Luxury Vacation Rentals 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 vacation rentals – enter your dates for availability.

Top-rated vacation rentals in Sherman

Home in Sherman

4 bedrooms•5 baths

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Welcome to Sherman

Experience luxury vacation rentals in Sherman, Connecticut, where calm countryside living meets high design. Wander blends the polish of a five-star hotel with the privacy of a standalone home for an effortless stay.

Expect light-filled living rooms, chef-grade kitchens, plush suites, and outdoor areas made for unhurried mornings. Every stay includes ultra fast WiFi, dedicated workspaces, meticulous cleaning, and 24/7 concierge support.

Set among rolling hills and quiet country roads, our Sherman homes create space to recharge, focus, and gather in style, all with the confidence that everything looks and feels exactly as promised.

All homes in Sherman

Home in Sherman

4 bedrooms•5 baths

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View all homes

Highlights in Sherman

Discover the scenic beauty of Sherman, offering tranquil lakeside retreats, lush nature preserves, and historic New England charm.

Candlewood Lake

Squantz Pond State Park

Great Hollow Nature Preserve

Deer Pond Farm

Bull's Bridge

Appalachian Trail at Hoyt Road

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 vacation rentals in Sherman

Other popular amenities & vacation types in Sherman

Private pool vacation rentals in Sherman

Discover more of Sherman

Sherman sits at the northern tip of Candlewood Lake on the New York line, surrounded by the rolling Litchfield Hills, stone-fenced meadows, and hardwood forests. The pace is easy, the skies feel expansive, and nights still glow with constellations.

Summer brings glassy mornings on the water and long golden evenings. Autumn paints the hills in brilliant color, while winter swaps in snow-dusted quiet. Come spring, country lanes, trails, and farm stands reawaken. Just about 90 minutes from New York City, it feels a world away, which is why Wander’s luxury vacation rentals in Sherman, Connecticut 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 vacation rentals?

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

Some of our most popular 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 vacation rentals does Wander have available in Sherman?

Wander offers 1 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 vacation rentals in Sherman?

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

Do Wander’s 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.