Rutland Vacation Homes

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Our top choices for Rutland holiday homes

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

1. Cozy Rutland Retreat

Rutland

Susan E.

HK$1,315 total

includes taxes & fees

16 Nov - 17 Nov

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

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

Mendon

Aurore H.

HK$1,728 total

includes taxes & fees

9 Nov - 10 Nov

A house with a wooden deck, solar panels, and a well-maintained garden.

3. Kingsley Homestead - 2 Bedroom retreat

Rutland

HK$1,563 total

includes taxes & fees

19 Nov - 20 Nov

A house with a covered deck, a barbecue grill, and a wooden pergola.

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

Mendon

Callison A.

HK$3,252 total

includes taxes & fees

15 Nov - 16 Nov

A dining area with a wooden table, four chairs, a coffee maker, and a trash can.

5. Chittenden Farmhouse: Historic 4BR/2BA, 20 Min to Killington, 7 Min to Mountaintop Resort

Chittenden

"Loved this stay - the farmhouse is authentic and oozes charm! Everything about this stay was easy - 20min drive to the slopes, 15 min to downtown Rutland, and an extremely well-equipped house to easily accommodate the six of us. Superb communication from the host both prior to and during our stay (promptly answered several questions for us). If you want a vintage farmhouse feel as opposed to a modern condo-style stay, this is the place for you!"

Carl P.

HK$4,074 total

includes taxes & fees

12 Nov - 13 Nov

A modern kitchen with a large island, white cabinetry, and a stainless steel refrigerator.

6. Susan Lane Hideaway: 4BR/4.5BA Renovated Home. Close to skiing and town.

Rutland

Matthew T.

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

7. Relaxing Rutland Retreat Near Skiing, Dining & Hiking

Rutland

HK$5,479 total

includes taxes & fees

13 Nov - 14 Nov

A hallway with a wooden wall, a white door, and a wooden staircase.

8. 4BR Home | Walk Downtown Rutland + Trails

Rutland

Dominic C.

HK$2,842 total

includes taxes & fees

10 Nov - 11 Nov

A rustic cabin with a stone fire pit, wooden deck, and a chimney.

9. Forest Mountain Ski Retreat. 20 min to Killington/14 to Pico.

Mendon

Heidi S.

A kitchen with white cabinetry, a stainless steel refrigerator, a coffee maker, and a dining area with two chairs.

10. Luxury Condo Tucked in the Heart of Killington

Killington

"We were very surprised. The accommodation's well worth the amount we paid. I was surprised how from the start to the close of our Anniversary get away It was such an easygoing experience. The host left fresh towels and bedding linens. The host kept in contact the entire way booking this condo. It was roomy nice Quiet!! I loved the privacy yet close to everything Killington has to offer. Our anniversary was special as we went with the host recommendation for a local resturaunt the Garlic. We have...

Melinda D.

HK$2,031 total

includes taxes & fees

9 Nov - 10 Nov

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.

11. CozyDen- Fireplace, Ski Off/ Shuttle On

Killington

Berni H.

HK$2,104 total

includes taxes & fees

9 Nov - 10 Nov

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

12. Liquid Lodge Lower: 2BR Duplex near Killington with 1 PM Checkout

Killington

HK$3,593 total

includes taxes & fees

9 Nov - 10 Nov

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

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

North Sherburne

"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.

HK$4,798 total

includes taxes & fees

9 Nov - 10 Nov

A wooden interior with a bench and shelves, a door with a handle, and a tiled floor.

14. The Outpost Double | Modern 2BR Ground Level Duplex | Exclusive Ski Deals

Killington

Gifford F.

HK$3,858 total

includes taxes & fees

9 Nov - 10 Nov

A hallway with a wooden beam ceiling, a door with a frosted glass panel, and a view of a living room with a sofa and a table.

15. Cozy 2BR Mountain Retreat Near Killington Resort - Pet Friendly w/ Fireplace

Killington

Smriti

HK$4,338 total

includes taxes & fees

9 Nov - 10 Nov

A bedroom with a bed, bedside table, lamp, dresser, mirror, and a painting on the wall.

16. Cozy 3BR, 2-Story Retreat with Hot Tub, Pet Friendly, Deck, Grill, Fire Table, 5 min to Killington

Killington

Sarah G.

HK$3,758 total

includes taxes & fees

9 Nov - 10 Nov

A red house with a gravel driveway and lush greenery.

17. The Coolidge Barn | Game Room, Firepit & Mountain Views | Sleeps 6

Plymouth

HK$4,871 total

includes taxes & fees

9 Nov - 10 Nov

A spacious living room with a fireplace, a television, and a large window.

18. 4BR Killington Home Perfect for Families, Pet-Friendly

North Sherburne

Christina V.

HK$5,554 total

includes taxes & fees

9 Nov - 10 Nov

A kitchen with granite countertops, stainless steel appliances, wooden cabinets, and a large island with seating.

19. Slopeside Estate Guesthouse: Hot tub, AC, Grill

Killington

HK$7,245 total

includes taxes & fees

9 Nov - 10 Nov

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

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

The Woods

HK$2,732 total

includes taxes & fees

9 Nov - 10 Nov

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Top Rutland Hotel Reviews

Mountain Meadows Lodge

10/10 Excellent

"I enjoyed my time so much, the staff were phenomenal. There were so many fun, family friendly activities. I also enjoyed the delicious breakfast. I will definitely return for an extended stay!! Parking was convenient & close, and the whole place was immaculately clean & fresh. I cannot wait for the next visit."

Woodstock Inn & Resort

10/10 Excellent

"Fantastic stay at Woodstock Inn this week! The room and property were spotless, and the staff was incredibly kind and welcoming. The spa was beautiful, the food at Red Rooster was excellent, and the athletic center, pool, and hot tub were all great. The entire property has a quiet, peaceful atmosphere that makes it easy to relax and unwind. Would absolutely recommend!"

Emrose Luxury Cabins

8/10 Good

"The cabins are new and well maintained. There are pots and pans and spatulas but incredibly no coffee maker. I don’t believe I’ve ever stayed in a room at any price point without a coffee maker. Also, the bed is up against a wall so you have to choose who has to crawl in and out of the bed to go to the bathroom, get a glass of water, etc. Not fun. There was also no contact information for management, so when we couldn’t figure out how to get the heater or fireplace working, we had to chat with Hotels.com who claimed our room did not have heat. Really? Vermont in the fall? Are you kidding me? After I almost lost my mind, they had someone from hotel management call me and instruct me how to turn the heat on. He was very nice and solved the problem, but how about providing contact information of someone on premises if there is an issue? The place is fairly new, and I like the concept, but they have a few things to iron out before they are ready for prime time. Let’s start with an $25 coffee maker in every room. Is that too much to ask? And Hotels.com really needs to get their chat proficiency together…."

Quality Inn Rutland - Killington

10/10 Excellent

"I had a great experience. It is classic Vermont. This giant (friendly) dog met me behind front desk. The desk clerk was a pretty rustic character. He had been on duty 48 hours, but he was so friendly and helpful. The poor guy was asleep in the desk chair when I went to check out but he was all about service when I woke him up. I slept better than I do at home. Price was right and I would stay there again."

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