Gloucester Holiday Rentals

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Holiday Rentals in Gloucester

Fridge, microwave, oven, stovetop
Charming Downtown Gloucester Retreat. Walk to Restaurants, Museums, Waterfront
10.0 out of 10, Exceptional, (3)
"Excellent location and perfect home for a girls trip. Owners were extremely responsive."
Charming Downtown Gloucester Retreat. Walk to Restaurants, Museums, Waterfront
Beach nearby, sun-loungers
Good Harbor Beach House - walk to beach, close to restaurants and shopping!
10.0 out of 10, Exceptional, (172)
"Laura's place is a gem and she is a terrific hostess. It is within walking distance to Good Harbor beach and drivable to all sorts of fun outings. It was the perfect size for our family of 8 - our four kids and to of their partners. The living area space, deck, and kitchen allowed for both full group moments and one on one time. Laura recently redid the kitchen and it was terrific. We highly recommend making pancakes on the stovetop griddle. Thanks for a great weekend in this special home."
Good Harbor Beach House - walk to beach, close to restaurants and shopping!
Property grounds
Walk to the ocean, very private. Secluded, woodsy location.
10.0 out of 10, Exceptional, (3)
"Clean and cozy studio. Was working in the area for a few days and was a relaxing place to come back to in the evening."
Walk to the ocean, very private. Secluded, woodsy location.
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On the beach
The Great Escape on Hampton Beach. Beach directly across the street.
10.0 out of 10, Exceptional, (37)
"The host was amazing, as well as the unit. Very clean and the perfect location! A 100% 5 star."
The Great Escape on Hampton Beach. Beach directly across the street.
Beach
The Warlock House: Speak Spells, Wave Wands, Ride Brooms - 5min Walk to Salem, Big TV, WiFi, Parking
10.0 out of 10, Exceptional, (24)
"Loved the house and it was convenient to everything we wanted to see in Salem. The decor was amazing and you can definitely tell there was attention to every detail. Clean and quiet. Would definitely recommend and would stay there again. "
The price is NZ$1,303
per night
28 May - 29 May
The Warlock House: Speak Spells, Wave Wands, Ride Brooms - 5min Walk to Salem, Big TV, WiFi, Parking
Aerial view
Blue Chill Cottage! Walk to Beach, restaurants, casino-Adorable Renovated-AC&WD
10.0 out of 10, Exceptional, (82)
"Blue Chill Cottage was such a wonderful place to stay with my family if 4. The decor was perfect, and everything was very well organized. Just a quick walk to the beach, and a wonderful place to relax after a day out!"
The price is NZ$769
per night
22 May - 23 May
Blue Chill Cottage! Walk to Beach, restaurants, casino-Adorable Renovated-AC&WD
Property grounds
Champaine Beach House
10.0 out of 10, Exceptional, (5)
"What a wonderful early season getaway! The house is absolutely gorgeous and impeccably taken care of.Loved listening to the ocean as I fell to sleep! Beautiful beachwalks would love to visit again!"
Champaine Beach House
Beach nearby, sun-loungers, beach towels
Oceanview Kingsize South End Studio (NO FINAL CLEANING FEE)
10.0 out of 10, Exceptional, (151)
"MUCH better than expected. Cutest little home!!! Highly recommend to stay here :)"
The price is NZ$366
per night
27 May - 28 May
Oceanview Kingsize South End Studio (NO FINAL CLEANING FEE)
1 bedroom, iron/ironing board, travel cot, free WiFi
♥ Historic Studio Minutes to Salem+Beaches Old Town Marblehead Private Parking ♥
10.0 out of 10, Exceptional, (29)
"This property was the perfect size for the two of us. It had all of the appliances and amenities that we could’ve asked for during our stay. The old house that this studio is in is a historic place. It was very nice to have our own parking place at the house to come back to after our daily sightseeing jaunts. It’s only 35 mins from the Logan airport and Boston and 5 mins to Salem."
The price is NZ$444
per night
10 Jun - 11 Jun
♥ Historic Studio Minutes to Salem+Beaches Old Town Marblehead Private Parking ♥
Aerial view
Upscale waterfront condo short walk to North Beach
10.0 out of 10, Exceptional, (28)
"We had an amazing. Tina and her husband were so easy and accommodating. The unit was exactly what we expected an extremely clean and well put together. They set up the fire put for us one night. All and all we enjoyed our stay so much and are going return for sure."
Upscale waterfront condo short walk to North Beach
Fridge, microwave, oven, stovetop
Lovely 3-Bedroom in Historic Downtown Ipswich
10.0 out of 10, Exceptional, (5)
"Nice location in the center of everywhere I needed to be. Clean and enough space for my needs. Everything was functional and had no issues whatsoever."
The price is NZ$544
per night
2 Jun - 3 Jun
Lovely 3-Bedroom in Historic Downtown Ipswich
Smart TV, streaming services
Oceanfront, private balcony, stunning panoramic views of the Atlantic
10.0 out of 10, Exceptional, (16)
"My husband and I wanted a long, relaxing weekend away. This was the perfect spot. In November it’s very quiet at the beach, which was nice. We walked on the beach, had some great seafood, went to the movies and enjoyed the beautiful view of the water from the condo. I would definitely stay here again."
The price is NZ$780
per night
22 May - 23 May
Oceanfront, private balcony, stunning panoramic views of the Atlantic
Terrace/patio
Marblehead. Cottage on Whittier, new construction
10.0 out of 10, Exceptional, (110)
"Well appointed space. Do comfortable, clean and modern. My girlfriend and I really enjoyed our time and would love to come back. Marblehead is very quaint. Great experience. Thank you!"
The price is NZ$653
per night
2 Jun - 3 Jun
Marblehead. Cottage on Whittier, new construction
Interior
Leslie's Retreat: Spacious home ideally located to everything
10.0 out of 10, Exceptional, (200)
"Very nice property in a quiet neighborhood right across the river from downtown Salem and most attraction. Very walkable when the weather is nice. Beds were comfortable and plenty of space for groups traveling together. Communication with the host was easy, Meg was very responsive. Decent sized outdoor space with a grill and patio furniture. Really enjoyed our Salem experience and would rent again the next time we come here. Only suggestion I have that would be a nice enhancement would be a hot...
Leslie's Retreat: Spacious home ideally located to everything
Beach nearby
The Lobster Claw - Perfect Location Near Beach/Boardwalk
10.0 out of 10, Exceptional, (2)
"The house was very clean, well maintained, and a great size for all of us. The neighborhood was very walkable and the house is super close to the beach which allowed for lots of walking. The host was very responsive and friendly and gladly answered any questions and concerns we had. The website provided when booking also made everything very clear and was referenced many times during the trip as it was so thorough. Would 100% recommend to anyone looking for a nice stay at the beach and would...
The price is NZ$533
per night
28 May - 29 May
The Lobster Claw - Perfect Location Near Beach/Boardwalk
Free WiFi, bed sheets
-Sleeps 2 - Hampton Beach Suite - Pet Friendly -
10.0 out of 10, Exceptional, (4)
"The perfect spot for a quick getaway with our dog! The weather was great and the beaches were spectacular!"
-Sleeps 2 - Hampton Beach Suite - Pet Friendly -
Fridge, microwave, stovetop, coffee/tea maker
Salem Vacation Rental: 1 Mi to Downtown!
10.0 out of 10, Exceptional, (4)
Salem Vacation Rental: 1 Mi to Downtown!
Aerial view
Beautiful Ocean Front Condo in Hampton Beach, NH
9.8 out of 10, Exceptional, (6)
"Highly recommend this place to stay. Breathtaking views of the Ocean. Highly recommend staying here."
The price is NZ$506
per night
27 May - 28 May
Beautiful Ocean Front Condo in Hampton Beach, NH
Fridge, microwave, oven, stovetop
Beach Life Bliss - steps to the beach
9.6 out of 10, Exceptional, (10)
"My friends and I had a lovely time at the house. It was quiet, sunny, and a nice break. It was nice to be close to options, but still quite secluded. We went for runs each morning, and enjoyed soaking up the warmth in the sunroom/patio area."
Beach Life Bliss - steps to the beach
View from property
Luxury 1900's romantic retreat steps from the beach - King Suite!
9.6 out of 10, Exceptional, (17)
"Cottage was very nice and it had everything we needed for a quiet getaway."
Luxury 1900's romantic retreat steps from the beach - King Suite!
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See all available properties in Gloucester
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Other types of properties in Gloucester you may be interested in

