House holiday rentals in Rutland County
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Top-rated house rentals in Rutland County
Guests agree: these houses are highly rated for location, cleanliness and more.
Holiday rentals for every style
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Popular amenities for house rentals in Rutland County
House rentals with a pool
Home in Killington
4.92 out of 5 average rating, 165 reviewsCozy Condo Tucked in the Heart of Killington
12–19 Jul
Home in Killington
5.0 out of 5 average rating, 28 reviews* Slope Side Sauna w/ Shuttle *
25 Jun – 2 Jul
Home in Pawlet
4.77 out of 5 average rating, 74 reviewsThe Vermont Experience A Magical Riverside Retreat
7–14 Jun
Home in Killington
5.0 out of 5 average rating, 31 reviewsBearmont! Pool, HotTub, AC, FirePit
31 May – 7 Jun
Home in Chittenden
4.9 out of 5 average rating, 81 reviewsComfortable, relaxing large country home
1–8 Sep
Home in Bridgewater
4.9 out of 5 average rating, 41 reviewsLuxurious family retreat home in the mountains
30 Oct – 6 Nov
Home in Granville
4.94 out of 5 average rating, 90 reviewsHistoric 1850’s Renovated Farmhouse w/ Pool!
30 Oct – 6 Nov
Home in Killington
4.97 out of 5 average rating, 37 reviews2 Minute Shuttle to the Slopes Unit 9
29 Sep – 6 Oct
Weekly house rentals
Home in Tinmouth
4.82 out of 5 average rating, 114 reviewsVermont Lakefront Getaway "The Wild Loon"
1–8 May
Home in Rutland
4.83 out of 5 average rating, 145 reviewsThe Green Mountain Getaway
9–16 Jun
Home in Weston
4.97 out of 5 average rating, 196 reviewsWeston Farmhouse-Clean, Fast WiFi, Generator!
5–12 May
Home in Killington
4.94 out of 5 average rating, 124 reviewsAtelier Killington, hottub and amazing location
6–13 Nov
Home in Shrewsbury
4.94 out of 5 average rating, 199 reviewsBaldwin House
27 May – 3 Jun
Home in Pittsfield
4.91 out of 5 average rating, 149 reviewsBeautiful Mountain Log Cabin with Scenic Views
24 Sep – 1 Oct
Home in Ludlow
4.97 out of 5 average rating, 147 reviewsSki Chalet with Hot Tub on Okemo Mountain
28 Feb – 7 Mar
Home in Brandon
4.93 out of 5 average rating, 120 reviewsRand’s Retreat
26 Feb – 5 Mar
Private house rentals
Home in Rutland
4.87 out of 5 average rating, 75 reviewsLovely 2-Bedroom on 25 acres
24–31 Oct
Home in Rutland
4.98 out of 5 average rating, 49 reviewsCheerful home near Killington, Okemo, Pico, trails
15–22 Dec
Home in Clarendon
5.0 out of 5 average rating, 9 reviewsMountain Cottage for ski weekend. Pet Friendly!
5–12 Jun
Home in Rutland
4.96 out of 5 average rating, 27 reviews*Pet Friendly* The Madden Mountain Home
16–23 Nov
Home in Castleton
4.95 out of 5 average rating, 20 reviewsWhat a View - Lake Bomoseen VT
7–14 Dec
Home in Castleton
5.0 out of 5 average rating, 16 reviewsNew Listing! Luxury waterfront Lake Bomoseen home!
13–20 Jan
Home in Hubbardton
5.0 out of 5 average rating, 12 reviewsBomoseen Luxury Waterfront -Great Family Getaway!
14–21 Apr
Home in Pittsfield
4.97 out of 5 average rating, 38 reviewsHideaway Mountain at Killington
7–14 Jun
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