A beach with a lifeguard tower, waves, and a large house with a tower on a rocky shore.

Gloucester Vacation Rentals

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Our top choices for Gloucester vacation rentals

1. Charming Retreat

Charming Retreat
East Gloucester
10.0 out of 10, Exceptional, (21 reviews)
"Nice place to stay, clean and comfortable."
United States
Anonymous traveller
The price is CA $188
CA $436 total
includes taxes & fees
Sep 24 - Sep 25
Charming Retreat

2. Quaint Neighborhood / Close to Beaches

Quaint Neighborhood / Close to Beaches
East Gloucester
10.0 out of 10, Exceptional, (14 reviews)
"A lovely place! Very clean with very comfortable beds! "
United States
Mariyana K.
The price is CA $200
CA $483 total
includes taxes & fees
Sep 23 - Sep 24
Quaint Neighborhood / Close to Beaches

3. 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, (13 reviews)
"Everything was great! Felt like I was in my own house"
United States
Bill D.
The price is CA $240
CA $574 total
includes taxes & fees
Oct 13 - Oct 14
Loft on Main - DWTN, Beach, PVT Deck, Coffee Bar

4. 3BR Harborside Home • Gloucester+Rockport • Ocean View

3BR Harborside Home • Gloucester+Rockport • Ocean View
East Gloucester
9.8 out of 10, Exceptional, (49 reviews)
"Beautiful, wonderfully well stocked home with everything anyone would need! And not just starter supplies either! They even have beach necessities in a shed out back! Quality and quantity amazing in everything! Beautiful views, comfortable rocking chairs on front porch. Everything was great!!"
United States
Michele V.
The price is CA $254
CA $725 total
includes taxes & fees
Sep 22 - Sep 23
3BR Harborside Home • Gloucester+Rockport • Ocean View

5. The Essex of Gloucester

The Essex of Gloucester
Gloucester
10.0 out of 10, Exceptional, (13 reviews)
"Very clean and perfect place to stay while we were in a wedding at the Beauport! The host checked in often and made us feel very welcomed and at home"
United States
Katie B.
The price is CA $274
CA $347 total
includes taxes & fees
Oct 21 - Oct 22
The Essex of Gloucester

6. Oceanside Village Home~Private Fenced Yard~Reserved Parking

Oceanside Village Home~Private Fenced Yard~Reserved Parking
Gloucester
9.6 out of 10, Exceptional, (15 reviews)
"Sparking clean property. Plenty of main floor gathering space (kitchen/dining/livingroom) with good separation of sleeping quarters, giving the opportunity for privacy and rest. Pretty back yard with Adirondack chairs to enjoy while reading or just resting. Easy drive to the main attractions of Gloucester and/or Rockport. All this and responsive owners too! "
United States
Karen T.
The price is CA $190
CA $526 total
includes taxes & fees
Sep 23 - Sep 24
Oceanside Village Home~Private Fenced Yard~Reserved Parking

7. 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, (22 reviews)
"For our one night stay it was perfect, Clean and comfortable, plenty of basic's, bedding, towels and kitchen supply's."
United States
CHARLES
The price is CA $294
CA $561 total
includes taxes & fees
Sep 27 - Sep 28
Cozy two bedroom house in the heart of Gloucester

8. Quirky 1-bedroom apartment with AC in delightful Gloucester, near water

Quirky 1-bedroom apartment with AC in delightful Gloucester, near water
Gloucester
10.0 out of 10, Exceptional, (1 review)
"Lovely, large room with beams on the ceiling and a very comfortable bed. Clean and inviting. Appreciated the detailed, friendly messages from the host. The building is near a pretty pond and the store downstairs sells coffee for a dollar!"
United States
Catherine C.
The price is CA $223
CA $308 total
includes taxes & fees
Oct 4 - Oct 5
Quirky 1-bedroom apartment with AC in delightful Gloucester, near water

9. Ocean Breeze / 8-Minute Walk to Beach

Ocean Breeze / 8-Minute Walk to Beach
East Gloucester
10.0 out of 10, Exceptional, (20 reviews)
"Very clean and quaint. There is definitely noise you can hear from upstairs but not in a way that was bothersome. We enjoyed our stay!"
United States
Jessica M.
The price is CA $298
CA $589 total
includes taxes & fees
Oct 15 - Oct 16
Ocean Breeze / 8-Minute Walk to Beach

