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
Tiny home in Culpeper
4.98 out of 5 average rating, 122 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
Cabin in Etlan
4.99 out of 5 average rating, 166 reviews

Mountain 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.

Superhost
Tiny home in Reva
4.93 out of 5 average rating, 355 reviews

K-9 Heaven Dogs Run Free

Welcome to K-9 Heaven! Escape the hustle and bustle of the city and embrace the beauty of clean, open spaces. Spend joyful moments with our friendly horses—don’t forget, they adore peppermints! Bring your furry friends along; it’s their vacation too! We offer a fantastic off-leash experience just 20 minutes from Old Rag Mountain, White Oak Falls, and downtown Culpeper, where you'll find endless hiking trails to explore. Plus, we're conveniently located near delightful wineries and breweries.

Guest favourite
Guest house in Syria
4.96 out of 5 average rating, 401 reviews

Little House on Strother Run

Nestled between Mount Tom and Double Top Mountain and at the edge of the Shenandoah National Forest, Little House is the perfect starting out and ending point for a peaceful and relaxing stay in the Appalachian Mountains. Little House is located at the edge of our 7 acre property. You'll enjoy the bucolic atmosphere of our farmette which includes use of our shared sitting area on Strother Run. The sitting area is shared with the main house which is rented or used by our family periodically.

Guest favourite
Cabin in Reva
4.94 out of 5 average rating, 166 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.

Guest favourite
Flat in Culpeper
4.96 out of 5 average rating, 195 reviews

TreeTop at Mt Run Lake (Private Guest Apartment)

Spacious one bedroom guest apartment with SEPARATE ENTRANCE, private separate patio and reserved parking in this newly decorated full apartment, set on four acres with lakefront views situated in the foothills of the Blue Ridge Mountains. One flight of stairs up to a beautiful apartment with fantastic views of the lake and surrounding property. Private and secluded yet only 10 minutes from Historic downtown Culpeper with its many restaurants, local shops, grocery stores and pharmacies.

Top guest favourite
Home in Boston
4.96 out of 5 average rating, 157 reviews

Peacefield - Blue Ridge views near Culpeper

Welcome to the Peacefield! This retreat is nestled in the rolling foothills of the Blue Ridge Mountains in the shadow of Old Rag, overlooking Hazel River Farm (160 acres). The spacious estate is perfect for escaping the city. There are many options for relaxing with a deck, hot tub, pool (summer only), home theater, and an open kitchen connecting the dining and family rooms. The beauty of the estate includes walking trails, glimpses of sheep, and local art (watercolor and photography).

Top guest favourite
Flat in Culpeper
4.98 out of 5 average rating, 111 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
Farm stay in Warrenton
4.98 out of 5 average rating, 670 reviews

Winters Retreat Farm Cottage - Entire house

Need a change of view? Unplug, and relax in this independent private cottage on the homestead. Watch for deer, turkeys and birds in the field from the sunroom or take a hike around the farm. Centered in Fauquier's wine country it is ideal for the weekend escape, or day trips West to the mountains, East to DC or points south. Also, a perfect solution for accommodating family at get-to-gathers, wedding guest, or your "Halfway overnight stay" traveler North/ South or to the beach.

Guest favourite
Home in Culpeper
4.95 out of 5 average rating, 452 reviews

Cute Home in Downtown Culpeper with many extras!

Enjoy our recently updated home in downtown Culpeper. Our small home sits in a prime location within 1-3 blocks of amazing restaurants, breweries, and interesting shops.The house is located in a safe and quiet part of town. Convenient distance from Blue Ridge Mountain hiking. This property is professionally cleaned and sanitized after each reservation. Perfect for a family getaway! We are now accepting longer-term reservations. Top-rated accommodation in Culpeper for 2018-2022

Top guest favourite
Guest house in Boston
4.99 out of 5 average rating, 205 reviews

The Bunkhouse- 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 bunkhouse 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, 108 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