
Holiday rentals in Cheshire
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Top-rated holiday rentals in Cheshire
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The Cottage
This is a rural location. Located on an open hill along a private drive, this newly built -"little house on the prairie"- is surrounded by fields on one end and woods on the other. The moon and lotsa stars at night -no neighbors nearby. Trails and ponds are available for your enjoyment. Swimming* and fishing is encouraged in the warmer months. A small outdoor fire ring is nearby. Hiking in the woods on the far side of the field will be off limits last week of October through thanksgiving.

629 on Main Rental A
The whole group will be comfortable in this spacious and unique space.This 100 year old 4 square home was previously a dentist office to a local dentist for many years. Located in the historical district of Main Street; this property is within 2 blocks of the world’s only Mothman Museum. Shops,restaurants, River Museum,flood wall murals showing the history of Point Pleasant and the river front and Tu-Endie-Wei parks are also some of the attractions within walking distance of the property.

The Retreat at Fox Lake
The retreat at Fox Lake is a newly constructed 1+ bedroom house featuring a private back deck and hot tub! This home has a bedroom with a king-sized bed and an additional room with a fold-out futon. Features include eclectic art, reclaimed materials, glass enclosed gas fireplace, Starlink high speed wifi, on-site parking and direct access to Fox Lake and more! This is the perfect retreat for a couple, a few friends or small family. The vibe is earthy, textured, cozy and modern.

Yellow Dog Barndominium
Our brand new barndominium is a 10 minute drive from Ohio University, yet sits on a 100+ acres in the country. You will find it located near the front of the property, feet away from a 16 acre private water ski lake with beautiful sunset views. Visitors can enjoy hiking, fishing and swimming during their stay. We designed this as a couples retreat, including a 4 person hot tub, but a second bedroom with a full bed and twin trundle can accommodate friends or family who may join you.

Frazier’s Cabin
Peaceful & beautiful views. Less than 2 miles from downtown. Your own private walking path. Escape from stress to this cozy cabin on 3.1 acres. A country setting with fruit trees and wild berries. Wake up to deer just outside your door. Visit downtown Pt. Pleasant where you’ll find multiple shops, restaurants and the Mothman Statue. There’s also Tu Endie Wei State Park and a river walk with hand painted murals along the flood wall. A PERFECT place for a Mothman enthusiast!!

Runaway Retreat - No Cleaning Fee
NO cleaning fee! 👫 I'll REIMBURSE for Kids under 12, just message! 🐾WELL BEHAVED dogs stay free! Enjoy the tranqulity of this space...just runaway for a bit! Come get some R&R for a weekend or a while. Perfect for couples, families/friends, hunters, traveling workers, etc. Enjoy a relaxing space where you can just breathe! Expect a clean & cozy spot you'll never want to leave. We're close enough to town to quickly grab groceries or shop, but quietly nestled in the country!

Cabin Retreat at Whitetail Run
Tranquil cabin, on private 17 acres with pond 90 minutes from central Ohio. Great for star gazing and amazing views. Welcome to our newly Amish built cabin overlooking a private stocked pond on 17 acres of rolling hills in Vinton County. Explore trails through mature woods and wildflower meadows. Enjoy scenic views from the spacious deck, patio, or in the hot tub. Whether you are up for a quiet get away or an adventure this cabin and surrounding area has much to offer.

Castaway Cares
Nestled on a quiet hilltop you will enjoy 360° privacy in this rustic cabin that's spacious and unique! On the main floor you will find the fully equipped kitchen, living room with DVD player and retro game system, dining space, full bathroom & 2 bedrooms each with a queen & twin size bed. Downstairs in the basement you will find another living room, master bedroom with en suite bath, and gym. It can be the perfect space for families, friends groups, hunters and more!

Camp Forever Cabin West
Escape to the rolling hills of Southeastern Ohio at Camp Forever! Our property is located in the countryside, perfect for a peaceful getaway. We offer amenities such as a hot tub, fire pit and lots of games! Camp Forever has a primary bedroom and lofted beds upstairs. Please note that there is another cabin 67 ft apart. Camp Forever is 20 minutes from Ohio University, and a Short 5 minute drive to 2 Wineries! We love pets and insist you bring them along for your stay.

River Siren: Suite 1 (River view balcony)
A unique, freshly restored historical building in the quaint town of Pomeroy, Ohio. Feel like you're staying in an artsy NYC loft in the heart of Appalachia! Featuring stunning views of the Ohio River and Main Street from a spacious balcony. Located in a great central location just a short walk to restaurants, bars, coffee shops, boutiques, churches and more. (Suite 1 of 2 apartments located up a two-story walk up in historical building. Not handicap accessible.)

Cozy 2-Bedroom River Cabin with Private Dock
Take it easy at this unique and tranquil getaway: The River Cabin has a large, covered porch overlooking Millcreek and exclusive access to a dock, fire-ring area, and deck with table, chairs and umbrella. It sleeps five (2 full size, 1 twin). Includes a fully stocked kitchen, a full bathroom, and linens. The dock sits right on Millcreek, and is a lovely place to relax and fish. Up to 2 pets allowed for a fee. Additional $5 daily charge the 5th guest.

Large Scenic Cabin with Amazing View
Nestled in the trees high above the water, the Overlook Cabin offers a peaceful, comfortable, and intimate experience of the Ohio River, with a large riverfront window, 8x12ft deck, & jacuzzi bath. The 12x40ft space has a queen, 2 twins, another bed in the loft, and a couch, and would be great for families, hunters, or couples. Local coffee provided. Owners live onsite should any issues arise. Pet friendly. Free wi-fi available.
Popular amenities for Cheshire holiday rentals
Other great holiday rentals in Cheshire

Grandpa's Loft

Chanoma Pines- Lake Hope / Athens / Hocking Hills

The Cottage on Lovers Lane

Rock Camp Cabin

Secluded Glamping A-Frame 15 minutes from Athens

Cozy Cottage on the Green Ravine

Kanauga Landing / Ohio River Cottage

New! Luxe Creekside Cabin | Hot Tub | Dog Friendly
Destinations to explore
- Western North Carolina Holiday rentals
- Washington Holiday rentals
- Gatlinburg Holiday rentals
- Charlotte Holiday rentals
- Pigeon Forge Holiday rentals
- Northeast Ohio Holiday rentals
- Pittsburgh Holiday rentals
- Rappahannock River Holiday rentals
- James River Holiday rentals
- Indianapolis Holiday rentals
- Asheville Holiday rentals
- Louisville Holiday rentals
- Hocking Hills State Park
- Lake Logan State Park
- Strouds Run State Park
- Ohio University
- Hocking Hills Winery
- Mothman Museum
- Burr Oak State Park
- Rock House
- Cantwell Cliffs
- Ash Cave
- Conkles Hollow State Nature Preserve
- Lake Hope State Park
- Hocking Hills Canopy Tours
- Marshall University
- Tar Hollow State Park
- Zaleski State Forest