10. New England Coastal Residence

New England Coastal Residence
Gloucester
10.0 out of 10, Exceptional, (3 reviews)
"Comfortable, clean and very much natural light. The beds are incredibly comfortable. A great place as a homebase when visiting the area."
United States
Richard B.
The price is CA $440
CA $1,230 total
includes taxes & fees
Sep 22 - Sep 23
New England Coastal Residence

11. 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, (19 reviews)
"Rachel was very responsive and attentive, excellent host. The house was in a great location, clean, and very comfortable. Would stay there again should the need arise."
United States
Betty
The price is CA $493
CA $1,003 total
includes taxes & fees
Oct 7 - Oct 8
3BR Oceanview Townhouse on Boulevard I Walk to downtown l Sleeps 8

12. 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, (5 reviews)
"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 $547
CA $1,484 total
includes taxes & fees
Sep 22 - Sep 23
Classic Coastal Family Home | Walk to Sea;King Bed

13. 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
10.0 out of 10, Exceptional, (1 review)
"We loved our stay. The property is beautiful with wonderful views. Convenient to get most places."
United States
Sara G.
Oceanview Home/Walk to Lanes Cove and Plum Cove beach I Sleeps 6

14. The Duval House

The Duval House
Downtown Gloucester
9.4 out of 10, Exceptional, (20 reviews)
"We had a wonderful stay. The house was very nice and the room was very clean. Can’t wait to come back!"
United States
Jennifer H.
The price is CA $288
CA $673 total
includes taxes & fees
Oct 21 - Oct 22
The Duval House

15. Stay at Rocky Neck

Stay at Rocky Neck
Rocky Neck
10.0 out of 10, Exceptional, (15 reviews)
"Our host was amazing and this was the perfect getaway for us in a beautiful location!"
United States
Joy B.
The price is CA $1,511
CA $2,373 total
includes taxes & fees
Oct 12 - Oct 13
Stay at Rocky Neck

16. Long Beach Suites

Long Beach Suites
2.0 star property
East Gloucester
9.2 out of 10, Wonderful, (86 reviews)
"We are so glad we found this beautiful property! The condo was very bright & spacious inside, clean and comfortable. Quick walk to the beach and ice cream shop. Perfect location in a quiet neighborhood."
United States
Kayse
Long Beach Suites

17. Harbor Retreat ★ Ocean View ★ Heart of Downtown ★

Harbor Retreat ★ Ocean View ★ Heart of Downtown ★
Rockport
9.8 out of 10, Exceptional, (43 reviews)
"This is our second year staying at Gigi's place. It's such a great location and value. It offers everything we like during the off season without the crowds and is such a clean and comfortable place to stay."
United States
Victoria P.
The price is CA $162
CA $391 total
includes taxes & fees
Sep 27 - Sep 28
Harbor Retreat ★ Ocean View ★ Heart of Downtown ★

18. Downtown Rockport · King Bed w/Parking · Walk to Train

Downtown Rockport · King Bed w/Parking · Walk to Train
Rockport
9.8 out of 10, Exceptional, (42 reviews)
"Perfect house for a stay in Rockport. Clean, well decorated and the perfect location for walking around the town and also exploring the east coast. "
United States
Leanna S.
The price is CA $222
CA $502 total
includes taxes & fees
Oct 5 - Oct 6
Downtown Rockport · King Bed w/Parking · Walk to Train

19. Harborside Oasis ★ Harbor View ★ Heart of Downtown

Harborside Oasis ★ Harbor View ★ Heart of Downtown
Rockport
9.8 out of 10, Exceptional, (38 reviews)
"I couldn’t have asked for a better experience or location!! We loved every second we were there"
United States
Nicholas L.
The price is CA $176
CA $414 total
includes taxes & fees
Sep 24 - Sep 25
Harborside Oasis ★ Harbor View ★ Heart of Downtown

20. Apartment with private rooftop deck with ocean views

Apartment with private rooftop deck with ocean views
Rockport
10.0 out of 10, Exceptional, (23 reviews)
"A beautiful home clean with everything we needed for our stay. We enjoyed our stay and I would definitely book again!"
United States
Ellen W.
The price is CA $245
CA $442 total
includes taxes & fees
Sep 27 - Sep 28
Apartment with private rooftop deck with ocean views
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?

Steps to Wingaersheek's Private 1.5 Mile White Dune Beach: This Gloucester vacation home rental is located near the beach and has a fireplace, a selection of games, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Some other top choices in Gloucester are Peaceful centrally located home: w/ yard & walking distance to town and Wingaersheek, Private & Public Beach, Luxury Home, Ext'd Family Show Annisquam.

How many vacation rentals are there in Gloucester?

Expedia has 175 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 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 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.