Holiday rentals in Cavendish

5 out of 5 average rating, 111 reviews

Home in Ludlow

Stunning Views of Okemo - 3 Bedrooms, 3 Bath Home

Recently constructed on ten private acres with captivating views of Okemo resort. Three bedroom, three full bath modern chalet, just 1.5 miles from downtown and 3 miles from Okemo’s base areas. Epic views of Okemo and surrounding mountains from every room. Cozy around the fireplace in the living room or enjoy smores outside by the firepit, or a glass of wine on the deck. Lower level has second living room great for kids with large TV, comfy couches, Pac Man arcade, foosball and board games.

5 out of 5 average rating, 115 reviews

Midcentury Hillside Retreat - Summer Paradise

Enjoy this peaceful retreat in the heart of the Green Mtns and surrounded by 130+ acres of private woodland. Dramatic field stone fireplace and spectacular panoramic views of Mt Ascutney into New Hampshire from the entire living space. Large chef's kitchen. Private master suite and two guest bedrooms. The perfect get-away for relaxing with family and friends. Exceptional hiking, biking and Connecticut River adventures. Near GMHA and Woodstock. Great restaurants, fun village shopping nearby.

4.93 out of 5 average rating, 153 reviews

Apartment in Ludlow

All Season Lovely and Zen Okemo Mt Lodge Condo

Tired of city life and want a fresh breath? Feel the call from nature while also desiring some sporty fun? Come enjoy our lovely and Zen Condo right at the foot of beautiful Okemo! True ski-in/ski-out in the winter. Enjoy your warm ski day lunch by sitting next to the wood-burning fireplace*, while watching all the activities on the slope. In the warm weather, enjoy the beautiful hiking trails and golf course that Okemo offers, as well as water activities at the nearby lakes and rivers.

4.94 out of 5 average rating, 1,270 reviews

Tiny home in Jamaica

Apple Blossom Cottage: A Tiny House

The ABC is located just 15 minutes from the Stratton Mountain Gondola and just 2 miles from the popular Jamaica State Park. Comfortable for up to 5 people. The private tiny house includes fresh linens, dedicated Wi-Fi, a kitchenette, hot shower, flushing toilet, fire pit and porch. The calendar is accurate. Stratton Mountain Resort 10 miles Grace Cottage Hospital 7 miles Magic Mtn 15 miles Bromley 18 miles Mount Snow 15 miles Brattleboro 24 miles Okemo 30 miles Killington 47 miles

4.99 out of 5 average rating, 646 reviews

Barn in Chester

Inviting studio apartment above barn in Vermont

This custom build apartment is located just 10 minutes from I91. In the winter you are 30 minutes away from some of the best skiing around. Located on 85 private acres with great views this is the perfect winter get away. In the summer you can relax by the firepit, hike in the woods, work in the gardens (just kidding), collect breakfast from the chickens or visit some of the local breweries. We are as close or as far away as you would like us to be with our house right next door.

4.97 out of 5 average rating, 395 reviews

Cottage in Windsor

Ogden's Mill Farm

Private guest house situated on over 250 acres, with fully equipped gourmet kitchen and great views of quiet fields and valley. Pond with diving board for swimming in the summer. Giant sledding hill is a favorite of children and adults alike. Trails on property for hiking, xc- skiing, and snowshoeing. 15 mins to Woodstock VT. 45 mins to Killington,Pico and Okemo. Great restaurants and shopping nearby. Hanover and Norwich VT 20 mins. Please note not handicapped accesible.

4.98 out of 5 average rating, 126 reviews

Home in West Windsor

Birdie's Nest Guesthouse

Welcome to our newly renovated studio apartment, nestled among the trees in the serene hills of West Windsor, Vermont. Elevated on the second floor, this separate structure offers a tranquil escape with breathtaking views of Mount Ascutney and our own private pond. Immerse yourself in the comforts of this thoughtfully designed studio apartment, surrounded by the natural beauty of the Vermont landscape. Every detail has been curated to ensure your utmost comfort and enjoyment.

4.99 out of 5 average rating, 175 reviews

Flat in Weathersfield

The Loft at Weathersfield

Close to Okemo, The Loft at Weathersfield, is just 1/2 hour south of Woodstock / Hanover area and 22 minutes from Okemo Mountain. The Loft, is located in a private agricultural setting with easy access to Vermont's best biking, hiking, fly fishing, skiing, and many equine trails. The loft is 900 square feet with a kitchen/dining room, living room, full bath, one bedroom with a queen bed and one twin bed. There is a spacious deck off the kitchen and a car port underneath.

