Search Condo Rentals in Winchester

Start date: Check-in selected.
To Date
End date: Check-out

  • 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
28 Nov - 30 Nov
In two months
9 Jan - 11 Jan
In three months
6 Feb - 8 Feb
In four months
6 Mar - 8 Mar

Condo Rentals in Winchester

No exact matches found, but these alternatives could be just right

Recommended hotels in Winchester

Suite, 1 King Bed, Jetted Tub (Oversized Room) | 1 bedroom, desk, laptop workspace, blackout drapes
Best Western Inn

Best Western Inn

2.5 star property
Winchester
8.8 out of 10, Excellent, (654)
"Staff was very efficient at check in. The room was nice and clean. Would stay there again. "
United States
Amanda
The price is AED 340
AED 389 total
includes taxes & fees
23 Nov - 24 Nov
Best Western Inn
Smart TV, fireplace
Luxurious Lakefront Home- Marina, Boats, and Kayaks!

Luxurious Lakefront Home- Marina, Boats, and Kayaks!

Winchester
10.0 out of 10, Exceptional, (1)
"We really enjoyed our stay. The home was great! Everything you need. Love the location. Close to Winchester and the lake. Highly recommend. Already planning to stay there again."
United States
Gary W.
The price is AED 159
AED 1,740 total
includes taxes & fees
21 Nov - 22 Nov
Luxurious Lakefront Home- Marina, Boats, and Kayaks!
Fridge, microwave, coffee/tea maker, toaster
Beautifully Renovated Studio 2 miles from the Marina

Beautifully Renovated Studio 2 miles from the Marina

Winchester
9.8 out of 10, Exceptional, (15)
"The place was exactly as pictured with an easy check-in and out process. Was a perfect little place for us to stay for a long weekend!"
United States
Anonymous traveler
The price is AED 275
AED 704 total
includes taxes & fees
21 Nov - 22 Nov
Beautifully Renovated Studio 2 miles from the Marina
Exterior
Tiny Home w/ RV Hookups

Tiny Home w/ RV Hookups

Winchester
8.8 out of 10, Excellent, (8)
"Very clean highly recommend if you are looking to get away and relax "
United States
Jeffrey
The price is AED 493
AED 921 total
includes taxes & fees
16 Nov - 17 Nov
Tiny Home w/ RV Hookups
Smart TV, fireplace
The Lakeside Getaway

The Lakeside Getaway

2.0 star property
Winchester
9.6 out of 10, Exceptional, (5)
"We had a great time and the home provided plenty of room for our large group. The only thing I would say would be to rename the property and change a few photos. The impression was given that the property is lakeside, which it is not."
United States
angela s.
The price is AED 364
AED 1,978 total
includes taxes & fees
9 Dec - 10 Dec
The Lakeside Getaway
Dining
Oasis on the Square

Oasis on the Square

Winchester
9.6 out of 10, Exceptional, (10)
"Great accommodations in downtown Winchester! "
United States
LeBron F.
The price is AED 200
AED 525 total
includes taxes & fees
16 Nov - 17 Nov
Oasis on the Square
TV, fireplace
Winchester's Premier Downtown Loft!

Winchester's Premier Downtown Loft!

Winchester
9.6 out of 10, Exceptional, (9)
"We thoroughly enjoyed our stay in this comfortable and beautiful apartment, right in the heart of Winchester. It’s walkable to several restaurants and a great ice cream shop. Check-in and communication were smooth. "
United States
Jennifer M.
The price is AED 200
AED 525 total
includes taxes & fees
16 Nov - 17 Nov
Winchester's Premier Downtown Loft!
Interior
Beautiful And Spacious Fully Renovated Farmhouse

Beautiful And Spacious Fully Renovated Farmhouse

Winchester
9.4 out of 10, Exceptional, (29)
"It was spacious and great for a family event. It really just needed a better cleaning job between guests or maybe it sat empty awhile. We had to wash sheets and towels before we used. Other than that it was very nice. "
United States
Marguerite
The price is AED 459
AED 1,311 total
includes taxes & fees
14 Dec - 15 Dec
Beautiful And Spacious Fully Renovated Farmhouse
Interior
Gorgeous Renovated Home with Open Floor Plan and Large Lot

Gorgeous Renovated Home with Open Floor Plan and Large Lot

Winchester
9.0 out of 10, Wonderful, (16)
"Great potential for outside features (firepits, grills, yard games)."
United States
Darrin S.
The price is AED 422
AED 1,261 total
includes taxes & fees
15 Nov - 16 Nov
Gorgeous Renovated Home with Open Floor Plan and Large Lot
Terrace/patio
Lakeview Luxe - Lake Access + Pool

Lakeview Luxe - Lake Access + Pool

2.0 star property
Winchester
10.0 out of 10, Exceptional, (3)
"Beautiful home. Very well kept. Hosts were very helpful. Short distance from restaurants and town square. "
United States
Tressa K.
The price is AED 559
AED 2,135 total
includes taxes & fees
16 Nov - 17 Nov
Lakeview Luxe - Lake Access + Pool
Fridge, microwave, oven, stovetop
Welcome to Tims Ford Lake! Free UTV/kayaks/canoe, firepit, complete privacy!

