Top 50 Rutland Vacation Rentals

Houses (412)
Condos (330)
Townhome (68)
Golf rental (793)
Mountain view (598)
Ski rental (329)

Discover popular destinations in and around Rutland

Vermont State Fairgrounds

924 vacation rentals

Paramount Theater

861 vacation rentals

Rutland Regional Medical Center

987 vacation rentals

Pine Hill Park

772 vacation rentals

Norman Rockwell Museum

1,016 vacation rentals

Paramount Theater

861 vacation rentals

Vermont State Fairgrounds

924 vacation rentals

Rutland Regional Medical Center

987 vacation rentals

Pine Hill Park

772 vacation rentals

Norman Rockwell Museum

1,016 vacation rentals

Explore a selection of Rutland vacation rentals

Killington Mountain Ski resort five minutes away
Guests10
Bedrooms2
Bathroom1
Wonderful 4.9 / 5
$160 avg/night
2 beds
1 Bathroom
Guests 10
41 reviews
GREAT WHITE VIEW-SKI ON SKI OFF
Guests12
Bedrooms4
Bathrooms4
Wonderful 4.9 / 5
$512 avg/night
4 beds
4 Bathrooms
Guests 12
13 reviews
Killington Condo with 3 Flat Screen TVs, pool & tennis !
Guests8
Bedrooms2
Bathroom1
Wonderful 4.9 / 5
$140 avg/night
2 beds
1 Bathroom
Guests 8
24 reviews
Killington Getaway In Private Community
Guests10
Bedrooms2
Bathroom1
Wonderful 4.3 / 5
$246 avg/night
2 beds
1 Bathroom
Guests 10
3 reviews
Pond View Condo Near Pico and Killington - Sleeps 5
Guests5
Bedrooms2
Bathroom1
Wonderful 4.6 / 5
$68 avg/night
2 beds
1 Bathroom
Guests 5
34 reviews
Mountain Views Large Family Friendly Ski Luxurious House w/ WIFI...
Guests16
Bedrooms5
Bathrooms3
Wonderful 4.9 / 5
$1,100 avg/night
5 beds
3 Bathrooms
Guests 16
16 reviews
3 Bedroom, 3 Bath Condo at Fox Hollow Village w/ Mountain View
Guests8
Bedrooms3
Bathrooms2
Wonderful 5 / 5
$330 avg/night
3 beds
2 Bathrooms
Guests 8
1 reviews
Spacious Modern Condos at Fox Hollow in Killington VT
Guests6
Bedrooms2
Bathrooms2
Wonderful 4.7 / 5
$190 avg/night
2 beds
2 Bathrooms
Guests 6
7 reviews
Pico Mountain Resort Ski Chalet, Ski-on/Ski-Off, 4BR/2BA
Guests12
Bedrooms4
Bathrooms2
Wonderful 5 / 5
$363 avg/night
4 beds
2 Bathrooms
Guests 12
13 reviews
Mountain Privacy 5 Miles from Pico/Killington with Hot Tub!
Guests8
Bedrooms3
Bathrooms2
Wonderful 5 / 5
$357 avg/night
3 beds
2 Bathrooms
Guests 8
11 reviews
Killington/Pico -- spacious and updated 4 BR home
Guests8
Bedrooms4
Bathrooms4
Wonderful 5 / 5
$1,000 avg/night
4 beds
4 Bathrooms
Guests 8
1 reviews
Come enjoy the beautiful green mountains of Vermont in this...
Guests11
Bedrooms4
Bathrooms2
Wonderful 0 / 5
$514 avg/night
4 beds
2 Bathrooms
Guests 11
Slopeside Private Home at Pico Mountain, pool & fitness center...
Guests10
Bedrooms4
Bathrooms3
Wonderful 5 / 5
$383 avg/night
4 beds
3 Bathrooms
Guests 10
1 reviews
Views of Killington and Pico!
Guests12
Bedrooms5
Bathrooms3
Wonderful 5 / 5
$469 avg/night
5 beds
