House holiday rentals in Cavendish

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Popular amenities for house rentals in Cavendish

House rentals with a pool

Guest favourite
Home in Killington
4.91 out of 5 average rating, 212 reviews

Luxury Condo Tucked in the Heart of Killington

KennethRating, 5 stars1 week ago
Very nice place easy access to routes 4 and 100 with plenty of things to do
Guest favourite
Home in Ludlow
4.92 out of 5 average rating, 13 reviews

Ski-In/Ski-Out Hike Okemo Mountain Condo

StephanieRating, 5 stars3 weeks ago
Words can’t describe the experience we had this weekend. Linda was the best host we have ever worked with and the place was extraordinary to say the least! Extremely clean, comfortable and well located! Kid friendly and close to downtown! We will highly recommend it to friends and family and if we could leave more stars than a 5-star review we would! Looking forward to booking this place again in the near future! Thank you Linda for your amazing hospitality!
Top guest favourite
Home in Mendon
4.89 out of 5 average rating, 247 reviews

Ranch at Mendon Mt Orchards

RobinRating, 5 stars1 month ago
We enjoyed our stay. we felt at home. very spacious and cozy. this house has everything you need for your stay. Very close to Rutland. The fresh baked apple pie was a bonus. It was so delicious. Everything was perfect for us! Thank you! We will definitely be back again!
Superhost
Home in Wilmington
4.87 out of 5 average rating, 171 reviews

Adams Farm-"The Little Farmhouse"

Catherine (Lou)Rating, 5 stars4 months ago
We had an amazing stay! The house is lovely and very comfortable, perfect for going skiing at mount snow and cross country skiing and prospect mountain. We were really glad to have picked it. The house is spacious, we all had a lot of room to ourselves, and the kitchen had everything we needed. The farm is gorgeous. Great grocery stores nearby. Sharon was amazing - so helpful when a winter storm threatened to make it hard for us to drive home. She offered us extra time or even another night discounted, which was really generous. She also communicated with friends to help us determine if the road back to NYC had been cleared. We are so grateful for her help! We hope to return in warmer weather to enjoy the farm even more.
Top guest favourite
Home in Killington
4.99 out of 5 average rating, 135 reviews

SugarBear- Pool, AC, Sauna, Gym, Tennis!

JennRating, 5 stars1 month ago
Dan & Holly are amazing hosts. They provided everything needed to make our week great. They left dining recommendations and all of the information we needed for the property. It was the perfect space for our family. The on-site amenities were great. The pool space was super clean and the staff was amazing. The property is well maintained and we had everything we needed to feel at home. We would definitely recommend this property to friends and family. Downtown Rutland was a short drive, and there was so much to see just minutes from the property. Dan & Holly are extremely responsive and truly think of everything. We had no questions and checking in and out was a breeze because they are so thorough. It was a wonderful experience from start to finish.
Guest favourite
Home in Keene
4.93 out of 5 average rating, 211 reviews

The Brick House on Washington Street

PaulRating, 5 stars1 week ago
Great stay and was exactly what we needed for our entire family for a weekend wedding!
Guest favourite
Home in Plainfield
4.89 out of 5 average rating, 139 reviews

Historic Home on 17 acres of land. Go escape!

BrandieRating, 5 stars3 months ago
Staying here is always a joy for the entire family! It has become an annual tradition that we all look forward to in winter. Thank you for being so accommodating with our schedule and a special thanks to Mitchell for going the extra mile to snow blow a waking path for me and the dogs to keep our daily routine of visiting the horses, after the last storm brought over 13” of snow. P.S. the new stove/oven is amazing!! 🤩
Guest favourite
Home in Granville
4.94 out of 5 average rating, 105 reviews

Historic 1850’s Renovated Farmhouse w/ Pool!

