Holiday rentals in Boston

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Top-rated holiday rentals in Boston

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

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Superhost
Cabin in Stanley
4.99 out of 5 average rating, 300 reviews

New, 5BD/4BA | hot tub, arcade, pool table, views

Welcome to this new, 2,880 sf LUXE retreat in Shenandoah Woods--a spacious cabin designed for unforgettable getaways. It features 5 king beds, 4 full baths (2 en suite, 1 adjoining, 1 hall), and stunning views from the porches, hot tub, and rooms. More highlights: ★Arcade, board games, 6 ft pool table ★Fire pit ★Elect fireplace ★Elect Grill on deck ★Smart TVs up to 70" ★Fast WiFi ★Dining for 10 ★Well-equipped kitchen ★5 mins-Stanley ★13-15 mins-Luray Caverns ★25 mins-Shenandoah National Park

Guest favourite
The image features a rustic stone fireplace, complemented by a cozy armchair with a floral pattern. The warm wooden floor and textured stone wall create an inviting atmosphere, while a small table and lamp are positioned on the mantel above the fireplace.
Chalet in Boston
4.84 out of 5 average rating, 117 reviews

The Manor House at Spring Haven Farm

Get your nature fix staying here. Perfect for family or friend gatherings since it sleeps 8; yet it's also romantic for just the 2 . Huge fireplace for warm evenings (extra charge for wood/cleaning), beautiful night sky and 10 foot beamed ceilings, 2 decks, walks around the lake. Cozy and comfortable formal with a first floor bedroom, if you have trouble with steps this home may be challenging. Pets allowed on a case by case basis, on a leash at all times outdoors and in restricted areas.

Top guest favourite
The guest house is framed by lush greenery and softly illuminated by hanging lights that create a welcoming ambiance. A spacious porch with potted plants invites relaxation, while the multi-gabled roof and cupola add character to the charming exterior. Gravel pathways lead to the entrance.
Guest house in Sperryville
4.99 out of 5 average rating, 150 reviews

Countryside getaway 5 min. from Old Rag parking!

Just 5 min away from Old Rag trailhead in Shenandoah National Park and merely minutes from wineries/breweries. Our guest house is close to White Oak Canyon, Skyline Drive, Three Blacksmiths, Washington, and Luray Caverns! Book here if you like: -Escaping the hustle and bustle, and relaxing in nature -Hearing birds sing while sipping coffee/tea/wine on the porch -Observing wildlife (including our chickens and bees) -Fishing on the Hughes River in our backyard -Stargazing and spotting fireflies

Top guest favourite
A spacious bedroom features a large bed with crisp white linens and a decorative blanket. Soft lighting is provided by two bedside lamps, and a comfortable seating area is visible beside a window with sheer curtains. A ceiling fan adds comfort to the room.
Home in Culpeper
4.99 out of 5 average rating, 116 reviews

Stylish & Cozy Getaway in Historic Culpeper

Welcome to your own private Culpeper retreat! This brand new house is the perfect place to unwind and soak in the experience of southern hospitality along with photo worthy moments. The outdoor space provides the perfect place to relax and take in the stunning sunset. You’ll love spending time outside, whether you’re grilling up a delicious meal or just lounging with a good book. Thoughtfully designed to provide a comfortable modern stay. Have fun with the whole family at this stylish place.

Top guest favourite
Cabin in Culpeper
4.95 out of 5 average rating, 111 reviews

Bison Farm - Cabin "Cielo"

Bison Farm cabin in a very secluded section toward the back side of a 300 acre working bison farm. This is a tiny home Park Model with 400 sq. ft. and a nice spacious covered deck providing an outdoor living room. The kitchen has a 2-burner induction cook-top, a convection oven that is also a microwave and a small refrigerator and freezer two drawer unit that has decent space but is not a full sized appliance. Note: bison rotate pastures daily. Please don't expect them in your cabin view.

Top guest favourite
The exterior of the country house showcases a rustic red façade complemented by a covered front porch. A welcoming entryway is flanked by lush greenery and a gravel driveway, evoking a serene rural atmosphere amid the surrounding trees.
Cabin in Reva
4.95 out of 5 average rating, 184 reviews

10-Acre Dog-Friendly House w Grill & Near Wineries

Welcome to the Reva Retreat! This country house sits on 10 acres, nestled between Shenandoah Nat'l Park & the Blue Ridge Mtns, with wineries and breweries nearby. Approx 1.5 hours from DC and 45 mins from Charlottesville makes this the perfect getaway destination to escape the city & unplug. Stocked with amenities: BBQ grill, dine al fresco, stargaze by the firepit, cook a feast in the new kitchen, play board games in the basement, or connect your laptop to a 32" monitor to work remotely.

