Gloucester Vacation Rentals

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Our top choices for Gloucester vacation rentals

Luxury 1900's romantic retreat steps from the beach - King Suite!

Luxury 1900's romantic retreat steps from the beach - King Suite!
Gloucester
9.8 out of 10, Exceptional, (54 reviews)
"We enjoyed every bit of our stay."
United States
Kathy B.
The price is CA $283
CA $585 total
includes taxes & fees
Jul 1 - Jul 2
Luxury 1900's romantic retreat steps from the beach - King Suite!

Long Beach Suites

Long Beach Suites
2.0 star property
East Gloucester
9.2 out of 10, Wonderful, (69 reviews)
"Location, spacious, clean and neat!"
United States
Henry
The price is CA $325
CA $636 total
includes taxes & fees
Jun 30 - Jul 1
Long Beach Suites

The Essex of Gloucester

The Essex of Gloucester
Gloucester
10.0 out of 10, Exceptional, (8 reviews)
"Perfect size for two couples! Extremely clean and well stocked!!!!"
United States
Kimberly
The price is CA $357
CA $455 total
includes taxes & fees
Jun 23 - Jun 24
The Essex of Gloucester

Long Beach Suites: Ocean Views

Long Beach Suites: Ocean Views
East Gloucester
9.2 out of 10, Wonderful, (22 reviews)
"Loved the stay Very close to beaches, beautiful area. "
United States
Jessica P.
The price is CA $226
CA $589 total
includes taxes & fees
Jun 16 - Jun 17
Long Beach Suites: Ocean Views

Cozy two bedroom house in the heart of Gloucester

Cozy two bedroom house in the heart of Gloucester
Gloucester
9.4 out of 10, Exceptional, (14 reviews)
"Wonderful spot to stay and would use it again if I visit later."
United States
Shelley S.
The price is CA $307
CA $614 total
includes taxes & fees
Jun 30 - Jul 1
Cozy two bedroom house in the heart of Gloucester

Ocean Breeze / 8-Minute Walk to Beach

Ocean Breeze / 8-Minute Walk to Beach
East Gloucester
10.0 out of 10, Exceptional, (19 reviews)
"Excellent location, very clean and good communication. Will definitely stay again when in the area. "
United States
Patrick M.
The price is CA $208
CA $480 total
includes taxes & fees
Jun 16 - Jun 17
Ocean Breeze / 8-Minute Walk to Beach

Loft on Main - DWTN, Beach, PVT Deck, Coffee Bar

Loft on Main - DWTN, Beach, PVT Deck, Coffee Bar
Downtown Gloucester
10.0 out of 10, Exceptional, (12 reviews)
"Excellent downtown location! The loft was clean and well stocked. Great communication from the time of booking through check-out. "
United States
Aimee C.
The price is CA $320
CA $675 total
includes taxes & fees
Jun 24 - Jun 25
Loft on Main - DWTN, Beach, PVT Deck, Coffee Bar

Beach Life Bliss - steps to the beach

Beach Life Bliss - steps to the beach
Gloucester
9.8 out of 10, Exceptional, (46 reviews)
"A wonderful place to stay!"
United States
rich k.
The price is CA $451
CA $844 total
includes taxes & fees
Jun 25 - Jun 26
Beach Life Bliss - steps to the beach

Quaint Neighborhood / Close to Beaches

Quaint Neighborhood / Close to Beaches
East Gloucester
10.0 out of 10, Exceptional, (14 reviews)
"Very nice place I loved it"
United States
Erika G.
The price is CA $334
CA $658 total
includes taxes & fees
Jun 28 - Jun 29
Quaint Neighborhood / Close to Beaches

3BR Oceanview Townhouse on Boulevard I Walk to downtown l Sleeps 8

3BR Oceanview Townhouse on Boulevard I Walk to downtown l Sleeps 8
Gloucester
10.0 out of 10, Exceptional, (12 reviews)
"Easy, clean, helpful host, great location!!"
United States
Brady D.
The price is CA $380
CA $860 total
includes taxes & fees
Jun 14 - Jun 15
3BR Oceanview Townhouse on Boulevard I Walk to downtown l Sleeps 8

New England Coastal Residence

New England Coastal Residence
Gloucester
The price is CA $485
CA $1,169 total
includes taxes & fees
Jun 15 - Jun 16
New England Coastal Residence

3BR/2 BA Harborside Home · Fenced Backyard+Grill · Ocean Views

3BR/2 BA Harborside Home · Fenced Backyard+Grill · Ocean Views
East Gloucester
9.8 out of 10, Exceptional, (46 reviews)
"House was wonderful and had everything we needed. Very clean and homey for three couples. Great location. Great contact with the host. "
United States
Monica W.
The price is CA $396
CA $908 total
includes taxes & fees
Jun 16 - Jun 17
3BR/2 BA Harborside Home · Fenced Backyard+Grill · Ocean Views