4.95 out of 5 average rating, 152 reviews

Guest house in Cavendish

Cozy Cavendish Bunkhouse

Enjoy a stylish & relaxing experience at this centrally-located guest home. Newly renovated with local interior designer! The bunkhouse is behind our main house. We're a quick 10 minute drive to Okemo Ski Resort! You can enjoy plenty of nature, hiking, snowmobiling, mountain biking, skiing/snowboarding and much more in the area! Follow the Bunk House on IG where we’ll share all the local happenings!! ‘at’cozycavendishbunk We look forward to hosting you!

4.9 out of 5 average rating, 120 reviews

Tiny home in Athens

LUXE Forest Retreat

Here you will experience a full sensory immersion in nature while simultaneously enjoying all the comforts of a custom built luxury home. The SY House derives its name from the Japanese expression Shinrin-yoku, which directly translates to "forest bathing... A practice of therapeutic relaxation where one spends time in a forest or natural atmosphere, focusing on sensory engagement to connect with nature." The essence of this house is nature.

4.93 out of 5 average rating, 104 reviews

Renovated Vermont Schoolhouse – Close to Okemo

Time for recess! Our totally renovated and expanded schoolhouse is a perfect retreat with all the comforts of home. It has high ceilings, lots of natural light, and plenty of spaces to gather or have some quiet time. Fully stocked kitchen w/DW. 3 bdrms (3 beds, 2 queen/1 full), 2.5 baths. W/D. Close to Ludlow, Okemo/Jackson Gore, Stratton, Killington, Castle Hill Spa and plenty of lakes and ponds.

4.97 out of 5 average rating, 133 reviews

Flat in Weathersfield

Cute VT Bungalow With 180 Degree View of NH

Located on a quiet country dirt road you will find this cozy apartment perfect for a weekend getaway. A short walk and you will be amazed at the 360 degree views of Vermont and New Hampshire. Centrally located near Okemo, Sunapee and Killington mountains, ski all 3 mountains in a weekend. Explore covered bridges, walking trails, scenic bike rides, or tubing on the Connecticut River.

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Popular amenities for Cavendish holiday rentals

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Air conditioning

Other great holiday rentals in Cavendish

5 out of 5 average rating, 28 reviews

Cabin in Weathersfield

Little Ascutney Post &Beam Chalet -Cozy near Okemo

VarunRating, 5 stars3 months ago

This was our first Airbnb stay, and it very much did not disappoint! We stayed over the weekend celebrating our family member’s 50th birthday, and the log cabin was pretty much perfect; the kitchen came well equipped with utensils and baking supplies, which we used for a few of our own homemade recipes, and the overall setting was really nice as well. The cabin came equipped with a few games as well which we played for a few hours. Nick and Emily were quick to respond as well, helping when needed. Overall 5/5!

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

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!

4.94 out of 5 average rating, 16 reviews

Cabin in West Windsor

Peaceful Vermont Cottage

LauraRating, 5 stars2 days ago

Great value. My son and I needed a comfortable place to crash with some elbow room. Huge laundry machines look new and worked great. Loved the big dining table. WiFi was excellent. TV worked great and was easy to stream our shows. Also, we liked the deck of cards and trivia board game. Fun! Brownsville Butcher and Pantry was very close drive for meals/groceries. Easy access to Hartland, Woodstock and I-91.

4.97 out of 5 average rating, 30 reviews

3BR 1Bth New England Cape - Experience Vermont!

MeganRating, 5 stars1 week ago

Stayed here for a wedding overnight, comfortable accommodations and quiet, peaceful area!

4.98 out of 5 average rating, 100 reviews

Flat in Ludlow

Law Office Apartment

LiliRating, 5 stars7 months ago

Alice’s place is as lovely as she is. She’s a great host! The apartment was everything I needed as a homebase whilst I was looking for property in the area. The kitchen is perfect, even for a professional chef! I was even able to have, a friend from Rutland over for dinner and cooked full fledged meal. Bed and linens were extremely clean and comfortable. Has all the New England charm you could ask for. Neighborhood is very cute. (if you are sensitive to noise, remember that it is an in town property and you will hear some truck traffic in the early morning. I always travel with earplugs, so not really an issue for me.) It’s next to the library and across from the green. There’s a great Shaws supermarket just two minutes drive from the apartment. The house itself is peaceful and full of natural light. The kitchen island with barstools made an ideal workspace for me. No issues with the Wi-Fi. Loved it. I would return. I recommend booking Alice’s place!

Apartment in Cavendish

4.78 out of 5 average rating, 60 reviews

Hotel Standard Condo Minutes from Okemo

PatriciaRating, 5 stars2 months ago

Clean, safe condo. A little dated, but still really good. Yiwen was quick to respond to an issue we had when we first checked in and the rest of the stay was perfect. The area had a lot of closed businesses, but we were able to find things to do and places to go. We recommend MacLomain's Scottish Pub and Lady Jane's Scottish Gift Shop both in Chester. The Curiosities Shop in Rutland was also nice.