Vacation rentals in Boston

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Top-rated vacation rentals in Boston

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Guest favorite

Tiny home in Reva

4.94 out of 5 average rating, 290 reviews

K-9 Heaven Dogs Run Free

K-9 Heaven ... Get away from the City. Enjoy clean open spaces. Spend time with the horses.They love peppermints. Don't leave your K-9 family at home, It's there vacation too. 100% off leash 20 min away Old Rag Mountain , White Oak Falls and downtown Culpeper. There are so many trails for a wonderful hiking experience. We are with in 10 min of nearby winerys, breweries We are off leash for dogs . Never leave the farm as we have Doordash to bring you whatever you desire, Wine, food anything.

May 31 – Jun 7

G$26,468 GYD per night

Guest favorite

Farm stay in Sperryville

4.98 out of 5 average rating, 121 reviews

The Roost at Upper Nonesuch

New for fall: Pickleball Court!. Located in the foothills of the Blue Ridge Mountains, Upper Nonesuch is the perfect place to get away and relax. Enjoy the serene view of the valley and rolling hills from the large screened-in porch and bedroom, the walking trails, the spring-fed pond on the adjacent farm. Take a short drive and enjoy hiking Old Rag and White Oak Canyon Falls. Explore Sperryville and Culpeper, the many orchards, wineries, breweries, all the Shenandoah Valley has to offer.

Aug 3 – 10

G$29,183 GYD per night

Guest favorite

Apartment in Madison

4.9 out of 5 average rating, 229 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*

May 22 – 29

G$17,100 GYD per night

Guest favorite

Cottage in Madison

4.91 out of 5 average rating, 138 reviews

Robinson River Roost - Cottage near Shenandoah NP

Enjoy a slice of country life in our rustic 3 BR, 1.5 bath cottage nestled along the Blue Ridge in Madison County. Great for a family or small group. Minutes to scenic hikes at White Oak and Old Rag in Shenandoah National Park, plus wineries, breweries and festivals at Graves Mountain Lodge. Steps away from trout fishing and swimming holes of the peaceful Robinson River, plus Possum's Store across the street. Convenient to Charlottesville, Culpeper, Blue Ridge Pkwy, Luray Caverns, Camp Varsity.

Sep 1 – 8

G$25,364 GYD per night

Guest favorite

Guesthouse in Syria

4.95 out of 5 average rating, 328 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.

Aug 9 – 16

G$20,327 GYD per night

Guest favorite

Guest suite in Culpeper

4.98 out of 5 average rating, 248 reviews

Spacious property-deluxe amenities; hot tub & more

Enjoy the beauty of nature in our beautiful private 2 room suite. Located in Culpeper County Virginia, you are minutes away from world class dining, wineries, great breweries while only 20 minutes from Shenandoah National Park. Retreat to the deck for an evening soak in the hot tub after a day of exploring the area. This space provides a queen bed, plenty of sitting space, full private bathroom, walk in closet, 50 inch smart TV, WIFI, mini fridge, ice maker, microwave, and coffee maker.

Dec 22 – 29

G$21,776 GYD per night

Guest favorite

Apartment in Culpeper

4.98 out of 5 average rating, 147 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.

Feb 12 – 19

G$21,154 GYD per night

Guest favorite

Home in Boston

4.97 out of 5 average rating, 116 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).

Aug 28 – Sep 4

G$98,950 GYD per night

Guest favorite

Farm stay in Culpeper

4.96 out of 5 average rating, 116 reviews

Charming cottage in farm country

Take it easy at this unique and tranquil getaway. Enjoy the beauty of farm country while being conveniently located to restaurants, wineries, breweries and fun activities. Close to downtown historical Culpeper and Amtrak train station. Whether you are interested in great food, outdoors, horse shows or just looking for a break, we got you covered. Small scale farm with pigs and free range chickens. Check my Guidebook! 40 min from Lake Anna 45 min from Shenandoah NP 70 min from DC

Sep 15 – 22

G$19,914 GYD per night

Guest favorite

Yurt in Etlan

4.95 out of 5 average rating, 192 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.

Aug 14 – 21

G$26,243 GYD per night

Guest favorite

Guest suite in Brandy Station

4.98 out of 5 average rating, 132 reviews

Studio apartment at historic Glenmore

Studio apartment with separate entry at historic Glenmore in scenic Brandy Station, VA. Beautiful farm location with newly renovated space featuring a kitchenette with refrigerator, microwave, coffeemaker and toaster. Bedroom/living area with queen bed and twin sofa bed. TV with dish and unlimited internet. Full bath with shower. We cannot accommodate children under the age of four because the space has an open wooden staircase that cannot be blocked off.

Sep 29 – Oct 6

G$19,076 GYD per night

Guest favorite

Guesthouse in Boston

4.98 out of 5 average rating, 146 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.

Jul 13 – 20

G$28,362 GYD per night