KimberlyRating, 5 stars3 weeks ago
9 adults and 3 children all met up for a family weekend! We came from NY, NH and Maine! The house was perfect! Plenty of room to gather or separate! Even tho it was a chilly rainy weekend the kids managed to get in plenty of pool time! Tanya was very responsive and Melvin was the greatest! Our first morning he came right over to fix a slow drain. Highly recommend!! Kim and family

Weekly house rentals

Superhost
Home in Cavendish
4.71 out of 5 average rating, 7 reviews

Mountain View 3-BR Cavendish Lodge

JoseRating, 5 stars3 weeks ago
Place was great
Top guest favourite
Home in Ludlow
5 out of 5 average rating, 32 reviews

Ludlow Lake & Ski Cottage - Adventure Awaits!

MdRating, 5 stars1 week ago
Exceptional experience! This is one of the relaxing place I have ever been! Large windows give you sense of experience living in nature. The stunning view gives you awesome feeling in any weather conditions.The house is nice, clean and equipped with pretty much everything. They have all the utensils for cooking and lots of toys for kids both indoor and outdoor. They also have paddles boat and kayak to use at anytime ! In addition, Brian is very respectful, responsible and quick to respond for any questions. All together Feel like you live in your own house. Great vacation spot without any doubt.
Top guest favourite
Home in Cavendish
4.98 out of 5 average rating, 48 reviews

Okemo <12 min Game room~Hot tub~Fire pit~Mtn Views

RickyRating, 5 stars2 months ago
Awesome place! All the games in the basement gave us something to do while hanging inside the house. It’s great being able to come back after a long day of snowboarding and relaxing in the hot tub. The kitchen had everything we needed to cook. Only thing “negative” I could say is we couldn’t find any trash bags for the trash cans but obviously not that big of a deal. Overall I would 100% recommend and would definitely stay here again, without a doubt
Guest favourite
Home in Ludlow
4.9 out of 5 average rating, 93 reviews

The Bluebird Day Chalet 2 bed dtwn Ludlow Village

NikkiRating, 5 stars4 days ago
Great place! Right downtown near everything and super walkable. Nice rooms, clean and tidy! Would recommend, perfect for a weekend get away.
Guest favourite
Home in Cavendish
4.98 out of 5 average rating, 97 reviews

Cottage on Main Okemo Mountain new decor AC, WIFI

SusanRating, 5 stars3 months ago
Jennifer’s place was perfect for a ski weekend for our family. We felt right at home and it had everything we needed. The place was very clean and had comfy beds. Easy drive to Okemo and surrounding restaurants. Jennifer was very helpful and responsive when needed. Would stay again for sure!
Top guest favourite
Home in Cavendish
4.98 out of 5 average rating, 44 reviews

Enjoy Vermont charm with fast Wi-Fi & Hot Tub!

CourtneyRating, 5 stars3 months ago
Amazing value! Very close to Okemo, great charming house and fantastic hot tub. Kitchen was very well stocked to cook for large groups. We really appreciated the well stocked glassware and the robes in each room. Will definitely come back!
Top guest favourite
Home in Chester
4.98 out of 5 average rating, 52 reviews

Cozy Chalet w/ Jacuzzi Hot Tub near Okemo Mountain

RitaRating, 5 stars3 days ago
Nice and quiet out of the way place. Perfect for a quick getaway for a few days. We will definitely be going back.
Guest favourite
Home in Mount Holly
5 out of 5 average rating, 10 reviews

Vermont Mountain Escape

CanerRating, 5 stars4 months ago
The house is fantastic and I highly recommend it to anyone who’s planning a trip to the area. Austin’s place is very stylish, comfortable and has everything that’ll make your stay an enjoying experience. You’ll find nice touches and well-thought details throughout the house the moment you step in. Location is also amazing to have a safe and peaceful stay with beautiful surroundings while being close to all nearby actions. We had a great ski trip overall and already planning to be back.

