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)
"This home in the center of Gloucester was the perfect accommodation for our weekend stay. It is a 5-10 minute walk to town, a 5 minute walk to the supermarket, and a 2 minute walk to a delightful local wine and cheese shop! The house was equipped with all we needed including a Nespresso machine and electric kettle. Having a parking space was a bonus. Would definitely stay again."
Charming Downtown Gloucester Retreat. Walk to Restaurants, Museums, Waterfront
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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Fridge, microwave, oven, stovetop
Beautiful, Cozy Ultra Convenient Salem Home
9.2 out of 10, Wonderful, (7)
"Convenient to dowtown"
The price is NZ$386
includes taxes & fees
27 May - 28 May
Beautiful, Cozy Ultra Convenient Salem Home
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.
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$1,267
includes taxes & fees
19 Jun - 20 Jun
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$832
includes taxes & fees
24 May - 25 May
Blue Chill Cottage! Walk to Beach, restaurants, casino-Adorable Renovated-AC&WD
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$507
includes taxes & fees
27 May - 28 May
Beautiful Ocean Front Condo in Hampton Beach, NH
Exterior
House near down town Salem
9.6 out of 10, Exceptional, (20)
"Clean, easy parking, easy entry. Quaint diner to walk to on corner of the street. A good spot to lay your head after exploring Salem."
The price is NZ$521
includes taxes & fees
28 May - 29 May
House near down town Salem
Property grounds
Champaine Beach House
10.0 out of 10, Exceptional, (5)
"Stunning house with great views from main bedroom! Grassy lawn for furry family members. Loved every moment of our stay and miss it already!"
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
includes taxes & fees
27 May - 28 May
Oceanview Kingsize South End Studio (NO FINAL CLEANING FEE)
Interior
Themed Stay in Historic Salem-Walk to Downtown!
The price is NZ$732
includes taxes & fees
3 Jun - 4 Jun
Themed Stay in Historic Salem-Walk to Downtown!
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$430
includes taxes & fees
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
includes taxes & fees
9 Jun - 10 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."
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$651
includes taxes & fees
9 Jun - 10 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
Fridge, oven, stovetop, coffee/tea maker
Walk to Beach. Private Nature and Bird Watching Trail. Quiet.
9.0 out of 10, Wonderful, (37)
"Perfect setting and location for our visit. Around the corner from the beach and a two minute drive to Parker River WMA."
Walk to Beach. Private Nature and Bird Watching Trail. Quiet.
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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

Reception
The Hotel at Cape Ann Marina
3.5 star property
8.2 out of 10, Very good, (519)
"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
includes taxes & fees
27 May - 28 May
The Hotel at Cape Ann Marina
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
includes taxes & fees
29 May - 30 May
Beauport Hotel Gloucester
Porch
Castle Manor Inn
2.5 star property
8.2 out of 10, Very good, (751)
"Clean and quiet"
The price is NZ$346
includes taxes & fees
27 May - 28 May
Castle Manor Inn
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
Expedia verified reviews