Rutland Holiday Houses | Expedia.co.nz

Rutland Holiday Homes
Vermont
United States of America
Holiday Homes
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A winding road surrounded by autumn foliage.

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Our top choices for Rutland holiday homes

A modern living room with a sofa, a round coffee table, and a chair. There is a painting on the wall and a door leading to another room.

A bedroom with a bed, curtains, and a window.

A modern kitchen with a dishwasher, a coffee maker, and a dining area with a wooden table set for two.

1. Cozy Rutland Retreat

Cozy Rutland Retreat

Rutland

9.8 out of 10, Exceptional, (16 reviews)

9.8/10

Exceptional

(16 reviews)

"The location was perfect, the property is very well maintained and comfortable. I would highly recommend this place!"

Valerie

The price is NZ$313

NZ$313

includes taxes & fees

8 Sept - 9 Sept

Cozy Rutland Retreat

A modern kitchen with a black stove, a red microwave, and a stainless steel sink. There are two black chairs and a black table.

A living room with a pool table, a leather sofa, and a billiards cue rack.

A view through a window with a metal screen, a grassy area, a wooden fence, and a hill in the background.

A residential property with a well-maintained lawn, a large flowering tree, and a house with a porch.

2. new 2 bedroom close to killington and bike trails this is pet ok downstairs unit

new 2 bedroom close to killington and bike trails this is pet ok downstairs unit

Mendon

9.8 out of 10, Exceptional, (6 reviews)

9.8/10

Exceptional

(6 reviews)

"Very pretty property, wish we could have spent more time there. Getting in and out was easy and there were plenty of options for food in town just a few minutes away. Great stay."

Aurore H.

The price is NZ$393

NZ$393

includes taxes & fees

7 Sept - 8 Sept

new 2 bedroom close to killington and bike trails this is pet ok downstairs unit

A spacious kitchen with a large island, wooden dining table, and chairs. There are multiple windows providing natural light and views of the outdoors.

A modern kitchen with a central island, bar stools, a stove, and a refrigerator.

A covered outdoor seating area with a wooden railing, surrounded by snow-covered trees.

A modern kitchen with a wooden counter, bar stools, and a black leather couch.

3. large ski ranch hot tub close to killington pets ok

large ski ranch hot tub close to killington pets ok

Mendon

9.2 out of 10, Wonderful, (5 reviews)

9.2/10

Wonderful

(5 reviews)

"The hot tub was great after a day of skiing."

Callison A.

The price is NZ$801

NZ$801

includes taxes & fees

7 Sept - 8 Sept

large ski ranch hot tub close to killington pets ok

A modern kitchen with white cabinets, stainless steel appliances, a window with a view, and a 'GATHER' sign above the window.

A two-story house with a front porch and a garage.

A modern living room with a wooden dining table, dark brown leather sofa, and a patterned rug.

A spacious living area with a wooden bench, a dining table with chairs, a kitchen in the background, and a view of the outdoors through a window.

4. Relaxing Rutland Retreat Near Skiing, Dining & Hiking

Relaxing Rutland Retreat Near Skiing, Dining & Hiking

Rutland

The price is NZ$1,219

NZ$1,219

includes taxes & fees

8 Sept - 9 Sept

Relaxing Rutland Retreat Near Skiing, Dining & Hiking

5. 4BR Home | Walk Downtown Rutland + Trails

4BR Home | Walk Downtown Rutland + Trails

Rutland

10.0 out of 10, Exceptional, (6 reviews)

10/10

Exceptional

(6 reviews)

"House was clean, organized and spacious. Great location as well, close to grocery, gas and restaurants. Host answered questions quickly. "

Dominic C.

The price is NZ$673

NZ$673

includes taxes & fees

3 Sept - 4 Sept

4BR Home | Walk Downtown Rutland + Trails

A cozy living room with a fireplace, a sofa, and a coffee table.

An indoor swimming pool with a wooden ceiling and large windows.

A two-story house with a covered porch and a chimney.

A bedroom with a bed, two bedside lamps, a nightstand, and a window with blinds.

