Winchester Holiday Rentals

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Check prices for these dates

Tonight
5 Jul - 6 Jul
Tomorrow
6 Jul - 7 Jul
Next weekend
11 Jul - 13 Jul
In two weeks
18 Jul - 20 Jul

Holiday Rentals in Winchester

Chesapeake Bay House with Dock & Private Beach
Outdoor dining

Chesapeake Bay House with Dock & Private Beach

10.0 out of 10, Exceptional, (162)
"Great place for a long weekend. Easy travel to surrounding areas to explore."
Chesapeake Bay House with Dock & Private Beach
Charming 2-bedroom cottage with BOAT SLIP, WiFi, and AC
Property grounds

Charming 2-bedroom cottage with BOAT SLIP, WiFi, and AC

10.0 out of 10, Exceptional, (4)
"We thoroughly enjoyed this cottage and location for weekend during lacrosse tournaments. Much better than staying in hotel and perfect on the water to enjoy some family time! Thanks Angela! "
Charming 2-bedroom cottage with BOAT SLIP, WiFi, and AC
Charming 2-bedroom cabin close to Fair Hill on horse farm
Exterior

Charming 2-bedroom cabin close to Fair Hill on horse farm

10.0 out of 10, Exceptional, (1)
"Good experience"
The price is NZ$1,119
includes taxes & fees
14 July - 15 July
Charming 2-bedroom cabin close to Fair Hill on horse farm
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.
Smart TV, books

Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.

10.0 out of 10, Exceptional, (14)
"Was a charming place to stay close to everything"
The price is NZ$347
includes taxes & fees
8 July - 9 July
Unique cottage built in the 1800s, Granite Cliffs of Port Deposit Maryland.
Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.
Property grounds

Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.

9.4 out of 10, Exceptional, (25)
"We were a group of all ages and everyone had a good time. It was quiet, peaceful and very relaxing. We were there for a baseball tournament and would definitely stay again."
Fully Equipped Docked Houseboat at Log Pond Marina in Havre de Grace, MD.
*** NEWLY RENOVATED**** Escape to a Beautiful Getaway on the Chesapeake Bay
Interior

*** NEWLY RENOVATED**** Escape to a Beautiful Getaway on the Chesapeake Bay

9.2 out of 10, Wonderful, (175)
"We throughly enjoyed our stay here! The house was absolutely spotless, check in was easy, and kitchen is well appointed. The views are beautiful too. Brian was super responsive and answered all of my questions. Can’t wait to go back! "
*** NEWLY RENOVATED**** Escape to a Beautiful Getaway on the Chesapeake Bay
Captivating Chesapeake experience
Beach

Captivating Chesapeake experience

10.0 out of 10, Exceptional, (265)
"This place is the definition of the perfect getaway for a quick weekend. The home is immaculate, the scenery is beautiful and we feel instantly relaxed here. "
Captivating Chesapeake experience
Saltwater Pool - Entire 4 BR Home + Yard is What You Need this Summer
Pool

Saltwater Pool - Entire 4 BR Home + Yard is What You Need this Summer

Saltwater Pool - Entire 4 BR Home + Yard is What You Need this Summer
Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay
Terrace/patio

Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay

10.0 out of 10, Exceptional, (83)
"We had a wonderful stay! Really enjoyed the eagles and osprey. The hot tub was amazing and the fire pit was nice to enjoy in the cold weather. All amenities were there that we needed, the location is great and the town is really cute. We will be back! "
Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
Beach nearby, sun-loungers

Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

9.8 out of 10, Exceptional, (50)
"This was our second time staying at the property with our two kids and the accommodations continue to impress. We will happily stay again."
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
Private townhouse near downtown and state park
2 bedrooms, WiFi

Private townhouse near downtown and state park

10.0 out of 10, Exceptional, (9)
"The house is clean and comfortable with many amenities and within walking distance of parks and restaurants and museums. The host was very easy to connect with."
The price is NZ$503
includes taxes & fees
9 July - 10 July
Private townhouse near downtown and state park
Underground Railroad 4 Bedroom Farmhouse
Interior

Underground Railroad 4 Bedroom Farmhouse

9.8 out of 10, Exceptional, (18)
"Great property for a girls' weekend. Super clean, helpful and friendly owner, cute property and grounds, well-maintained."
The price is NZ$475
includes taxes & fees
9 July - 10 July
Underground Railroad 4 Bedroom Farmhouse
Nature's Haven Tiny Home
Terrace/patio

Nature's Haven Tiny Home

10.0 out of 10, Exceptional, (2)
"Enjoyed"
The price is NZ$390
includes taxes & fees
10 July - 11 July
Nature's Haven Tiny Home
Spacious and luxurious 3 bed/1.5 bath townhome with free parking, sleeps 6
Dining

Spacious and luxurious 3 bed/1.5 bath townhome with free parking, sleeps 6

10.0 out of 10, Exceptional, (1)
"Property is beautiful, host answered our questions in a timely manner. Would stay again "
Spacious and luxurious 3 bed/1.5 bath townhome with free parking, sleeps 6
Cozy studio in charming Elkton with AC and WiFi included. 3 miles from Fair Hill
Iron/ironing board, WiFi, bed sheets

Cozy studio in charming Elkton with AC and WiFi included. 3 miles from Fair Hill

2.0 star property
9.6 out of 10, Exceptional, (4)
"Great stay. Everything you need, quiet and clean. "
The price is NZ$266
includes taxes & fees
6 July - 7 July
Cozy studio in charming Elkton with AC and WiFi included. 3 miles from Fair Hill
WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD
Fridge, microwave, oven, stovetop

WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD

9.8 out of 10, Exceptional, (41)
"This property was perfect for our trip. It was very clean, comfortable and feels like home. Description and photos on the website were accurate. The owners were very attentive and hospitable. This is definite a place I’ll return to."
WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD
Kennett Square, Near Longwood Gardens & Downtown
Interior

Kennett Square, Near Longwood Gardens & Downtown

7.8 out of 10, Good, (10)
"Great place, very difficult check in process. It was a nice stay overall "
The price is NZ$824
includes taxes & fees
9 July - 10 July
Kennett Square, Near Longwood Gardens & Downtown
Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio
Fridge, microwave, oven, stovetop

Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio

9.8 out of 10, Exceptional, (38)
"Perfect property with cute details and thoughtful touches. Host is phenomenal. "
Trendy Cozy Cottage Clean Bright Three bed, Two bath Patio
Waterfront house with amazing views. Top of the Chesapeake
On the beach, sun-loungers, beach towels

Waterfront house with amazing views. Top of the Chesapeake

10.0 out of 10, Exceptional, (97)
"From booking to check out Matt was great! Property was clean and felt like home. The water view was beautiful and just sitting out and enjoying the water from the deck, the kids were in the water our entire stay or fishing off the pier. We definitely will be booking again!"
Waterfront house with amazing views. Top of the Chesapeake
Cozy 2-bedroom townhome in charming Elkton
Fridge, microwave, oven, stovetop

Cozy 2-bedroom townhome in charming Elkton

8.8 out of 10, Excellent, (5)
"We stayed for two nights and the beds were very comfortable. The house met our needs for the short time we were in town. I do wish somewhere it was disclosed that it backed up to a railroad track that is used day and night for commuter rail and we had a large freight train come by both nights at roughy 345am. "
Cozy 2-bedroom townhome in charming Elkton
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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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?

*** NEWLY RENOVATED**** Escape to a Beautiful Getaway on the Chesapeake Bay: This holiday home rental outside of Winchester is located on a lake, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as 1 hot tub.

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.