Condo vacation rentals in Gloucester

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Popular amenities for Gloucester condo rentals

Weekly condo rentals

Guest favorite
Condo in Rockport
4.97 out of 5 average rating, 67 reviews

Gorgeous apartment, short walk to beach&downtown!

CourtneyRating, 5 stars2 weeks ago
This is a thoughtfully organized and stocked apartment in an adorable neighborhood, walkable to all of the Rockport sights and easy to find. I appreciated the adjustable desk, the amazingly easy to use tv, the Nespresso and the laundry. There were a lot of nice aesthetic details, too: real books, a lovely courtyard, pretty upholstery. Highly recommend.
Top guest favorite
Condo in Swampscott
5 out of 5 average rating, 90 reviews

Newly Renovated Victorian close to Boston

DouglasRating, 5 stars3 days ago
Excellent hosts - great access to train to Boston (15 minutes) - Swampscott is beautiful- near Salem and Marblehead - what a wonderful location near an historic harbor …
Superhost
Condo in Gloucester
5 out of 5 average rating, 3 reviews

Marina View, Walk to Niles Beach & Rocky Neck

DouglasRating, 5 stars5 months ago
This comfortable apartment has a charming view of Gloucester harbor. It's location adjacent to a live theater and around the corner from Rocky Neck is perfect for entertainment and exploration. It's a five-minute car ride into the downtown, or if you're feeling a need to stretch your legs - it's a long, easy walk.
Top guest favorite
Condo in Salem
4.99 out of 5 average rating, 68 reviews

Artsy Condo | High Ceilings | Modern Industrial

GiaoRating, 5 stars1 week ago
Great place. We loved how central the location was to everything. The house was clean and comfortable. Owners were very responsive and easy to work with.
Superhost
Condo in Salem
4.92 out of 5 average rating, 12 reviews

Luxury Sand Castle Beach House Historic SALEM

EmilyRating, 5 stars6 months ago
Gary provided an amazing experience during our stay! The home was spotless, beautifully decorated, and equipped with everything we needed for a comfortable visit. The location was perfect, close to main attractions, yet peaceful and relaxing. Gary was incredibly thoughtful and responsive, making us feel right at home. Small touches like a welcoming Thanksgiving card and chocolates really stood out. We couldn’t have asked for a better place to stay and would absolutely recommend this Airbnb to anyone visiting the area. We hope to return soon! Thank you for the exceptional hospitality!
Superhost
Condo in Peabody
4.94 out of 5 average rating, 82 reviews

Peabody Penthouse Top of the World Sunset View

NoraRating, 5 stars1 week ago
i loved this place so much, the photos do not do the place justice. I had a great time, the place was so relaxing and i felt right at home. Peabody is such a nice place and there are so many stores right near by, even walkable. The best part of the place is the outdoor patio which have seats and such a nice view. i love how much light the place got during the day and during the sunsets. the place was super clean and nicely decorated. Demetri was such a great host and was so helpful, friendly and responsive! Thank you for a great stay!
Guest favorite
Condo in Rockport
4.86 out of 5 average rating, 94 reviews

Quintessential Charm, Private, Walk to Beach/Town

Alex And IndiaRating, 5 stars1 month ago
Cute and clean accommodations! Walking distance to downtown Rockport, quiet and private. Definitely recommend!
Top guest favorite
Condo in Rockport
4.96 out of 5 average rating, 78 reviews

Rockport Oceanfront 1 Bed Apt Heart of Downtown

TessaRating, 5 stars2 weeks ago
A truly fantastic stay! The apartment was just as described, very clean and exactly what we needed. Maureen was extremely responsive and delightful to communicate with - we can’t wait to come back!

Pet-friendly condo rentals

Superhost
Condo in Bay Village
4.89 out of 5 average rating, 114 reviews

Condo in downtown Boston

SusanRating, 5 stars3 weeks ago
This was such a charming place in a wonderful location. Griffin and Carolyn were responsive and took really good care of us. They are great hosts who we highly recommend and would book with again!
Guest favorite
Condo in Somerville
4.85 out of 5 average rating, 221 reviews

A Cozy 3 Bedroom Home Close To Boston & Parking

DanielleRating, 5 stars1 week ago
Shirley & Marie were great hosts. The house was clean and tidy upon our arrival. Check-in & check-out were very easy. They were very easy to communicator with before our arrival. Highly recommend staying here. We will definitely be back!
Guest favorite
Condo in East Boston
4.95 out of 5 average rating, 202 reviews

Family Home + Near Downtown + Cool Backyard!

