Cavendish Vacation Rentals from $233: Search Short-Term Rentals

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Our top choices for Cavendish vacation rentals

1. Luxury Adventure Cabin Kayaks, Trails, Lakes Hot Tub

Cavendish

Michael L.

$373 nightly

Oct 20 - Oct 21

Total with taxes and fees

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

Cavendish

Ania H.

$479 nightly

Sep 21 - Sep 22

Total with taxes and fees

3. Cozy Chic Resort Cabin! Hot-Tub Private Fire Pit

Cavendish

Joe C.

$375 nightly

Sep 21 - Sep 22

Total with taxes and fees

4. Upscale Cabin hot-tub, private fire pit, complimentary kayaks paddleboards

Cavendish

David V.

$436 nightly

Oct 18 - Oct 19

Total with taxes and fees

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

Ludlow

Keath

$240 nightly

Sep 21 - Sep 22

Total with taxes and fees

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

Clock Tower Base Area

tiliger01

$205 nightly

Sep 21 - Sep 22

Total with taxes and fees

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

Ludlow

Brian

$273 nightly

Sep 21 - Sep 22

Total with taxes and fees

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

Ludlow

$261 nightly

Sep 30 - Oct 1

Total with taxes and fees

9. Efficient condo near slopes with kitchenette & great location

Ludlow

Frank R.

$205 nightly

Sep 21 - Sep 22

Total with taxes and fees

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

Clock Tower Base Area

"Property is on 4th floor almost at the end, so you have to walk the most with heavy bags..that was pain.. had problems with heating and cooling system. Also requested for 1 hour late check out at the time of booking, never received any response on top cleaning stuffs were sent to the property sharp at 10 am. Our friends rented another property on the same building and they could easily checked out late at 12:00 pm. Otherwise we enjoyed our stay and proximity to the slope is unparallel."

Indrajit A.

$236 nightly

Oct 19 - Oct 20

Total with taxes and fees

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

Ludlow

Tyler

$280 nightly

Sep 21 - Sep 22

Total with taxes and fees

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

Ludlow

Carey S.

$446 nightly

Sep 21 - Sep 22

Total with taxes and fees

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

Mt Holly

Cheri V.

$429 nightly

Sep 22 - Sep 23

Total with taxes and fees

14. Fat Sheep Farm & Cabins

Windsor

Jessica

$288 nightly

Oct 21 - Oct 22

Total with taxes and fees

15. Bridgewater Living - Ben&Jerry Suite

Bridgewater

$216 nightly

Sep 23 - Sep 24

Total with taxes and fees

16. New Ludlow Village Home with Stunning Okemo Mountain View

Ludlow

Nancy F.

$529 nightly

Sep 22 - Sep 23

Total with taxes and fees

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

Ludlow

$374 nightly

Sep 21 - Sep 22

Total with taxes and fees

18. Charming Fully Renovated One-Room Schoolhouse on 22+ acres

Grafton

Eleanor D.

$323 nightly

Sep 22 - Sep 23

Total with taxes and fees

19. Okemo | Spacious Executive Room w Amenities Nearby

Jackson Gore Base Area

David K.

$242 nightly

Sep 22 - Sep 23

Total with taxes and fees

20. Luxury Farmhouse Mins 2 Okemo w/Hot Tub & Fire Pit!

Mount Holly

Chi L.

$730 nightly

Sep 21 - Sep 22

Total with taxes and fees

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Top Cavendish Hotel Reviews

The Jackson

10/10 Excellent

"Very characterful property a little way out of Woodstock. Friendly staff, good to meet other guests at the complimentary wine and cheese event every evening. Room was small, bed comfortable but if the patio door was open there was a noisy aircon unit a couple of feet away. But the room was hot! So this was not ideal. Beautiful grounds but wouldn’t have wanted to sit outside the room as it was so noisy!"

