Luxury Vacation Rentals for Families 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 family vacation rentals – enter your dates for availability.

Top-rated family 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 family adventures in Gloucester

Plan an effortless family escape to Cape Ann with Wander. Our collection of luxury family vacation rentals in Gloucester, Massachusetts blends the polish of a five-star stay with the space and privacy you need.

Expect multi-bedroom floor plans, kid-friendly lounges, and bright ocean-view living areas designed for together time. Chef's kitchens, laundry, and ultra fast WiFi keep routines smooth, while dedicated work nooks make hybrid schedules simple.

Each home is professionally cleaned and thoughtfully outfitted, with hotel-grade amenities, inspiring views, and 24/7 concierge support. From sunrise coffees on the deck to movie nights that actually feel like home, a Wander makes family travel feel easy.

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 Gloucester’s sandy shores, historic castles, and exciting marine adventures perfect for an unforgettable family seaside getaway.

Good Harbor Beach

Wingaersheek Beach

Maritime Gloucester

Hammond Castle Museum

Stage Fort Park

7 Seas Whale Watch

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 family vacation rentals in Gloucester

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Discover more family fun in Gloucester

Gloucester pairs storied maritime character with wide, family-friendly beaches. Good Harbor rolls out soft sand and boogie-board waves, while Wingaersheek reveals tidal flats and warm shallows perfect for sandcastle architects.

Beyond the shore, schooners glide past the working harbor, and the Fishermen’s Memorial watches over sunset strolls. Whale-watching boats depart seasonally, lighthouses crown the headlands, and nearby Rockport adds galleries and coastal charm to a day’s wandering.

Summer brings sea breezes and St. Peter’s Fiesta, autumn lights up coastal trails, and winter rewards with dramatic surf and quiet streets. This is why Wander’s luxury family vacation rentals in Gloucester, Massachusetts are the perfect choice, whether you are traveling for work or leisure.

FAQs: Vacation Rentals in Gloucester

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

Wander offers a level of consistency and quality you won’t find with most family 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 family vacation rentals in Gloucester?

Some of our most popular family 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 family vacation rentals does Wander have available in Gloucester?

Wander offers 2 family 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 family vacation rentals in Gloucester?

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

Do Wander’s family 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.