Luxury Vacation Rentals for Families in Massachusetts

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 19 family vacation rentals – enter your dates for availability.

Top-rated family vacation rentals in Massachusetts

Home in Egremont

5 bedrooms•4 baths

•

Home in Becket

5 bedrooms•2 baths

•

Home in Becket

6 bedrooms•4 baths

•

Wander Cape Cod Village

5 bedrooms•5 baths

•

Home in Barnstable

5 bedrooms•4 baths

•

Home in Barnstable

3 bedrooms•2 baths

•

Home in Sandwich

3 bedrooms•2.5 baths

•

Home in Dennis

3 bedrooms•1 bath

•

Welcome to family adventures in Massachusetts

Bring the whole crew to a better kind of getaway. Our Massachusetts collection is built for space, privacy, and ease, with coastal homes in Barnstable, Chatham, and Dennis and a wooded escape in Becket for Berkshire calm. Every stay matches the photos and is professionally operated, so you can settle in without the guesswork.

Choose from luxury family vacation rentals in Massachusetts with multi-bedroom floor plans, expansive living rooms, chef-ready kitchens, ultra fast WiFi, and dedicated workspaces. Expect hotel-grade cleanliness, 24/7 concierge support, and thoughtful details that make traveling with kids feel effortless.

Available soon in Massachusetts

Home in Egremont

5 bedrooms•4 baths

•

Home in Barnstable

3 bedrooms•2 baths

•

Home in Dennis

3 bedrooms•1 bath

•

Home in Yarmouth

3 bedrooms•2 baths

•

Featured family vacation rentals in Massachusetts

Home in Egremont

5 bedrooms•4 baths

•

Wander Cape Cod Village

5 bedrooms•5 baths

•

Home in Barnstable

5 bedrooms•4 baths

•

Home in Barnstable

5 bedrooms•3 baths

Luxury

Home in Dennis

6 bedrooms•5 baths

•

Home in Barnstable

7 bedrooms•5.5 baths

•

Home in Barnstable

6 bedrooms•4 baths

•

Luxury

Home in East Falmouth

5 bedrooms•4 baths

•

Highlights in Massachusetts

From revolutionary history in Boston to sandy shores on Cape Cod, Massachusetts offers endless family adventures and educational fun.

Freedom Trail

Museum of Science

New England Aquarium

Plimoth Patuxet Museums

Cape Cod National Seashore

The Witch House at Salem

Dr. Seuss National Memorial Sculpture Garden

Fenway Park

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.

All homes in Massachusetts

Home in Egremont

5 bedrooms•4 baths

•

Home in Becket

5 bedrooms•2 baths

•

Home in Becket

6 bedrooms•4 baths

•

Wander Cape Cod Village

5 bedrooms•5 baths

•

Home in Barnstable

5 bedrooms•4 baths

•

Home in Barnstable

3 bedrooms•2 baths

•

Home in Sandwich

3 bedrooms•2.5 baths

•

Home in Dennis

3 bedrooms•1 bath

•

View all homes

Most popular amenities for family vacation rentals in Massachusetts

Beach essentials (11)

More popular family destinations in Massachusetts

Family vacation rentals in Barnstable

Family vacation rentals in Becket

Family vacation rentals in Chatham

Family vacation rentals in Dennis

Other popular amenities & vacation types in Massachusetts

Large group vacation rentals in Massachusetts

Pet-friendly vacation rentals in Massachusetts

Beachfront vacation rentals in Massachusetts

Hot tub vacation rentals in Massachusetts

Private pool vacation rentals in Massachusetts

Discover more family fun in Massachusetts

Massachusetts rewards family time with variety. On Cape Cod, gentle beaches and tidal flats invite easy days by the water, while rail trails weave through pine forests. In the Berkshires, mountain views, glassy ponds, and winding trails set the tone for unplugged afternoons and brilliant autumn color.

From lighthouse-dotted coastlines to country roads lined with farm stands, the state offers four seasons of simple pleasures and standout scenery. Plan a trip that blends seaside mornings with hillside sunsets, all within one destination. This is why Wander's luxury family vacation rentals in Massachusetts are the perfect choice, whether you're traveling for work or leisure.

FAQs: Vacation Rentals in Massachusetts

Why should I book a Wander in Massachusetts 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 Massachusetts 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 Massachusetts?

Some of our most popular family vacation rentals in Massachusetts include Wander Berkshires Serenity, Wander Berkshires Lakeside, and Wander Berkshires Lodge. 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 Massachusetts?

Wander offers 19 family vacation rentals in Massachusetts, 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 Massachusetts?

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

Do Wander’s family vacation rentals in Massachusetts have WiFi access?

Yes. Every Wander home in Massachusetts 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.