Proctorsville Vacation Rentals

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Our top choices for Proctorsville vacation rentals

10.0 out of 10, Exceptional, (19)
"Amazing place! "
United States
Tara
$481 nightly
The price is $539
Jan 4 - Jan 5, 2026
Total with taxes and fees
Beautiful Condominium at Castle Hill Resort, 10 Minutes from Okemo Ski Resort
9.8 out of 10, Exceptional, (14)
"The treehouse was so cool and well maintained. We were very warm and everything was clearly laid out for where to go, where to park, etc. "
United States
Ethan
$171 nightly
The price is $187
Jan 7 - Jan 8, 2026
Total with taxes and fees
Treehouse at Wise Pines- NoBo
10.0 out of 10, Exceptional, (11)
"Super easy check in, beautiful and peaceful. Will def be back "
United States
Tyler S.
$377 nightly
The price is $413
Jan 20 - Jan 21, 2026
Total with taxes and fees
Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit
10.0 out of 10, Exceptional, (14)
"Really enjoyed the setup at the location and the owners were very responsive to any queries!"
United States
Ed N.
$517 nightly
The price is $579
Jan 5 - Jan 6, 2026
Total with taxes and fees
Pet-friendly winter retreat in the woods with fireplace near Okemo + Killington
10.0 out of 10, Exceptional, (2)
"On a farm in the country…..stars blazing at night for hot tub. Cozy loft had amazing mattress and pillows! Our dog enjoyed the surrounding field. Beautiful! "
United States
Laurel
$319 nightly
The price is $360
Jan 1 - Jan 2, 2026
Total with taxes and fees
Beautiful country cabin with hot tub and outdoor shower in Londonderry

Apartment in Bromley Mountain

Cozy Bromley Retreat
9.8 out of 10, Exceptional, (8)
"As always, an excellent stay. Wonderful unit, very nicely stocked in a perfect location. Communication was quick and easy. Easily my favorite place to stay!"
United States
Vanessa P.
$303 nightly
The price is $342
Jan 5 - Jan 6, 2026
Total with taxes and fees
Cozy Bromley Retreat
9.6 out of 10, Exceptional, (166)
"Very nice and clean cabin, not too far from small towns, decently supplied for expected conveniences, charming area - a small stream nearby provides a pleasant background noise. "
United States
Philip
$327 nightly
The price is $366
Jan 5 - Jan 6, 2026
Total with taxes and fees
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
10.0 out of 10, Exceptional, (10)
"Great location, well-designed house, and a beautiful view."
United States
Marcel P.
$1,046 nightly
The price is $1,182
Jan 5 - Jan 6, 2026
Total with taxes and fees
Newly built Vermont secluded cabin retreat with AC and brand new Hot Tub!!!
9.2 out of 10, Wonderful, (7)
"Close to Woodstock and market. Easy check in. Very quiet. Kurig, no cups for coffee."
United States
Nancy
$209 nightly
The price is $229
Jan 12 - Jan 13, 2026
Total with taxes and fees
Ben & Jerry’s Studio | 10 Min to Killington
8.8 out of 10, Excellent, (9)
"After a long month of work I needed a weekend in VT to calm the nerves. This was a beautiful spot to be in, glad I was here!"
United States
Paul S.
$181 nightly
The price is $203
Jan 4 - Jan 5, 2026
Total with taxes and fees
Whimsical Room & Private Bathroom in Historic Inn
3.0 star property
Sunrise Bear Ridge C4 4 Bedroom Condo

Condo resort in Killington

Mountain Green
2.0 star property
6.8 out of 10, (17)
"Great communication from Jeff."
United States
Dennis
$260 nightly
The price is $286
Jan 11 - Jan 12, 2026
Total with taxes and fees
Mountain Green

