Luxury Vacation Rentals with a Private Pool 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 private pool vacation rentals – enter your dates for availability.
Welcome to private poolside luxury in Chatham
Experience Wander in its element with luxury private-pool vacation rentals in Chatham, Massachusetts. Our homes bring hotel-grade consistency to the serenity of a private residence, so every arrival feels effortless and every detail is dialed in.
Slip into your heated pool for a morning swim, lounge on sunlit terraces, and wind down by the fire as the evening cools. Inside, find chef-ready kitchens, plush linens, smart home tech, dedicated workspaces, and ultra fast WiFi. Each stay includes meticulous housekeeping, 24/7 concierge support, and thoughtful touches like fitness zones and stocked essentials.
From long weekends to extended stays, this Chatham collection makes work and leisure flow with ease.
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
Chatham Main Street
Chatham Fish Pier
Lighthouse Beach
Monomoy National Wildlife Refuge
Chatham Shark Center
Chatham Marconi Maritime Center
Hardings Beach
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 private pool vacation rentals in Chatham
More popular private pool destinations near Chatham
Other popular amenities & vacation types in Chatham
Discover more beyond the pool in Chatham
Set on the elbow of Cape Cod, Chatham marries maritime heritage with easygoing sophistication. Greet sunrise at Lighthouse Beach, watch seals and trawlers at the Fish Pier, and wander Main Street’s galleries, bookshops, and classic storefronts.
Days here move between sandy stretches like Hardings and Ridgevale, sailing or paddling on Pleasant Bay, and birding across the dunes of Monomoy National Wildlife Refuge. Summer brings hydrangeas and bandstand nights, fall glows with crisp light, and winter offers quiet walks by the Atlantic. With so much to enjoy year-round, Wander’s luxury private-pool vacation rentals in Chatham, Massachusetts are the perfect choice, whether you are traveling for work or leisure.
FAQs: Vacation Rentals in Chatham
Why should I book a Wander in Chatham over other private pool vacation rentals?
Wander offers a level of consistency and quality you won’t find with most private pool 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 private pool vacation rentals in Chatham?
Some of our most popular private pool 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 private pool vacation rentals does Wander have available in Chatham?
Wander offers 2 private pool 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 private pool vacation rentals in Chatham?
You can check-in to Wander private pool vacation rentals in Chatham after 4.00pm and check-out before 10.00am.
Do Wander’s private pool 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.