Charming Retreat

Charming Retreat
East Gloucester
9.8 out of 10, Exceptional, (17 reviews)
"Nice place to stay, clean and comfortable."
United States
Anonymous traveller
The price is CA $375
CA $675 total
includes taxes & fees
Jun 30 - Jul 1
Charming Retreat

Classic Coastal Family Home | Walk to Sea;King Bed

Classic Coastal Family Home | Walk to Sea;King Bed
Gloucester
10.0 out of 10, Exceptional, (1 review)
"Property was excellent, beautifully decorated with good taste, location was beautiful, everyone enjoyed the weekend stay. Rooms were clean, beds were comfortable."
United States
Maarij K.
The price is CA $566
CA $1,513 total
includes taxes & fees
Jun 16 - Jun 17
Classic Coastal Family Home | Walk to Sea;King Bed

Stay at The Neck

Stay at The Neck
Rocky Neck
10.0 out of 10, Exceptional, (1 review)
"Beautiful home with incredible view! Perfect location!! We would definitely stay here again!"
United States
Chris W.
Stay at The Neck

Oceanview Home/Walk to Lanes Cove and Plum Cove beach I Sleeps 6

Oceanview Home/Walk to Lanes Cove and Plum Cove beach I Sleeps 6
Gloucester
The price is CA $1,239
CA $2,078 total
includes taxes & fees
Jul 4 - Jul 5
Oceanview Home/Walk to Lanes Cove and Plum Cove beach I Sleeps 6

Long Beach Suites: 3 Mins Toes To Sand!

Long Beach Suites: 3 Mins Toes To Sand!
East Gloucester
8.8 out of 10, Excellent, (19 reviews)
"Excellent location. Walkable to Long Beach. Enjoyed daily walks on the beach. Well appointed condo unit. Plenty of towels and kitchen supplies. Two king sized beds was ideal. Would stay here again."
United States
Molly P.
The price is CA $271
CA $694 total
includes taxes & fees
Jun 14 - Jun 15
Long Beach Suites: 3 Mins Toes To Sand!

Oceanview Kingsize South End Studio NO FINAL CLEANING FEE

Oceanview Kingsize South End Studio NO FINAL CLEANING FEE
Rockport
9.8 out of 10, Exceptional, (206 reviews)
"What a wonderful, clean place to stay. The view was amazing and for our first ever experience in Massachusetts just couldn't have been better!!"
United States
Jamie L.
The price is CA $272
CA $344 total
includes taxes & fees
Jun 30 - Jul 1
Oceanview Kingsize South End Studio NO FINAL CLEANING FEE

Harborside Oasis ★ Harbor View ★ Heart of Downtown

Harborside Oasis ★ Harbor View ★ Heart of Downtown
Rockport
10.0 out of 10, Exceptional, (24 reviews)
"good location"
United States
Bruce S.
The price is CA $191
CA $417 total
includes taxes & fees
Jun 16 - Jun 17
Harborside Oasis ★ Harbor View ★ Heart of Downtown

Harbor Retreat ★ Ocean View ★ Heart of Downtown ★

Harbor Retreat ★ Ocean View ★ Heart of Downtown ★
Rockport
9.8 out of 10, Exceptional, (33 reviews)
"This is a really beautiful property that's great for a weekend getaway in an incredible little town!"
United States
Travis G.
The price is CA $182
CA $411 total
includes taxes & fees
Jun 15 - Jun 16
Harbor Retreat ★ Ocean View ★ Heart of Downtown ★
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.
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Top Gloucester Hotel Reviews

Find out more about Gloucester

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation 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 or room. 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 vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . 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 . 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 vacation rental 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 vacation 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 short-term rentals, that won’t be hard to do.

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Frequently asked questions

Can I find a vacation rental in Gloucester?

Yes, we offer vacation rentals in Gloucester close to Maritime Gloucester, or you can choose a more remote option if you'd like a relaxing place to 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.

What are some of the best vacation rentals that Gloucester has to offer?

Beach Life Bliss - steps to the beach: This Gloucester vacation home rental is located near the beach and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games. Another good choice for your trip to Gloucester is Steps to Wingaersheek's Private 1.5 Mile White Dune Beach.

How many vacation rentals are there in Gloucester?

Expedia has 169 vacation rentals for your stay in Gloucester.

What can I see and do in Gloucester?

Family-friendly attractions include Maritime Gloucester and Schooner Adventure, whereas Pavilion Beach and Half Moon Beach 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 vacation rentals like in Gloucester?

Vacation rentals are private properties you can stay in for a short or long stay in Gloucester. Vacation rentals offer amenities such as hot tubs, fire pits, and patios so you'll have all the conveniences of home. If you're concerned about a sanitized environment, vacation rentals can offer a sense of privacy away from public hotel elevators and busy concierge desks while still allowing you a great travel experience. You'll also find more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is an attractive option for a family getaway.