Rutland vacation rentals

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Top-rated vacation rentals in Rutland

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

Guest favorite

Condo 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

Aug 25 – Sep 1

€ 115 per night
Guest favorite

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.

Apr 24 – May 1

€ 100 per night
Guest favorite

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.

Aug 16 – 23

€ 124 per night

Popular amenities for Rutland vacation 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 vacation rentals in Rutland

Guest favorite

Cabin in Granville

4.98 out of 5 average rating, 132 reviews

Quaint log cabin nestled in the woods

Apr 21 – 28

€ 118 per night
Superhost

Bungalow in Castleton

4.81 out of 5 average rating, 299 reviews

Lake Bomoseen Bungalow

Oct 8 – 15

€ 114 per night
Guest favorite

Tiny home in Pittsford

4.96 out of 5 average rating, 154 reviews

Charming tiny house with great VT location!

Jun 2 – 9

€ 127 per night
Superhost

Condo in Killington

4.84 out of 5 average rating, 341 reviews

Winter is coming! Cute Mountain Getaway!

Jun 5 – 12

€ 114 per night
Guest favorite

Guesthouse in Granville

4.9 out of 5 average rating, 780 reviews

Moon Valley Country Retreat no clean fee pets yes

Feb 18 – 25

€ 99 per night
Guest favorite

Cabin in Leicester

4.98 out of 5 average rating, 709 reviews

Log Cabin Getaway near Middlebury and Green Mtns

Jan 23 – 30

€ 127 per night
Guest favorite

Cabin in Rochester

4.95 out of 5 average rating, 387 reviews

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

Feb 23 – Mar 2

€ 147 per night
Guest favorite

Cottage in Poultney

4.97 out of 5 average rating, 109 reviews

The Cottage in East Poultney

Feb 27 – Mar 6

€ 140 per night
Guest favorite

Condo in Killington

4.92 out of 5 average rating, 143 reviews

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

May 26 – Jun 2

€ 137 per night
Guest favorite

Guesthouse in Pawlet

4.91 out of 5 average rating, 282 reviews

Picturesque Cabin on the Mettowee

Oct 31 – Nov 7

€ 121 per night
Guest favorite

Apartment in Chittenden

5.0 out of 5 average rating, 222 reviews

Vermont Country Suite

Nov 19 – 26

€ 153 per night
Guest favorite

Castle in Clarendon

4.98 out of 5 average rating, 433 reviews

Kingsley Grist Mill, Covered Bridge and Waterfall.

Nov 18 – 25

€ 398 per night

Other great vacation rentals in Rutland

Guest favorite

Home in Rutland

5.0 out of 5 average rating, 120 reviews

ONE ROOM SCHOOL HOUSE

Sep 21 – 28

€ 252 per night
Guest favorite

Cabin in West Rutland

4.88 out of 5 average rating, 153 reviews

VT MOUNTAIN LOG CABIN, CLOSE TO KILLINGTON/PICO

Oct 11 – 18

€ 203 per night
Guest favorite

Condo in Killington

4.94 out of 5 average rating, 148 reviews

Bright Ski on/off Condo Full Kitchen-Free Shuttle!

Apr 26 – May 3

€ 145 per night
Guest favorite

Apartment in Hancock

4.95 out of 5 average rating, 144 reviews

Suite in the Green Mountains

Oct 30 – Nov 6

€ 101 per night
Guest favorite

Condo in Ludlow

4.92 out of 5 average rating, 119 reviews

Okemo Ski-in/Ski-out, Steps to lift Condo

Aug 7 – 14

€ 116 per night
Guest favorite

Townhouse in Killington

4.92 out of 5 average rating, 226 reviews

Modern Mountain Condo with Spa, Pool, Sauna, Gym

May 8 – 15

€ 169 per night
Guest favorite

Home in Rutland

4.87 out of 5 average rating, 75 reviews

Lovely 2-Bedroom on 25 acres

May 12 – 19

€ 103 per night
Guest favorite

Apartment in Rutland

4.89 out of 5 average rating, 47 reviews

Cozy apt mins to the mountain

Jun 9 – 16

€ 104 per night
Guest favorite

Apartment in Rutland

4.95 out of 5 average rating, 58 reviews

Baby Queens Barbiecore Studio Apt Dog Friendly

Jun 20 – 27

€ 95 per night
Guest favorite

Apartment in Rutland

4.94 out of 5 average rating, 32 reviews

Nice, Large Modern Apartment

Oct 8 – 15

€ 153 per night
Guest favorite

Apartment in Killington

5.0 out of 5 average rating, 12 reviews

Jack S'Bearo - Slopeside at Pico! Shuttle to Killy

Apr 13 – 20

€ 136 per night
Guest favorite

Apartment in West Rutland

4.96 out of 5 average rating, 26 reviews

Mountain View Apartment

Oct 6 – 13

€ 148 per night

Quick stats about vacation 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

Frequently Asked Questions

  • Are there pet-friendly vacation rentals in Rutland?

    Four-legged friends are welcome in Rutland. Choose from more than 20 vacation rentals for guests traveling with pets.

  • Are there vacation rentals with a dedicated workspace in Rutland?

    Yes! Work meets play with ease at over 50 vacation rentals in Rutland featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • How much does it cost to stay in house rentals in Rutland?

    Experience the best of Rutland with our house rentals, starting at about $40 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do house rentals in Rutland have a bbq area?

    Absolutely! We offer over 10 house rentals with a bbq area in Rutland. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Rutland have wireless internet?

    Absolutely! We offer over 50 house rentals with wireless internet in Rutland. Enjoy a tailored experience with all the comforts you desire.

  • Are there family-friendly apartment rentals in Rutland?

    Rutland has more than 20 family-friendly apartment rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Do house rentals in Rutland have air conditioning?

    Absolutely! We offer over 30 house rentals with air conditioning in Rutland. Enjoy a tailored experience with all the comforts you desire.

  • What are the most popular amenities for Apartment Rentals in Rutland?

    Enhance your stay in our Apartment Rentals with the most popular amenities: over 40 homes with wireless internet, over 30 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.

Destinations to explore

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  4. Rutland County
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