Woodstock Inn & Resort

8/10 Good

"Woodstock itself is absolutely beautiful and has a wonderful atmosphere. However, we had a few issues in both common areas, and our room that significantly impacted our experience. First, the cleanliness of the lobby was disappointing. I noticed that it was noticeably dusty and had visible spiderwebs in several areas, which did not create a welcoming first impression. Second, the bathroom and bed did not live up to the luxurious standard expected. Both the bathroom sink and bathtub drained incredibly slowly. This resulted in an unpleasant backflow of water whenever I tried to use them, which felt very unhygienic. Lastly, the bed was lopsided and very uncomfortable. The boxspring on both sides of the bed was covered in stains, which took away from the charm and comfort of the room. Everything else was great, and with a little more attention to room cleanliness, this place would be flawless."

Castle Hill Resort And Spa

10/10 Excellent

"We stayed in a two bedroom condo that was fabulous. It was very clean. It had a fireplace and anything we needed was available. One thing that was upsetting is that there was a wedding Saturday night at the castle so we were unable to have dinner there and then they were closed on Sunday so both nights of our stay we could not have dinner at the castle, which we were actually looking forward to. We had a great time regardless of that, we ended up having dinner at Murdock which was sooooo good highly recommend. We didn't use the pool because it was a little chilly, but it looked great. Would go back again especially for ski season."

Find out more about Cavendish

Everything you need to know about Cavendish 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 Cavendish 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 Cavendish vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Cavendish vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Cavendish. 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 Cavendish 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 $233 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 Cavendish rentals

At Expedia, we put the best Cavendish 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 Cavendish 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 Cavendish 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 Cavendish. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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Frequently asked questions

Can I find vacation rentals in Cavendish?

Yes, there are vacation rentals close to popular attractions in Cavendish, or you can choose a more secluded option if you want a relaxing place to stay. The ski slopes and spas are just a few reasons why tourists like Cavendish. Allow lots of time to check out the mountain landscape and restaurants during your visit.

What's the top vacation rental in Cavendish?

Traveling with kids? Try this secluded & updated 3-bedroom home close to Okemo: This vacation home rental outside of Cavendish is located on a lake and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 3 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 selection of games.

How many vacation rentals are there in Cavendish?

Choose from 27 Expedia vacation rentals in Cavendish for a memorable vacation.

What’s there to see and do in Cavendish?

Explore the area and family-friendly sights such as Maple Lanes, or get out into nature at a spot like Lake Rescue. Phineas Gage Memorial and Fox Run Golf Course are a couple of places you'll find in the larger area.

What’s a vacation rental in Cavendish like?

A vacation rental is a private property where you can stay for a few weeks or just a few days in Cavendish. Vacation rentals provide amenities like laundry facilities and kitchens to help you enjoy your stay. If you're concerned about cleanliness, vacation rentals can provide a sense of security away from public hotel elevators and lobbies bustling with people while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a popular choice for family trips.

Cavendish Vacation Rentals

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Check prices for these dates

Our top choices for Cavendish vacation rentals

1. Luxury Adventure Cabin Kayaks, Trails, Lakes Hot Tub

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

3. Cozy Chic Resort Cabin! Hot-Tub Private Fire Pit

4. Upscale Cabin hot-tub, private fire pit, complimentary kayaks paddleboards

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

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

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

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

9. Efficient condo near slopes with kitchenette & great location

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

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

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

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

14. Fat Sheep Farm & Cabins

15. Bridgewater Living - Ben&Jerry Suite

16. New Ludlow Village Home with Stunning Okemo Mountain View

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

18. Charming Fully Renovated One-Room Schoolhouse on 22+ acres

19. Okemo | Spacious Executive Room w Amenities Nearby

20. Luxury Farmhouse Mins 2 Okemo w/Hot Tub & Fire Pit!

Find vacation rentals that suit your style

Top Cavendish Hotel Reviews

The Jackson

Find out more about Cavendish

Explore a world of travel with Expedia

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