Guesthouse holiday rentals in James River

Stylish Creekside Cabin w/ HotTub, Parklike views.

Escape to this beautifully remodeled guest cottage, designed for an unforgettable stay. Nestled in a serene 6.5-acre setting with private creek views, it's just minutes from shopping, breweries, and dining. Wake up to breathtaking scenery, unwind in a peaceful setting, and enjoy modern amenities. Relax by the fire pit or soak in the hot tub. Perfect for a romantic retreat or a fun-filled family getaway in the Historic Triangle. Unmatched comfort, charm, and relaxation—your perfect escape awaits!

Family · Location · Check-in

Lulu's Peaceful Cottage

Enjoy a relaxing stay at this great located cottage. Lulu's Peaceful cottage is brand new, stylishly decorated for comfort. Private little cottage in a park like setting amongst trees & nature. Inside is an equipped kitchenette, coffee/tea bar, & is meal prep friendly. Relax in the soaking tub, or shower if you prefer. Lulu's is close to everything. Shopping, gyms, parks, & recs, hospitals, museums, & airport, and just a few miles from all major highways. Easy driveway parking & keyless entry.

Family · Value · Breakfast

Historic HomeTract Cottage UVA/Charlottesville/Ivy

Hometract Cottage is a historic one bedroom home (NRHP, circa 1800) centrally located 15 minutes or less from Charlottesville, UVA, Crozet, Monticello, wineries and more. The cottage features ensuite bath, fully stocked kitchen, living/workspace with comfortable sleeper sofa, mature landscaping for privacy, and covered front porch. Hometract is a quiet 3-acre property with terraced garden views. Visit our chicken coop, relax in the hammock, or walk to the garden shop or Duner's restaurant.

Value · Family · Air conditioning

Waterfront Guesthouse II on the Rappahannock

The “Beach House” is a guest cottage at Snug Harbor, a 2 acre private property overlooking the Rappahannock River and Chesapeake Bay. Perfect for a couple’s getaway, this well-appointed cottage has beautiful water views and includes access to our private beach & dock (with guest slip) with use of our paddle boards and kayaks. The cottage’s 1st floor features an open liv/din/kit area, full bath with large shower and a covered patio. The 2nd floor features a large loft bedroom with a queen bed.

Location · Family · Parks

Solar-powered Guesthouse at Peak Time Property

This cozy guesthouse is a perfect getaway. It has SPECTACULAR views of the Priest and Three Ridges. Located in Massies Mill, it is a 20-30 minute drive to the Appalachian Trail, Wintergreen, breweries, wineries, and distilleries. It is also practically around the corner from Pharsalia Events. There are several convenience stores close by, but the closest grocery store is an 18 minute drive. Situated on 26 acres, there is more than a mile of marked trails available to walk as you wish.

Family · Location · Comfort

Funky, Private Guesthouse Near Richmond Food Scene

Welcome to the Yellow Tiger’s Den, a private, tucked-away guesthouse filled with bold color, thoughtful design, and a little Richmond edge. Set above a spiral staircase for total privacy, this sunny studio blends mid-century modern style with curated yellow accents, a cozy private patio, and everything you need for a relaxed stay. Located in Richmond’s historic Battery Park neighborhood, you’re minutes from the city’s growing food scene, local attractions, and easy highway access.

Value · Location · Wi-Fi

Homestead at HeartRock

Welcome to HeartRock Homestead. Our sweet spot offers rustic charm and modern comfort. Come for a private grownup nature camp! A getaway for couples, friends, and families. There is something for everyone! We have great check in and check out times to maximize your stay! Have you ever heard the whippoorwill sing while watching the stars? Or felt grazed organic cut flowers amongst the morning dew? Or felt a seasoned sunset kiss your heart? We hope to see you soon!

Family · Value · Outdoor spaces

Cozy, Spacious, and Scenic Retreat~13 min to LU

Sleeps 6! *no longer ADA* This cozy 3BR 2BA home is perfect for any small or large group! -Clean & spacious -Large living room, kitchen, 3 bedrooms (4 beds total), washer/dryer, and 2 FULL bathrooms! -Back deck overlooking large field with wildlife -15 minutes from Liberty University -20 minutes from downtown Lynchburg -5-20 minutes from: Restaurants, churches, River Ridge Mall, and local colleges -Smart TV's -Self check-in Please read all house rules before booking.

Family · Location · Bathroom

2 Bdrms★Pet Friendly★4K Theater★Fire Pit★Fast Wifi

Minutes from I-95 "The Cottage" is a great stop along your journey just 15 minutes to Kings Dominion or Meadow Event Park. Surf high speed internet, catch up on laundry, dine in Ashland or have a cookout and share stories around the campfire. You’ll love the Cottage because of the clean accommodations, complete kitchen, quiet neighborhood, home theater, comfy beds & pet friendly! The Cottage is great for Families, Couples, Business Travelers & Fun Seekers!

Location · Value · Pool

The Skyhouse- simple & serene w/mountain views

Enjoy the solace and beauty of the Blue Ridge Mountains with modern and local comforts. Retreat and explore on this old 100acre farm- via foot- or float on the tiny pond in a kayak or SUP. Or venture out to Shenandoah National Park, the local coffee shops, eateries, wineries, and breweries. Whatever you choose the skyhouse is stocked with roasted coffee, farm-fresh eggs, fresh-baked bread, teas and soaps from our incredible local homesteaders and artisans.

Family · Value · Nearby

Your Perfect Blue Ridge Mountain Hideaway near 151

A luxury tiny home built without compromise. This six-figure, custom-built retreat features high-end finishes, premium materials, and a refined layout that feels both elevated and comfortable. Set in the Blue Ridge Mountains, it offers privacy and tranquility with easy access to scenic drives, hiking, renowned breweries, and local wineries—ideal for a relaxed weekend escape focused on slowing down, good food and drinks, and returning home refreshed.

Value · Location · Laundry

Cozy Fall Retreat - Creek Views & Fire Pits

A cozy waterfront escape tucked into 10 wooded acres above Bland Creek. Perfect for crisp fall days and peaceful evenings. - Elevated screened porch with colorful water and wooded views - Creekside fire pits for crisp fall nights - Dock, kayaks, fishing, and direct water access - Outdoor dining and hammocks beneath the trees - Immaculately clean and thoughtfully stocked for a seamless stay - Just 15 minutes from downtown Gloucester

Location · Family · Barbecue