Rooftop pool
Beauport Hotel Gloucester
3.5 star property
9.6 out of 10, Exceptional, (714)
"The Beauport is a beautiful hotel, with a roof top deck and pool, and lovely ocean views. The staff is friendly and very willing to help with anything and everything. The bed was very comfortable and both the bedroom and bathroom were immaculately clean. Top notch hotel in every respect."
The price is NZ$501
per night
22 May - 23 May
Beauport Hotel Gloucester
Exterior detail
Ocean House Hotel at Bass Rocks
4.0 star property
9.0 out of 10, Wonderful, (620)
"Great hotel, we really enjoyed it. Beautiful location on the ocean, wonderful waking up to the sounds of the surf. Property was immaculate. bed comfortable as well. We were visiting family so we did not get a chance to enjoy breakfast but it looked delicious and people were smiling."
The price is NZ$312
per night
22 May - 23 May
Ocean House Hotel at Bass Rocks
Reception
The Hotel at Cape Ann Marina
3.5 star property
8.2 out of 10, Very good, (518)
"The room was dated, but the rooms are being remodeled. It was clean, had easy access and had a beautiful view!"
The price is NZ$364
per night
23 May - 24 May
The Hotel at Cape Ann Marina
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Gloucester holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Gloucester. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Gloucester. Seeing all the best attractions is bound to make you fall in love with Gloucester. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Gloucester short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find a holiday rental in Gloucester?

Yes, there are holiday rentals in Gloucester close to Maritime Gloucester, or you can select a more secluded option if you're looking for a relaxing stay. Visitors like the scenic seaside and waterfront in Gloucester. Make sure you have time to check out the seafood restaurants and monuments during your trip.

How many holiday rentals are there in Gloucester?

Expedia has 152 holiday rentals for your stay in Gloucester.

What can I see and do in Gloucester?

Family-friendly attractions include Maritime Gloucester and Schooner Adventure, whereas Half Moon Beach and Stage Fort Park are a couple of great spots to enjoy the outdoors. Capt Bill & Sons Whale Watch and Cape Ann Museum are other places to visit while you're in town.

What are holiday rentals like in Gloucester?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Gloucester. Holiday rentals provide amenities such as patios, hot tubs and fire pits so you'll feel just like you're at home. If you're concerned about a clean environment, a holiday rental can provide a sense of seclusion away from public hotel lifts and busy front desks while still allowing you the enjoyment of travel. You'll also find more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is an attractive choice for a family trip or a small group gathering.

Recent reviews of Gloucester properties
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