teresa has thought of EVERYTHING, and it is available for you to use on your stay. The location is fantastic, a short walk to North Beach in a nice quiet residential neighborhood. We would highly recommend and would stay here again!
Top guest favorite
Home in Lakeside Marblehead
5 out of 5 average rating, 16 reviews

Large Pool, Nature Trails, Redd's Pond, 4-Bed

AlanaRating, 5 stars1 week ago
Amy was very responsive and communicative. The house was clean and maps took us right to the home. It was too early in the season to enjoy the pool but it was pristine and would have been great for hot summer weather. Amy was wonderful with trying to accomodate any requests and we liked the location from easy access to Salem and within a one hour drive to Boston!
Superhost
Home in Rockport
5 out of 5 average rating, 5 reviews

Rockport Pool House|4BR/3BA Walk to Bearskin Neck

MarthaRating, 5 stars5 days ago
Beautiful house in a lovely quiet neighborhood. Kitchen was amazing! Very walkable to Bearskin Neck and Old Garden Beach. We had a few little glitches the first night, but Rachel was very responsive and everything was perfect within 24 hours. Would absolutely be happy to stay there again. To future guests: Rockport is light on grocery stores, so even though most things are walkable, for groceries you might want a car.
Guest favorite
Home in Arlington
4.94 out of 5 average rating, 34 reviews

Beautiful Spacious 4BRM House!

NicholasRating, 5 stars2 days ago
I loved everything Maxine said and how she helped navigate around every even in the house, everything was so clean, very quite place good for professional working, everything was just beyond, amazing & lovely place you feel right at home with so much space to move around the house. Being free having your privacy. Thank you Maxine 🙏👏🏽
Top guest favorite
Home in Norwood
4.95 out of 5 average rating, 42 reviews

the house of id; vintage shop, accessible space

KassiaRating, 5 stars1 week ago
We absolutely loved our stay at this home! It was extremely clean, cozy, and beautifully prepared — every detail made us feel so comfortable and welcome. You can truly feel the love and care the host put into the space. It felt like a warm home from the moment we arrived. We are already looking forward to coming back again. Thank you for such a special experience! 🙏✨💕☀️

House rentals with a hot tub

Top guest favorite
Home in Chelmsford
5 out of 5 average rating, 18 reviews

* * Crooked_Spring_Colonial * *

LoriRating, 5 stars3 weeks ago
The home is beautiful, exactly as pictured on the site, located on a very quiet street in a wooded area. Very clean, with access to a whole array of kitchenware and other items around the house. Excellent, detailed set of instructions for the home with info on TV controls, gaming system, thermostat control, local recommendations, and departure instructions. This would be an amazing house to stay with small children, as there is a fun playroom with toys in the basement and a great backyard. It's about 45 minutes to Boston without traffic, and about 1 1/4 hours at peak times, so plan accordingly if you are planning travel to downtown Boston. Great local ice cream place just down the street and local shopping about 10 minutes away.
Guest favorite
Home in Scituate
4.94 out of 5 average rating, 16 reviews

Beach Cottage in Scituate w/ HOT TUB

AdilyaRating, 5 stars3 weeks ago
We absolutely loved this AirBnB!! Stayed in Scituate for a college graduation in BU and was the perfect location to come home to and walk on the beach and spend time with family and host. James was super helpful and responsive, we definitely recommend!!
Superhost
Home in Salem
4.8 out of 5 average rating, 10 reviews

5BR Luxe Lakehouse: Theater, Gym, Spa, Bar, Garage

Juan ManuelRating, 5 stars5 months ago
beautiful home great for large quiet family gatherings!
Guest favorite
Home in Sandown
4.95 out of 5 average rating, 19 reviews

Sunrise Beach Escape

AshenafiRating, 5 stars1 week ago
We had great time with family and friends. Very beautiful place, quiet and peaceful. Lake view is amazing. Kids enjoyed jacuzzi and many games in the house. There are kayaks and life jackets for everyone. Adults had fun on the deck and by the fire near the lake. House is very clean. Hiking places are close. We really enjoyed and recommend for families who love nature and quiet neighborhood.
Guest favorite
Home in Danville
5 out of 5 average rating, 43 reviews

Elm Farm

AdreannaRating, 5 stars1 day ago
This property was absolutely amazing & it made my wedding party and I feel right at home the second we showed up! Plenty of space, very clean & we all still had our own privacy. The grounds were well kept and stunning. We kept discovering new areas of the home all weekend that we didn’t know about behind each door! The host was so kind , flexible and amazing at communicating. I highly recommend for any family or friend gatherings you may have. The best home we have stayed in so far!
Guest favorite
Home in Scituate
5 out of 5 average rating, 5 reviews

BOOK NOW! Beathtaking Ocean front Estate w/HotTub!

SaadRating, 5 stars1 week ago
I had a wonderful stay! The place looked exactly like the photos—clean, serene, and thoughtfully put together. It was the perfect spot to relax. Kimberly was very responsive and provided great local recommendations. Would definitely stay here again!
Top guest favorite
Home in South Boston
4.95 out of 5 average rating, 81 reviews

Heart of Southie - Hot Tub + Walk to Top Bars

KathleenRating, 5 stars2 weeks ago
We stayed at Alex’s place for 2 nights. Both he and Kaleen were extremely helpful and kind. The place is just perfect for a large group. We were 8 people in town for a college graduation. Great recommendation with PS Gourmet coffee. Went morning and afternoon both days for coffee and hot chocolate (which is amazing for the kids. They make it fresh w steamed milk.) The weather was absolutely horrible - a Nor’ Eastern on Memorial Day weekend - so we didn’t get to enjoy the hot tub but it looked lovely :) Definitely recommend.
Guest favorite
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

Quick stats about house rentals in Gloucester

  • Total rentals

    270 properties

  • Total number of reviews

    7.1K reviews

  • Family-friendly rentals

    250 properties are a good fit for families

  • Pet-friendly rentals

    80 properties allow pets

  • Rentals with dedicated workspaces

    140 properties have a dedicated workspace

  • Wifi availability

    270 properties include access to wifi

Destinations to explore

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  2. United States
  3. Massachusetts
  4. Essex County
  5. Gloucester
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