Gloucester holiday rentals

We found 764 holiday rentals — enter your dates for availability
Discover a selection of 173 homes, 46 apartments and other holiday rentals in Gloucester that are perfect for your trip. Holiday homes provide the best amenities for you and your friends, family or even pets, such as a hot tub and a washer and dryer. Whatever you're looking for, you'll find a property to rent for everyone's needs, including a place that's non-smoking or offers accessibility.

Holiday rentals with weekly discounts – Gloucester

Showing deals for:25 Dec - 1 Jan

Beach Room View
Front Porch overlooking Front Beach
Main Room View
Motif Number 1, located on Bradley Wharf in the harbor town of Rockport, Ma.
Exceptional
(58 reviews)

Beach & King - Stunning Ocean Views!

Rockport

8% off
S$14,399
for 7 nights, 1 home
S$2,057 per night
includes taxes & fees
Beach & King - Stunning Ocean Views!
Patio with panoramic view of our lawn and miles of beautiful marshes - see video
Lawn and gardens below patio, overlooking hundreds of acres of beautiful marshes
Interior
Breakfast table (kitchen) with a view
Exceptional
(51 reviews)

PREMIUM Modern Home on 2 Acres - Panoramic Marsh Views - NEW Video Tour

Gloucester

8% off
S$6,607
for 7 nights, 1 home
S$944 per night
includes taxes & fees
PREMIUM Modern Home on 2 Acres - Panoramic Marsh Views - NEW Video Tour
Exterior detail
Exterior
Interior
Private kitchen
Exceptional
(27 reviews)

❤️ of Cape Ann, - Historic Antique Colonial yet new & modern Close 2 Everything

Essex

20% off
S$3,549
for 7 nights, 1 home
S$507 per night
includes taxes & fees
❤️ of Cape Ann, - Historic Antique Colonial yet new & modern Close 2 Everything
Interior
Terrace/patio
The garden
Marina
Exceptional
(157 reviews)

Charming private townhouse-style lodging, a block from Marblehead Harbor

Marblehead

8% off
S$2,276
for 7 nights, 1 home
S$325 per night
includes taxes & fees
Charming private townhouse-style lodging, a block from Marblehead Harbor
Dining
Exterior
Exterior
Living area
Excellent
(8 reviews)

Walk to Good Harbor and Long Beach -Vacation Home

Gloucester

8% off
S$3,990
for 7 nights, 1 home
S$570 per night
includes taxes & fees
Walk to Good Harbor and Long Beach -Vacation Home
Property grounds
Property grounds
Interior
Exterior
Exceptional
(69 reviews)

Ocean views just steps to Back Beach, Front Beach, and downtown Rockport

Rockport

8% off
S$5,580
for 7 nights, 1 home
S$797 per night
includes taxes & fees
Ocean views just steps to Back Beach, Front Beach, and downtown Rockport
Living room with decorative fireplace.
View of Marblehead Harbor from Fort Sewall
Bar area next to a stain-glass window.
Living room with smart TV.
Exceptional
(11 reviews)

Old Town Cottage Near Crocker Park and the Marblehead Harbor. Includes Parking!

Marblehead

7% off
S$4,638
for 7 nights, 1 cottage
S$663 per night
includes taxes & fees
Old Town Cottage Near Crocker Park and the Marblehead Harbor. Includes Parking!
Exterior detail
Living area
Interior
Room
Exceptional
(39 reviews)

Lovely Downtown Beverly

Beverly

8% off
S$2,911
for 7 nights, 1 home
S$416 per night
includes taxes & fees
Lovely Downtown Beverly
Living area
Exterior detail
Interior
Dining
Exceptional
(34 reviews)

The Anchor House Marblehead Retreat - Minutes to Old Town and Historic Salem!

Marblehead

12% off
S$4,527
for 7 nights, 1 home
S$647 per night
includes taxes & fees
The Anchor House Marblehead Retreat - Minutes to Old Town and Historic Salem!
Living area
Living area
Room
Interior
Exceptional
(16 reviews)

Fresh Design-Walk to Salem-Food-Train Station

Beverly

8% off
S$2,635
for 7 nights, 1 apartment
S$376 per night
includes taxes & fees
Fresh Design-Walk to Salem-Food-Train Station
outside shower and garden area
kitchen, dining area
Living area
Private kitchen
Exceptional
(100 reviews)

Good Harbor Beach Apt.- 6/10 mile

Gloucester

8% off
S$2,462
for 7 nights, 1 apartment
S$352 per night
includes taxes & fees
Good Harbor Beach Apt.- 6/10 mile
Exterior
View from kitchen window to rear fruit trees and vegetable gardens.
Private kitchen
Sunny eat-in kitchen.
Exceptional
(32 reviews)

