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.

Guest favourite

Home in Celina

4.97 out of 5 average rating, 33 reviews

Luxe & Spacious Family Gem: Hot Tub, Pool, Dog OK!

Step into the luxurious and spacious 4BR 2.5BA nestled near the scenic Grand Lake St. Marys. It promises a relaxing retreat just a few minutes from local restaurants, shops, breweries, exciting attractions, and natural landmarks. ✔ 4 Comfortable Bedrooms ✔ Lounge & Living Area ✔ Fully Equipped Kitchen ✔ Loft Playroom ✔ Game Room ✔ Workspace ✔ Yard (Pool, Hot Tub, Fire Pit, BBQ, Dining, Lounge, Lawn) ✔ Smart TVs ✔ High-Speed Wi-Fi ✔ Free Parking ✔ Private Dock (0.4 miles away) Learn more below!

Guest favourite

Home in Celina

4.96 out of 5 average rating, 45 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 Saint Marys

5 out of 5 average rating, 21 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, 53 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, 44 reviews

Luxury Waterfront Lakehouse

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!

Superhost

Cottage in Celina

4.89 out of 5 average rating, 9 reviews

Liv for Dayz: A Rustic Lakeside Cottage w/HOT TUB!

Plan your getaway to Boardwalk Village and stay in this brand new, cozy, beautifully furnished lakefront cottage on Grand Lake St. Mary’s in Celina, OH! This 2 bedroom, 1 loft, 2 bath cottage boasts spectacular views of the lake AND pool. Boardwalk Village, an all-in-one experience alongside Greater Grand Lake, is a walking and biking paradise. We're perfect for a unique and relaxed getaway that is still in close proximity to shopping, dining, and other entertainment options!

Guest favourite

Cottage in Minster

4.76 out of 5 average rating, 264 reviews

Best Cottage on Lake Loramie!

Nicest place on beautiful Lake Loramie. Lake front view from the living area. The Fort Loramie state park is right across the road. This park offers over 400 acres and 1655 acres of land to explore complete with a beach. Our State Park is one of the original canal feeder lakes with more than eight miles of hiking trails that follow a portion of the Miami-Erie Canal. Kayaking is a big hit at Lake Loramie also! Everything you need for a getaway. Other rentals also available!

Guest favourite

Home in Oxford

4.95 out of 5 average rating, 192 reviews

Perfect get away steps from town and campus

Redhawk Retreat--3800 sq. ft of luxury in this Frank Lloyd Wright inspired retreat. One Minute from Uptown Oxford, one minute to Miami campus, and minutes to Hueston Woods. Whether you are an individual or a party of ten, you will find our 4 bedroom, 3.5 bath home warm and inviting. First floor master with en suite master bath. Three bedrooms in full walkout lower level. Relax in our home surrounded by nature with all the amenities of a five star hotel.

Guest favourite

Cottage in Lewisburg

4.99 out of 5 average rating, 111 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, 26 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!

Guest favourite

Home in Saint Marys

4.95 out of 5 average rating, 22 reviews

Cozy Cottage in Saint Marys

2 bedroom cottage. Located across the street from lake channel. Walking distance to Otterbein Senior Community and lake access at saint marys park. Minutes away from public boat ramp and multiple restaurants.