6. The Woods Resort Killington - 2B Townhouse with Spa, Pool & Jacuzzi

The Woods Resort Killington - 2B Townhouse with Spa, Pool & Jacuzzi

2.0 star property

The Woods

The price is NZ$653

NZ$653

includes taxes & fees

13 Sept - 14 Sept

The Woods Resort Killington - 2B Townhouse with Spa, Pool & Jacuzzi

A spacious living room with wooden floors, a high ceiling with exposed beams, a dining area with a table and chairs, and large windows offering a view of the outdoors.

A spacious living area with a wooden staircase, a dining area, and large windows providing natural light.

A spacious living area with wooden flooring, a leather chair, a bookshelf, and a television.

A two-story house with a balcony, surrounded by trees and a grassy yard.

7. Killington Retreat | Deck-Fire Pit-Mountain Views!

Killington Retreat | Deck-Fire Pit-Mountain Views!

Clarendon

9.2 out of 10, Wonderful, (5 reviews)

9.2/10

Wonderful

(5 reviews)

"The living area is bigger than we expected, and we loved watching the horses next door. It's a short drive to downtown Rutland, and it's quiet. "

Ahmad H.

The price is NZ$656

NZ$656

includes taxes & fees

20 Sept - 21 Sept

Killington Retreat | Deck-Fire Pit-Mountain Views!

A living room with a sofa, coffee table, and chairs, a television mounted on the wall, and a kitchen area with a stone wall and wooden beams.

A compact kitchen with a central island, white cabinetry, and stainless steel appliances.

A living room with a beige sofa set, a wooden coffee table, and a lamp. There are framed pictures on the wall and a window with curtains.

8. Luxury Condo Tucked in the Heart of Killington

Luxury Condo Tucked in the Heart of Killington

Killington

The price is NZ$462

NZ$462

includes taxes & fees

15 Sept - 16 Sept

Luxury Condo Tucked in the Heart of Killington

A modern living room with a flat-screen TV, grey sofas, a dining table with chairs, and a large window with a view of greenery.

A modern living room with a sofa, coffee table, and a dining area with chairs and a table.

A compact kitchen with wooden cabinets, stainless steel appliances, and a checkered floor mat.

A neatly made bed with a checkered bedspread, a bedside lamp, and a shelf with decorative items.

9. CozyDen - AC, Bike to Mountain, Porch!

CozyDen - AC, Bike to Mountain, Porch!

Killington

9.4 out of 10, Exceptional, (3 reviews)

9.4/10

Exceptional

(3 reviews)

"Place was clean and location was great"

Berni H.

The price is NZ$458

NZ$458

includes taxes & fees

7 Sept - 8 Sept

CozyDen - AC, Bike to Mountain, Porch!

A cozy living room with a sectional sofa, a coffee table, and a fireplace.

A spacious living area with a fireplace, a television, and a dining area with natural light.

A spacious dining area with a dark wooden table, white chairs, and woven placemats.

A kitchen with a large island, bar stools, and a view of the outdoors.

10. Breakaway House by Killington Vacation Rentals

Breakaway House by Killington Vacation Rentals

3.0 star property

Killington

The price is NZ$1,394

NZ$1,394

includes taxes & fees

3 Sept - 4 Sept

Breakaway House by Killington Vacation Rentals

A living room with a wooden table, two chairs, a leather sofa, a coffee table, and a brick wall.

A two-story house with a deck, surrounded by a snowy landscape and trees.

A bedroom with two beds, a dresser, a mirror, a door, and a small table.

A bathroom with a shower, toilet, sink, and cabinets.

11. Liquid Lodge Lower: 2BR Duplex near Killington with 4 PM Checkout

Liquid Lodge Lower: 2BR Duplex near Killington with 4 PM Checkout

2.0 star property

Killington

The price is NZ$816

NZ$816

includes taxes & fees

3 Sept - 4 Sept

Liquid Lodge Lower: 2BR Duplex near Killington with 4 PM Checkout

A cozy cabin interior with a stone fireplace, leather sofas, and large windows offering a view of the forest.

