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
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, 162 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, 234 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
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, 143 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

Guest favourite
The cabin's exterior displays a modern A-frame design complemented by warm autumn foliage. A multi-level deck features a hot tub, while large windows provide views into the inviting living space. The driveway is visible, winding through the surrounding natural landscape.
Cabin in Luray
4.97 out of 5 average rating, 100 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).

Top guest favourite
A modern cabin is viewed amid tall green trees, featuring a distinctive angular design. Large windows create a seamless connection with the natural surroundings. A covered deck is furnished with outdoor chairs, providing a comfortable space for relaxation.
Cabin in Culpeper
4.96 out of 5 average rating, 113 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.

Top guest favourite
The dark wooden cabin, framed by lush greenery, sits at a hillside location with panoramic mountain views. A deck extends from the cabin, featuring a hanging basket chair. A warm sunset casts a golden hue across the sky, enhancing the serene atmosphere.
Cabin in Free Union
4.99 out of 5 average rating, 236 reviews

Shenandoah Stargazer with Sauna

Stargazer is the perfect place to get away from it all! The stillness and serenity of being nestled in a bird and wildlife sanctuary is so good for your soul. Watch the sunrise from a hanging basket chair at 2700 feet of elevation, or wait for moonrise and toast spectacular star views! Relax in the sauna after a day filled with hiking and an al fresco meal on the deck. Roast s’mores at the deck fire table or over the side yard fire pit. There's magic in the air at this mountaintop retreat!

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, 264 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, 188 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.

Top guest favourite
Cabin in Etlan
5 out of 5 average rating, 217 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
Treehouse in Stanardsville
4.98 out of 5 average rating, 122 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, 237 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
An aerial view showcases the A-frame cabin surrounded by lush greenery and tall trees. The warm glow of the cabin's exterior lights contrasts with the moody sky, creating a striking presence on the mountainside. A stone path leads to the entrance from the circular driveway.
Cabin in Luray
4.95 out of 5 average rating, 325 reviews

The Sparrow Luxury A-Frame w/Hot Tub in Shenandoah

Soak in a private hot tub under Shenandoah stars at The Sparrow a newly built luxury A-frame in Virginia’s Shenandoah Valley, a scenic drive from Washington, DC. This African-inspired retreat offers two bedrooms, a full kitchen, a cozy fireplace, a deck, a workspace with fast WiFi, 4K TVs, and a PlayStation 5. Minutes from Luray Caverns, Skyline Drive, and Shenandoah National Park, with hiking trails, wineries, and stunning fall foliage close by.

Popular amenities for Boston holiday rentals