Holiday Rentals in Winchester

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Holiday Rentals in Winchester

Homey Retreat in Historic Kennett Square!!
10.0 out of 10, Exceptional, (50)
"Super cute and within walking distance of a plethora of places to eat."
The price is €311
includes taxes & fees
1 Oct - 2 Oct
Homey Retreat in Historic Kennett Square!!
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
9.8 out of 10, Exceptional, (43)
"We really enjoyed the water views & walking by the water. It was a very enjoyable and relaxing stay."
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay
10.0 out of 10, Exceptional, (73)
"A hidden gem! Beautiful location on the bay with the cutest town!!! "
Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay
Cozy loft tucked away on the beautiful Chester and Lancaster County line.
10.0 out of 10, Exceptional, (85)
"We have been to this beautiful loft several times now, and every time, it is such a joy. The owners, Stayce and Judd, could not be more accommodating, kind, and helpful, and the loft is just immaculate. The grounds are stunning, and the farm animals and pups are the icing on the cake. We can’t wait to come back!"
Cozy loft tucked away on the beautiful Chester and Lancaster County line.
Captivating Chesapeake experience
10.0 out of 10, Exceptional, (249)
"We had a wonderful stay at this beautiful property. The water views are amazing and it was so relaxing! The house was very clean and well maintained. Everything we expected it to be from the listing, actually more charming and comfortable than the pictures show. Thank you. "
Captivating Chesapeake experience
Historic Kennett Square
9.4 out of 10, Exceptional, (39)
"We had a very pleasant stay. The property was clean & as pictured. "
Historic Kennett Square
WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD
10.0 out of 10, Exceptional, (27)
"The accomodations were VERY nice. The wifi was not sufficient for me to work in the room, but they allowed us to sit on the deck and work instead."
WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD
Cozy home with fenced in yard-Pet Friendly . 2 block walk to historic downtown!
9.6 out of 10, Exceptional, (52)
"Nice. Close to downtown. Great backyatd"
Cozy home with fenced in yard-Pet Friendly . 2 block walk to historic downtown!
Veazey Cove | 8,000 sq ft Waterfront Home w/ Pool + Hot Tub!
9.4 out of 10, Exceptional, (32)
"We had a great time in the pool, fishing off dock, paddle boarding, kayaking and swimming. The kids (5 under 8) loved playing in the bAsement."
Veazey Cove | 8,000 sq ft Waterfront Home w/ Pool + Hot Tub!
Lancaster co. farmhouse in the heart of amish country
10.0 out of 10, Exceptional, (128)
"Gorgeous property. Extremely family friendly - toys, pac-n-play, and sound machine which were amazing to have! Really couldn’t ask for anything better. Thank you for hosting us! "
Lancaster co. farmhouse in the heart of amish country
House on 3 acres near Fair Hill Nature Park. Close to Pa, and De.
9.8 out of 10, Exceptional, (95)
"Older home that was very clean. met our needs well. was close to the University of Delaware. "
House on 3 acres near Fair Hill Nature Park. Close to Pa, and De.
Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.
9.4 out of 10, Exceptional, (19)
"Everything would have been wonderful except for the attitude of the owner who was quick to blame us for something we had no control of. We were quite content and lucky the bath house was so convenient because one of the toilets on the boat did not work. He insisted it was our fault and was quick to blame. In his defense he did send someone out very quickly to see if it could be fixed. "
Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.
Top of the Chesapeake - Minutes from Historic Charlestown
9.8 out of 10, Exceptional, (133)
""Oh, down in Chesapeake Catching rock around fishing creek The soft-shell crabs play hide and seek Down in Chesapeake." We LOVE the Chesapeake area and have stayed up and down the bay, mostly midway and lower. This area on the upper bay is so close to Philadelphia and, although there are tourists around like us, it doesn't feel touristy unless you go into North East, downtown (which is still worth eating a meal or getting ice cream in that cute little town)! Our stay felt private, and we had...
The price is €567
includes taxes & fees
30 Sept - 1 Oct
Top of the Chesapeake - Minutes from Historic Charlestown
Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio
9.8 out of 10, Exceptional, (33)
"The house is cute and clean small house perfect for 9. Comfortable clean linens were provided. Easy to get to. Close to food and easy to get to University of Delaware. Host was easy to get in touch with. The only thing was no TV at all but we enjoyed our time."
Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio
Adventure Mobile
Adventure Mobile
Historic home in the heart of Main Street- walkable to shops and restaurants
10.0 out of 10, Exceptional, (9)
"We really enjoyed the property. The location was within walking distance to the downtown area providing many food and shopping options. We were in MD for a lacrosse tournament which was minutes away from the house. The house was recently renovated, clean and bright. We had more than enough space for our group of 8."
Historic home in the heart of Main Street- walkable to shops and restaurants
Stunning waterfront villa with indoor pool and kids swing set and play area.
10.0 out of 10, Exceptional, (8)
"The house is very impressive! We loved many things about it. It was very clean. The pool and porches were very good. . The setting is impressive. We were 11 family members ranging from 62-82. For us, getting in and out of the tall beds was a challenge. Besides that all was good . Thank you for sharing your beautiful home"
Stunning waterfront villa with indoor pool and kids swing set and play area.
Beautiful Colonial Style Home in Nottingham PA
10.0 out of 10, Exceptional, (5)
"Loved the house! Would have loved the details about house, when & how it was built! Daughter in Delaware had graduation celebration for son in Delaware, 2 daughters & family up from North Carolina, my husband & me from West Virginia! 16 in all! But, ice didn’t dispensed and refrigerator was not clean! I took pictures!"
Beautiful Colonial Style Home in Nottingham PA
Kennett Home away from Home!
7.4 out of 10, Good, (6)
"Home provided a wonderful gathering place for friends reunion. Lots of space to spread out and a big kitchen/ living area to gather in. Only caution is lots of stairs, might be a caution for older adults."
The price is €635
includes taxes & fees
29 Sept - 30 Sept
Kennett Home away from Home!
Chesapeake City Quiet Overlook
10.0 out of 10, Exceptional, (11)
"My wife and I booked Jane’s house for our wedding weekend in Chesapeake city. Jane allowed us to use her property for our wedding of 40 ppl. She could not have been nicer or more accommodating for this special occasion. She responded to all of our questions quickly and even made special offers to make our wedding weekend even more special. I cannot say enough nice things about Jane. The house and property were gorgeous in a really great location along the canal in Chesapeake city. The views...
Chesapeake City Quiet Overlook
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See all available properties in Winchester
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 types of properties in Winchester you may be interested in

