Apartment holiday rentals in Gloucester

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Popular amenities for Gloucester apartment rentals

Weekly apartment rentals

Superhost
Apartment in Gloucester
4.74 out of 5 average rating, 38 reviews

Cozy

FrancescaRating, 5 stars1 week ago
Although our stay was short the place fit all our expectations and needs. The coffee bar was great! The only hiccup was the parking lot was a little crowded/full and we had to find parking elsewhere. But would highly recommended staying at Donny’s Place.
Superhost
Apartment in Gloucester
4.84 out of 5 average rating, 68 reviews

Close to Half Moon Beach!

LesleyRating, 5 stars8 months ago
A lovely and spacious apartment with beautiful views and a warm cozy feel. Walkable to the bay, various trails along the coast, local shops, restaurtants, the waterfront and the train. Sabine was very helpful and considerate when we had some TV issues - which were promptly dealt with along with a gift basket for the inconvenience. Another one followed later for a birthday celebration!! Thank you! I would definitely recommend this location for anyone visiting New England and/or Boston.
Top Guest favourite
Apartment in Magnolia
5 out of 5 average rating, 42 reviews

Blue Magnolia

LukeRating, 5 starstoday
Had a wonderful night that was comfortable and perfect for my needs. Clean and cozy. Great communication.
Guest favourite
Apartment in Gloucester
4.96 out of 5 average rating, 53 reviews

CbytheSea - Ocean View Penthouse

InvaRating, 5 stars2 days ago
Spent Father’s Day weekend in Gloucester with immediate and extended family, and rented both units from Nick and Emily. I must say the whole family absolutely loved everything in the units. I feel like pictures don’t do it justice as it felt way bigger in person. So well decorated. Super clean. Amazing location!! Finding parking wasn’t teeeerrible, just slightly inconvenient. There was always plenty if you were willing to take a short walk. Nick and Emily were super responsive and extremely accommodating. Hoping we can all return once this New England weather warms up enough to enjoy the beaches.
Guest favourite
Apartment in Gloucester
4.95 out of 5 average rating, 59 reviews

New Design - Walk to DNTN, Beauport, Beach, Train

ChrisRating, 5 stars4 days ago
Perfect location to stay, and very clean and orderly. The host was responsive, and answered all our questions. I would definitely stay here again.
Superhost
Apartment in Rockport
4.85 out of 5 average rating, 101 reviews

Long Beach Suites: Steps Away From Surf!

ShoshanaRating, 5 stars3 days ago
Wonderful wonderful. I can express how amazing this spot was. I keep thinking about it. We stayed another 2 nights at a hotel but it is nothing like this place. We will definitely come back and the price was great too compared to hotels with no kitchen. It was clean, just absolutely perfect and few walking feet to south shore beach. I can keep going about how wonderful this Airbnb apartment is. Thank you!
Guest favourite
Apartment in Gloucester
5 out of 5 average rating, 32 reviews

White Sand beach in a private enclave

EddyRating, 5 stars10 months ago
Great location within walking distance to some of the best beaches in MA. The house is at the highest point in elevation in the area, so every night you had a refreshing breeze from all directions, no need for AC. The host's were friendly, accommodating and responsive. I would definitely stay at the same place again in a heartbeat.
Guest favourite
Apartment in Kittery
4.97 out of 5 average rating, 78 reviews

Charming retreat in Kittery

Angela LopesRating, 5 stars2 weeks ago
I loved my stay! It was the perfect place to celebrate my birthday and wedding. The beach is very close, and the downtown area is charming. Everything exceeded my expectations. I would definitely come back! ☺️

Private apartment rentals

Guest favourite
Apartment in Gloucester
4.88 out of 5 average rating, 33 reviews

East Gloucester Beach house

AshleyRating, 5 stars4 days ago
We really enjoyed our time here! The location of this house was a great home base for us. We were able to easily travel to Boston & Salem on day trips. Gloucester and the surrounding areas had so much to offer so we were able to do a lot of fun things! Matthew provided great local recommendations as well which was perfect! The house was nice and clean and was easy to find and access. We would stay again!
Guest favourite
Apartment in Rockport
4.87 out of 5 average rating, 75 reviews