RogerRating, 5 stars3 months ago
We had a great stay! Quiet, safe neighborhood, easy to get to the city. Lots of space for the six of us to eat and relax together. Beautiful view of the Boston skyline just minutes walk from the place. Comfortable beds and soft sheets too! We also had no troubles parking nearby and leaving our car (for free) for our entire stay.
Guest favorite
Condo in Cambridge
4.89 out of 5 average rating, 138 reviews

#1A Harvard MIT Central location! in unit W/D

ScottRating, 5 stars1 month ago
Louisa’s place is awesome. Lots of room, great kitchen, living room, bed, etc. She is super responsive and even gave us something important that we forgot, which made a big difference to our trip. We would definitely stay there again.
Guest favorite
Condo in South Boston
4.88 out of 5 average rating, 136 reviews

Right Near Convention Center and Train Station

MollyRating, 5 stars2 days ago
We had a great stay at this South Boston condo! The location was perfect—just a short walk to the Convention Center, and the Seaport area, making getting around the city extremely simple. The space was spotless and clearly well cared for. Communication with the host was smooth and responsive throughout. The main bedroom was quiet and had a great work setup with a desk. The lower bunk bed is set directly on the floor, which actually worked out well—smaller adults in our group found it comfy and easy to sleep on. Parking was limited, but we found street parking without much trouble. Overall, a clean, convenient, and well-located spot—we’d definitely stay here again!
Guest favorite
Condo in Roxbury
4.97 out of 5 average rating, 108 reviews

Spacious Dorchester Retreat | 2-bdrm condo

JosefRating, 5 stars1 week ago
The house was adorable and very clean. We weren't there much, but we had everything we needed when we were there. The hosts were very responsive and helpful when needed.
Guest favorite
Condo in Roslindale
4.89 out of 5 average rating, 108 reviews

Transit friendly condo on quiet street

HarvinderRating, 5 stars3 weeks ago
It’s a lovely and peaceful neighborhood. The home was really good. Very spacious bedrooms, well stocked kitchen and living room. Wish we had more time to spend indoors. Andy was else quick on responses and proactively addressed any questions we had. Grocery store is just around the corner so that’s a big plus too. Overall a great experience
Guest favorite
Condo in Jamaica Plain
4.88 out of 5 average rating, 540 reviews

Historic JP Brownstone with Parking. Pets Welcome!

ChristopherRating, 5 stars2 weeks ago
Adorable brownstone in JP! Close to the orange line, quiet neighborhood with lots of families. House was great, lots of space.

Condo rentals with a pool

Guest favorite
Condo in Hampton Beach
4.88 out of 5 average rating, 50 reviews

Nautical Bliss - Luxury Studio Condo w/ Pool

Rae-LynnRating, 5 stars9 months ago
Great location, close by to the beach and right at the beginning of all the shops and food. We will be back!
Top guest favorite
Condo in Hampton
5 out of 5 average rating, 18 reviews

Lovely 2 BR beach condo with inground pool

PhyllisRating, 5 stars8 months ago
We had a wonderful vacation in NH especially due to the beautiful condo we stayed in. Every morning we took a short walk to the beach at sunrise. We also enjoyed sitting out on the deck overlooking the pool as well. It was a short drive to most places of interest, shops and restaurants. Our host Sue was very responsive via text. The place was clean and full of many things to help make our stay special. We’ll definitely be back in the future.
Guest favorite
Condo in Hampton Beach
4.89 out of 5 average rating, 36 reviews

Hampton 100 yards to beach

KrystinaRating, 5 stars10 months ago
Clean and good storage for a small space. Good location
Superhost
Condo in Hampton
4.82 out of 5 average rating, 17 reviews

Serenity by the Sea

JamesRating, 5 stars8 months ago
Great place to stay with an awesome view of the beach right from the balcony. This is where every morning we would have our coffee to plan out our day and every evening sit back with a glass of wine and watch the moon rise over the ocean. The accommodations were good, the place was clean and had all the things to make our stay enjoyable. We would stay here again as well as recommend it to friends and family.
Guest favorite
Condo in Hampton Beach
4.97 out of 5 average rating, 38 reviews

Ocean View - Steps to the Beach!

AngeloRating, 5 stars9 months ago
We stay at Hampton Beach every year for a few days. This has by far been the best. It seemed we were at home. Copmmunication with the owner and the facility was exceptional.
Superhost
Condo in Hampton Beach
4.85 out of 5 average rating, 87 reviews

Rising Tides | Steps to Beach | Parking | A/C

FabiolaRating, 5 stars1 month ago
I loved the stay, excellent location and very cozy place. I would go back 100%
Guest favorite
Condo in Londonderry
4.88 out of 5 average rating, 41 reviews

Village Hideaway

VinnieRating, 5 stars1 month ago
This condo was a place that’s lived in, not JUST for use as an AirBNB. It felt homey. Donald explained to me the weird shower spout. Donald’s wife responded to me about the WiFi information when I asked about it. We enjoyed it.
Top guest favorite
Condo in Hampton Beach
4.97 out of 5 average rating, 74 reviews

406 Co. Seascape

JoeRating, 5 stars7 months ago
Great stay at this condo in Hampton Beach! Very walkable location and stunning sunrises each morning. Will definitely come back.

Quick stats about condo rentals in Gloucester

  • Total rentals

    20 properties

  • Nightly prices starting at

    ﺩ.ﺇ331 before taxes and fees

  • Total number of reviews

    1.8K reviews

  • Family-friendly rentals

    10 properties are a good fit for families

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    20 properties include access to wifi

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