Quaint Simplicity on Quiet Lane, Spacious and Relaxing, Walk to Shops, Beaches

Rockport

8% off
S$2,697
for 7 nights, 1 home
S$385 per night
includes taxes & fees
Quaint Simplicity on Quiet Lane, Spacious and Relaxing, Walk to Shops, Beaches
Room
Private kitchen
Exterior
Living area
Exceptional
(32 reviews)

Moody Salem Home Away From Home

Salem

8% off
S$2,494
for 7 nights, 1 home
S$356 per night
includes taxes & fees
Moody Salem Home Away From Home
Outdoor dining
Dining
Living area
Interior
Exceptional
(42 reviews)

Samuel Tucker House - Downtown Luxury 2 Bedroom Condo

Marblehead

8% off
S$2,502
for 7 nights, 1 apartment
S$357 per night
includes taxes & fees
Samuel Tucker House - Downtown Luxury 2 Bedroom Condo
Room
Living area
Living area
Interior
Exceptional
(22 reviews)

Charming Retreat

Gloucester

6% off
S$2,703
for 7 nights, 1 apartment
S$386 per night
includes taxes & fees
Charming Retreat
Interior
Exterior
Dining
Living area
Wonderful
(36 reviews)

Quiet neighborhood and Walking destination to Downtown Salem

Salem

16% off
S$1,734
for 7 nights, 1 apartment
S$248 per night
includes taxes & fees
Quiet neighborhood and Walking destination to Downtown Salem
Property grounds
Interior
Living area
Private kitchen
Exceptional
(12 reviews)

C by the Sea - Ocean View Penthouse

Gloucester

8% off
S$4,830
for 7 nights, 1 apartment
S$690 per night
includes taxes & fees
C by the Sea - Ocean View Penthouse
Living room, Instagram worthy!
Marina
Interior
Interior
Exceptional
(23 reviews)

Roomy Themed 3BR Historic Salem, Near Boston, with Parking, Walk to Attractions.

Salem

8% off
S$4,281
for 7 nights, 1 apartment
S$612 per night
includes taxes & fees
Roomy Themed 3BR Historic Salem, Near Boston, with Parking, Walk to Attractions.
Living area
Living area
Interior
Private kitchen
Exceptional
(14 reviews)

Quaint Neighborhood / Close to Beaches

Gloucester

6% off
S$2,831
for 7 nights, 1 apartment
S$404 per night
includes taxes & fees
Quaint Neighborhood / Close to Beaches
Room
Living area
Private kitchen
Exterior
Excellent
(50 reviews)

Friendly family with. Sweet home

Salem

16% off
S$1,988
for 7 nights, 1 apartment
S$284 per night
includes taxes & fees
Friendly family with. Sweet home

  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

The historical area of Gloucester awaits your stay

Come and experience Gloucester and its monuments, history and art galleries. This city's seaside, beaches and whale watching draw many visitors. Are you looking for specific amenities for your getaway? Many of our holiday rentals feature full kitchens and laundry facilities.

Activities and attractions in Gloucester

Are you searching for things to do in the city? Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that makes Gloucester a fun place to get away to. Here are some of the top attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Bewitched in Salem (13.2 mi / 21.2 km)
  • Water Park of New England (15.6 mi / 25.2 km)
  • Salem Willows Park (11.8 mi / 19 km)
  • Mill River Winery (14.5 mi / 23.4 km)
  • Appleton Farms Grass Rides (11.1 mi / 17.9 km)
  • Mud Puddle Toys (12 mi / 19.4 km)

Exploring the natural features in Gloucester

Whether you're looking for adventure or just want to spend some time taking in the scenery, you'll be sure to find the perfect setting for your holiday in Gloucester. Here are a few of the area's most eye-catching features, all within 30 miles (48.2 km) of the city centre:

  • Half Moon Beach (0.9 mi / 1.4 km)
  • Stage Fort Park (0.9 mi / 1.4 km)
  • Niles Beach (1.2 mi / 1.9 km)
  • Good Harbor Beach (1.7 mi / 2.8 km)
  • Long Beach (2.7 mi / 4.3 km)
  • Wingaersheek Beach (2.9 mi / 4.7 km)

Seasonal weather averages in Gloucester

If you're planning a holiday around the weather, July, August, September and June are the hottest months to visit, when temperatures average 19°C.

Travelling to and around Gloucester

The nearest airport is in Beverly, MA (BVY-Beverly Municipal), located 12.8 mi (20.6 km) from the city centre. If you can't find a flight that's convenient for your trip, you could also fly into Lawrence, MA (LWM-Lawrence Municipal), which is 24.3 mi (39.1 km) away.