Apartment in Killington

Mountain Green Resort
4.0 star property
6.0 out of 10, (1)
"Clean room, elevator broken and not enough bathroom towels."
United States
Jing
$841 nightly
The price is $925
Jan 5 - Jan 6, 2026
Total with taxes and fees
Mountain Green Resort
2.0 star property
8.0 out of 10, Very Good, (1)
"I was "sold" & excited when I saw the pictures online bc the barn looked really neat. Although the barn was a neat concept, the pictures ARE NOT accurate, it is not as updated as pictured & it was VERY DISAPPOINTING. I now understand the non-refundable policy bc what you see online is definitely NOT what you walked into when you opened the door & they don't want to have to give people their back. Although we had fun, the accommodations were VERY misleading & disappointing. "
United States
Christine M.
$439 nightly
The price is $496
Jan 5 - Jan 6, 2026
Total with taxes and fees
Enjoy this authentic and cozy VT Barn with Brand New Hot Tub
9.4 out of 10, Exceptional, (9)
"Great property, as advertised."
United States
Chris A.
$299 nightly
The price is $338
Jan 7 - Jan 8, 2026
Total with taxes and fees
5th-floor mountain-view condo, easy access to the slopes free shuttle or walk
9.0 out of 10, Wonderful, (74)
"Perfect location for a quick ski trip. "
United States
Michael D.
$284 nightly
The price is $321
Jan 11 - Jan 12, 2026
Total with taxes and fees
Ski-in/out mountainside condo close to everything with full kitchen - tranquil
10.0 out of 10, Exceptional, (2)
"We had a great stay. The cabin was well lit and perfect for two people. Very clean, warm, and comfortable. There was a snow storm the night before we left and they kept the driveway plowed for us. Gorgeous views and close to everything."
United States
Karen L.
$567 nightly
The price is $641
Jan 12 - Jan 13, 2026
Total with taxes and fees
Romantic Riverbed Treehouse - hot tub & new sauna!

Vacation Home in Chester Depot

Chester Farmhouse Ski Retreat near Slopes
9.6 out of 10, Exceptional, (17)
"This was my second time staying at this property. Everything was great just like last year. I highly recommend it if you are staying in Chester, VT. "
United States
Lori N.
$299 nightly
The price is $335
Jan 20 - Jan 21, 2026
Total with taxes and fees
Chester Farmhouse Ski Retreat near Slopes
7.2 out of 10, Good, (44)
"Perfect place for a long weekend"
United States
Patrick D.
$255 nightly
The price is $288
Jan 11 - Jan 12, 2026
Total with taxes and fees
Clean & bright condo with mountain views & modern kitchen - walk to lifts
10.0 out of 10, Exceptional, (43)
"Such a comfortable home and property! It was the perfect place to celebrate the 4th with family and friends. Loved the private pond that was delightful for swimming. Teenagers enjoyed the games and hot tub. Patrick, the host, responded quickly to texts and was very helpful. We definitely want to come back!"
United States
Barbara S.
$2,362 nightly
The price is $2,645
Dec 30 - Dec 31
Total with taxes and fees
Hot Tub - Fire Place - Sauna - Gym - 4 min to Bromley on a Private Lake
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 Proctorsville Hotel Reviews

Find out more about Proctorsville

Everything you need to know about Proctorsville vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Proctorsville vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Proctorsville vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Proctorsville vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Proctorsville. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Proctorsville in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $187 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Proctorsville rentals

At Expedia, we put the best Proctorsville vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Proctorsville rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Proctorsville vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Proctorsville. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently asked questions

Are there vacation rentals in Proctorsville?

Yes, we give you a choice of vacation rentals close to top points of interest in Proctorsville, or you can go with a secluded option if you'd like a relaxing place to stay. The ski slopes and spas are just a few reasons why tourists like Proctorsville. Allow lots of time to check out the mountain landscape and restaurants during your visit.

What are some of the best vacation rentals in Proctorsville?

Ground-floor apartment with pool, hot tub, tennis & gym access - near skiing: This highly rated vacation home rental in Proctorsville is located in the mountains and has an indoor pool, a patio, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a microwave, kitchenware, and a coffee maker. You can relax into your vacation with a garden and a hot tub.

How many vacation rentals are there in Proctorsville?

Expedia has 9 vacation rentals for your stay in Proctorsville.

What’s there to see and do in Proctorsville?

While exploring the area, visit family-friendly sights like Green Mountain Sugar House, or get outside and enjoy nature at Lake Rescue. While in the area, you can also visit popular places like Okemo Mountain Resort and Killington Resort.

What’s a vacation rental in Proctorsville like?

Vacation rentals are privately owned properties you can stay in for a couple of days or more in Proctorsville. Vacation rentals offer extras such as laundry facilities and kitchens so you'll have everything you need. If you're concerned about a sanitized environment, a vacation rental can offer a sense of seclusion away from public hotel elevators and lobbies packed with people while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a popular option for a small group gathering.