Search Cottages in Winchester

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Check prices for these dates

Next weekend
9 May - 11 May
In two weeks
16 May - 18 May
In one month
30 May - 1 Jun
In two months
27 Jun - 29 Jun

Compare 7 Cottages in Winchester with updated reviews, rates, and availability.

Quaker Hill Cottage on gated estate with fire pit & hiking trails
Exterior

Quaker Hill Cottage on gated estate with fire pit & hiking trails

9.8 out of 10, Exceptional, (22)
"Such an interesting place. It was a great stay. We would definitely stay there again!"
The price is AEDĀ 422
AEDĀ 802 total
includes taxes & fees
6 May - 7 May
Quaker Hill Cottage on gated estate with fire pit & hiking trails
Pet-friendly Greenville Home w/ Private Yard
House (3 Bedrooms) | Interior

Pet-friendly Greenville Home w/ Private Yard

3.0 star property
Pet-friendly Greenville Home w/ Private Yard
Cozy Richmond Home w/ Fire Pit: Walk, Bike & More!
House (2 Bedrooms) | Interior

Cozy Richmond Home w/ Fire Pit: Walk, Bike & More!

3.0 star property
Cozy Richmond Home w/ Fire Pit: Walk, Bike & More!
Close to Earlham / IU / Reid! <br>- Nice neighborhood -
Fridge, microwave, oven, stovetop

Close to Earlham / IU / Reid! <br>- Nice neighborhood -

9.0 out of 10, Wonderful, (6)
"This was a great home and the hosts are great! Enjoyed my stay as I completed a summer internship in the area."
Close to Earlham / IU / Reid! <br>- Nice neighborhood -
Exquisite Hagerstown Home With Deck & Gazebo!
Interior

Exquisite Hagerstown Home With Deck & Gazebo!

3.0 star property
Exquisite Hagerstown Home With Deck & Gazebo!
Quaint Economy Retreat w/ Patio & Spacious Yard!
House (3 Bedrooms) | Interior

Quaint Economy Retreat w/ Patio & Spacious Yard!

3.0 star property
Quaint Economy Retreat w/ Patio & Spacious Yard!
Bright Muncie Home w/ Yard ~ 2 Mi to Downtown!
Terrace/patio

Bright Muncie Home w/ Yard ~ 2 Mi to Downtown!

3.0 star property
Bright Muncie Home w/ Yard ~ 2 Mi to Downtown!
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.
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Other property types in Winchester

Indoor Pool, Hot Tub, Fireplaces, Golf, Park-like setting. Family Reunion Place!
Outdoor dining

Indoor Pool, Hot Tub, Fireplaces, Golf, Park-like setting. Family Reunion Place!

9.8 out of 10, Exceptional, (182)
"Plenty of room for our 25 that stayed. The pool is wonderful. Very clean and communication is excellent. This was our second stay and will do it again. Thank you Ted"
Indoor Pool, Hot Tub, Fireplaces, Golf, Park-like setting. Family Reunion Place!
Inviting family retreat with a seasonal saltwater pool, gymnasium and privacy
Sport court

Inviting family retreat with a seasonal saltwater pool, gymnasium and privacy

10.0 out of 10, Exceptional, (187)
"An awesome place to stay with a large group. The indoor pickleball was a huge hit!!"
Inviting family retreat with a seasonal saltwater pool, gymnasium and privacy
Stunning 3 bed, 2.5 bath home, nestled in a quiet woodsy setting.
Living area

Stunning 3 bed, 2.5 bath home, nestled in a quiet woodsy setting.

9.8 out of 10, Exceptional, (7)
"The atmosphere and views are stunning. The home is spacious for families. We enjoyed our stay. "
Stunning 3 bed, 2.5 bath home, nestled in a quiet woodsy setting.
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.