Private house rentals

Guest favourite
Home in Plymouth
5 out of 5 average rating, 10 reviews

Pet-friendly escape to hike, bike, golf, swim

MorganRating, 5 stars3 months ago
This house is perfect for a family ski weekend getaway! Beautifully tucked away on a quiet road yet a super short drive from lots to do, skiing, etc. Beautiful and comfortable interior, our son and dogs were right at home too. Jeanne really thought of everything with the welcome basket! We have added this one to our favorites 😊👏🏻
Guest favourite
Home in Cavendish
4.94 out of 5 average rating, 81 reviews

Close to Okemo, 25 Acre Mountain Playground

MichaelRating, 5 stars5 months ago
A beautiful place with an incredible view of the mountains- cozy and warm and extra comfy beds! Sheryl’s kitchen had everything we needed. And close to okemo
Top guest favourite
Home in Windsor
4.99 out of 5 average rating, 94 reviews

Stylish Ascutney Cabin •View •Chef’s Kitchen •Pets

AmandaRating, 5 stars1 week ago
We had a great stay! The house was well-appointed and comfortable. We especially loved the covered porch and beautiful view. It was a great home base for exploring the area, including several nearby hiking trails, Woodstock and Quechee (about a half hour away), and Brattleboro (less than an hour away). Ab was a fantastic host. He was proactive with communication and even checked in with us to make sure we had power after some strong thunderstorms that had moved through the area.
Top guest favourite
Home in Cavendish
5 out of 5 average rating, 22 reviews

The Carol

LaurenRating, 5 stars2 months ago
The Carol is a stunning and beautifully decorated historic home that was the perfect getaway for our ski trip!!! We stayed one night but wish we had stayed longer! It is located only 10 mins from Okemo which was perfect. The beds were super comfy and the bathroom and kitchen were stocked with everything we needed. Sarah was super helpful and responsive to everything and provided tons of recommendations to make our stay worthwhile. Would 100% recommend this place to anyone looking to ski Okemo!
Guest favourite
Home in Reading
4.91 out of 5 average rating, 70 reviews

Private, Large 4BR home | Pet friendly | 10 Acres

PhilipRating, 5 stars2 weeks ago
The place was in a wonderful quiet setting and the owners had left a thoughtful gift bag. They were great about communicating throughout and would definitely recommend the place
Top guest favourite
Home in Charlestown
4.99 out of 5 average rating, 70 reviews

Private & Cozy Farmhouse in New Hampshire

KarenRating, 5 stars2 weeks ago
This was our second stay at the farmhouse. We love this place! Wes and Lindsey are so nice and welcoming. The house is roomy, clean, and the property is beautiful. We most enjoyed walking our dog on the path out back, and spending time with family we have in the area. Hope to stay many more times!
Guest favourite
Home in West Windsor
4.97 out of 5 average rating, 95 reviews

3BR Country Retreat | Private and Peaceful

MarchantRating, 5 stars3 days ago
It’s a beautiful house in a private area. Great outdoor seating with tables, a sitting area and a fire pit area. Super clean and lots of space!
Top guest favourite
Home in Cavendish
4.97 out of 5 average rating, 60 reviews

Okemo Mountain Area with River View

JaspreetRating, 5 stars3 months ago
We had a great time in Jay's home. There were two days of heavy snow while we were there, and we had to stay indoors for most of that time, and it was great to have that warm, cozy home to hunker down in, with TV, games etc. There was a lot of snow and the kids enjoyed building a snow castle in the front area. Our car got stuck while we were trying to exit, but thanks to Jay's quick help and a bucket of sand/salt we were able to get going again. The near by Singleton Country Store is an interesting and fun place to visit, and was useful for all our needs. We were visiting the area to ski at Okemo, which is an easy 10-12 minute drive. Also, there are plenty of interesting farms within 30-40 minutes drive from the home. The one we visited this time was the Billings Farm & Museum, which was really awesome. Highly recommend the home if you are in the area!

Quick stats about house rentals in Cavendish

  • Total rentals

    60 properties

  • Nightly prices starting at

    $77 SGD before taxes and fees

  • Total number of reviews

    2K reviews

  • Family-friendly rentals

    50 properties are a good fit for families

  • Pet-friendly rentals

    20 properties allow pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

Destinations to explore

  1. Airbnb
  2. United States
  3. Vermont
  4. Windsor County
  5. Cavendish
  6. House rentals