Walk To Downtown and Ocean, Large Private Yard

AnthonyRating, 5 stars7 months ago
Very quiet and beautiful place close to Rockport warf
Top Guest favourite
Apartment in Essex
5 out of 5 average rating, 63 reviews

R. Hill Tree Top Studio!

JamiRating, 5 stars2 months ago
My family and I have stayed at Finella's a few different times. Each time our experience has been wonderful. We enjoy staying at her place. It is close our daughter's college. Finella is a wonderful host. We look forward to staying at Finella's when we visit our daughter.
Superhost
Apartment in Annisquam
4.88 out of 5 average rating, 81 reviews

Annisquam Village Abode - access to private beach

JohnRating, 5 stars7 months ago
overall, this was a wonderful stay. Susan is extremely friendly, honest, and a very gracious host. She had a bowl of fresh fruit waiting for us along with Milk, Orange juice, English muffins, butter, and cereal; things I was not expecting and have never had before at an Airbnb. The unit was immaculate and exactly as the pictures showed. I asked for recommendations on a few things to do and she provided links to yelp pages almost immediately. I believe Susan lives in a different part of the house, but we still felt like we had so much privacy. The unit is in a gorgeous little private wooded development not far from the water, and we enjoyed a few walks around the neighborhood admiring some of the beautiful houses and the water view. We had no issue getting an uber to and from Glaucester to attend the wedding we were in town for, despite the area being so private. I would absolutely stay here again if we ever find ourselves back in the area!
Guest favourite
Apartment in Peabody
5 out of 5 average rating, 13 reviews

Large Modern Queen Room near Salem & Dining- 204

MannyRating, 5 stars2 weeks ago
Daniella’s space was perfect for the last leg of our trip to visit Salem. Everything was as the listing description indicated.Daniella was very prompt and professional in her communication. Everything was clean. Lots of places for shopping/eating nearby if needed. Would stay again!
Top Guest favourite
Apartment in Essex
4.97 out of 5 average rating, 77 reviews

Friendship Acres Barn Apartment B

AbigailRating, 5 stars1 week ago
Couldn’t recommend Jayne’s place more. It was so cozy and secluded, with two beautiful horses constantly grazing right outside our windows/screened in porch. The farm was beautifully kept, with flowers everywhere, a fire pit, and chickens. The inside was big, bright, sleek, and clean. It was just me and my husband but there was plenty of room for two more guests. The kitchen had everything you need and we used the screened in porch every chance we could. It’s a quick walk to the water where all the restaurants are. We enjoyed walking to Googan’s in the morning for coffee and a breakfast burrito. We spent a day at Crane beach nearby, an absolutely gorgeous spot. We also drive nearby to Gloucester and our favorite, Rockport. Jayne was quick to answer if I had any questions and made some great local recs for our stay. This was such a peaceful getaway, you get country coziness, salty marshlands, and the oceans/beach right near by. Definitely book!
Top Guest favourite
Apartment in Rockport
5 out of 5 average rating, 29 reviews

Treehouse By-the-Sea

MarianneRating, 5 stars1 week ago
our stay here was lovely. ellen and rusty were waiting for us when we arrived and helped us park. the space itself is cozy and clean. a treehouse indeed, up a bunch of stairs and surrounded by lovely oaks! ellen was an excellent communicator. she was flexible with our checkout as no one was following us and our first day was totally rained out. the location is lovely; a nearby beach and just under a mile walk to downtown. would recommend!
Guest favourite
Apartment in Gloucester
4.97 out of 5 average rating, 58 reviews

Charming Rocky Neck Rental - No cleaning fee!

MelissaRating, 5 stars8 months ago
We had a great stay at Lisa’s place! Was a beautiful area and great location!

