Castleton, VT Vacation Homes from AED 535

A lakeside community with houses and docks.

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Our top choices for Castleton vacation homes

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

1. Historic Victorian Estate 4 Bed 2 Bath Fast Wifi

Fair Haven

Amy G.

AED 1,116 total

includes taxes & fees

25 Oct - 26 Oct

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

2. Cozy Rutland Retreat

Rutland

Valerie

AED 719 total

includes taxes & fees

3 Nov - 4 Nov

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

3. Cozy 2 Bedroom close distance to downtown.

Rutland

AED 535 total

includes taxes & fees

27 Oct - 28 Oct

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

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

Mendon

Aurore H.

AED 851 total

includes taxes & fees

26 Oct - 27 Oct

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

5. Relaxing Rutland Retreat Near Skiing, Dining & Hiking

Rutland

AED 2,703 total

includes taxes & fees

2 Nov - 3 Nov

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

6. 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.

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

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

Mendon

Callison A.

AED 1,659 total

includes taxes & fees

3 Nov - 4 Nov

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

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

Rutland

Matthew T.

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

9. 4BR Home | Walk Downtown Rutland + Trails

Rutland

Dominic C.

AED 1,517 total

includes taxes & fees

9 Nov - 10 Nov

A kitchen with a central island, two bar stools, pendant lights, and a view of the living area through an open archway.

10. Cozy Killington A-Frame w/ Hot Tub, Modern Kitchen & Forest Views – Near Skiing & Hiking Trails

North Sherburne

Robert R.

AED 2,750 total

includes taxes & fees

11 Nov - 12 Nov

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

11. 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.

AED 2,364 total

includes taxes & fees

25 Oct - 26 Oct

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

12. 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.

AED 1,033 total

includes taxes & fees

3 Nov - 4 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.

13. CozyDen- Location, Ski Off/ Shuttle On

Killington

Berni H.

AED 1,040 total

includes taxes & fees

26 Oct - 27 Oct

A cozy living room with a fireplace, a television, and a view of a snowy deck.

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

Killington

Mark B.

AED 2,691 total

includes taxes & fees

25 Oct - 26 Oct

A cozy living room with a fireplace, a sofa, and a staircase.

15. 25 Rocky Ridge Rd - Killington Retreat: Group Ski House! Close to Mountain! Hot Tub.

Killington

Matthew P.

AED 2,822 total

includes taxes & fees

25 Oct - 26 Oct

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

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

Killington

Patrick B.

AED 2,723 total

includes taxes & fees

25 Oct - 26 Oct

A covered porch with a sliding glass door leading to a room, a seating area with chairs, and a view of a garden.

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

The Woods

AED 1,300 total

includes taxes & fees

1 Nov - 2 Nov

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.

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

North Sherburne

"On our 30th Anniversary trip to Vermont, New Hampshire and Maine we fell in love with Killington, Vermont. So much so we left the coast of Maine and last minute booked our remaining two nights back in Killington at the Poweder Run Lodge. The lodge was a wonderful experience! The location was beautiful, spacious, clean, had a fully stocked kitchen and spectacular views. The hosts were kind and easy to communicate with. We are older and need a continuous running fan and a little softer bed when we...

Heidi P.

AED 2,564 total

includes taxes & fees

26 Oct - 27 Oct

A modern house with a stone facade, a large deck, and outdoor seating.

19. Lakewood Lodge: 4BR/2.5BA Killington Home | Private Hot Tub, Wood Fire, Kent Pond & EV Charging

Killington

SHEEPDOG 1.

AED 3,181 total

includes taxes & fees

25 Oct - 26 Oct

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

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

Killington

AED 3,780 total

includes taxes & fees

26 Oct - 27 Oct

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Top Castleton Hotel Reviews

Mountain Meadows Lodge

10/10 Excellent

"A wonderful lodge, in a perfect location. We came for the first time in August and liked it so much that we returned two months later. It was even prettier now with the foliage. The staff is wonderful and very accommodating. Both Mike and Victoria are excellent hosts. The property is very clean, cozy an well maintained. We had a wonderful weekend and will come back again soon!"

Econo Lodge Rutland City near Hwy 7

8/10 Good

"I asked the girl at check-in for a first-floor room with 2 double beds. I am handicapped in a wheelchair, and she got us exactly what we wanted. Very clean room. Only one light in the room, so kind of on the dim side. The bed was too soft for me. The location was located to all kinds of stores and restaurants. They accept dogs for a small fee, which was great for us and our beloved Harleyquinn. Breakfast was supposed to be between 7 a.m.- 10 a.m., but at 7:15 am when I went to check out, the lobby was not open yet. I believe the worst thing is the parking. I do believe there is more in the back, but the front was pretty packed. I had to wait a few minutes for a truck to move so I could park in front of my room. Would stay here again, especially the price of the room."

Room 1

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Treat yourself

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Check prices for these dates

Our top choices for Castleton vacation homes

1. Historic Victorian Estate 4 Bed 2 Bath Fast Wifi

2. Cozy Rutland Retreat

3. Cozy 2 Bedroom close distance to downtown.

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

5. Relaxing Rutland Retreat Near Skiing, Dining & Hiking

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

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

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

9. 4BR Home | Walk Downtown Rutland + Trails

10. Cozy Killington A-Frame w/ Hot Tub, Modern Kitchen & Forest Views – Near Skiing & Hiking Trails

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

12. Luxury Condo Tucked in the Heart of Killington

13. CozyDen- Location, Ski Off/ Shuttle On

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

15. 25 Rocky Ridge Rd - Killington Retreat: Group Ski House! Close to Mountain! Hot Tub.

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

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

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

19. Lakewood Lodge: 4BR/2.5BA Killington Home | Private Hot Tub, Wood Fire, Kent Pond & EV Charging

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

Find vacation rentals that suit your style

Top Castleton Hotel Reviews

Mountain Meadows Lodge

North Star Lodge and Resort

The Mountain Inn at Killington

Bentley House Bed and Breakfast

Days Inn by Wyndham Rutland/Killington Area

Après Inn Killington

Best Western Inn & Suites Rutland-Killington

Killington Mountain Lodge, Tapestry Collection by Hilton

Econo Lodge Rutland City near Hwy 7

Search Vacation Homes in Castleton

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Castleton vacation homes

1. Historic Victorian Estate 4 Bed 2 Bath Fast Wifi

2. Cozy Rutland Retreat

3. Cozy 2 Bedroom close distance to downtown.

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

5. Relaxing Rutland Retreat Near Skiing, Dining & Hiking

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

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

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

9. 4BR Home | Walk Downtown Rutland + Trails

10. Cozy Killington A-Frame w/ Hot Tub, Modern Kitchen & Forest Views – Near Skiing & Hiking Trails

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

12. Luxury Condo Tucked in the Heart of Killington

13. CozyDen- Location, Ski Off/ Shuttle On

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

15. 25 Rocky Ridge Rd - Killington Retreat: Group Ski House! Close to Mountain! Hot Tub.

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

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

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

19. Lakewood Lodge: 4BR/2.5BA Killington Home | Private Hot Tub, Wood Fire, Kent Pond & EV Charging

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

Find vacation rentals that suit your style

Top Castleton Hotel Reviews

Mountain Meadows Lodge