Vacation rentals in Chesapeake

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Top-rated vacation rentals in Chesapeake

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Guest favorite

A cozy cabin is depicted with a welcoming front porch, featuring a swing and a large, round table surrounded by green chairs. A grill is positioned nearby, with lush greenery and colorful plants adding to the outdoor setting against a backdrop of rolling hills.

Campsite in Argillite

4.96 out of 5 average rating, 28 reviews

Cozy cabin hideaway with kitchen 2.

This adorable cabin is within a popular campground resort with many amenities. Centrally located near several main travel routes, you'll find multiple options of nearby restaurants, local festivals, events and historical sites. Take a few days to explore the many attractions of nearby Country Music Highway or enjoy simple country drives to the many local historical sites in the area! We have the friendly family atmosphere and tranquility you desire. Come stay with us , you'll be glad you did!

Guest favorite

An open concept living space features a sectional sofa with a coffee table, offering floor-to-ceiling windows that showcase city views. Modern kitchen appliances and a dining area with seating are visible. Sleek light fixtures enhance the welcoming atmosphere.

Loft in Ashland

4.97 out of 5 average rating, 319 reviews

Sky Loft on 10 . 2 bed . 2 bath + Modern luxuries

Lay your head in the clouds. Sky Loft on 10 is a brand new, state-of-the-art loft furnished with modern luxuries. It is conveniently located in the center of the city blocks away from downtown, Paramount Arts Center, KDMC, Central Park and the Ashland Town Center Mall. Tenth floor views and access to two private balconies provide stunning views of the city, riverfront and Tri-State area. Perfect for hosting or a relaxing getaway. Your next stay, retreat or celebration is just on the horizon.

Top guest favorite

An outdoor dining area is showcased with a rectangular table surrounded by six chairs. A patterned rug lies beneath the table, and lush greenery is visible in the background, enhancing the serene setting. The deck offers a tranquil space for meals among nature.

Home in Gallipolis

4.97 out of 5 average rating, 58 reviews

Creekside a piece of heaven

Creekside is a little piece of heaven located on Racoon Creek in Gallia County Ohio about two miles from the Ohio River with River access. When you stay with us you will enjoy seeing nature's beauty. Fishing, boating, and kayaking are right in your backyard (we have 3 kayaks available for rent). If hunting is what you love, we are a 15 min. drive to Crown City Wildlife area. November starts our small-town winter wonderland in 2022 Gallipolis was named the Today Show’s Merriest Main Street!

Guest favorite

The cabin is elevated above the water, featuring a wooden deck and a ramp leading to a white door. A scenic view of the river is provided, with the surrounding natural landscape visible. Two propane tanks are positioned beside the structure.

Cabin in Gallipolis

4.93 out of 5 average rating, 146 reviews

The Overlook @ River's Edge Bed & Breakfast

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. Each day includes 2 made-from-scratch Breakfasts & coffee (up to a $26 value) and owners live onsite should any issues arise. Pet friendly. Free wi-fi available.

Top guest favorite

A vibrant entrance to an indoor theme park features large, colorful sculptures of a pineapple, surfboards, and sports equipment. The façade is painted in bright colors, complemented by tropical palm tree graphics, inviting visitors to enjoy a fun-filled experience inside.

Home in Ashland

4.96 out of 5 average rating, 122 reviews

Cozy Cottage

Fully Equiped Kitchen with new stainless appliances including dishwasher , pots & pans, silverware New Central Heat & Air New Bathroom Washer & Dryer Off street Parking Minutes to Kingsdaughters Hospital, Mall, Marathon Refinery Approx 15 minutes away, Restaurants, Grocery , Schools Residential Area Owners close by if you need to call with questions Wifi Recliners Big Screen TV Discount on Monthly Rentals Travel Size Soap, Shampoo, Detergent provided Bed linens & towels provided Clean

Superhost

A cozy living room space features a comfortable sofa with decorative pillows, accompanied by an armchair. A rustic coffee table sits at the center, adorned with plants and decorative items. A large area rug covers the floor, leading to a door framed by patterned curtains.

Apartment in Proctorville

5 out of 5 average rating, 4 reviews

Private, Country Townhouse Retreat, 8 Min. to SMM

Don't need 2 beds?? Let us know and we'll adjust to a lower rate so you can book a 1 bedroon rate instead! This stylish place to stay is centrally located to businesses, restaurants and stores, yet is situated in a country setting far enough away from it all. Our home fosters a quiet getaway for those who'd like a break from the everyday hustle of life. Slow your pace and rest easy. Whether you're in search of a weekend, or an extended stay, our lil cozy spot will not disappoint!