Apartment rentals with a hot tub

Guest favourite
Apartment in Woburn
4.94 out of 5 average rating, 152 reviews

Your Cozy 1 BR Apt & Relaxing Retreat

VivianaRating, 5 stars1 week ago
We had a fantastic stay at this place! The house was spotless, with a fully stocked kitchen and bathroom that made everything super convenient. Thiago was incredibly helpful, attentive, and kind throughout our stay, which made the experience even better. We especially loved the jacuzzi area and the large, comfy couch in the living room. The entire place offered great privacy. Would definitely recommend it!
Guest favourite
Apartment in Revere
4.85 out of 5 average rating, 13 reviews

Step Into Spacious Vintage Charm in West Revere

LindaRating, 5 stars3 days ago
Our stay was wonderful, everything was very clean and cozy. We had plenty of room for our group and was very convenient going to and from Boston for all of our activities. The host(s) were quick to respond to any questions or concerns we had. Thank you!
Superhost
Apartment in Hampton Beach
5 out of 5 average rating, 5 reviews

Condo with pool sleeps 4

ChristopherRating, 5 stars11 months ago
Great stay. Nice clean place. Good view of fireworks from the balcony.
Top Guest favourite
Apartment in Winthrop
4.96 out of 5 average rating, 243 reviews

Oceanfront Pool. Close to Boston. Free Parking.

LillianRating, 5 stars2 days ago
This place was great! Conveniently located outside the city close to many T stations. The hosts were proactive communicators and very helpful! Beach access, hot tub, pool, local shops, it was the perfect spot for a getaway.
Superhost
Apartment in Cambridgeport
4.87 out of 5 average rating, 38 reviews

Central Square Upscale Penthouse near MIT/Harvard

MichaelRating, 5 stars3 weeks ago
The unit we rented ended up not being available at the last moment but Jonah was able to find and arrange comparable accommodation set away
Guest favourite
Apartment in Arlington
4.98 out of 5 average rating, 196 reviews

Lakeside apartment, patio, hot tub, outside shower

PietroRating, 5 stars1 week ago
Everything was absolutely exceptional! My parents stayed here for two weeks and had a wonderful experience. The hosts were incredibly kind and responsive — they replied to our messages and requests immediately, which made everything so easy and stress-free. My parents left extremely happy and are already talking about coming back. Highly recommended!
Guest favourite
Apartment in Windham
4.86 out of 5 average rating, 244 reviews

The Estate Escape with Hottub

LauraRating, 5 stars2 weeks ago
This home served us perfectly. It matched the description and with the bedrooms not side by side, it was perfect with a crying baby in the other room 👶🏻 - we didn’t hear a peep!
Superhost
Apartment in Derry
4.77 out of 5 average rating, 381 reviews

Downtown Derry, Studio Apartment

IanRating, 5 stars2 weeks ago
I stayed with Evan and Rachel previously in the apartment located upstairs from the Hideaway Studio. Once again, I was not disappointed! Spotlessly clean, great location, clear instructions, and perfect for a single guy looking to stay a few nights in Derry. No complaints except I was unable to find any dish soap, so I had to wash everything with hand soap. Also, when using the hot tub, I was bothered by a musty smell coming from the water, especially when all the jets were turned on. Perhaps I’m just overly sensitive to mold. Also, some of the pictures should be updated. While I didn’t need it for my stay, the bunk bed was not set up, so it was just the full bed with the twin trundle underneath. Wonderful stay overall, and I would not hesitate to book this location again!

Quick stats about apartment rentals in Gloucester

  • Total rentals

    110 properties

  • Nightly prices starting at

    $123 AUD before taxes and fees

  • Total number of reviews

    7K reviews

  • Family-friendly rentals

    40 properties are a good fit for families

  • Pet-friendly rentals

    20 properties allow pets

  • Rentals with dedicated workspaces

    50 properties have a dedicated workspace

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