3 Bathrooms
Guests 12
1 reviews
Bed & Breakfast: The Red Clover Inn and Restaurant - Maggie's
Guests2
Bedroom1
Bathroom1
Wonderful 0 / 5
$165 avg/night
1 bed
1 Bathroom
Guests 2
Bed & Breakfast: Mendon MountainView Lodge - Economy
Guests4
Bedroom1
Bathroom1
Wonderful 0 / 5
$116 avg/night
1 bed
1 Bathroom
Guests 4
Spacious private home away from the hussle and bussle.
Guests10
Bedrooms4
Bathrooms3
Wonderful 0 / 5
$437 avg/night
4 beds
3 Bathrooms
Guests 10
Carriage House Apartment in Central Vermont
Guests2
Bedroom1
Bathroom1
Wonderful 0 / 5
$116 avg/night
1 bed
1 Bathroom
Guests 2
Contemporary Spacious 7br/6.5 bath home near Killington VT
Guests22
Bedrooms7
Bathrooms6
Wonderful 4 / 5
$727 avg/night
7 beds
6 Bathrooms
Guests 22
1 reviews
4 Bedroom 4 Bathroom Luxury Mountain Getaway
Guests12
Bedrooms4
Bathrooms4
Wonderful 0 / 5
$367 avg/night
4 beds
4 Bathrooms
Guests 12
New Lakeside Cottage near Okemo and Killington
Guests5
Bedrooms2
Bathrooms2
Wonderful 4.8 / 5
$175 avg/night
2 beds
2 Bathrooms
Guests 5
33 reviews
Charming Converted Horse Barn
Guests6
Bedrooms4
Bathroom1
Wonderful 4.8 / 5
$106 avg/night
4 beds
1 Bathroom
Guests 6
41 reviews
Beautiful house minutes from Lake Bomoseen - Dogs Welcome
Guests6
Bedrooms3
Bathrooms2
Wonderful 4.8 / 5
$99 avg/night
3 beds
2 Bathrooms
Guests 6
60 reviews
Newly Remodeled 3-Bd, 2-Ba, on Quiet Country Road
Guests6
Bedrooms3
Bathrooms2
Wonderful 5 / 5
$250 avg/night
3 beds
2 Bathrooms
Guests 6
6 reviews
Newly Built Killington Vermont Ski House
Guests14
Bedrooms5
Bathrooms3
Wonderful 5 / 5
$500 avg/night
5 beds
3 Bathrooms
Guests 14
15 reviews
Beautiful Killington Vermont Ski House located on VAST snowmobile...
Guests14
Bedrooms5
Bathrooms3
Wonderful 5 / 5
$221 avg/night
5 beds
3 Bathrooms
Guests 14
15 reviews
Hot Tub Home in Wooded Setting
Guests13
Bedrooms5
Bathrooms2
Wonderful 4.9 / 5
$303 avg/night
5 beds
2 Bathrooms
Guests 13
43 reviews
SKI KILLINGTON $99 Avg/nt. 2 Br 1 &1/2 B Four Season Resor...
Guests6
Bedrooms2
Bathroom1
Wonderful 4.5 / 5
$156 avg/night
2 beds
1 Bathroom
Guests 6
22 reviews
Okemo Mountain - Family Affordable Winter & Summer
Guests6
Bedrooms2
Bathrooms2
Wonderful 4.8 / 5
$100 avg/night
2 beds
2 Bathrooms
Guests 6
32 reviews
Lakefront house, with huge two tiered deck and dock!
Guests10
Bedrooms4
Bathrooms2
Wonderful 4.6 / 5
$212 avg/night
4 beds
2 Bathrooms
Guests 10
17 reviews
Luxurious, Secluded, Ski Chalet, w/ Country Decor & Hot Tub Near...
Guests14
Bedrooms4
Bathrooms3
Wonderful 4.9 / 5
$224 avg/night
4 beds
3 Bathrooms
Guests 14
46 reviews
Super-Comfy Immaculate Studio at the base of Killington Mountain
Guests4
Bedroom1
Bathroom1
Wonderful 4.9 / 5
$151 avg/night
1 bed
1 Bathroom
Guests 4
18 reviews
Splendid Green Mountain Retreat with Views & Pond
Guests12
Bedrooms4
Bathrooms3
