Guesthouse holiday rentals in Charlottesville
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Top-rated Guesthouses in Charlottesville
Guests agree: These guesthouses are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Charlottesville guesthouses
Family-Friendly guesthouses
Guesthouse in Crozet
4.86 out of 5 average rating, 281 reviewsStylish Carriage House Suite near Crozet center
6–13 Jun
Guesthouse in Crozet
4.92 out of 5 average rating, 184 reviewsCrozet Carriage House
11–18 Aug
Guesthouse in Charlottesville
5.0 out of 5 average rating, 110 reviewsHidden Gem near town and Monticello with a pool
24 Nov – 1 Dec
Guesthouse in Schuyler
4.9 out of 5 average rating, 356 reviewsHomestead at HeartRock
7–14 Mar
Guesthouse in Ruckersville
4.98 out of 5 average rating, 255 reviewsMountain Guesthouse*Hot Tub*WiFi*Firepit*Grill*SNP
9–16 Oct
Guesthouse in Boston
4.98 out of 5 average rating, 148 reviewsThe Bunkhouse- simple & serene w/mountain views
13–20 Oct
Guesthouse in Charlottesville
4.92 out of 5 average rating, 135 reviewsThe Cottage at Eastwood Farm and Winery
1–8 Aug
Guesthouse in Madison
4.97 out of 5 average rating, 229 reviewsHebron Valley Cottage
8–15 Sep
Guesthouses with a patio
Guesthouse in Reva
4.97 out of 5 average rating, 146 reviewsAdorable cottage with partial blue ridge views
25 Oct – 1 Nov
Guesthouse in Mount Crawford
4.95 out of 5 average rating, 108 reviewsCountry Cabin near JMU/ Skyline Dr / Massanutten
29 Oct – 5 Nov
Guesthouse in Fort Valley
4.9 out of 5 average rating, 144 reviewsRomantic Mountain Getaway⛰ hot tub*king bed*sauna
16–23 Jul
Guesthouse in Barboursville
4.95 out of 5 average rating, 21 reviewsBurnley Cottage
6–13 Jun
Guesthouse in Keswick
4.92 out of 5 average rating, 51 reviewsElegant Keswick guest house with luxurious pool
10–17 Feb
Guesthouse in Charlottesville
5.0 out of 5 average rating, 30 reviewsHome Tract Cottage UVA/Charlottesville/Ivy
13–20 Sep
Guesthouse in Waynesboro
4.89 out of 5 average rating, 54 reviewsNona's Cottage-Waynesboro/Shenandoah Valley, VA
24 Sep – 1 Oct
Guesthouse in Keswick
4.85 out of 5 average rating, 26 reviewsThe Woodhouse Cottage
3–10 May
Guest house rentals with a washing machine and dryer
Guesthouse in Afton
4.92 out of 5 average rating, 514 reviewsTiny House Bliss. Brew Ridge. Trail. Ski. Wineries
7–14 Jun
Guesthouse in Afton
5.0 out of 5 average rating, 223 reviewsMountain Cottage / Pool, heart of 151 Brew Trail
7–14 Jun
Guesthouse in Midland
4.97 out of 5 average rating, 151 reviewsModern Farm Stay
14–21 Oct
Guesthouse in Gordonsville
4.91 out of 5 average rating, 171 reviewsLa Petite Maison at Hedgeapple Hollow
31 Jul – 7 Aug
Guesthouse in Shenandoah
4.87 out of 5 average rating, 256 reviewsGuest House with Game Room & Massage Chair
10–17 Jul
Guesthouse in Faber
5.0 out of 5 average rating, 40 reviewsRelaxing Cottage with Firepit
30 Nov – 7 Dec
Guesthouse in Charlottesville
4.98 out of 5 average rating, 43 reviewsCharming one room cottage with parking.
4–11 Oct
Guesthouse in Nellysford
5.0 out of 5 average rating, 38 reviewsThe Nest...lovely 2 bedroom apartment in the woods
4–11 Mar
Quick stats about guesthouse rentals in Charlottesville
Total rentals
30 properties
Local attractions
Shenandoah National Park Trust, University of Virginia and John Paul Jones Arena
Popular amenities
Kitchen, Wi-Fi and Pool
Wi-Fi availability
30 properties include access to Wi-Fi
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Total number of reviews
3.6K reviews
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