Luxury Vacation Rentals with a Private Pool in Sherman

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 private pool vacation rentals – enter your dates for availability.

Top-rated private pool vacation rentals in Sherman

Home in Sherman

4 bedrooms•5 baths

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Welcome to private poolside luxury in Sherman

Find your private oasis in the Connecticut countryside. Our handpicked collection of luxury private pool vacation rentals in Sherman blends five-star standards with the comfort of a beautiful home.

Every stay includes a secluded pool for unhurried swims, elegant living rooms, chef-ready kitchens, plush bedding, and dedicated work areas with fast WiFi. Count on pristine cleaning, inspiring views, smart home touches, and 24/7 concierge support.

Settle in, power down, or power through. With hotel-grade consistency and total privacy, booking a Wander in Sherman elevates every stay.

All homes in Sherman

Home in Sherman

4 bedrooms•5 baths

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View all homes

Highlights in Sherman

Experience the quiet charm of Sherman, where scenic vineyards, pristine lakes, and lush hiking trails offer a peaceful New England escape.

Candlewood Lake

White Silo Farm & Winery

Great Hollow Nature Preserve

Squantz Pond State Park

Appalachian Trail Access

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 private pool vacation rentals in Sherman

Discover more beyond the pool in Sherman

At the northern reach of Candlewood Lake, Sherman blends shimmering water with rolling hills and stone-lined backroads. Dawn brings glassy coves for paddling, afternoons invite boat days, and sunsets wash the shoreline in soft color.

Scenic byways link farm stands, tasting rooms, and classic New England greens, with nearby stretches of the Appalachian Trail offering ridgeline hikes and river overlooks. Summer is all about the lake, fall delivers brilliant foliage, and winter slows to a peaceful hush.

Choose the serenity of Sherman for your next escape. That is why Wander’s luxury private pool vacation rentals in Sherman are the perfect choice, whether you are traveling for work or leisure.

FAQs: Vacation Rentals in Sherman

Why should I book a Wander in Sherman 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 Sherman 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 Sherman?

Some of our most popular private pool vacation rentals in Sherman include Lakeshore Crest Estate - Private Dock & Pool and Lakeshore Crest Estate - Private Dock & Pool. 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 Sherman?

Wander offers 1 private pool vacation rentals in Sherman, 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 Sherman?

You can check-in to Wander private pool vacation rentals in Sherman after 4.00pm and check-out before 10.00am.

Do Wander’s private pool vacation rentals in Sherman have WiFi access?

Yes. Every Wander home in Sherman 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.