Holiday rentals in Winchester

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Top-rated holiday rentals in Winchester

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite

Home in Dayton

4.94 out of 5 average rating, 160 reviews

TOP AIRBNB IN DAYTON! | SOUTH PARK | FENCED YARD

Stunning Three Bedroom Historical South Park bungalow - located just steps away from UD, downtown Dayton, and Miami Valley Hospital. This home features an open concept living space with white oak hardwood flooring through-out. The kitchen is fully equipped with all the modern amenities: stainless steal appliances, soft close cabinetry, granite countertops. Two Gorgeous bathrooms w/ custom tile work including a master w/ walk-in shower. Completely fenced in rear yard w/ privacy. Magical space!

Guest favourite

Home in Celina

4.95 out of 5 average rating, 44 reviews

Lake View Cottage with Boat Dock

Relax with the whole family in our spacious 2 bedroom, 2 bath UPDATED HOME featuring beautiful lake views, a boat dock & sea wall. Large kitchen with all your kitchen necessities for your home away from home. Master bedroom has a king size bed with private attached full bath. Spare bedroom has 2 twin beds. Washer and Dryer. Large screened in porch to enjoy your morning coffee or relax reading a book. Grand Lake St. Marys has many restaurants around the lake for your enjoyment. **NO PETS

Guest favourite

Home in Celina

4.97 out of 5 average rating, 31 reviews

Lakeside Retreat | Boat Dock • Pet Friendly • Pool

Make lasting memories at The Pearl, Comfort Acres' top-rated retreat. ★ Relax in your private pool (seasonal). ★ Gather round the cozy outdoor fire pit. ★ Access the boat dock & rent a boat. ★ Unwind on spacious patio. ★ Entertain with fully equipped chef’s kitchen. ★ Enjoy fireplace, game room & fun treasure hunt. ★ Let kids explore playroom. ★ Rest in luxurious beds (3 kings, 2 queens). ★ Near golf course, dining & more! ★ Bring your pet! Book now for an exceptional, 5 star experience!

Guest favourite

Home in Saint Marys

5 out of 5 average rating, 20 reviews

Bayshore Beach Bungalow w/ BIKES. "New for 2024"

NEW LISTING... WELCOME to our 3-bedroom beachside home bordering Grand Lake St Marys State Park with its POOL/splashpad, and bike rentals. We have everything you need including sheets, towels and BEACH toys, towels & chairs. Our outside boasts stunning lake views and sunsets, easy water access, and FREE firewood for your evening campfires! You'll never run out of things to do with the Visitor Center walkable up the street…Come and see the new Eagles nest display today and make some memories!

Guest favourite

Home in Celina

4.96 out of 5 average rating, 52 reviews

Cottonwood Cottage on Grand Lake

Grand Lake areas newest, cozy and modern cottage with a boat dock, fire pit, screened in porch and hot tub- all in a peaceful and private setting. Comfort and cleanliness are our top priority and you will feel instantly at home! Rent a pontoon from next door, Lakeshore Marina. Stroll or bike for miles from the Franklin Township bike path situated just around the corner & end your day with the best pizza on the lake at the nearby iconic Shingle Shack bar and restaurant. Lake life awaits you!

Guest favourite

Home in Saint Marys

4.98 out of 5 average rating, 41 reviews

Luxury Waterfront Lakehouse 20% off special

Largest listing around, perfect for your groups vacation! Amenities abound! Relax and unwind with lake front views from the front, and channel-front privacy from the back. Stretch out and play on our massive custom deck. Inside, you will find over 4000 sq ft of space, with 5 bedrooms, nursery, fireplace, game room and plenty of activities for the whole group. With plenty of parking and plenty of space to explore and enjoy, this vacation home is the perfect getaway during any season!

Guest favourite

Home in Dayton

4.97 out of 5 average rating, 259 reviews

Spacious 4BR/3.5BA Home Near UD, Oregon &DT Dayton

Situated in Dayton's historic South Park, this home, revamped in 2019, retains its 1800s charm. Ideal for families and friends keen on downtown Dayton proximity. Perfect for UD or local events, offering a homely feel. Please note: local bookings are not accepted. This neighborhood is currently undergoing revitalization, with several homes, including the one adjacent, at different stages of remodeling and rehabilitation. It's an urban area experiencing a dynamic transformation.

Guest favourite

Home in New Palestine

4.98 out of 5 average rating, 85 reviews

2 Bedroom House in New Palestine, Close 2 Downtown

A completely remodeled two bedroom, one bathroom home... all yours. It's fully equipped with everything you need - towels, dishes, laundry detergent, books, and bedding. Just bring your clothes! The home has WiFi and premium TV channels. You can relax and drink your coffee from the front porch or keep up with your busy life by doing laundry and working from the desk. It's approximately $22 for an Uber ride to downtown Indy. Enjoy the quiet but stay close to the city!

Guest favourite

Cottage in Lewisburg

4.99 out of 5 average rating, 100 reviews

The Cottage Retreat

Whether you are looking for a place to spend some time or just passing through we think you’ll find it quite lovely here. We are just 5 mile off of I70 and centrally located among many places of interest. Go out or stay in. The outdoor living space is pretty spectacular! Private, with a hot tub, fire pit (wood provided), turf to play corn hole. Inside delivers all the comforts of home with full kitchen, laundry, workspace and cozy fireplace.

Guest favourite

Home in Saint Marys

4.92 out of 5 average rating, 24 reviews

Lovely Lake Cottage

Relax with the whole family at this Grand Lake St. Marys lake cottage overlooking the lake. 2 beaches just steps away, Mariana, fishing, playground, state park grounds for all kinds of family fun. Relax on the huge porch grilling out or roast marshmallows over the fire. Explore the many restaurants & shopping in 2 nearby towns. Enjoy annual festivals, fishing and bird watching from this unique lake property.

Superhost

Tiny home in New Paris

4.72 out of 5 average rating, 25 reviews

Cozy Lakefront Tiny House - Romantic OH Cabin

Reconnect with nature at this unforgettable escape. Enjoy a relaxing afternoon in the hammock, swim and fish in the lake, or take advantage of the birding opportunities while you're here! Only catch + release fishing is permitted at this time. Our lake has bass, bluegill, catfish, crappie, largemouth bass, and sunfish!