A cozy room with a leather sofa, a recliner, and a small table. Large windows offer a view of the outdoors.

A kitchen with wooden cabinets, a granite countertop, a microwave, three black stools, and a window with a forest view.

A covered deck with outdoor seating and a barbecue grill.

12. Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore

Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore

Mt Holly

9.8 out of 10, Exceptional, (42 reviews)

9.8/10

Exceptional

(42 reviews)

"This house has great hang out space and plenty of space for a big family!"

Cheri V.

The price is NZ$824

NZ$824

includes taxes & fees

3 Sept - 4 Sept

Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore

A two-story cabin with a covered porch, a hot tub, and a fire pit area.

A bedroom with a bed, dresser, bedside tables, and artwork on the walls.

13. 25 Rocky Ridge Rd - Killington Retreat: Group Ski House! Close to Mountain! Hot Tub.

25 Rocky Ridge Rd - Killington Retreat: Group Ski House! Close to Mountain! Hot Tub.

Killington

9.6 out of 10, Exceptional, (70 reviews)

9.6/10

Exceptional

(70 reviews)

"Great stay. Killer location!"

Matthew P.

The price is NZ$1,277

NZ$1,277

includes taxes & fees

3 Sept - 4 Sept

25 Rocky Ridge Rd - Killington Retreat: Group Ski House! Close to Mountain! Hot Tub.

A cozy living room with a stone fireplace, a large sectional sofa, and a wooden ceiling.

A wooden staircase with a metal handrail and a view of the outdoors through a window.

A hot tub on a wooden deck with a view of a forest.

14. The Tower House | Hot Tub | Firepit | Dog-Friendly

The Tower House | Hot Tub | Firepit | Dog-Friendly

Killington

9.0 out of 10, Wonderful, (2 reviews)

9.0/10

Wonderful

(2 reviews)

"Great place, near everything and great customer service!!"

Patrick B.

The price is NZ$1,116

NZ$1,116

includes taxes & fees

3 Sept - 4 Sept

The Tower House | Hot Tub | Firepit | Dog-Friendly

A modern living room with a red sectional sofa, a round coffee table, wooden ceiling beams, a kitchen area, and a balcony with a view of trees.

A dining area with a wooden table and chairs, large windows, and a ceiling with recessed lighting.

A building with a red exterior, a white door, and a wooden porch with steps leading to it.

A modern kitchen with wooden cabinets, a stainless steel refrigerator, and a large island with bar stools.

15. NEW! Smart 3BR Basecamp w/ Hot Tub, AC, EV Charger & Flat Parking

NEW! Smart 3BR Basecamp w/ Hot Tub, AC, EV Charger & Flat Parking

North Sherburne

The price is NZ$1,059

NZ$1,059

includes taxes & fees

3 Sept - 4 Sept

NEW! Smart 3BR Basecamp w/ Hot Tub, AC, EV Charger & Flat Parking

A spacious living area with a red sectional sofa, a wooden dining table, and a kitchen in the background.

A spacious kitchen with wooden cabinets, a stainless steel refrigerator, and a large island with stools.

A modern kitchen with wooden cabinets, a large island with stools, and stainless steel appliances.

A spacious living area with a red sectional sofa, a brick fireplace, and a dining table with chairs.

16. Experience the charm of Peak Hill Home, Entire home in Killington/Pittsfield, Vermont

Experience the charm of Peak Hill Home, Entire home in Killington/Pittsfield, Vermont

North Sherburne

10.0 out of 10, Exceptional, (1 review)

10/10

Exceptional

(1 review)

"Peak Hill, is a lovely and very clean home, with a fully stocked kitchen and comfy beds. This home is exactly as the pictures that are shown. We had a very small issue with the door lock (battery), called and it was fixed right away, wonderful service. The owner, Geri, we had the opportunity to meet and she is very kind and a pleasure to speak with. We travel alot and l bring pretty much my own kitchen, pillow...... with me where ever l go. However, l would of been fine using all at this...

Essa R.

