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$1,299 total

includes taxes & fees

22 Nov - 23 Nov

A small, enclosed room with wooden walls and a single electric heater on a stone base.

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

Mendon

Aurore H.

HK$2,188 total

includes taxes & fees

16 Nov - 17 Nov

A house with a wooden deck, a pink flamingo decoration, and a small garden with green plants.

3. Kingsley Homestead - 2 Bedroom retreat

Rutland

HK$1,565 total

includes taxes & fees

23 Nov - 24 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$4,044 total

includes taxes & fees

16 Nov - 17 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$4,912 total

includes taxes & fees

16 Nov - 17 Nov

A modern kitchen with white cabinetry, a stainless steel refrigerator, and a wooden dining table.

6. Relaxing Rutland Retreat Near Skiing, Dining & Hiking

Rutland

HK$5,483 total

includes taxes & fees

16 Nov - 17 Nov

A modern kitchen with white cabinets, a central island, pendant lighting, and a rustic wooden ceiling.

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

Rutland

Matthew T.

HK$7,614 total

includes taxes & fees

16 Nov - 17 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$2,844 total

includes taxes & fees

16 Nov - 17 Nov

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

9. 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$1,935 total

includes taxes & fees

23 Nov - 24 Nov

A kitchen with a wood stove, microwave, and wooden cabinets.

10. CozyDen- Fireplace, Ski Off/ Shuttle On

Killington

Berni H.

HK$2,106 total

includes taxes & fees

16 Nov - 17 Nov

A two-story house with a porch, a chimney, and a small garden.

11. Historic Victorian Estate 4 Bed 2 Bath Fast Wifi

Fair Haven

Natalie B.

HK$2,270 total

includes taxes & fees

16 Nov - 17 Nov

A residential building with a white exterior, a grey roof, and a number '304' sign.

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

The Woods

HK$2,895 total

includes taxes & fees

16 Nov - 17 Nov

An outdoor deck with a fire pit and wicker furniture.

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$5,505 total

includes taxes & fees

16 Nov - 17 Nov

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

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

Killington

HK$4,235 total

includes taxes & fees

16 Nov - 17 Nov

A two-story house with a stone facade, a large garage, and a gravel driveway.

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

Killington

HK$7,717 total

includes taxes & fees

16 Nov - 17 Nov

A hot tub in a lush garden with a wooden deck and stairs leading to a cabin.

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

Killington

Sarah G.

HK$4,433 total

includes taxes & fees

16 Nov - 17 Nov

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

17. Breakaway House: Renovated Killington Duplex, Unit B. Great location! Close to Skiing.

Killington

Ron L.

HK$4,066 total

includes taxes & fees

16 Nov - 17 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.

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

Killington

Smriti

HK$4,977 total

includes taxes & fees

16 Nov - 17 Nov

A wooden deck with outdoor furniture, including chairs and a table, surrounded by trees.

19. Tanglewood Vista at Killington: Great Group Ski Home Close to Mountain. Hot Tub.

Killington

Mary C.

HK$7,215 total

includes taxes & fees

16 Nov - 17 Nov

A red house with a gravel driveway and lush greenery.

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

Plymouth

HK$5,627 total

includes taxes & fees

16 Nov - 17 Nov

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Top Rutland Hotel Reviews

Hampton Inn Rutland

10/10 Excellent

"large comfortable room great breakfast warm cookies"

Pointe at Castle Hill Resort

10/10 Excellent

"We booked a deluxe suite, and it was fantastic — basically a full one-bedroom apartment with a kitchen equipped with all the essentials, including a washing machine and dryer. The location is quiet and peaceful, and the property itself is clean, cozy, and well-maintained. The hotel also has great amenities like a pool, gym, and hot tub — unfortunately, we didn't get a chance to use them this time, but it's a wonderful bonus to have! There were only two small issues: it was a bit tricky to find our room at first since it was located in the far wing of the building, and the heater was rather hard to adjust. Aside from that, our stay was wonderful. We love staying at this hotel and will definitely be back again!"

Mountain Sports Inn

8/10 Good

"It's in a good location close to the Killington ski area. The employees were very friendly and were very helpful. The breakfast was awesome and cooked to order. Get a room on the back side of the building so you don't have to listen to the cars. If your looking for a place to sleep with a great breakfast at a reasonable price then this is your place."

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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