Book Holiday Homes in Rutland

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Featured Holiday Homes in Rutland

Quiet Modern Luxury Home w/  Memory Foam Beds, A/C, FAST WiFi and Full Kitchen

Quiet Modern Luxury Home w/ Memory Foam Beds, A/C, FAST WiFi and Full Kitchen

Bridgewater
With a stay at this vacation home in Bridgewater Corners, you'll be on a river, within a 15-minute drive of Killington Resort and Long Trail Brewing ...
Quiet Modern Luxury Home w/ Memory Foam Beds, A/C, FAST WiFi and Full Kitchen
Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle

Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle

Ludlow
The price is AU$559 per night from 7 Nov to 8 Nov
AU$559
includes taxes & fees
7 Nov - 8 Nov
With a stay at this vacation home in Ludlow, you'll be in the mountains, within a 5-minute drive of Okemo Mountain Resort and Dorsey Park.
Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle
Lake front house about 1 mile from Okemo's Jackson Gore Base Lodge

Lake front house about 1 mile from Okemo's Jackson Gore Base Lodge

Ludlow
With a stay at this vacation home in Ludlow, you'll be on the waterfront, within a 5-minute drive of Okemo Mountain Resort and Green Mountain Sugar House.
Lake front house about 1 mile from Okemo's Jackson Gore Base Lodge
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Spectacular 4 Bed Killington Home

Spectacular 4 Bed Killington Home

Killington
When you stay at this vacation home in Killington, you'll be in the mountains, a 2-minute drive from Killington Resort and 8 minutes from Pico Mountain at Killington ...
Spectacular 4 Bed Killington Home
Slopeside Chalet - Ski to and from your home!

Slopeside Chalet - Ski to and from your home!

Killington
The price is AU$1,098 per night from 3 Nov to 4 Nov
AU$1,098
includes taxes & fees
3 Nov - 4 Nov
When you stay at this vacation home in Killington, you'll be in the mountains, just steps from Killington Resort and a 4-minute drive from Bear Mountain Quad ...
Slopeside Chalet - Ski to and from your home!
Spacious 6-bedroom house in charming Quechee. Family friendly, all seasons!

Spacious 6-bedroom house in charming Quechee. Family friendly, all seasons!

2 out of 5
Quechee
With a stay at this vacation home in Quechee, you'll be a 5-minute walk from Quechee Ski Hill and within a 5-minute drive of The Strong House Spa.
Spacious 6-bedroom house in charming Quechee. Family friendly, all seasons!
Ski-On/Off - private sauna - right next to lift - 1GB WiFi - Renovated

Ski-On/Off - private sauna - right next to lift - 1GB WiFi - Renovated

Killington
When you stay at this vacation home in Killington, you'll be in the mountains, just steps from Killington Resort and 15 minutes by foot from Sunrise Village ...
Ski-On/Off - private sauna - right next to lift - 1GB WiFi - Renovated
Dog-Friendly Cottage with Deck & Beautiful Views - Close to Golf, Skiing & Trail

Dog-Friendly Cottage with Deck & Beautiful Views - Close to Golf, Skiing & Trail

Killington
With a stay at this vacation home in Killington (North Sherburne), you'll be within a 15-minute drive of Killington Resort and Pico Mountain at Killington Ski ...
Dog-Friendly Cottage with Deck & Beautiful Views - Close to Golf, Skiing & Trail
Okemo Mountain Lodging

Okemo Mountain Lodging

3.5 out of 5
77 Okemo Ridge Rd, Ludlow, VT
With a stay at Okemo Mountain Lodging in Ludlow (Clock Tower Base Area), you'll be within a 10-minute walk of Okemo Mountain Resort and General Parking.
Okemo Mountain Lodging
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Rutland Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Rutland vacation homes are the perfect way for you to wing it.

Holiday houses in Rutland let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Rutland in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Rutland adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Rutland with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Rutland vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Rutland Holiday Homes essential information

Accommodation
698 Holiday Homes
Lowest Price
AU$186
Highest Price
AU$1,098
Popular accommodation
Quiet Modern Luxury Home w/ Memory Foam Beds, A/C, FAST WiFi and Full Kitchen, Gorgeous Village Home 3 bd, 2 ba Short Walk To Shops, Restaurants, Ski Shuttle, Lake front house about 1 mile from Okemo's Jackson Gore Base Lodge, Spectacular 4 Bed Killington Home, Slopeside Chalet - Ski to and from your home!, Spacious 6-bedroom house in charming Quechee. Family friendly, all seasons! , Ski-On/Off - private sauna - right next to lift - 1GB WiFi - Renovated, Dog-Friendly Cottage with Deck & Beautiful Views - Close to Golf, Skiing & Trail, Okemo Mountain Lodging

Top trending hotels in Rutland

Comfort Inn Trolley Square

Comfort Inn Trolley Square

2.5 out of 5
19 Allen St, Rutland, VT
Fully refundableReserve now, pay when you stay
The price is AU$186 per night from 17 Nov to 18 Nov
AU$186
includes taxes & fees
17 Nov - 18 Nov
With a stay at Comfort Inn Trolley Square in Rutland, you'll be 0.6 mi (1 km) from Rutland Regional Medical Center and 9.8 mi (15.7 km) from Pico Mountain at ...
Comfort Inn Trolley Square
Days Inn by Wyndham Rutland/Killington Area

Days Inn by Wyndham Rutland/Killington Area

2.5 out of 5
401 US-7, Located At The Junction Of Us 4 And Us 7, Rutland, VT
Fully refundableReserve now, pay when you stay
The price is AU$187 per night from 12 Nov to 13 Nov
AU$187
includes taxes & fees
12 Nov - 13 Nov
When you stay at Days Inn by Wyndham Rutland/Killington Area in Rutland, you'll be near ski lifts, within a 5-minute drive of Vermont State Fairgrounds and Rutland ...
Days Inn by Wyndham Rutland/Killington Area
Best Western Inn & Suites Rutland-Killington

Best Western Inn & Suites Rutland-Killington

2.5 out of 5
5 Best Western Place, Rutland, VT
Fully refundableReserve now, pay when you stay
The price is AU$270 per night from 10 Nov to 11 Nov
AU$270
includes taxes & fees
10 Nov - 11 Nov
With a stay at Best Western Inn & Suites Rutland-Killington in Rutland, you'll be in the mountains, within a 10-minute drive of Pico Mountain at Killington Ski ...
Best Western Inn & Suites Rutland-Killington
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Hampton Inn Rutland

Hampton Inn Rutland

2.5 out of 5
47 Farrell Rd, Rutland, VT
Fully refundableReserve now, pay when you stay
The price is AU$241 per night from 3 Nov to 4 Nov
AU$241
includes taxes & fees
3 Nov - 4 Nov
Located in Rutland, Hampton Inn Rutland is in the mountains, within a 5-minute drive of Diamond Run Mall and Vermont State Fairgrounds.
Hampton Inn Rutland
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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^Subject to availability and chosen travel dates.