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Proctorsville Rentals

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186 Houses

4 Minutes to Okemo Mountain

Proctorsville house

3 bedrooms / 2 bathrooms / sleeps 10

Price per night from

$519

Chester Farmhouse on 100 Acres, 15 Min to Okemo!

Proctorsville house

5 bedrooms / 2 bathrooms / sleeps 14

Responds fast! avg. 4 minutes

Price per night from

$297

Vermont 1828 Reunion House, sleeps 20, 5 miles to Okemo

Proctorsville house

8 bedrooms / 4 bathrooms / sleeps 20

Price per night from

$472

Elegant victorian with free wifi, private washer/dryer - Near Okemo

Proctorsville house

5 bedrooms / 3 bathrooms / sleeps 12

Responds fast! avg. 3 hours 1 minutes

Price per night from

$461

Great rentals within 20 miles that match your search

Responds fast! avg. 2 hours 25 minutes

Price per night from

$264

Price per night from

$440

Cozy Historic Hilltop Cottage

Brownsville house

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$171

Minutes from Killington + Okemo + Woodstock, VT come and experience The Cabin

Bridgewater log cabin

4 bedrooms / 3 bathrooms / sleeps 24

Price per night from

$942

☆ SKI ON & OFF! ☆ Luxury Trailside Condo! NEW Steam Shower, Hot Tub, Pool

Killington condo

2 bedrooms / 2 bathrooms / sleeps 6

“First Family Ski Trip with the Kids” I have a 4 year old and an 11 month old and neither my wife nor I had been skiing since both kids were born. Our eldest was ready for his first skiing vacation and Killington was a great spot since they have a great ski school and child care for the little one. We booked somewhat late but had another couple that wanted to bring their 4 year old daughter as well, so we found this awesome rental. Unfortunately we didn't really get to use the ski on/off to its fullest potential since we had to drop the kids off at their base each day but it would have been extremely convenient. The condo was the perfect size, wifi was key along with the other amenities. The clubhouse was close and convenient, awesome to be able to take the kids to the pool after a day on the slopes and sit myself in the hot tub while they played. I will definitely be coming back here!

Responds fast! avg. 12 minutes

Price per night from

$177

2 mins to Okemo, Shuttle Route and Hot Tub!

Ludlow house

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 1 hour 13 minutes

Price per night from

$148

Reading Farms Estate/ Vermont Luxury Rental

Reading villa

15 bedrooms / 12 bathrooms / sleeps 44

Price per night from

$2,885

Fox Run -- Sleeps 10 - 12, Only 1 mile from Okemo Jackson Gore Base

Ludlow townhouse

4 bedrooms / 4 bathrooms / sleeps 12

Price per night from

$471

Slopeside Townhome in Bromley Village

Peru townhouse

4 bedrooms / 3 bathrooms / sleeps 11

Price per night from

$324

Amare Guesthouse, renovated in-town victorian

Chester house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$271

Large, Lovely, Affordable Mountain Home

Windham house

5 bedrooms / 3 bathrooms / sleeps 10

“I rented a house for a weekend and received much more than a pla” I rented the Windham County House for a weekend to hold a retreat for first year students at Middlebury College who are still adjusting to college life. This house provided us with an intimate setting that allowed the members of the retreat to feel comfortable, considerate, and expressive. Micheal helped make our weekend the best as possible by always providing assistance whenever needed. Mary and I communicated very well from when I inquired about the house to when we returned to campus after the weekend. There are beautiful hiking trails close to the house in the fall that greatly add to the experience of renting this house. If you're looking for comfortable, family oriented, you should strongly consider renting this house.