Wonderful 4.8 / 5
$166 avg/night
4 beds
3 Bathrooms
Guests 12
15 reviews
Best Spot on Pauline! (Book now for fall & winter! 5 mins from...
Guests8
Bedrooms4
Bathrooms3
Wonderful 4.9 / 5
$330 avg/night
4 beds
3 Bathrooms
Guests 8
31 reviews
LARGEST BIG GROUP SKI ON & OFF HOME FOR RENT WITH PARKING FOR OVER...
Guests26
Bedrooms7
Bathrooms5
Wonderful 4.8 / 5
$748 avg/night
7 beds
5 Bathrooms
Guests 26
5 reviews
Affordable country living in beautiful South Woodstock.
Guests10
Bedrooms4
Bathrooms2
Wonderful 5 / 5
$278 avg/night
4 beds
2 Bathrooms
Guests 10
49 reviews
Killington 2 Bdrm Condo with Health Spa and Pool
Guests6
Bedrooms2
Bathrooms2
Wonderful 4.8 / 5
$185 avg/night
2 beds
2 Bathrooms
Guests 6
41 reviews
Woodstock Four Season Family Estate Has It All!
Guests12
Bedrooms6
Bathrooms2
Wonderful 5 / 5
$636 avg/night
6 beds
2 Bathrooms
Guests 12
62 reviews
Winter On The Slopes, Summer On The Lake! 3 Br, 2 Baths, Sleeps 8
Guests8
Bedrooms3
Bathrooms2
Wonderful 4.8 / 5
$316 avg/night
3 beds
2 Bathrooms
Guests 8
25 reviews
Amazing Mountain Condo - Outdoor pool, Walk to Golf, Mountain...
Guests4
Bedroom1
Bathroom1
Wonderful 4.8 / 5
$210 avg/night
1 bed
1 Bathroom
Guests 4
28 reviews
Ski House on Lake Rescue, 3.5 Miles from Okemo
Guests8
Bedrooms4
Bathrooms3
Wonderful 4.8 / 5
$254 avg/night
4 beds
3 Bathrooms
Guests 8
19 reviews
Waterfront home with stunning views on Lake Bomoseen
Guests6
Bedrooms3
Bathrooms2
Wonderful 4.7 / 5
$207 avg/night
3 beds
2 Bathrooms
Guests 6
12 reviews
Mountain Top Home With Unequaled Views/ Minutes To Okemo/ Sleeps 14
Guests14
Bedrooms4
Bathrooms4
Wonderful 4.9 / 5
$638 avg/night
4 beds
4 Bathrooms
Guests 14
39 reviews
NEW - Base Lodge - Downtown on shuttle route - 10 BR, 5 Bath...
Guests34
Bedrooms10
Bathrooms5
Wonderful 4.9 / 5
$529 avg/night
10 beds
5 Bathrooms
Guests 34
19 reviews
Log Cabin - Lake Pauline Waterfront - 2 Miles To Okemo...
Guests8
Bedrooms3
Bathrooms2
Wonderful 5 / 5
$230 avg/night
3 beds
2 Bathrooms
Guests 8
23 reviews
Artisan Farmhouse for Groups! - 7 Minutes to Killington Skyeship...
Guests24
Bedrooms7
Bathrooms4
Wonderful 5 / 5
$639 avg/night
7 beds
4 Bathrooms
Guests 24
25 reviews
2 Bed,2 Bath Condo at The Woods Resort and Spa at Killington.
Guests4
Bedrooms2
Bathrooms2
Wonderful 4.3 / 5
$171 avg/night
2 beds
2 Bathrooms
Guests 4
6 reviews
Luxury 1 Bed Condo with Indoor (and Outdoor) Swimming Pools...
Guests4
Bedroom1
Bathroom1
Wonderful 4.7 / 5
$103 avg/night
1 bed
1 Bathroom
Guests 4
90 reviews
Waterfront Home on Lake Bomoseen
Guests6
Bedrooms3
Bathroom1
Wonderful 4.5 / 5
$157 avg/night
3 beds
1 Bathroom
Guests 6
19 reviews
Cozy Ski Retreat close to Okemo doubles as a Wonderful Lakefront...
Guests12
Bedrooms3
Bathrooms3
Wonderful 4.9 / 5
$471 avg/night
3 beds
3 Bathrooms
Guests 12
33 reviews

