Gloucester Vacation Rentals

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Our top choices for Gloucester vacation rentals

Wingaersheek, Private & Public Beach, Luxury Home, Ext'd Family Show Annisquam

Gloucester
9.4 out of 10, Exceptional, (61)
"Beautiful home, close to the beach. Air conditioning wasn’t great and fridge didn’t get very cold. Enjoyed the deck space "
United States
Jess K.
Wingaersheek, Private & Public Beach, Luxury Home, Ext'd Family Show Annisquam

Steps to Wingaersheek's Private 1.5 Mile White Dune Beach

Gloucester
9.8 out of 10, Exceptional, (39)
"We had a great stay here - the house was very comfortable and welcoming and just steps away from the beach! The owner is very responsive and helpful. Would absolutely stay here again!"
United States
Piper T.
Steps to Wingaersheek's Private 1.5 Mile White Dune Beach

Good Harbor Beach House - walk to beach, close to restaurants and shopping!

Gloucester
10.0 out of 10, Exceptional, (218)
"We absolutely loved our stay! The house was beautiful. We especially loved the main living area, kitchen and porches. "
United States
Erinn M.
Good Harbor Beach House - walk to beach, close to restaurants and shopping!

Cranberry Hill l 9 BR 22 Acre Estate l Sleeps 24

Gloucester
10.0 out of 10, Exceptional, (3)
"It was a beautiful home. Clean, up-to-date, and conveniently located. The host was very attentive and helpful. "
United States
Charlie L.
Cranberry Hill l 9 BR 22 Acre Estate l Sleeps 24

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

Gloucester
9.8 out of 10, Exceptional, (49)
"Very nice spot - very clean - nice bathroom"
United States
Mary M.
Luxury 1900's romantic retreat steps from the beach - King Suite!

Peaceful centrally located home: w/ yard & walking distance to town

2.0 star property
Gloucester
8.6 out of 10, Excellent, (11)
"Everything was perfect thank you so much for having us "
United States
Ryan
Peaceful centrally located home: w/ yard & walking distance to town

Steps Away from Good Harbor & Long Beach! Spacious Home for Groups of All Sizes!

Gloucester
10.0 out of 10, Exceptional, (37)
"The stay was wonderful. Stocked clean house, great location-walk to beach and lobster rolls! Lovely patio and ample parking. Superior responsive and flexible host. I’m planning to return next year - that says it all, I think. "
United States
Jeanne S.
Steps Away from Good Harbor & Long Beach! Spacious Home for Groups of All Sizes!

Edgemoor Estate 13 Beds 6.5 Bath (Sleeps 26) - Heated Pool Jacuzzi Beach

Gloucester
6.8 out of 10, (3)
"This was the perfect property for our family. The house is wonderful and the hosts are super responsive. We can’t wait to return!"
United States
Bridget D.
Edgemoor Estate 13 Beds 6.5 Bath (Sleeps 26) - Heated Pool Jacuzzi Beach

The Warlock House: Spellbound Stay - Sleep Where the Magic and Spells Happens!

Downtown Salem
9.6 out of 10, Exceptional, (61)
"Amazing place to stay! Love the attention to decorating details, from the spooky lighting to the Alexa “Scroll of Spells” and it’s within close walking distance to many Salem attractions! Would recommend to anyone!"
United States
More M.
$657 nightly
The price is $751
Dec 10 - Dec 11
Total with taxes and fees
The Warlock House: Spellbound Stay - Sleep Where the Magic and Spells Happens!

Leslie's Retreat: Spacious home ideally located to everything

Salem
10.0 out of 10, Exceptional, (251)
"Great location, walking distance to everything! Beautiful well kept home."
United States
Susan G.
Leslie's Retreat: Spacious home ideally located to everything

Apartments in Salem

3.0 star property
Salem
8.0 out of 10, Very Good, (48)
"Property was fine. It is well located to see the sites in Salem. Only negative was that the neighbors were a bit loud at night. "
United States
Wes
$268 nightly
The price is $293
Dec 10 - Dec 11
Total with taxes and fees
Apartments in Salem

Cozy Salem Getaway. Historic Home Near All the Sights

Salem
9.6 out of 10, Exceptional, (58)
"it was very nice and cozy definitely go back there again "
United States
Doreen
$399 nightly
The price is $446
Jan 8 - Jan 9, 2026
Total with taxes and fees
Cozy Salem Getaway. Historic Home Near All the Sights

Ocean views from every window. 5min walk to the quiet end of the beach!