Price per night from

$98

Clifford Country Bed & Breakfast, open May-October

Mount Holly b&b

3 bedrooms / 2 bathrooms / sleeps 6

“Unspoiled Vermont at it's finest!” Located on a quiet country lane in the picturesque little village of Mount Holly Vermont the traveller to the Okemo Valley region will discover the charmingly delightful Clifford Country Bed and Breakfast. The Inn is owned and operated by a lovely women named Emily Clifford Jackson and quite honestly the only thing nicer than your stay at the Inn itself will be the opportunity to meet and become friends with Ms. Jackson. Clifford Country offers it's quests all the warmth and amenities of a country inn including extremely clean and comfortable accommadations complete with old-fashioned home-style hospitality and affordable rates. Breakfast is served daily and features all the old favorites such as fresh fruit and juices, farm fresh milk ,eggs and maple syrup from the farms of local friends and neighbors. Emily also offers a wide variety of freshly home made breads, muffins, pancakes, etc. all of which seem to just be the perfect way to start off your Vermont morning. This was my second visit to Clifford Country and although there is much more that I could tell folks about both the area and the Inn I would like to share this with the viewers of Tripadvisor. As a "Green Hotel in the Green Mountain State" for the traveller looking to experience the epitome of "unspoiled Vermont" Clifford Country is an absolute gem and typifies all that is special about this beautiful place. I suspect there may be places to stay in Vermont that are more pretentious than Clifford Country but I can guarantee there are non more pleasurable. Clifford Country is a totally charming B & B run by an equally charming owner and it really doesn't get any better than that. I shall return to Clifford Country as soon as possible.

Price per night from

$122

Serene, Modern Escape, Overlooking Quiet Brook

Woodstock apartment

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$266

The I.B. Munson House Inn - All Bedrooms

Wallingford b&b

4 bedrooms / 4 bathrooms / sleeps 8

Price per night from

$738

Perfect Hideaway Cabin - lake, trails, forest, meadows

Mount Holly log cabin

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 3 hours 12 minutes

Price per night from

$107

Premier Ski-in / Ski-out - 3 Bed, Sunrise Mountain

Killington apartment

3 bedrooms / 2 bathrooms / sleeps 10

Price per night from

$767

The 1843 Stone House - Chester, VT (3bdrm/ 2 ba)

Chester house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$236

The I.B. Munson House Inn - Bedroom 4

Wallingford b&b

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$230

Ski Killington, Pico, Snow Mobile, Summer Fun

Killington house

5 bedrooms / 3 bathrooms / sleeps 12

Price per night from

$590

South Face Village

Ludlow condo

2 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$649

Private Cabin / Minutes to Okemo

Mount Holly cottage

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$148

2 bedroom premium AAA rated condo across from the slopes-2C4

Killington condo

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$230

Oma"s Kottage

Ludlow house

6 bedrooms / 2 bathrooms / sleeps 11

Responds fast! avg. 25 minutes

Price per night from

$236

KILLINGTON GOLFING, BIKING SKI 2 Bd 1&1/2 B $79 av nt. 4 Season Resort Sleeps 8

Killington condo

2 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 1 hour 49 minutes

Price per night from

$114

Vermont Cottage Lake Amherst

Plymouth cottage

5 bedrooms / 4 bathrooms / sleeps 12

Price per night from

$826

Queen room in peaceful country B&B, open May-Oct.

Mount Holly private room

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$122

Lakefront vacation home - 4 BR - sleeps 10

Ludlow house

4 bedrooms / 2 bathrooms / sleeps 10

Price per night from

$63

The Lodges Bear Mountain Luxury ski-on/ski-off 3 bed 3 Bath LOW RATES-Mar/Apr

Killington condo

3 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$348

Clean, Affordable, 2 BR Apt 5 min drive to Okemo & 25 min drive to Killington Mt

Ludlow apartment

2 bedrooms / 1 bathroom / sleeps 5

Price per night from

$89

Vermont Cottage on Lake Amherst 6 Bedrooms 4 Bathrooms

Plymouth cottage

5 bedrooms / 4 bathrooms / sleeps 10

Price per night from

$826

Hugging Bear Inn - Bear's Den Room

Chester b&b

1 bedroom / 1 bathroom / sleeps 5

Price per night from

$164

Vermont Country Lake House

Ludlow house

5 bedrooms / 3 bathrooms / sleeps 14

Responds fast! avg. 2 hours 25 minutes

Price per night from

$177

Newly Remodeled Townhome

Jamaica townhouse

3 bedrooms / 2 bathrooms / sleeps 12

Price per night from

$590

Log Home w/ first class amenities near OKEMO Mtn

Mount Holly log cabin

5 bedrooms / 4 bathrooms / sleeps 15

Price per night from

$531

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