Search Vacation Homes in Winchester

Plan, book, stay with confidence

Be picky

Search almost a million properties worldwide

Treat yourself

Change your mind

Book hotels with free cancellation

Check prices for these dates

Next weekend

In two weeks

In one month

In two months

Compare 38 Vacation Homes in Winchester with updated reviews, rates, and availability.

Winston Vacation Rental | 4BR | 2BA | Stairs Required | 1,704 Sq Ft

"Rooms are spacious and each have their own controller for heat or air conditioning so you can keep the room temp to your liking. The deck is huge and perfect for hanging outside even in wet weather because it’s totally covered. Nice fully stocked kitchen with a variety of appliances and kitchen utensils. The nice surprise was the garage with the ping pong table and work out equipment. They also provide a stroller high chair and pak n play if you have a baby"

Spacious living room with a large 65” Smart TV, perfect for a fun movie night.

"Gary was amazing, the house was super clean and well stocked. I was on a work trip so i was only there in the evenings, but it was perfect! Id love to ce back!"

"Perfect! We needed a place to stay on our way up to Washington. We have a dog over 100 lbs and it’s very hard to find a hotel that will take him. This place was very clean, beautiful renovations and very dog friendly. Wish we could have stayed longer, will definitely stay again! "

AED 606 total

includes taxes & fees

16 Feb - 17 Feb

"Love this little abode and recommend "

AED 800 total

includes taxes & fees

19 Feb - 20 Feb

"The home was comfortable for all. Kitchen was very functional for preparing food for 8. Wished for better weather so we could have enjoyed the fire pit in the beautiful backyard."

AED 1,583 total

includes taxes & fees

16 Feb - 17 Feb

"Enjoyed our stay. Had everything we needed"

AED 1,749 total

includes taxes & fees

16 Feb - 17 Feb

"We had a great stay and home was just what was advertised. There were so many personal touches and the owner was great to deal with. There was a problem with the A/C before we arrived which was quickly relayed to us by owner and they had it fixed just after our arrival. We will definitely be back next time we are in town. "

AED 1,323 total

includes taxes & fees

19 Feb - 20 Feb

"We have stayed at this property now multiple times and it has been clean, easy, great location, everything works and we will definitely be back"

"Inviting and comfortable "

Roseburg Vacation Rental | 1BR | 1BA | 880 Sq Ft | 2 Steps Required for Access

"12 day stay small would be good for couple gŕeat appliances ken who lives next door was easy to get along with had things all ready to go when i arrived "

"Usually staying near or in the mountains nets you with a long drive to go get anything let the bar combined with the deli across the street makes it really easy to stock up on food or just get general necessities without having to hop in your car."

"We had an amazing time here it was so quite and peaceful and the host were amazing we will be going back"

A comfortable living space to kick your feet up and watch your favorite show!

"This place is worth your money! The beds and bedding are very comfortable. The shower pressure is great. The amenities excel. Very quiet neighborhood. Communication with host is excellent. I will recommend this place to my friends and family. Would stay here again for sure."

AED 664 total

includes taxes & fees

17 Feb - 18 Feb

"The Monroe River House in Roseburg, OR was the perfect home for us. The master bedroom was spacious, and the bed was super comfortable. Having an additional BR and bathroom was a bonus, too. The house and kitchen were well-stocked and had everything we needed and more - like plastic bags to keep food in, etc. The yard was huge, and we spent a few afternoons hanging out at the little beach on the river at the bottom of the property. The area is beautiful with lots of local wineries nearby. We...

"Excellent experience! We were passing through and wanted a cozy experience from multiple hotel stays. Our hosts were outstanding and so friendly, attentive to every little detail to make us feel welcomed and comfortable. An outstanding bed and breakfast experience!"

AED 812 total

includes taxes & fees

14 Feb - 15 Feb

"*"

"Love this place, very accommodating, clean, and great owners! Will be booking with them again "

AED 541 total

includes taxes & fees

14 Feb - 15 Feb

"I loved the wild river right out the door"

"We were able to check in early, which helped us greatly in preparing for Christmas . Hosts were very easy to communicate with. The hot tub had an issue before we arrived but they had that swapped out the day we arrived. "

"Renee was an absolute delight to communicate with and I’m appreciative of her hospitality. This place is absolutely adorable and secluded. It was a nice and peaceful New Year’s Eve. "