Luxury Vacation Rentals in Chatham
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.
Welcome to Chatham
Set your sights on luxury vacation rentals in Chatham, Massachusetts, where classic Cape style meets modern comfort. Our collection features refined coastal homes with bright, open interiors and outdoor spaces designed to catch the sea breeze.
Expect hotel-grade consistency every time you book a Wander. Think pristine cleaning, 24/7 concierge, ultra fast WiFi, chef-ready kitchens, premium linens, and thoughtful smart tech. Choose a serene hideaway near the harbor or a light-filled retreat beside peaceful salt marshes, and settle into a polished home that feels effortless from arrival to checkout.
Destinations near Chatham
Highlights in Chatham
Discover classic Cape Cod charm with picturesque lighthouses, stunning beaches, a quaint downtown, and abundant marine wildlife in this seaside town.
Chatham Lighthouse
Main Street
Chatham Fish Pier
Lighthouse Beach
Monomoy National Wildlife Refuge
Hardings Beach
Chatham Shark Center
Chatham Marconi Maritime Center
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.
Most popular amenities for vacation rentals in Chatham
Other popular amenities & vacation types in Chatham
Discover more of Chatham
At the elbow of Cape Cod, Chatham balances maritime character with easygoing sophistication. Working harbors, cedar-shingled roofs, and sweeping views toward the Atlantic and Nantucket Sound create a backdrop that feels both storied and fresh.
Summer brings hydrangeas and band concerts on the lawn, autumn paints the marshes gold, and quiet winters reward those who love open horizons. Lighthouse vistas, seal-dotted shoals, and the wild beauty of nearby Monomoy make every season memorable. This is why Wander's luxury vacation rentals in Chatham are the perfect choice, whether you're traveling for work or leisure.
FAQs: Vacation Rentals in Chatham
Why should I book a Wander in Chatham over other vacation rentals?
Wander offers a level of consistency and quality you won’t find with most vacation rentals.
Every home in Chatham 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 Chatham?
Some of our most popular vacation rentals in Chatham include Wander Cape Cod Dunes, Wander Chatham Oasis, and Wander Chatham Oasis. 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 Chatham?
Wander offers 2 vacation rentals in Chatham, 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 Chatham?
You can check-in to Wander vacation rentals in Chatham after 4.00pm and check-out before 10.00am.
Do Wander’s vacation rentals in Chatham have WiFi access?
Yes. Every Wander home in Chatham 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.