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.

Guest favourite

Tiny home in Reva

4.94 out of 5 average rating, 287 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.

16–23 Apr

$171 SGD per night
Guest favourite

Farm stay in Sperryville

4.98 out of 5 average rating, 120 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.

14–21 Jun

$188 SGD per night
Guest favourite

Guest house in Syria

4.95 out of 5 average rating, 324 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.

16–23 Jul

$128 SGD per night

Popular amenities for Boston holiday rentals

Other great holiday rentals in Boston

Guest favourite

Flat in Madison

4.9 out of 5 average rating, 227 reviews

The Studio at Dark Run Retreat

8–15 Apr

$110 SGD per night
Guest favourite

Home in Brightwood

4.99 out of 5 average rating, 297 reviews

Hilltop Haven Luxury lodging in Wine country

4–11 Nov

$199 SGD per night
Guest favourite

Cottage in Madison

4.9 out of 5 average rating, 135 reviews

Robinson River Roost - Cottage near Shenandoah NP

7–14 May

$164 SGD per night
Guest favourite

Cottage in Etlan

4.97 out of 5 average rating, 159 reviews

Amy's Place

2–9 Apr

$191 SGD per night
Guest favourite

Guest suite in Stanley

4.98 out of 5 average rating, 158 reviews

Tranquility in the Mountains

20–27 Aug

$165 SGD per night
Guest favourite

Guest house in Madison

4.97 out of 5 average rating, 227 reviews

Hebron Valley Cottage

4–11 Jun

$197 SGD per night
Guest favourite

Farm stay in Rixeyville

4.97 out of 5 average rating, 266 reviews

Historic Tiny Log Cabin at Beechwood View Farm

30 Jul – 6 Aug

$145 SGD per night
Guest favourite

Guest suite in Brandy Station

4.95 out of 5 average rating, 116 reviews

Threlkeld Farm,quiet, restful, fat pillows!

21–28 Aug

$165 SGD per night
Guest favourite

Tiny home in Linville

4.99 out of 5 average rating, 593 reviews

The spring house at Thistle Hollow

25 Jul – 1 Aug

$155 SGD per night
Guest favourite

Cabin in Rixeyville

4.98 out of 5 average rating, 190 reviews

Cedarfield Cabin

10–17 Nov

$346 SGD per night
Guest favourite

Cottage in Midland

4.97 out of 5 average rating, 124 reviews

The Stoney Cottage Hideaway

17–24 Nov

$188 SGD per night
Guest favourite

Home in Madison

4.96 out of 5 average rating, 134 reviews

Spacious Shenandoah Home on 35 Private Acres

29 Jul – 5 Aug

$350 SGD per night

Destinations to explore

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