Top guest favorite

A charming cabin features a red roof and wooden exterior reflected in the calm water of a nearby pond. Lush greenery surrounds the structure, creating a serene atmosphere. A wrap-around porch with seating is visible at the front, inviting relaxation in nature.

Cabin in Catlettsburg

4.96 out of 5 average rating, 308 reviews

The Luxury Cabin

The Cabin is a fully furnished , 3 bedroom home on 13 acres, a pond 2 fire-pits, wildlife. The house has a gas fireplace, and a fully stocked kitchen, also we provide a gas grill outside on the wrap around porch. The porch has a swing and plenty of seating. A wash room with full size washer and dryer. The pond has a dock and is fully stocked. A king master suite with a shower ,bath tub. A bunk room w/ 4 long bunks. Upstairs a balcony / queen bedroom overlooking the downstairs.

Guest favorite

The exterior of the guesthouse is displayed, featuring a wooden deck with steps leading up to a door. Soft evening light highlights the structure's features, including the metal roof and large windows with sheer curtains. Trees border the area, enhancing the natural setting.

Guesthouse in Huntington

4.94 out of 5 average rating, 181 reviews

Entire Guesthouse 2 minutes from I-64

Hello, Our guest house is very private, quiet, cozy, secure and exceptionally clean. A great couples retreat with 2+miles of hiking trails and a vast space for outdoor activities and wildlife viewing. The beds are comfortable and the heat and air conditioning are great. We have all the amenities...all linens are furnished. There is a washer, dryer, iron and hair dryer and detergent. We are nestled on over 100 acres of land and are 1000 feet from the nearest highway.

Top guest favorite

A view of the kitchen featuring a dark countertop with bar stools. An open archway leads to the living room, which contains a sectional sofa. A trash can is positioned against the wall, and the textured flooring contributes to the overall warm ambiance.

Home in Ashland

4.97 out of 5 average rating, 120 reviews

Roosevelt Retreat - 2BR, 2 Bath Craftsman

Charming, updated Craftsman in South Ashland which is 1 of 2 on the property (home located at the front of the property). You will find a 2 bedroom (1 king, 1 full bed/1 xl twin bed), 2 bath (one bathroom contains the washer and dryer), fully furnished kitchen, living room with sectional, and 3 flat-screen smart TV's. This is a quiet, residential neighborhood within a 10-minute walk of Putnam Stadium and a 5 -minute drive to downtown. NO SMOKING - NO ANIMALS

Superhost

A view of a large grassy yard is presented, featuring lush green grass and a mature tree with abundant foliage. The image captures a serene outdoor environment, unfolding from the perspective of a classic porch column.

Home in Kitts Hill

4.83 out of 5 average rating, 144 reviews

House in the country to just get away !

Farm house in the country . About 6 miles from Lake Vesuvius in Pedro , Ohio Large yard. Near a small creek . Great for hunters or if you just want to get away. The house has window air conditioners. There is a front porch where you can sit and rock or swing and just take it easy . NO INTERNET OR WI-FI. But there is a landline for local calls or 911 There is a camper in the back yard that is rented also. Call or email me for more info.

Guest favorite

Home in Ashland

4.93 out of 5 average rating, 137 reviews

Cozy 2 bed 1 bath home, minutes from everything!

The whole group will enjoy easy access to everything from this centrally located home. Brand new appliances will make the chef feel right at home. Watch TV on the 65 inch smart TV in the living room, or sit outside on the front or back porch to unwind. Less then a 5 minute drive to downtown Ashland/KDMC, and less then 10 to Camp Landing/Malibu Jacks. Make this house your home while you take in our small and lovely city.

Guest favorite

Farm stay in Lesage

4.92 out of 5 average rating, 122 reviews

True North Farm & Events

Nature lovers dream! A romantic escape for couples or bring the whole gang. Plenty of room to relax, play, explore or just watch our friendly herd of horses and donkeys. Consistently earning Airbnb Super Host status since 2020, we take your vacation seriously so you can rejuvenate and relax. TO NOTE: to reduce chance of miscommunication please read listing in it’s entirety.