
Holiday rentals in Boston
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Top-rated holiday rentals in Boston
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Old Rag Mountain Cabin w/WiFi, TV, Fire Pit, Patio
Come escape to our cozy retreat amidst the stunning beauty of the Shenandoah National Park region. Our unique 400 sq ft tiny home offers all the modern amenities, fully equipped kitchen, private patio w/ fire pit, loft bedroom , and spacious bathroom. Only minutes from Old Rag Mountain, wineries, breweries, horseback riding, trout fishing, and more. Unwind & relax after a day of exploring on your spacious patio.Are your desired dates already booked? Check out our other listing, Bald Eagle Cabin
4.99 out of 5 average rating, 214 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
4.99 out of 5 average rating, 306 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.
4.84 out of 5 average rating, 118 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
4.99 out of 5 average rating, 156 reviews
Horizon | Hot/Cold Tub, Fireplaces, Sauna, EV Plug
The Horizon cabin at Arête, your luxury 2 BR mountain A-frame retreat with breathtaking views. Enjoy a private two-level deck with a hot tub, cold plunge, and cedar steam sauna for ultimate relaxation. Inside, the spa-inspired bathroom offers heated floors & towel rack, and a soothing shower with five massaging heads. The kitchen is fully equipped, and you can enjoy al fresco dining using the outdoor Napoleon grill. Relax by the indoor wood fireplace or outdoor fire pit (firewood provided).
4.97 out of 5 average rating, 105 reviews
Bison Farm - Cabin "Brisa"
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.
4.97 out of 5 average rating, 122 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.
4.95 out of 5 average rating, 186 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.
4.99 out of 5 average rating, 102 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.
4.96 out of 5 average rating, 192 reviews
Mountain Retreat — 4 Bdrm Blue Ridge / Shenandoah
🌲 Wide Pine Shenandoah 🌲 ⛰️ Beautiful and relaxing country retreat with wraparound decks surrounded by 20+ private acres near the Blue Ridge Mountains, Skyline Drive, and Shenandoah National Park 🧭 Just 1.5 hours from DC, and 10-15 minutes from Sperryville and Culpeper 🥾 Enjoy the private trails or popular hikes in the National Park 🍷 Designed to create a relaxing experience away from it all 8️⃣ Ideal for groups of 8 or less 🐶 pet friendly 🧹 Professionally cleaned
5.0 out of 5 average rating, 69 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.
4.98 out of 5 average rating, 240 reviews
Pet Friendly Cottage on 21 acre farm
Enjoy the lovely, quiet setting on 21 acres. Newly renovated 2 story bank barn will be your home away from home. Soft, muted colors, zen feel. Come relax, hike, ride your bike, go wine and craft beer tasting, Copper Fox Distillery, has nice gin and bourbon if you prefer. Visit Luray Caverns and Shenandoah National Park, or shop at Sperryville gift shops, restaurants, antique markets and art galleries. Old Rag Mountain is only 20 minutes away!
5.0 out of 5 average rating, 134 reviewsPopular amenities for Boston holiday rentals
Other great holiday rentals in Boston

1830 Log Cabin Retreat • 35 Min to Shenandoah NP
5.0 out of 5 average rating, 89 reviews
The Sanado | Views | Hot Tub | Sauna
5.0 out of 5 average rating, 6 reviews
Refurbished 1880s Victorian Farm House~ Sleeps 6.
4.81 out of 5 average rating, 31 reviews
Kovi Bear Cabin ~ Woodland hiking/biking trails!
5.0 out of 5 average rating, 10 reviews
Cloud Haven - Soaking Tub in the Sky - King Bed
4.83 out of 5 average rating, 6 reviews
Fall is almost here - Come to The Country
4.93 out of 5 average rating, 14 reviews
Historic Manor | Hot Tub & Pickleball | SNP nearby
5.0 out of 5 average rating, 25 reviews
The Mill House at Ragged Ridge Farm
4.96 out of 5 average rating, 25 reviewsDestinations to explore
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- Shenandoah National Park
- Luray Caverns
- Bryce Resort
- Lake Anna State Park
- Early Mountain Winery
- University of Virginia
- George Mason University
- Monticello
- Glass House Winery
- Blenheim Vineyards
- James Madison University
- Shenandoah River Outfitters
- Sky Meadows State Park
- Prince Michel Winery
- The Rotunda
- Downtown Mall
- Jiffy Lube Live
- White Oak Lavender Farm & The Purple WOLF Vineyard
- Bluemont Vineyard
- John Paul Jones Arena
- IX Art Park
- James Monroe's Highland
- Grand Caverns
- Massanutten Indoor WaterPark