The price is NZ$1,075

NZ$1,075

includes taxes & fees

3 Sept - 4 Sept

Experience the charm of Peak Hill Home, Entire home in Killington/Pittsfield, Vermont

A cabin with a wooden deck, surrounded by lush greenery and a garden with purple flowers.

A modern kitchen with white cabinets, stainless steel appliances, a marble countertop, and wooden stools.

A modern living room with a fireplace, leather sofas, and a stone accent wall.

A two-story house with a stone facade, a wooden deck, and a grassy yard with outdoor seating.

17. Fun In Fun Out Lower: 3BR with Den, Sauna and Sheltered Hot Tub

Fun In Fun Out Lower: 3BR with Den, Sauna and Sheltered Hot Tub

Killington

10.0 out of 10, Exceptional, (1 review)

10/10

Exceptional

(1 review)

"Such an awesome place! The booking/check-in process was seamless and the location cannot be beat! Will definitely be booking again. "

Catherine S.

The price is NZ$1,072

NZ$1,072

includes taxes & fees

3 Sept - 4 Sept

Fun In Fun Out Lower: 3BR with Den, Sauna and Sheltered Hot Tub

A two-story house with a covered porch and a gabled roof.

A living room with a Christmas tree, a flat-screen TV, and a fireplace.

A bedroom with a bed, a ceiling fan, a window with blinds, a nightstand with a lamp, and a wardrobe.

A living room with a brown leather sofa, a wooden coffee table, a TV, and speakers.

18. Historic Victorian Estate 4 Bed 2 Bath Fast Wifi

Historic Victorian Estate 4 Bed 2 Bath Fast Wifi

Fair Haven

9.0 out of 10, Wonderful, (34 reviews)

9.0/10

Wonderful

(34 reviews)

"Very nice house to stay in Fair Haven VT. Worked perfectly for us and beautiful area. Clean and has everything you need."

Amy G.

The price is NZ$590

NZ$590

includes taxes & fees

7 Sept - 8 Sept

Historic Victorian Estate 4 Bed 2 Bath Fast Wifi

A cozy living room with a stone fireplace, a sofa set, and a dining table.

An indoor swimming pool with clear lanes, wooden beams, and a view of greenery outside.

A dining table set for six with white plates, clear glasses, and cutlery, in a room with a stone wall, a mounted TV, and a cross on the wall.

A patio with two wicker chairs, a fire pit, and a small garden with rocks and plants.

19. Bearmont- Pool, HotTub, FirePit, AC, Gym, Sauna

Bearmont- Pool, HotTub, FirePit, AC, Gym, Sauna

The Woods

10.0 out of 10, Exceptional, (7 reviews)

10/10

Exceptional

(7 reviews)

"Great location and a great place. Felt right at home"

Tyler B.

The price is NZ$1,101

NZ$1,101

includes taxes & fees

3 Sept - 4 Sept

Bearmont- Pool, HotTub, FirePit, AC, Gym, Sauna

A cozy living room with a brick fireplace, comfortable seating, and large windows offering a view of the outdoors.

A kitchen with wooden cabinets, a black stove, a refrigerator, and a window with a view of trees.

A red cabin with a porch, surrounded by trees and a dirt path leading to it.

A living room with a brown sofa, a wooden coffee table, and a patterned rug.

20. Cozy Vermont House Near Killington and Woodstock. Mountainside. Close to Slopes.

Cozy Vermont House Near Killington and Woodstock. Mountainside. Close to Slopes.

Bridgewater

8.8 out of 10, Excellent, (3 reviews)

8.8/10

Excellent

(3 reviews)

"Great place for a ski weekend"

Kathryn F.

The price is NZ$1,179

NZ$1,179

includes taxes & fees

3 Sept - 4 Sept

Cozy Vermont House Near Killington and Woodstock. Mountainside. Close to Slopes.

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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Top Rutland Hotel Reviews

Days Inn by Wyndham Rutland/Killington Area

10/10 Excellent

"Very quiet, great ac. Pool was great"

Nathanael 2-night trip

Posted 7 hours ago

Days Inn by Wyndham Rutland/Killington Area

Hampton Inn Rutland

10/10 Excellent

"Great hotel, not there long enough to use amenities. Very expensive for area we thought. But definitely nice!"

