Holiday houses in Boston

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Top-rated holiday rentals in Boston

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Guest favourite
The exterior of the tiny house is shown, featuring a light-colored siding and several windows that allow natural light inside. A wooden deck with steps leads to the entrance, and a fenced area provides privacy. Lush greenery surrounds the home, adding a natural backdrop.
Tiny home in Culpeper
4.96 out of 5 average rating, 137 reviews

3 Bed Tiny House in Culpeper w/ Kitchen & Firepit!

Welcome to our cozy tiny house in Culpeper, VA! This is the perfect retreat for couples/small groups looking for a unique & memorable experience. W/ open 2 lofts & a pull out couch this home sleeps up to 6 guests. The fully equipped kitchen allows for easy cooking. The composting toilet is an eco-friendly alternative w/o giving up convenience. Enjoy the outdoor fire pit & lounge area or visit some of the nearby attractions like Shenandoah National Park, shops downtown, & Death Ridge Brewery!

Top Guest favourite
An A-frame cabin is nestled in a green landscape, surrounded by lush trees. A welcoming front door is flanked by flower beds, while rolling hills rise in the background, suggested by the faint evening light. The property features a well-maintained lawn with visible pathways.
Cabin in Etlan
4.99 out of 5 average rating, 185 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
Apartment in Madison
4.91 out of 5 average rating, 264 reviews

The Studio at Dark Run Retreat

Quiet studio on a secluded 5 acres only 3 miles from town. Kick back and relax by the pool in the warmer months, or in the hot tub in the cooler months. Small trails lead to the creek running along the property, maybe you'll even catch a glimpse of the deer or turkey that wander thru...we've even seen a lil bear once! There is an apartment above the studio, so we ask that you be mindful of those guests if occupied. *The studio got a make-over! As of 10/6/20, we will no longer be hosting pets*

Top Guest favourite
A historic log cabin is set on a grassy expanse, with a red metal roof contrasting against the wooden logs. The porch area features a small table and chairs, surrounded by trees and farmland. Horses are visible in the background, enhancing the rural setting.
Farm stay in Rixeyville
4.97 out of 5 average rating, 302 reviews

Historic Tiny Log Cabin at Beechwood View Farm

Enjoy the beauty of each season at our historic Tiny Log Cabin, built in the 1800s and newly renovated on a beautiful farm setting. Please read all of the description below, and scroll to the bottom before booking! Note—the cabin can be warm in the summer and chilly in the winter due to the logs and chinking. There is a window unit AC and heater in the winter. Also note—the full restroom/shower is a 30 yard walk to the basement of our home. Kuerig with coffee. No refrigerator or microwave.

Guest favourite
A cozy bedroom features a spacious bed with plush bedding and a decorative throw. A large wall clock and framed artwork add character, while teal curtains frame the windows. Soft lighting from bedside lamps creates a warm ambiance against the wood-paneled wall.
Bungalow in Culpeper
4.95 out of 5 average rating, 492 reviews

Chic and comfortable downtown home. Many extras!

Located only 1.5 blocks from the center of Downtown Culpeper on the quietest hidden street in the area! Within 1-3 blocks of amazing restaurants, breweries, and interesting shops. This 1960s bungalow has been completely remodeled and professionally decorated to create a very luxurious and comfortable experience. Convenient distance from Blue Ridge Mountain hiking. This property is professionally cleaned and sanitized after each reservation. We are now accepting longer-term reservations!

Top Guest favourite
Apartment in Culpeper
4.98 out of 5 average rating, 127 reviews

Red Fox Retreat

Easily walkable to Downtown Culpeper! This restored and newly renovated historic property allows easy access to Downtown Culpeper. It features a large outdoor fire pit and expansive grounds to spread out and relax. This 1000 sqft unit is located in the upper level with views of the surrounding grounds and trees. Brightly decorated and designed in partnership with Lets Go and Stay properties; the Red Fox retreat is a great place to stay while visiting Culpeper and the surrounding area.

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, 248 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
A colorful sunset fills the sky with hues of orange and pink, viewed from the property. The silhouette of the house is complemented by the warm light from the windows. Green foliage and flowers adorn the foreground, enhancing the serene atmosphere.
Guesthouse in Boston
4.99 out of 5 average rating, 220 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
The exterior of a two-story cottage is visible, featuring a welcoming porch. Large windows allow for natural light, and seating is arranged on the porch. Surrounding greenery and a gravel pathway add to the peaceful ambiance, with a gently sloped landscape in the background.
Barn in Boston
5 out of 5 average rating, 113 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!

Guest favourite
A view from within a cozy space, showcasing a deck with wooden railings. Sheer curtains filter sunlight, highlighting a grassy yard and a distant barn surrounded by trees. The natural scenery provides a serene backdrop, inviting relaxation and connection with nature.
Farm stay in Boston
4.75 out of 5 average rating, 147 reviews

HB1 at Spring Haven Farm

This is a horsebarn converted into a duplex, hence the name, HB1. It has all the comforts of home including private entrance and a full equipped kitchen. It might be a bit cozy if you use the air mattress, but it can easily fit in the foyer or the living room. Children under 12 years of age stay free. We like to provide interesting objects both inside and outside the dwelling; anything from a camo shower curtain to shadow box decor.

Guest favourite
The cabin is illuminated at dusk, showcasing warm light from multiple windows. A small porch features two chairs, inviting relaxation. The surrounding greenery enhances the cabin's secluded feel in a natural setting.
Guesthouse in Syria
4.87 out of 5 average rating, 691 reviews

Cozy 1 room cabin in the mountains.

In the heart of the Shenandoah mountains. 1 mile from White Oak Canyon and Old Rag for amazing hikes. Perfect for the fly fisherman (lots of local streams) or a nice quiet get-away for a couple. Once you park your car you can sit back and just listen to the river flowing in the back yard & enjoy a nice beverage next to the fire pit. The property is a very special place! UPDATE: New kitchen counters and new table and chairs

Top Guest favourite
A white post bearing the address '9114' stands in a green lawn, with a charming white house featuring red shutters and a covered porch visible in the background. A clear sky with scattered clouds is overhead, and trees line the property.
Cottage in Culpeper
4.91 out of 5 average rating, 116 reviews

The Cottage at Old Salem School

Charming, fully renovated 1800's school house conveniently located between Culpeper and Sperryville. Enjoy dining on the covered porch or patio and sharing stories at the fire pit, or explore the many local breweries, wineries, or world class restaurants nearby. Easily accessible from Skyline Drive or Northern Virginia, this private cabin has everything you need to relax after a day of hiking, shopping, or working.

Popular amenities for Boston holiday rentals

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