Holiday Rentals in Proctorsville

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Our top choices for Proctorsville holiday rentals

Beautiful Condominium at Castle Hill Resort, 10 Minutes from Okemo Ski Resort

Beautiful Condominium at Castle Hill Resort, 10 Minutes from Okemo Ski Resort
Cavendish
10.0 out of 10, Exceptional, (19)
"Amazing place! "
United States
Tara
The price is €469
includes taxes & fees
4 Jan - 5 Jan 2026
Beautiful Condominium at Castle Hill Resort, 10 Minutes from Okemo Ski Resort

Treehouse at Wise Pines- NoBo

Treehouse at Wise Pines- NoBo
Woodstock
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
The price is €163
includes taxes & fees
7 Jan - 8 Jan 2026
Treehouse at Wise Pines- NoBo

Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit

Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit
2.0 star property
Cavendish
10.0 out of 10, Exceptional, (11)
"Super easy check in, beautiful and peaceful. Will def be back "
United States
Tyler S.
The price is €353
includes taxes & fees
7 Jan - 8 Jan 2026
Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit

Pet-friendly winter retreat in the woods with fireplace near Okemo + Killington

Pet-friendly winter retreat in the woods with fireplace near Okemo + Killington
2.0 star property
Plymouth
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.
The price is €504
includes taxes & fees
5 Jan - 6 Jan 2026
Pet-friendly winter retreat in the woods with fireplace near Okemo + Killington

Beautiful country cabin with hot tub and outdoor shower in Londonderry

Beautiful country cabin with hot tub and outdoor shower in Londonderry
2.0 star property
Londonderry
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
The price is €315
includes taxes & fees
7 Jan - 8 Jan 2026
Beautiful country cabin with hot tub and outdoor shower in Londonderry

Cozy Bromley Retreat

Cozy Bromley Retreat
Bromley Mountain
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.
The price is €293
includes taxes & fees
5 Jan - 6 Jan 2026
Cozy Bromley Retreat

Charming Fully Renovated One-Room Schoolhouse on 22+ acres

Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Grafton
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
The price is €318
includes taxes & fees
7 Jan - 8 Jan 2026
Charming Fully Renovated One-Room Schoolhouse on 22+ acres

Newly built Vermont secluded cabin retreat with AC and brand new Hot Tub!!!

Newly built Vermont secluded cabin retreat with AC and brand new Hot Tub!!!
Londonderry
10.0 out of 10, Exceptional, (10)
"Great location, well-designed house, and a beautiful view."
United States
Marcel P.
The price is €1,028
includes taxes & fees
5 Jan - 6 Jan 2026
Newly built Vermont secluded cabin retreat with AC and brand new Hot Tub!!!

Ben & Jerry’s Studio | 10 Min to Killington

Ben & Jerry’s Studio | 10 Min to Killington
Bridgewater
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
The price is €199
includes taxes & fees
12 Jan - 13 Jan 2026
Ben & Jerry’s Studio | 10 Min to Killington

Whimsical Room & Private Bathroom in Historic Inn

Whimsical Room & Private Bathroom in Historic Inn
Chester Depot
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.
The price is €177
includes taxes & fees
4 Jan - 5 Jan 2026
Whimsical Room & Private Bathroom in Historic Inn

Sunrise Bear Ridge C4 4 Bedroom Condo

Sunrise Bear Ridge C4 4 Bedroom Condo
3.0 star property
Killington
Sunrise Bear Ridge C4 4 Bedroom Condo

Mountain Green

Mountain Green
2.0 star property
Killington
6.8 out of 10, (17)
"Great communication from Jeff."
United States
Dennis
The price is €263
includes taxes & fees
11 Jan - 12 Jan 2026
Mountain Green

Mountain Green Resort

Mountain Green Resort
4.0 star property
Killington
6.0 out of 10, (1)
"Clean room, elevator broken and not enough bathroom towels."
United States
Jing
The price is €786
includes taxes & fees
5 Jan - 6 Jan 2026
Mountain Green Resort

Enjoy this authentic and cozy VT Barn with Brand New Hot Tub

Enjoy this authentic and cozy VT Barn with Brand New Hot Tub
2.0 star property
Londonderry
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.
The price is €431
includes taxes & fees
26 Jan - 27 Jan 2026
Enjoy this authentic and cozy VT Barn with Brand New Hot Tub

5th-floor mountain-view condo, easy access to the slopes free shuttle or walk

5th-floor mountain-view condo, easy access to the slopes free shuttle or walk
Killington
9.4 out of 10, Exceptional, (9)
"Great property, as advertised."
United States
Chris A.
The price is €294
includes taxes & fees
7 Jan - 8 Jan 2026
5th-floor mountain-view condo, easy access to the slopes free shuttle or walk

Ski-in/out mountainside condo close to everything with full kitchen - tranquil

Ski-in/out mountainside condo close to everything with full kitchen - tranquil
Clock Tower Base Area
9.0 out of 10, Wonderful, (74)
"Perfect location for a quick ski trip. "
United States
Michael D.
The price is €280
includes taxes & fees
11 Jan - 12 Jan 2026
Ski-in/out mountainside condo close to everything with full kitchen - tranquil

Romantic Riverbed Treehouse - hot tub & new sauna!

Romantic Riverbed Treehouse - hot tub & new sauna!
londonderry
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.
Romantic Riverbed Treehouse - hot tub & new sauna!

Chester Farmhouse Ski Retreat near Slopes

Chester Farmhouse Ski Retreat near Slopes
Chester Depot
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.
The price is €291
includes taxes & fees
20 Jan - 21 Jan 2026
Chester Farmhouse Ski Retreat near Slopes

Clean & bright condo with mountain views & modern kitchen - walk to lifts

Clean & bright condo with mountain views & modern kitchen - walk to lifts
Killington
7.2 out of 10, Good, (44)
"Perfect place for a long weekend"
United States
Patrick D.
The price is €255
includes taxes & fees
11 Jan - 12 Jan 2026
Clean & bright condo with mountain views & modern kitchen - walk to lifts

Hot Tub - Fire Place - Sauna - Gym - 4 min to Bromley on a Private Lake

Hot Tub - Fire Place - Sauna - Gym - 4 min to Bromley on a Private Lake
Peru
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.
The price is €2,303
includes taxes & fees
30 Dec - 31 Dec
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 holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Proctorsville holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Proctorsville holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Proctorsville holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Proctorsville holiday rentals we have selected for you start as low as €163 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Proctorsville rentals

At Expedia, we put the best Proctorsville holiday 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 holiday.

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 holiday rentals in Proctorsville?

Yes, there are holiday rentals close to the most popular sights in Proctorsville, or you can select a more secluded option if you're looking for a relaxing 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 holiday rentals that Proctorsville has to offer?

Ground-floor apartment with pool, hot tub, tennis & gym access - near skiing: This highly rated holiday home rental in Proctorsville is located in the mountains, and has an indoor pool, a patio and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a microwave, kitchenware and a coffee maker. You can relax into your holiday with a garden and 1 hot tub.

How many holiday rentals are there in Proctorsville?

Expedia has 9 holiday 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 such as Okemo Mountain Resort and Killington Resort.

What’s a holiday rental in Proctorsville like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Proctorsville. Holiday rentals feature amenities like kitchens and laundry facilities so you'll have all the comforts of home. If you're concerned about a clean environment, a holiday rental can offer a sense of security away from public hotel lifts and busy reception areas while still allowing you the experience of travel. You'll also get more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is an attractive choice for family trips.