Red Roof Inn PLUS+ Wilmington - Newark
2.5 star property
6.6 out of 10, (1002)
"I like the room the bed is very comfy the staff are nice and smily the hotel is very quiet and calm"
The price is €77
includes taxes & fees
1 Oct - 2 Oct
Red Roof Inn PLUS+ Wilmington - Newark
Ramada by Wyndham Newark/Wilmington
3.0 star property
6.8 out of 10, (1004)
"Nothing "
The price is €61
includes taxes & fees
27 Oct - 28 Oct
Ramada by Wyndham Newark/Wilmington
Hilton Wilmington/Christiana
4.0 star property
8.8 out of 10, Excellent, (1001)
"Breakfast and dinner were great. Staff was pleasant. Only one elevator was working and assume animals are allowed in this hotel, due to many areas smelling like a dog. "
The price is €135
includes taxes & fees
4 Oct - 5 Oct
Hilton Wilmington/Christiana
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.

Frequently asked questions

Are there holiday rentals in Winchester?

Yes, there are holiday rentals close to the most popular sights in Winchester, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Winchester has to offer?

Cozy home with fenced in yard-Pet Friendly . 2 block walk to historic downtown!: This holiday home rental outside of Winchester is located on a river, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Make the most of games in this rental home to help you unwind.

What can I see and do in Winchester?

While exploring the area, visit family-friendly sights like Fred Rust Ice Arena, or get outside and enjoy nature at Fair Hill State Natural Resources Management Area. University of Delaware and University of Delaware Botanic Gardens are a couple of places you'll find in the wider area.

What are holiday rentals like in Winchester?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Winchester. Holiday rentals feature extras like kitchens and laundry facilities so you'll have everything you want. If you're concerned about a sanitised environment, holiday rentals can provide a sense of safety away from public hotel lifts and busy front desks while still allowing you to travel. You'll also get more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a popular choice for a small group gathering.