Rutland Vacation Rentals

Discover popular destinations in and around Rutland

Killington Mountain Ski resort five minutes away

GREAT WHITE VIEW-SKI ON SKI OFF

Killington Condo with 3 Flat Screen TVs, pool & tennis !

Killington Getaway In Private Community

Pond View Condo Near Pico and Killington - Sleeps 5

Mountain Views Large Family Friendly Ski Luxurious House w/ WIFI...

3 Bedroom, 3 Bath Condo at Fox Hollow Village w/ Mountain View

Spacious Modern Condos at Fox Hollow in Killington VT

Pico Mountain Resort Ski Chalet, Ski-on/Ski-Off, 4BR/2BA

Mountain Privacy 5 Miles from Pico/Killington with Hot Tub!

Killington/Pico -- spacious and updated 4 BR home

Come enjoy the beautiful green mountains of Vermont in this...

Slopeside Private Home at Pico Mountain, pool & fitness center...

Views of Killington and Pico!

Bed & Breakfast: The Red Clover Inn and Restaurant - Maggie's

Bed & Breakfast: Mendon MountainView Lodge - Economy

Spacious private home away from the hussle and bussle.

Carriage House Apartment in Central Vermont

Contemporary Spacious 7br/6.5 bath home near Killington VT

4 Bedroom 4 Bathroom Luxury Mountain Getaway

New Lakeside Cottage near Okemo and Killington

Charming Converted Horse Barn

Beautiful house minutes from Lake Bomoseen - Dogs Welcome

Newly Remodeled 3-Bd, 2-Ba, on Quiet Country Road

Newly Built Killington Vermont Ski House

Beautiful Killington Vermont Ski House located on VAST snowmobile...

Hot Tub Home in Wooded Setting

SKI KILLINGTON $99 Avg/nt. 2 Br 1 &1/2 B Four Season Resor...

Okemo Mountain - Family Affordable Winter & Summer

Lakefront house, with huge two tiered deck and dock!

Luxurious, Secluded, Ski Chalet, w/ Country Decor & Hot Tub Near...

Super-Comfy Immaculate Studio at the base of Killington Mountain

Splendid Green Mountain Retreat with Views & Pond

Best Spot on Pauline! (Book now for fall & winter! 5 mins from...

LARGEST BIG GROUP SKI ON & OFF HOME FOR RENT WITH PARKING FOR OVER...

Affordable country living in beautiful South Woodstock.

Killington 2 Bdrm Condo with Health Spa and Pool

Woodstock Four Season Family Estate Has It All!

Winter On The Slopes, Summer On The Lake! 3 Br, 2 Baths, Sleeps 8

Amazing Mountain Condo - Outdoor pool, Walk to Golf, Mountain...

Ski House on Lake Rescue, 3.5 Miles from Okemo

Waterfront home with stunning views on Lake Bomoseen

Mountain Top Home With Unequaled Views/ Minutes To Okemo/ Sleeps 14

NEW - Base Lodge - Downtown on shuttle route - 10 BR, 5 Bath...

Log Cabin - Lake Pauline Waterfront - 2 Miles To Okemo...

Artisan Farmhouse for Groups! - 7 Minutes to Killington Skyeship...

2 Bed,2 Bath Condo at The Woods Resort and Spa at Killington.

Luxury 1 Bed Condo with Indoor (and Outdoor) Swimming Pools...

Waterfront Home on Lake Bomoseen

Cozy Ski Retreat close to Okemo doubles as a Wonderful Lakefront...