Search Winchester Cottage Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

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

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
Aug 29 - Aug 31
In two weeks
Sep 5 - Sep 7
In one month
Sep 19 - Sep 21
In two months
Oct 17 - Oct 19

Browse Select Winchester Cottages

Our top choices for Winchester cottages

1830's Luxury Brick Cottage, Cozy Fireplace, right off the Cobblestone Streets!
Exterior

1830's Luxury Brick Cottage, Cozy Fireplace, right off the Cobblestone Streets!

10.0 out of 10, Exceptional, (204)
"Beautiful cottage in the perfect location. "
1830's Luxury Brick Cottage, Cozy Fireplace, right off the Cobblestone Streets!
Historic headquarters of city founder! Gated parking!
Exterior

Historic headquarters of city founder! Gated parking!

10.0 out of 10, Exceptional, (51)
"Great location, great cottage, great host! We would definitely stay here again. "
Historic headquarters of city founder! Gated parking!
Delightful Cottage by Clayton
Exterior

Delightful Cottage by Clayton

10.0 out of 10, Exceptional, (2)
"The stay was great! Iā€™d recommend doing something for the slippery bathtub. My grandmother and I almost fell and we are both disabled. "
Delightful Cottage by Clayton
Unique Cottage - Dog Friendly - Close to Purina
Exterior

Unique Cottage - Dog Friendly - Close to Purina

9.6 out of 10, Exceptional, (7)
"Such a cute cottage! Enjoyed our stay! Comfy beds "
Unique Cottage - Dog Friendly - Close to Purina
Quaint St Louis Home ~ 6 Mi to Downtown!
House (2 Bedrooms) | Interior

Quaint St Louis Home ~ 6 Mi to Downtown!

3.0 star property
Quaint St Louis Home ~ 6 Mi to Downtown!
The Reubling House - Modern-rustic Cabin!
House (1 Bedroom) | Interior

The Reubling House - Modern-rustic Cabin!

3.0 star property
10.0 out of 10, Exceptional, (1)
The Reubling House - Modern-rustic Cabin!
Serene Pacific Getaway: Deck, Grill & Fire Pit!
House (3 Bedrooms) | Interior

Serene Pacific Getaway: Deck, Grill & Fire Pit!

3.0 star property
Serene Pacific Getaway: Deck, Grill & Fire Pit!
Pet-friendly Pacific Cottage Near Purina Farms!
Interior

Pet-friendly Pacific Cottage Near Purina Farms!

3.0 star property
Pet-friendly Pacific Cottage Near Purina Farms!
Beautiful Cottage on Large one Acre Private Lot
Terrace/patio

Beautiful Cottage on Large one Acre Private Lot

10.0 out of 10, Exceptional, (18)
"Even tho our trip was cut short with Mother Nature shenanigans. We had a great time here. The host was very responsive and helpful. Will stay here again "
Beautiful Cottage on Large one Acre Private Lot
St Louis Home < 1 Mi to Forest Park!
Interior

St Louis Home < 1 Mi to Forest Park!

3.0 star property
10.0 out of 10, Exceptional, (2)
"We really enjoyed our stay. A great house in a really fun residential area. Close to an area with a main town st with cool restaurants, bars and shops to walk around. "
St Louis Home < 1 Mi to Forest Park!
St Louis Vacation Rental 4 Mi to Airport!
Exterior

St Louis Vacation Rental 4 Mi to Airport!

3.0 star property
10.0 out of 10, Exceptional, (2)
"The house was spacious and nice "
St Louis Vacation Rental 4 Mi to Airport!
Saint Charles House Near Historic Downtown!
House (4 Bedrooms) | Interior

Saint Charles House Near Historic Downtown!

3.0 star property
Saint Charles House Near Historic Downtown!
Spacious O'fallon Vacation Home: 30 Mi to St Louis
Exterior

Spacious O'fallon Vacation Home: 30 Mi to St Louis

3.0 star property
Spacious O'fallon Vacation Home: 30 Mi to St Louis
Home 2 Mi to Dtwn St Louis: Great for Families!
House (3 Bedrooms) | Interior

Home 2 Mi to Dtwn St Louis: Great for Families!

3.0 star property
Home 2 Mi to Dtwn St Louis: Great for Families!
Missouri Retreat w/ Deck, Grill & Shuffleboard!
House (3 Bedrooms) | Interior

Missouri Retreat w/ Deck, Grill & Shuffleboard!

3.0 star property
10.0 out of 10, Exceptional, (1)
"Picked this house as it is close to the wedding venue Haue Valley. Literally a 5 min drive from there. Large beautiful home that kept all the craftsmen woodwork and charm but with modern appliances lighting etc. Roomy and comfortable furniture stocked with everything you need. Steve was very attentive to his communications. Would stay there again!! Pacific has a cute downtown with shops and restaurants within walking distance!"
Missouri Retreat w/ Deck, Grill & Shuffleboard!
9 Mi to Forest Park: Pet-friendly Home in St Louis
House (3 Bedrooms) | Interior

9 Mi to Forest Park: Pet-friendly Home in St Louis

3.0 star property
9 Mi to Forest Park: Pet-friendly Home in St Louis
9 Mi to Dtwn: Vibrant St Louis Home!
House (2 Bedrooms) | Interior

9 Mi to Dtwn: Vibrant St Louis Home!

3.0 star property
9 Mi to Dtwn: Vibrant St Louis Home!
Pet-friendly St Louis Home w/ Grill & Backyard
Property grounds

Pet-friendly St Louis Home w/ Grill & Backyard

3.0 star property
10.0 out of 10, Exceptional, (1)
"Good service thank you."
Pet-friendly St Louis Home w/ Grill & Backyard
Vino Villa Wine Country Gem: Patio & Grill
House (3 Bedrooms) | Interior

Vino Villa Wine Country Gem: Patio & Grill

3.0 star property
Vino Villa Wine Country Gem: Patio & Grill
'the Cabernet Cabin' Defiance Home on Katy Trail!
House (2 Bedrooms) | Front of property

'the Cabernet Cabin' Defiance Home on Katy Trail!

3.0 star property
'the Cabernet Cabin' Defiance Home on Katy Trail!
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.
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

Drury Plaza Hotel St. Louis at the Arch

Drury Plaza Hotel St. Louis at the Arch

10/10 Excellent
"Absolutely thrilled with our decision to stay at this hotel. Wonderful staff eager to please. Lots of room in eating area and many staff members to keep things moving. Hotel location is close to centered between Busch Stadium and the Arch. $32 onsite parking is offset with the free evening food and cocktails. Room was large and bed was comfortable. All clean & nice. "
philip 3-night trip
Posted 8 hours ago
Drury Plaza Hotel St. Louis at the Arch