Welcome to Tims Ford Lake! Free UTV/kayaks/canoe, firepit, complete privacy!

Winchester
9.8 out of 10, Exceptional, (12)
"Property was just as stated. Owners were very accommodating. Great peaceful wooded area. Everything you could possibly want!"
United States
Chris
The price is AED 441
AED 1,281 total
includes taxes & fees
16 Nov - 17 Nov
Welcome to Tims Ford Lake! Free UTV/kayaks/canoe, firepit, complete privacy!
Interior
Winchester TN lake house rental, Tims Ford Lake vacation home,private boat ramp

Winchester TN lake house rental, Tims Ford Lake vacation home,private boat ramp

2.0 star property
Winchester
10.0 out of 10, Exceptional, (4)
"We were only there for 1 night but the house was clean and comfortable and perfectly suited our needs. "
United States
Gwen K.
The price is AED 909
AED 2,573 total
includes taxes & fees
17 Nov - 18 Nov
Winchester TN lake house rental, Tims Ford Lake vacation home,private boat ramp
Outdoor dining
"The Hawk Nest" cabin on Tims Ford Lake

"The Hawk Nest" cabin on Tims Ford Lake

Winchester
9.6 out of 10, Exceptional, (18)
"This was a nice and very unique place to stay. We really appreciated that we had a place to dock the boat. "
United States
Dawn D. C.
The price is AED 1,010
AED 1,912 total
includes taxes & fees
21 Nov - 22 Nov
"The Hawk Nest" cabin on Tims Ford Lake
Terrace/patio
Gather at Tims Ford Lake

Gather at Tims Ford Lake

Winchester
9.6 out of 10, Exceptional, (19)
"Great time nice and quiet"
United States
David C.
The price is AED 5,542
AED 8,337 total
includes taxes & fees
15 Dec - 16 Dec
Gather at Tims Ford Lake
Outdoor dining
Cozy 2-bedroom RV in awesome Winchester with WiFi, AC

Cozy 2-bedroom RV in awesome Winchester with WiFi, AC

Winchester
The price is AED 463
AED 790 total
includes taxes & fees
15 Dec - 16 Dec
Cozy 2-bedroom RV in awesome Winchester with WiFi, AC
Property grounds
Lakeview Retreat: Dock, Boat Slip, Spacious for multi-family

Lakeview Retreat: Dock, Boat Slip, Spacious for multi-family

Winchester
10.0 out of 10, Exceptional, (34)
"We had a great time gathering for my sister's birthday with family! Love this place will come back again!"
United States
Merideth H.
The price is AED 915
AED 2,294 total
includes taxes & fees
19 Nov - 20 Nov
Lakeview Retreat: Dock, Boat Slip, Spacious for multi-family
Property grounds
4-bedroom Lake house in tranquil Winchester with Lakeview's, hot tub, pool.

4-bedroom Lake house in tranquil Winchester with Lakeview's, hot tub, pool.

2.0 star property
Winchester
10.0 out of 10, Exceptional, (1)
"Very clean, many extras in the house. Nice location, close to Winchester and the marina. We all enjoyed it from 11 years old, teenagers to adults."
United States
Greg S.
The price is AED 1,128
AED 1,922 total
includes taxes & fees
15 Dec - 16 Dec
4-bedroom Lake house in tranquil Winchester with Lakeview's, hot tub, pool.
Terrace/patio
Lakefront Luxury on Tims Ford Lake

Lakefront Luxury on Tims Ford Lake

Winchester
10.0 out of 10, Exceptional, (10)
"Very relaxing stay in a quiet neighborhood on the lake. The house is very nice and as advertised. Owner is very communicative and helpful."
United States
Clay W.
The price is AED 1,745
AED 3,224 total
includes taxes & fees
15 Dec - 16 Dec
Lakefront Luxury on Tims Ford Lake
Property grounds
Lake View Prime Location, Community Dock w swim ladders, covered boat slip,

Lake View Prime Location, Community Dock w swim ladders, covered boat slip,

Winchester
10.0 out of 10, Exceptional, (22)
"We were mesmerized when we walked through the doors of the beautiful home! There were 3 different levels of living areas, perfect for our family Thanksgiving! The owner was very attentive and responsive. I don’t think I’ve ever had a better time!"
United States
Cindy L.
The price is AED 823
AED 2,177 total
includes taxes & fees
18 Nov - 19 Nov
Lake View Prime Location, Community Dock w swim ladders, covered boat slip,
Restaurant
Holiday Inn Express Hotel & Suites Tullahoma by IHG

Holiday Inn Express Hotel & Suites Tullahoma by IHG

2.5 star property
Tullahoma
8.8 out of 10, Excellent, (628)
"Yes"
United States
Joseph
The price is AED 404
AED 474 total
includes taxes & fees
13 Dec - 14 Dec
Holiday Inn Express Hotel & Suites Tullahoma by IHG
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

The Smokehouse Lodge and Cabins

The Smokehouse Lodge and Cabins

10/10 Excellent
"Great staff "
Matthew 3-night trip
Posted 2 days ago
The Smokehouse Lodge and Cabins