A calm lake with autumn foliage, a dock, and houses along the shore.

Search Chalets in Winchester

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
20 Nov - 22 Nov
In two months
1 Jan - 3 Jan
In three months
29 Jan - 31 Jan
In four months
26 Feb - 28 Feb

Our top choices for Winchester chalets

A hot tub on a deck surrounded by trees.

1. Nature’s Oasis | Hot Tub | Walkable to Deer Lick Falls

Nature’s Oasis | Hot Tub | Walkable to Deer Lick Falls
Monteagle
8.8 out of 10, Excellent, (5 reviews)
The price is AED 568
AED 1,312 total
includes taxes & fees
18 Nov - 19 Nov
Nature’s Oasis | Hot Tub | Walkable to Deer Lick Falls
A modern cabin with a wooden exterior, a porch with steps, and two chairs.

2. Foster's Cabin 3 | 2 Minutes from Foster Falls

Foster's Cabin 3 | 2 Minutes from Foster Falls
Sequatchie
9.4 out of 10, Exceptional, (3 reviews)
"Best stay for groups"
United States
DIVYA S.
The price is AED 334
AED 757 total
includes taxes & fees
5 Nov - 6 Nov
Foster's Cabin 3 | 2 Minutes from Foster Falls
A cabin with a porch, a staircase, and a view of the surrounding trees.

3. Bluebonnet | Sleeps 6 | Lake Access

Bluebonnet | Sleeps 6 | Lake Access
Tracy City
10.0 out of 10, Exceptional, (1 review)
"Great place to stay"
United States
Haley F.
The price is AED 317
AED 1,113 total
includes taxes & fees
18 Nov - 19 Nov
Bluebonnet | Sleeps 6 | Lake Access
A lakeside deck with outdoor seating and a fire pit.

4. Settle Down on the Lake – Your Waterfront Escape in Tracy City

Settle Down on the Lake – Your Waterfront Escape in Tracy City
Tracy City
10.0 out of 10, Exceptional, (17 reviews)
"Quiet and beautiful setting for a girls weekend"
United States
Meaghan D.
The price is AED 839
AED 1,858 total
includes taxes & fees
18 Nov - 19 Nov
Settle Down on the Lake – Your Waterfront Escape in Tracy City
A modern cabin with a wooden exterior, a porch with steps, and two chairs.

5. Foster's Cabin 4 | 2 Minutes from Foster Falls

Foster's Cabin 4 | 2 Minutes from Foster Falls
Sequatchie
9.4 out of 10, Exceptional, (6 reviews)
"It was cute for what we needed."
United States
Amanda S.
Foster's Cabin 4 | 2 Minutes from Foster Falls
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Winchester Hotel Reviews

Best Western Inn

Best Western Inn

10/10 Excellent
"I had an issue with the TV and the attendant fixed it right away... very cordial."
Gary 3-night trip
Posted 12 hours ago
Best Western Inn

Explore a world of travel with Expedia