Proctorsville Vacation Rentals from $230: Search Short-Term Rentals

Q: What are some of the best vacation rentals in Proctorsville?

Mountainside 5-BR Ski-In/Out Okemo Villa : You might want to consider this vacation home rental near Proctorsville, which is located in the mountains and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a hot tub.

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Our top choices for Proctorsville vacation rentals

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

Cavendish

Ania H.

$483 nightly

Sep 7 - Sep 8

Total with taxes and fees

2. Ski-In/Out condo with patio, mountain views, washer/dryer, & cable

Clock Tower Base Area

AMY K.

$205 nightly

Sep 7 - Sep 8

Total with taxes and fees

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

Clock Tower Base Area

serena m.

$236 nightly

Sep 7 - Sep 8

Total with taxes and fees

4. Downtown Condo w/ Electric Fireplace, WiFi & Shuttle Stop Across the Street

Ludlow

Keath

$240 nightly

Sep 7 - Sep 8

Total with taxes and fees

5. Efficient condo near slopes with kitchenette & great location

Ludlow

Frank R.

$204 nightly

Sep 8 - Sep 9

Total with taxes and fees

6. Cozy Studio Condo with Great Location, WiFi & Kitchenette

Ludlow

Mikhail R.

$211 nightly

Sep 7 - Sep 8

Total with taxes and fees

7. Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails

Ludlow

$262 nightly

Sep 30 - Oct 1

Total with taxes and fees

8. Ski-In/Out Condo with Mountain Views, and Washer/Dryer

Ludlow

Carey S.

$381 nightly

Sep 7 - Sep 8

Total with taxes and fees

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Top Proctorsville Hotel Reviews

Lincoln Inn & Gallery

10/10 Excellent

"That property is excellent!"

Pointe at Castle Hill Resort

10/10 Excellent

"I found this interesting "resort" by accident when I needed to spend time with my mom who was about 40 minutes away in the Lebanon/Hancock, NH area. Wished I'd had more time to spend at there! I would have brought a bathing suit, tried the hot tub, booked a massage at the Spa, and had another delicious meal at the restaurant in the historic building. The non-historic lodging part of the property seems more like a place families and couples might stay when they ski: very comfortable and casual, older (but not historic), not too fancy, allows dogs!! Staff was lovely! Nice, friendly, available for questions, and willing to make more coffee when I slept in and everyone else beat to me to it."

The Jackson

10/10 Excellent

"We had a lovely 1 night stay at the quaint Jackson. We enjoyed the wine & cheese hour, had dinner at Oakes & Evelyn (on site but not part of the hotel) and enjoyed a nightcap on the porch. The bed was super comfortable, sheets were clean and crisp, robes were Frette and products smelled great. The property is gorgeous and Woodstock as a town is a delight."

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 $230 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?

Mountainside 5-BR Ski-In/Out Okemo Villa: You might want to consider this vacation home rental near Proctorsville, which is located in the mountains and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a hot tub.

How many vacation rentals are there in Proctorsville?

Expedia has 5 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 Maple Lanes, or get outside and enjoy nature at Lake Rescue. In the larger area, you’ll find Fox Run Golf Course and Okemo Mountain 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.

Room 1

Check prices for these dates

Our top choices for Proctorsville vacation rentals

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

2. Ski-In/Out condo with patio, mountain views, washer/dryer, & cable

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

4. Downtown Condo w/ Electric Fireplace, WiFi & Shuttle Stop Across the Street

5. Efficient condo near slopes with kitchenette & great location

6. Cozy Studio Condo with Great Location, WiFi & Kitchenette

7. Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails

8. Ski-In/Out Condo with Mountain Views, and Washer/Dryer

9. Luxury Adventure Cabin #2—Kayaks, Trails, Lakes & 24/7 Hot Tub Access

10. Okemo Mountain, Family Affordable 2 fl village walk to town, Dogs OK.fireplace.

11. Well-appointed studio right downtown - less than a mile to Okemo Mountain

12. 2nd-floor downtown Ludlow studio condo with kitchenette, streaming

13. Bear`s Den in Ludlow, Okemo Views + Epic Game Room

14. Condo in the heart of town near skiing - less than a mile to Okemo Mountain

15. Terrific 3-bedroom cottage with AC in charming Cavendish

16. Cozy Chic! Cabin #3: wooded delights with year-round hot-tub and private firepit

17. Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore

18. Upscale Cabin 1: hot-tub, private firepit, complimentary kayaks + paddleboards!

19. New Ludlow Village Home with Stunning Okemo Mountain View

20. Ground Floor ski-in/out condo, full kitchen & high-speed WiFi

Find vacation rentals that suit your style

Top Proctorsville Hotel Reviews

Lincoln Inn & Gallery

On The River Inn

Pointe at Castle Hill Resort

The Jackson

Sleep Woodstock Motel

The Common Man Inn & Restaurant

Woodstock Inn & Resort

Killington Mountain Lodge, Tapestry Collection by Hilton

Find out more about Proctorsville

Frequently asked questions