If you prefer train travel, make your way to Gloucester Station or West Gloucester Station to see more of the city.

Frequently asked questions

What is the best area to stay in Gloucester when booking a holiday rental?
One of the most popular areas to get a holiday home in Gloucester is Annisquam. Discover a dream stay on Vrbo and explore this area as a local.
What is the most popular type of holiday rental accommodation in Gloucester?
The most popular types of holiday rentals in Gloucester are houses. Searching for something different? Vrbo has plenty of options to match our guests' needs, so you'll see holiday homes in lots of shapes and sizes. The ideal home away from home is waiting for you — grab yours today.
How much does it cost to rent a holiday rental in Gloucester?
Season, property type and length of stay are some things that can affect the price of a holiday home. Simply enter your travel dates to find your perfect fit. From cosy cabins to plush villas, all Vrbo holiday rentals offer unbeatable value.
How much does it cost to rent a beach house in Gloucester?
The average price for a holiday rental close to the beach in Gloucester depends on when you're travelling and the size and style of property you want. You can quickly and easily find prices on Vrbo by entering your preferred travel dates and destination. Then make use of the filter tool to select the number of bedrooms and amenities essential to you, like air conditioning, a pool and WiFi.
Are there pet-friendly holiday rentals in Gloucester?
Yes. You'll have your pick of 74 holiday rentals that allow pets in Gloucester. Lots of our pet-friendly holiday rentals even come with an outdoor space for your furry friend to run around in, doggie beds, complimentary treats and proximity to parks and green space. Apply the "Pets allowed" filter to find your pawfect holiday home on Vrbo.
Can I rent a house with a pool in Gloucester?
Grab your swimsuit and goggles, because there are two houses with a private pool in Gloucester. Kick back at one of these popular holiday rentals and you'll enjoy pool days every day. Simply enter your travel dates into Vrbo, then use the "pool" filter to find the perfect place to make a splash!
What are popular rental amenities in Gloucester?
When it comes to rental amenities that people search for in Gloucester, a firepit, a chef and tennis are the most popular. With Vrbo holiday homes, you'll find options to suit your style and taste, whether you're travelling with family, friends or even pets.
Are there large group holiday rentals in Gloucester?
Choose from 13 holiday rentals in Gloucester that can accommodate 10 or more people. Whether you're organising a trip with the family or an event like a party, there's enough space to get your group together under the same roof.
Are there holiday rentals in Gloucester that welcome kids?
Bring the whole group together for a fun-filled adventure in Gloucester at one of our 74 family-friendly holiday homes. Many of these stays feature amenities that are suitable for trips with children, including dining rooms, living rooms and swimming pools. Just click on the "Properties good for families" filter and select your favourite.
What are the top attractions for families in Gloucester?
Keep your kids occupied at these fun family-friendly attractions in Gloucester:
  • Good Harbour Beach
  • Hammond Castle
  • Wingaersheek Beach
Are there one-bedroom holiday rentals in Gloucester?
You'll find 11 one-bedroom properties in Gloucester to select from. A one-bedroom holiday property is a superb choice if it's just two of you or if you're travelling on your own. Add in more space, convenience and privacy than a hotel, and you're bound to have a memorable getaway.
Can I find two-bedroom holiday rentals in Gloucester?
Take off with your loved ones and enjoy a relaxing escape in one of the 18 two-bedroom holiday properties Gloucester has to offer.
Are there holiday rentals with WiFi in Gloucester?
Gloucester has 22 holiday rentals with WiFi, so you can stay connected while you're away. Simply check the "WiFi" box in our handy search filter for a list of properties with this feature. From streaming movies with the family to updating your social media, these Vrbo homes make it a cinch to go online.
How can I find holiday rentals with air conditioning in Gloucester?
Pick from 59 Vrbo holiday rentals with air conditioning in Gloucester providing that gentle, cool breeze and extra level of comfort. Just enter your travel dates and then use our handy filters to look for properties with air conditioning.
How old do you have to be to rent a holiday rental in Gloucester?
It's a good idea to check with the Gloucester holiday property you want on Vrbo as age restrictions vary. However, it's typically 16, 18 or 21.
How long can I rent a holiday rental in Gloucester for?
It all depends on the Gloucester property. To see a list of options offering extended stays, just type your travel dates and number of people into Vrbo. Enjoy having the whole place to yourself, as well as amenities such as air conditioning, a kitchen and a yard where your little ones can play. Keep an eye out for long-term stays that offer discounted weekly or monthly prices.

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