Top guest favourite
The exterior of a rustic cottage is highlighted at night, featuring a welcoming entrance illuminated by soft lighting. A pathway leads to the door, surrounded by well-maintained lawn and trees. Windows offer glimpses of the interior, contributing to the cozy ambiance.
Guest house in Culpeper
4.99 out of 5 average rating, 100 reviews

The Wheelhouse at Mount Airy

Welcome to The Wheelhouse, our charming and rustic cottage on the grounds of Mount Airy, a historic Civil War era home in Culpeper County, Virginia. Steeped in history and surrounded by tranquility, this idyllic retreat offers modern comfort and convenient access to wineries, downtown shops and restaurants, and the beautiful Shenandoah National Park. The location is also ideal for cycling enthusiasts who want to enjoy riding on less traveled country roads that offer spectacular scenery.

Guest favourite
An open living area features high wooden ceilings with exposed beams, creating a spacious atmosphere. A large kitchen island with bar seating is situated near a dining table. Two spiral staircases lead to upper levels, while large windows frame views of the surrounding nature.
Home in Robertson
4.93 out of 5 average rating, 256 reviews

One Of A Kind Home in VA Wine Country on 50 acres

Welcome to Lumusa Lodge. Leave your cares behind as you turn onto the windy road that leads you to this beautiful 50-acre retreat. We are proud to share our home and hope your time here is rejuvenating. Designed/built by a Hollywood actor and situated in wine country, this home is an hour from Dulles, 45 minutes from Charlottesville & 15 minutes from Culpeper. We have an adjacent farmhouse if you need additional space. Great venue for weddings, bachelorettes, and other special events.

Superhost
The spacious deck extends along the length of the house, featuring several white rocking chairs positioned for scenic views of the surrounding landscape. Cloudy skies create a serene atmosphere, highlighting the natural beauty of the nearby hills and fields.
Home in Madison
4.96 out of 5 average rating, 190 reviews

Spacious Shenandoah Home on 35 Private Acres

Sitting on 35 acres of private land to be explored, this classic countryside vacation rental ticks all the boxes for a relaxing outdoors-geared getaway! You can practically picture yourself enjoying a glass of wine after a long day of exploring the natural beauty of Virginia from this perched hillside home, sporting a long private drive, and an expansive furnished deck. This 2-bed, 2.5-bath outdoors oasis is sure to have everyone unplugged, outside and enjoying living in the moment.

Guest favourite
The exterior of a blue farmhouse is framed by lush greenery and a vibrant garden. A large tree provides shade, and an American flag hangs from the porch, welcoming guests. The house features multiple windows, highlighting its spacious design.
Home in Culpeper
4.95 out of 5 average rating, 449 reviews

Charming Restored Farmhouse Minutes from Culpeper

STRICT NO PETS POLICY! This spacious farmhouse, built in 1898, has been tastefully restored to accommodate modern living without sacrificing the charm of history. It is bright and airy, with open, spacious rooms and some smaller rooms for fun or quiet times. The house has a calming feel, with all the comforts of home. The farmhouse is a celebration of the richness of all things Virginia; its history, its vineyards, its fox hunts and the alluring charm of Old Virginia.

Top guest favourite
Cabin in Etlan
5.0 out of 5 average rating, 223 reviews

Old Rag Mountain Stay w/WiFi, TV, Fire Pit, Patio

This unique, modern A Frame cabin is located at the foothills of The Shenandoah Mountains only minutes from Old Rag Mountain, White Oak Canyon, trout fishing, horseback riding, wineries, breweries, and more! This 400 sq ft. tiny home has all the modern amenities you need to feel right at home. Step outside, enjoy the mountain air, and relax on your private patio with a cozy,private fire. Are your desired dates already booked? Check out our other listing, Black Bear Cabin!

Top guest favourite
A modern studio space features large windows that allow natural light to fill the room. A cozy yellow chair sits beside a small coffee table, with a guitar resting on a stand nearby. The bed area is visible in the background, framed by a stylish shelf.
Guest house in Boston
4.97 out of 5 average rating, 238 reviews

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.

Popular amenities for Boston holiday rentals