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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Top guest favourite
Cabin in Etlan
4.99 out of 5 average rating, 198 reviews

Mountain Cabin Getaway 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

Top guest favourite
The log cabin exterior is highlighted by a stone chimney and a welcoming porch with steps leading to the entrance. Lush green trees surround the cabin, creating a serene atmosphere in the tranquil forest setting.
Cabin in Madison
5 out of 5 average rating, 161 reviews

Log Cabin at Ragged Rock Ridge

Mountaintop log cabin nestled in a mature, tranquil forest with spectacular views, ideally located near adventures like hiking in Shenandoah National Park (including Old Rag & White Oak Canyon), many local wineries/breweries/distilleries and quaint towns of Sperryville & Madison, VA. The authentic log cabin includes a cozy stone fireplace, porch, and patio with Old Rag views. Ponds, wildlife and hiking also available on the sprawling 300-acre property. Escape to the Cabin at Ragged Rock Ridge.

Guest favourite
An A-frame cabin nestled among trees features a wrap-around deck overlooking the landscape. The kitchen showcases modern appliances and a spacious counter with bar stools, while a gentle waterfall flows over rocks nearby, surrounded by lush greenery.
Cabin in Bentonville
4.96 out of 5 average rating, 222 reviews

Timber Creek: Falls - A Shenandoah Cabin

Nestled on 8 acres, the Timber Creek Falls A-frame sits on the Shenandoah National Park border overlooking a beautiful cascading waterfall. A 90-min drive from DC, this cabin getaway will have you unwinding in tranquility. A hot tub offers views stretching 50mi to West Virginia on a clear day, and the closest neighbor is a half mile away. A truly private retreat comes w/ modern conveniences including: EV charger, smart devices, flat-screen TV, standing desk, wood burning stove & spa bathrobes.

Top guest favourite
A rustic cabin is illuminated by warm golden light from its windows, set against a soft twilight sky. The log exterior reflects the vintage charm of the structure, while the surrounding trees create a serene atmosphere, inviting guests to relax on the front porch.
Place to stay in Bentonville
4.99 out of 5 average rating, 520 reviews

John Pope Cabin Browntown Va. We now have Starlink

Our cabin, located in the foothills of the Appalachian Mountains is uniquely positioned overlooking a large open field where hawks hunt and bears leisurely stroll. Our neighbors have horses that peer over the fence (nosy) pet them but don’t feed them, please. Our cabin was built in 1865 by a Confederate soldier returning from the Civil War. Eleven children were born and raised in John Pope Cabin. Our cabin is rustic. An inviting front porch with swing is waiting for you @walnuthillcabin

Top guest favourite
The yurt is set against a starry night sky, surrounded by towering trees. A spacious deck leads to the yurt's entry, while warm light emanates from its windows. The scene showcases a natural ambiance highlighted by foliage and a gravel path leading to the entrance.
Yurt in Etlan
4.96 out of 5 average rating, 253 reviews

Peaceful Secluded Old Rag Retreat

The spacious one bedroom yurt is located high on a forested hillside in the middle of 15+ acres. Come enjoy a natural and serene getaway with all the comforts of home- a full kitchen (ie, all utensils, setting for four), a bathroom with shower and laundry, a queen bedroom, and a queen foldout sofa in the living room by the wood burning stove. The windows roll up from the outside and have permanent screens inside. There is also a BBQ grill, a separate firepit, and WiFi via satellite.

Top guest favourite
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, 181 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
An open-plan kitchen and living area is showcased with wooden beams and large windows, allowing natural light to illuminate the space. A kitchenette features wooden cabinetry, a microwave, and a small dining bar with three tall stools. A rocking chair is positioned beside a window overlooking the woodland.
Farm stay in Brightwood
4.94 out of 5 average rating, 162 reviews

Robinson River Cabin - Tri Creek Farm

If you spend most of your career glued to a computer and other screens, this place is for you. TriCreek Farm is a place for you to disconnect, reboot, and fuel your soul. This riverfront cabin is situated on ~100 acres, over 1/2 mile of Robinson River frontage, with breathtaking views. There are creeks, fishing, and hiking trails to explore and enjoy. The cabin is located in Brightwood, Virginia, a small town located in Madison County between Culpeper and Charlottesville Virginia.

Guest favourite
A charming blue farmhouse is framed by lush greenery, showcasing white trim and a welcoming front porch. An American flag is displayed prominently, complemented by colorful flowers in the landscaping. The surrounding trees provide shade and a serene atmosphere.
Home in Culpeper
4.95 out of 5 average rating, 435 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
A classic A-frame cabin is surrounded by trees, featuring a spacious deck with comfortable lounge seating. Soft lighting accentuates the inviting outdoor space, while large glass doors provide a glimpse into the cozy interior. The modern roof complements the rustic wooden facade.
Cabin in Front Royal
4.96 out of 5 average rating, 289 reviews

The Wizard's Chalet • Cozy nature escape • Hot Tub

Looking for a fun getaway in a relaxing, secluded spot? Come visit The Wizard's Chalet, a cozy & upgraded cabin located in the Shenandoah Valley just one mile from Shenandoah River access and a few miles from restaurants, wineries, basketball & volleyball courts, and more! With a fully stocked kitchen, three cozy bedrooms, high speed WIFI, hot tub, and several beautiful outdoor gathering spaces, this magical cabin is perfect for couples, friends, or the entire family!

Top guest favourite
Treehouse in Stanardsville
4.98 out of 5 average rating, 101 reviews

CloudPointe Retreat

Rare Appalachian Treehouse Gem! Luxurious, one-of-a-kind retreat for couples. Elevated tiny house among the treetops, private parking, plush bedroom, sleek bathroom, beautiful kitchenette, loveseat, lounge, private double-level decks, fireside lounging (wood provided), gas grill, and patio with a hot tub! Surrounded by nature, with wineries, hikes, restaurants and shopping all nearby. Please come and relax and revel in the beauty of nature! 4WD is recommended.

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, 231 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.

Top guest favourite
Barn in Boston
5 out of 5 average rating, 122 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!

Popular amenities for Boston holiday rentals

  1. Airbnb
  2. United States
  3. Virginia
  4. Culpeper County
  5. Boston