Hampton Beach
9.6 out of 10, Exceptional, (28)
"It was quick but memorable next time we will stay longer, accomodations were great, location has everything."
United States
Bonnie B.
Ocean views from every window. 5min walk to the quiet end of the beach!

Premier, modern, fully renovated, Beach home...stroll to the beach in 3 minutes!

Hampton Beach
10.0 out of 10, Exceptional, (102)
"This is an amazing property to stay at! The property owner is extremely responsive to ALL texts and requests. I highly recommend staying here!"
United States
Darlene S.
$571 nightly
The price is $620
Dec 10 - Dec 11
Total with taxes and fees
Premier, modern, fully renovated, Beach home...stroll to the beach in 3 minutes!

The Lighthouse - Perfect Location Near Beach

Hampton Beach
9.8 out of 10, Exceptional, (17)
"Tight squeeze but very nice for a HB stopover."
United States
Richard Brian T.
The Lighthouse - Perfect Location Near Beach

Unit1 Beautiful PRIVATE LARGE 3 bedroom/2 bath townhome. Close to ALL HISTORIC

Salem
9.6 out of 10, Exceptional, (146)
"Great place The one and only negative was the smell of POT when you opened door to unit. Otherwise, what a great place, beautiful, clean, close to everything. Would definitely stay again "
United States
HEATHER
Unit1 Beautiful PRIVATE LARGE 3 bedroom/2 bath townhome. Close to ALL HISTORIC

*NEW Spooky Halloween 2BR|Downtown|Parking

Salem
9.2 out of 10, Wonderful, (47)
"Very clean, quiet and convenient location! The owners checked in with me through the app to make sure we had everything we needed. I would stay again!"
United States
Rebecca T.
$256 nightly
The price is $293
Dec 14 - Dec 15
Total with taxes and fees
*NEW Spooky Halloween 2BR|Downtown|Parking

2 Bed/2 Bath Private Beach House One Block from the ocean.

Hampton Beach
10.0 out of 10, Exceptional, (18)
"Everything was wonderful! Location is perfect, we can’t wait to come back!"
United States
Melanie L.
2 Bed/2 Bath Private Beach House One Block from the ocean.

Classic New England: Big Family Home; Spas|Garden|FirePit; walk to beach, shops.

Rockport
10.0 out of 10, Exceptional, (22)
"The house was a perfect home base for our extended family vacation. The house is the best equipped of any of the VRBOs I have ever stayed at. We all loved it. "
United States
Mark B.
$1,076 nightly
The price is $1,202
Dec 17 - Dec 18
Total with taxes and fees
Classic New England: Big Family Home; Spas|Garden|FirePit; walk to beach, shops.

Luxury and Modern Apt near Mall/ Hospital

Danvers
10.0 out of 10, Exceptional, (48)
"Amazing stay! Met our needs perfectly. Walkable restaurants and coffee shop. Highly recommend this property."
United States
Paul M. P.
$429 nightly
The price is $479
Dec 10 - Dec 11
Total with taxes and fees
Luxury and Modern Apt near Mall/ Hospital
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

Everything you need to know about Gloucester vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Gloucester vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Gloucester vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Gloucester vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Gloucester. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Gloucester in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $293 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Gloucester rentals

At Expedia, we put the best Gloucester vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Gloucester rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Gloucester vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Gloucester. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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?

Cranberry Hill l 9 BR 22 Acre Estate l Sleeps 24: This Gloucester vacation home rental offers a patio, a garden, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 9 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. Some other top choices in Gloucester are Steps to Wingaersheek's Private 1.5 Mile White Dune Beach and Peaceful centrally located home: w/ yard & walking distance to town.

How many vacation rentals are there in Gloucester?

Expedia has 158 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.