Luxury Vacation Rentals for Large Groups in Gloucester

Luxury Vacation Rentals for Large Groups 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 1 large group vacation rentals – enter your dates for availability.

Top-rated large group vacation rentals in Gloucester

Oceanfront Dock Escape Kayaks & Paddleboards property photo 1

Oceanfront Dock Escape Kayaks & Paddleboards

4 bedrooms•3 baths
2,063 US dollars for 3 nights•
New

~$180 less than other sites

Welcome to your large group retreat in Gloucester

Welcome to your large group retreat in Gloucester

Bring everyone together in style with Wander’s luxury vacation rentals for large groups in Gloucester, Massachusetts. Our collection features expansive coastal homes designed for connection and comfort, each one professionally managed to a five star standard.
Spread out across multiple ensuite bedrooms and generous gathering spaces. Cook for the whole crew in entertainer kitchens with premium appliances, seat everyone at oversized dining tables, and unwind in dual living rooms or on broad outdoor terraces.
Every stay includes ultra fast WiFi, pristine cleaning, and 24/7 concierge. Select homes add gyms, pools or hot tubs, and quiet work nooks, so coordinating reunions, corporate retreats, or multi family getaways feels effortless from arrival to checkout.

All homes in Gloucester

Oceanfront Dock Escape Kayaks & Paddleboards property photo 1

Oceanfront Dock Escape Kayaks & Paddleboards

4 bedrooms•3 baths
2,063 US dollars for 3 nights•
New

~$180 less than other sites

View all homes

Highlights in Gloucester

Gather your group to experience Gloucester's historic maritime charm, scenic sandy beaches, and unforgettable coastal excursions perfect for large gatherings.
Good Harbor Beach
Wingaersheek Beach
Hammond Castle Museum
Cape Ann Whale Watch
Stage Fort Park
Rocky Neck Art Colony

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 large group vacation rentals in Gloucester

Bbq area (1)
Garden (1)
Dryer (1)
Washer (1)
Oven (1)
Tv (1)
Kitchen (1)
Wifi (1)
Microwave (1)
Dishwasher (1)
Heating (1)
Coffee maker (1)
Toys (1)
Free parking (1)
Iron (1)
Hair dryer (1)

Other popular amenities & vacation types in Gloucester

Family vacation rentals in Gloucester
Discover more large groups activities in Gloucester

Discover more large groups activities in Gloucester

Gloucester pairs working waterfront energy with the wild beauty of Cape Ann. Expect sweeping beaches, granite headlands, and a maritime legacy that animates every season.
Swim and sun at Good Harbor or Wingaersheek, hike the ledges of Halibut Point State Park, and watch schooners pass the Twin Lights of Thatcher Island. Browse Rocky Neck’s studios, cheer on St. Peter’s Fiesta, and savor the day’s catch overlooking the harbor.
With year round coastal drama and easy access to Boston and the rest of New England, it is ideal for gatherings of all sizes. This is why Wander’s luxury vacation rentals in Gloucester 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 large group vacation rentals?

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

Some of our most popular large group vacation rentals in Gloucester include Oceanfront Dock Escape ~ Kayaks & Paddleboards 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 large group vacation rentals does Wander have available in Gloucester?

Wander offers 1 large group 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 large group vacation rentals in Gloucester?

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

Do Wander’s large group 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.