Book Holiday Homes in Rutland

Start date: Check-in selected.
To Date
End date: Check-out

More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)

We keep it easy with the option to pay now or later on select accommodation

Book up 'til the last second - millions of rooms to crash tonight^

Featured Holiday Homes in Rutland

Traveling with kids? Try this secluded & updated 3-bedroom home close to Okemo

Traveling with kids? Try this secluded & updated 3-bedroom home close to Okemo

Ludlow
With a stay at this vacation home, you'll be centrally located in Ludlow, within a 10-minute drive of Okemo Mountain Resort and Fletcher Farm School for the ...
Opens in a new windowTraveling with kids? Try this secluded & updated 3-bedroom home close to Okemo
Classic ski home with hot tub, washer/dryer, mountain views, fireplace, & cable

Classic ski home with hot tub, washer/dryer, mountain views, fireplace, & cable

Ludlow
With a stay at this vacation home, you'll be centrally located in Ludlow, within a 5-minute drive of Okemo Mountain Resort and Red Lot.
Opens in a new windowClassic ski home with hot tub, washer/dryer, mountain views, fireplace, & cable
Brand new 2021 Reno of Federal Style House, steps from Downtown Brandon

Brand new 2021 Reno of Federal Style House, steps from Downtown Brandon

Brandon
A stay at this vacation home places you in the heart of Brandon, within a 10-minute walk of Judith Reilly Gallery and Stephen A Douglas Birthplace.
Opens in a new windowBrand new 2021 Reno of Federal Style House, steps from Downtown Brandon
Save an average of 15% on thousands of hotels when you're signed in
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 ...
Opens in a new windowQuiet Modern Luxury Home w/ Memory Foam Beds, A/C, FAST WiFi and Full Kitchen
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.
Opens in a new windowOkemo Mountain Lodging
Beautifully renovated with fireplace and coffee bar

Beautifully renovated with fireplace and coffee bar

Hartford
Located in White River Junction, this vacation home is on a river, within a 15-minute walk of The Strong House Spa and Route 4 Glassblowing Studio.
Opens in a new windowBeautifully renovated with fireplace and coffee bar
Classic VT Ski Chalet - Walkable to Okemo Ski Lift w/Fit Pit & Pool Table

Classic VT Ski Chalet - Walkable to Okemo Ski Lift w/Fit Pit & Pool Table

Ludlow
When you stay at this vacation home in Ludlow, you'll be in the mountains, within a 5-minute walk of Okemo Mountain Resort and Sunshine Ski Lift.
Opens in a new windowClassic VT Ski Chalet - Walkable to Okemo Ski Lift w/Fit Pit & Pool Table
Spacious Vermont Getaway 7 BR/4.5 BA - Close to Skiing - Biking - Golf - Hiking

Spacious Vermont Getaway 7 BR/4.5 BA - Close to Skiing - Biking - Golf - Hiking

Killington
With a stay at this vacation home in Killington, you'll be in the mountains, within a 10-minute drive of Killington Resort and Green Mountain National ...
Opens in a new windowSpacious Vermont Getaway 7 BR/4.5 BA - Close to Skiing - Biking - Golf - Hiking
Dog-friendly lake escape with sunroom, high-speed WiFi, water views & central AC

Dog-friendly lake escape with sunroom, high-speed WiFi, water views & central AC

Castleton
When you stay at this vacation home in Bomoseen, you'll be on the waterfront, within a 5-minute drive of Prospect Bay Country Club and Lake Bomoseen.
Opens in a new windowDog-friendly lake escape with sunroom, high-speed WiFi, water views & central AC
Don't see what you're looking for?
See all available properties in Rutland
View all properties
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
827 Holiday Homes
Lowest Price
AU$184
Highest Price
AU$271
Popular accommodation
Traveling with kids? Try this secluded & updated 3-bedroom home close to Okemo, Classic ski home with hot tub, washer/dryer, mountain views, fireplace, & cable, Brand new 2021 Reno of Federal Style House, steps from Downtown Brandon, Quiet Modern Luxury Home w/ Memory Foam Beds, A/C, FAST WiFi and Full Kitchen, Okemo Mountain Lodging, Beautifully renovated with fireplace and coffee bar, Classic VT Ski Chalet - Walkable to Okemo Ski Lift w/Fit Pit & Pool Table, Spacious Vermont Getaway 7 BR/4.5 BA - Close to Skiing - Biking - Golf - Hiking, Dog-friendly lake escape with sunroom, high-speed WiFi, water views & central AC

Top trending hotels in Rutland

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$184 per night from 4 Nov to 5 Nov
AU$184
4 Nov - 5 Nov
includes taxes & fees
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 ...
Opens in a new windowDays Inn by Wyndham Rutland/Killington Area
Comfort Inn Rutland - Killington

Comfort Inn Rutland - Killington

2.5 out of 5
19 Allen St, Rutland, VT
Fully refundableReserve now, pay when you stay
The price is AU$184 per night from 5 Nov to 6 Nov
AU$184
5 Nov - 6 Nov
includes taxes & fees
With a stay at Comfort Inn Rutland - Killington 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 ...
Opens in a new windowComfort Inn Rutland - Killington
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$271 per night from 9 Nov to 10 Nov
AU$271
9 Nov - 10 Nov
includes taxes & fees
Located in Rutland, Best Western Inn & Suites Rutland-Killington is in the mountains, a 3-minute drive from Green Mountain Rock Climbing Center and 5 minutes ...
Opens in a new windowBest Western Inn & Suites Rutland-Killington
Save an average of 15% on thousands of hotels when you're signed in
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$219 per night from 24 Nov to 25 Nov
AU$219
24 Nov - 25 Nov
includes taxes & fees
With a stay at Hampton Inn Rutland in Rutland, you'll be in the business district, just a 4-minute walk from Green Mountain Shopping Plaza and 10 minutes by ...
Opens in a new windowHampton Inn Rutland
Don't see what you're looking for?
See all available properties in Rutland
View all properties
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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.