Raymond 1-night trip

Posted 8 hours ago

Hampton Inn Rutland

On The River Inn

10/10 Excellent

"We had a wonderful stay at On the River. The room was large, clean, and very quiet. It's a short, quick drive into town. The staff was pleasant and helpful. A good choice when staying near Woodstock."

Marc 1-night trip

Posted 12 hours ago

On The River Inn

Woodstock Inn & Resort

10/10 Excellent

"Our room was beautiful, clean, and quiet. The bed was comfortable, and the amenities in the bathroom were a real indulgence."

Mary Beth 1-night trip

Posted 13 hours ago

Woodstock Inn & Resort

The Shire Woodstock

10/10 Excellent

"Great Location. great views of the river, lawn and firepits for relaxing. Rooms recently redone and well done."

Timothy 2-night trip

Posted 16 hours ago

The Shire Woodstock

The Jackson

10/10 Excellent

"Love this B&B - very well located, the food is amazing and the bedrooms are very comfy! Highly recommend!"

Yanil 1-night trip

Posted 17 hours ago

The Jackson

Comfort Inn Rutland - Killington

8/10 Good

"A good solid hotel."

Andrew C 2-night trip

Posted 19 hours ago

Comfort Inn Rutland - Killington

Killington Mountain Lodge, Tapestry Collection by Hilton

10/10 Excellent

"A great place to stay when you’re visiting Killington!"

Mason 3-night trip

Posted 19 hours ago

Killington Mountain Lodge, Tapestry Collection by Hilton

Best Western Inn & Suites Rutland-Killington

10/10 Excellent

"Staff are always very friendly and welcoming. The rooms are immaculate and the breakfasts are very nice"

KATHLEEN 2-night trip

Posted 1 day ago

Best Western Inn & Suites Rutland-Killington

Find out more about Rutland

Rutland Holiday Homes information

Number of reviews	201
Accommodation	880 Holiday Homes
Lowest Price	NZ$313
Highest Price	NZ$1,394

Explore a world of travel with Expedia

More ways to book

Book Holiday Homes in Rutland on Expedia.com

Holiday Homes in Rutland

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Rutland holiday homes

1. Cozy Rutland Retreat

2. new 2 bedroom close to killington and bike trails this is pet ok downstairs unit

3. large ski ranch hot tub close to killington pets ok

4. Relaxing Rutland Retreat Near Skiing, Dining & Hiking

5. 4BR Home | Walk Downtown Rutland + Trails

6. The Woods Resort Killington - 2B Townhouse with Spa, Pool & Jacuzzi

7. Killington Retreat | Deck-Fire Pit-Mountain Views!

8. Luxury Condo Tucked in the Heart of Killington

9. CozyDen - AC, Bike to Mountain, Porch!

10. Breakaway House by Killington Vacation Rentals

11. Liquid Lodge Lower: 2BR Duplex near Killington with 4 PM Checkout

12. Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore

13. 25 Rocky Ridge Rd - Killington Retreat: Group Ski House! Close to Mountain! Hot Tub.

14. The Tower House | Hot Tub | Firepit | Dog-Friendly

15. NEW! Smart 3BR Basecamp w/ Hot Tub, AC, EV Charger & Flat Parking

16. Experience the charm of Peak Hill Home, Entire home in Killington/Pittsfield, Vermont

17. Fun In Fun Out Lower: 3BR with Den, Sauna and Sheltered Hot Tub

18. Historic Victorian Estate 4 Bed 2 Bath Fast Wifi

19. Bearmont- Pool, HotTub, FirePit, AC, Gym, Sauna

20. Cozy Vermont House Near Killington and Woodstock. Mountainside. Close to Slopes.

Find holiday rentals that suit your style

Top Rutland Hotel Reviews

Days Inn by Wyndham Rutland/Killington Area

Find out more about Rutland

Rutland Holiday Homes information

Explore a world of travel with Expedia