Luxury Vacation Rentals in Gloucester

Never book a bad vacation home again. Every Wander comes with hotel-grade amenities, inspiring views, pristine cleaning and 24/7 concierge service.

We found 2 vacation rentals – enter your dates for availability.

Top-rated vacation rentals in Gloucester

Home in Gloucester

4 bedrooms•3 baths

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New

Home in Gloucester

4 bedrooms•3 baths

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New

Welcome to Gloucester

Set your sights on Gloucester, Massachusetts with Wander. Our luxury vacation rentals in Gloucester, Massachusetts combine the polish of a five star stay with the privacy of a coastal home. Every space is beautiful, expertly operated, and exactly as pictured, so you can step into a flawless setting the moment you arrive.

Expect hotel grade essentials across the board, including ultra fast WiFi, premium linens, pristine cleaning, and 24/7 concierge. Homes are designed for work and play with inspiring views, dedicated workstations, fitness options, and, in select residences, pools or hot tubs. Positioned to showcase Gloucester’s shoreline and light, each stay feels effortless and elevated.

Destinations near Gloucester

Available soon in Gloucester

Home in Gloucester

4 bedrooms•3 baths

•

New

Home in Gloucester

4 bedrooms•3 baths

•

New

All homes in Gloucester

Home in Gloucester

4 bedrooms•3 baths

•

New

Home in Gloucester

4 bedrooms•3 baths

•

New

View all homes

Highlights in Gloucester

Discover America's oldest seaport, where historic lighthouses, pristine sandy beaches, and a vibrant arts scene await your coastal adventure.

Gloucester Fisherman's Memorial

Hammond Castle Museum

Good Harbor Beach

Rocky Neck Art Colony

Eastern Point Lighthouse

Cape Ann Museum

IT'S A VACATION HOME, BUT BETTER

The Wander difference

Wander is different because we combine the quality of a luxury hotel with the comfort of a private vacation home. Your best trip ever is just a few clicks away.

Only the best homes

We’ll never not look like the pictures. Every Wander is beautiful and expertly operated, so you can leave any stress at the door.

Hotel-grade amenities

We’ll never leave you with nothing to do. From ultra fast WiFi to gyms and pools, our homes make it easy to blend work and play.

24/7 concierge service

We’ll never leave you hanging. Our chat-based Concierge is always available to help – from trip questions to special requests.

Inspiring and stunning views

We’ll never leave you uninspired. Every Wander has stunning views to refresh and inspire your soul. Adventure awaits.

Meticulous cleaning

We’ll never have you check in to a dirty house. Our cleaning teams are meticulous, and there are no chores at checkout.

Safety and security

We’ll never pass you off to a stranger. Every Wander location meets our industry-leading safety standards to give you peace of mind.

Most popular amenities for vacation rentals in Gloucester

Other popular amenities & vacation types in Gloucester

Family vacation rentals in Gloucester

Discover more of Gloucester

On Cape Ann’s rocky edge, Gloucester blends a working waterfront with sweeping Atlantic vistas. Watch schooners from the Dog Bar Breakwater, browse Rocky Neck’s galleries, or stretch out at Good Harbor and Wingaersheek, where soft sand and broad tidal flats set the scene for luminous sunsets.

Then venture to Halibut Point State Park for granite ledges and crashing surf, or trace maritime history at Eastern Point Lighthouse and Stage Fort Park. Whale watching boats reach Stellwagen Bank within minutes. This is why Wander’s luxury vacation rentals in Gloucester, Massachusetts are the perfect choice, whether you travel for work or leisure.

FAQs: Vacation Rentals in Gloucester

Why should I book a Wander in Gloucester over other vacation rentals?

Wander offers a level of consistency and quality you won’t find with most vacation rentals.

Every home in Gloucester delivers the quality of a luxury hotel, paired with the comfort and space of a private vacation home. You get hotel-grade amenities, meticulous cleaning, stunning views, and 24/7 concierge support in every stay. Why would you want to stay anywhere else?

Which are Wander’s most popular vacation rentals in Gloucester?

Some of our most popular vacation rentals in Gloucester include Oceanfront Dock Escape ~ Kayaks & Paddleboards, Gloucester Waterfront | Dock & Kayaks, and Oceanfront Dock Escape ~ Kayaks & Paddleboards. Guests love the quality of a luxury hotel, the comfort of a private vacation home, and the consistently exceptional experience Wander is known for. Explore the full collection to find the perfect home for your next stay.

How many different vacation rentals does Wander have available in Gloucester?

Wander offers 2 vacation rentals in Gloucester, each carefully designed and expertly operated. Browse the full collection to see what’s available for your trip.

What time is check-in and check-out at Wander’s vacation rentals in Gloucester?

You can check-in to Wander vacation rentals in Gloucester after 4.00pm and check-out before 10.00am.

Do Wander’s vacation rentals in Gloucester have WiFi access?

Yes. Every Wander home in Gloucester has ultra fast, reliable WiFi so you can stay connected throughout your stay.

What is Wander’s cancellation policy?

You can cancel your reservation within 24 hours of booking for a full refund.

For stays of less than 15 nights, you can cancel or reschedule up to 14 days before check-in for a full refund. For stays of 15 nights or longer, the cancellation window is 60 days.

For some homes, a 30-day deadline applies; this will be clearly shown before you book.