Holiday rentals in Rutland

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Top-rated holiday rentals in Rutland

Guests agree: these stays are highly rated for location, cleanliness and more.

Guest favourite

Apartment in Killington

4.95 out of 5 average rating, 124 reviews

🎿Cozy Fireplace Condo-Mins. to Everything 🚵

Seeking Adventure? This end unit garden level condo is 6 minutes to Killington AND Pico! Quick access to the Appalachian Trail to ATV, mountain bike, hike, and swim. Relaxing? Work remotely with fast Wi-Fi, hang on the porch swing, or unwind in front of the wood fireplace. Hop in the power adjustable king bed, pull the darkening shades, and turn on the sound machine for restful sleep so you can wake up and do it again! A portion of each stay is donated to local VT nonprofits

25 Aug – 1 Sep

$134 SGD per night
Guest favourite

Farm stay in Salisbury

4.95 out of 5 average rating, 263 reviews

Quaint 1-bedroom cottage on Blue Ledge Farm

This adorable cottage is on Blue Ledge Farm- a working goat dairy. It is a one-bedroom with a double fold-out futon in living room to potentially fit 4 guests. It is within 15 minutes of both Brandon and Middlebury, 1 hour south of Burlington. Pets are allowed, on leash. It can possibly include a farm and cheese tasting for an extra $20 per person (contact host in advance). It is the perfect place if you're an animal or cheese lover looking for a rustic and relaxing stay on a beautiful farm.

24 Apr – 1 May

$125 SGD per night
Guest favourite

Guest suite in Castleton

4.98 out of 5 average rating, 111 reviews

Mi Casa es su Casa!

Relax in this refurbished quiet Lake view rental. Minutes from Lake Bomoseen/Crystal Beach. Large family room, Cast iron wood-stove. Wall of windows w/lake views. 65" 4K TV, surround sound system. Wi-Fi access. Galley kitchen includes range, microwave, Keurig, fridge & wine cooler. Spacious bedroom, queen size bed w/ heated mattress pad. Lots of storage. Full bathroom. Private deck w/Adirondack chairs. Kayaks & boat launch. 25 min to Rutland, 35 min to Pico & 47 min Killington Ski Resorts.

16–23 Aug

$159 SGD per night

Popular amenities for Rutland holiday rentals

Stay near Rutland's top sights

Walmart3 locals recommend
Vermont Tap House11 locals recommend
Hannaford Supermarket24 locals recommend
Gill's Delicatessen6 locals recommend
Johnny Boys Pancake House20 locals recommend
ALDI4 locals recommend

Other great holiday rentals in Rutland

Superhost

Bungalow in Castleton

4.81 out of 5 average rating, 299 reviews

Lake Bomoseen Bungalow

8–15 Oct

$152 SGD per night
Guest favourite

Cabin in Granville

4.98 out of 5 average rating, 132 reviews

Quaint log cabin nestled in the woods

21–28 Apr

$154 SGD per night
Guest favourite

Tiny home in Pittsford

4.96 out of 5 average rating, 154 reviews

Charming tiny house with great VT location!

2–9 Jun

$161 SGD per night
Superhost

Apartment in Killington

4.84 out of 5 average rating, 341 reviews

Winter is coming! Cute Mountain Getaway!

5–12 Jun

$135 SGD per night
Guest favourite

Guest house in Granville

4.9 out of 5 average rating, 779 reviews

Moon Valley Country Retreat no clean fee pets yes

18–25 Feb

$138 SGD per night
Guest favourite

Cottage in Poultney

4.97 out of 5 average rating, 109 reviews

The Cottage in East Poultney

10–17 Dec

$172 SGD per night
Guest favourite

Cabin in Leicester

4.98 out of 5 average rating, 709 reviews

Log Cabin Getaway near Middlebury and Green Mtns

23–30 Jan

$170 SGD per night
Guest favourite

Apartment in Killington

4.92 out of 5 average rating, 143 reviews

Renovated, w/Covered Parking-Shuttle-Walk to Lifts

26 May – 2 Jun

$159 SGD per night
Guest favourite

Guest house in Pawlet

4.91 out of 5 average rating, 282 reviews

Picturesque Cabin on the Mettowee

17–24 Jan

$162 SGD per night
Guest favourite

Home in Rutland

4.81 out of 5 average rating, 287 reviews

Home Sweet Home

30 May – 6 Jun

$184 SGD per night
Guest favourite

Flat in Chittenden

5.0 out of 5 average rating, 222 reviews

Vermont Country Suite

19–26 Nov

$195 SGD per night
Guest favourite

Cabin in Rochester

4.95 out of 5 average rating, 387 reviews

Black haus: a hip, cool house hidden in a forest.

23 Feb – 2 Mar

$188 SGD per night

Quick stats about holiday rentals in Rutland

Total rentals

110 properties

Wifi availability

110 properties include access to wifi

Rentals with dedicated workspaces

50 properties have a dedicated workspace

Pet-friendly rentals

20 properties allow pets

Family-friendly rentals

70 properties are a good fit for families

Total number of reviews

4.5K reviews

Destinations to explore

  1. Airbnb
  2. United States
  3. Vermont
  4. Rutland County
  5. Rutland