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Holiday rentals in Cavendish

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Top-rated holiday rentals in Cavendish

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Holiday home in Cavendish

4.84 out of 5 average rating, 32 reviews

Cozy 1 bd Apt Minutes to Okemo & Pet Friendly

Looking for an affordable getaway near the scenic mountains of VT? Look no further! Our cozy one-bedroom apartment is just five minutes from the center of Ludlow and Okemo. Offering an open floor plan with a king bed, kitchenette with convection oven, open living space. Perfect for those looking to explore nature while enjoying comfortable, modern amenities. Book now and enjoy this hidden space above the carriage house where you will walk up the steep Vermont staircase to a Vermont hideaway.

1–8 Jun

€ 86 per night

Guest favourite

Guest house in Springfield

4.86 out of 5 average rating, 321 reviews

Connecticut River-Cozy Cottage

This cozy cottage is located on the beautiful Connecticut River, nestled between fertile farmland and Skitchewaug Mountain with views abound. The cottage design utilizes a small footprint while offering functionality and basic comforts, including a small kitchen. Great for all seasons, close to Okemo, Sunapee, Ascutney and other worthy attractions. Hiking and snowshoeing options at your front door. Secrete fishing and swimming holes located on the property. Boat dock available upon request.

18–25 Aug

€ 98 per night

Apartment in Ludlow

4.92 out of 5 average rating, 122 reviews

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.

19–26 May

€ 122 per night

Guest favourite

Barn in Chester

4.99 out of 5 average rating, 492 reviews

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.

22–29 Sep

€ 110 per night

Guest favourite

Home in Ludlow

4.92 out of 5 average rating, 139 reviews

149 Upper Crossroad Unit A

Renovated in the Summer of 2018, the Townhomes at Clock Tower are a beautiful, spacious year-mountain retreat. It sleeps 8 and has been beautifully appointed, with 2 Family rooms, 3 bedrooms, 2 bathrooms, a large open concept Kitchen, and Dining room with Gas Stove. The kitchen boasts granite countertops, dishwasher, with essentials. A short 5-minute walk to the Okemo Clock Tower Base Lodge, or a weekend/holiday shuttle that stops at the home for those who prefer not to walk it.

18–25 Jun

€ 120 per night

Guest favourite

Flat in Weathersfield

4.99 out of 5 average rating, 157 reviews

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.

23 Feb – 2 Mar

€ 136 per night

Guest favourite

Cabin in West Windsor

4.98 out of 5 average rating, 205 reviews

Sunset Cabin - your private romantic hideaway

Your private woodlands retreat awaits. Nestled atop a beautiful 10 acre meadow with 25 acres of woods for you to enjoy; this rustic, pet friendly cabin is a perfect romantic hideaway. Two trout ponds are steps from your door for fishing and swimming. Just a few minutes from Mt. Ascutney's hiking and mountain-biking trails and in the middle of fantastic cycling country. WiFi now available! Sunset Cabin is a marvelous spot for enjoying fall foliage and exploring Vermont.

2–9 Jul

€ 170 per night

Guest favourite

Guest house in Cavendish

4.95 out of 5 average rating, 106 reviews

Cozy Cavedish 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!

1–8 Oct

€ 257 per night

Guest favourite

Cottage in Ludlow

4.92 out of 5 average rating, 120 reviews

Ludlow Village Guest Cottage with Prime Location

Renovated one bedroom, one bath guest cottage in Ludlow, Vermont. Prime ski location, 12 houses down from the Mountain Road entrance to Okemo Base Lodge. Anything you need can be found a short walk from the front door including a wide variety of restaurants, shops and bars for Après Ski. Sitting on the weekend and holiday shuttle route to Okemo, its the perfect spot to be! Cottage has a fully equipped kitchen and wifi for your technology needs.

2–9 Sep

€ 126 per night

Guest favourite

Cottage in Windsor

4.97 out of 5 average rating, 316 reviews

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.

24 Nov – 1 Dec

€ 151 per night

Guest favourite

Apartment in Ludlow

4.92 out of 5 average rating, 122 reviews

Okemo Ski-in/Ski-out, Steps to lift Condo

Just steps of walk to the amazing Okemo slopes, C Building is the closest property to the A-Quad/B-Quad lift and this building offers convenient parking right downstairs and free wi-fi (dedicated Xfinity modem, no issue video conference). You’ll love this cozy place with hardwood floor and private balcony and sunshine after skiing. Great sun exposure. Fireplace has been updated to electric fireplace starting from 2023-2024 season.

18–25 May

€ 120 per night

Guest favourite

Guest suite in West Windsor

4.9 out of 5 average rating, 102 reviews

Newly renovated private space on Ascutney Trails

Newly renovated space on Ascutney trails--walking distance Ascutney Outdoors Center, hotel, restaurant, skiing, and Brownsville Butcher & Pantry. Trail access in back yard with miles of hiking, mountain biking, running and skiing. Parking for 2 cars. Close to Woodstock shops and Okemo adventure center. Private keycode entrance with self-check in. Microwave, refrigerator, Keurig, coffee and tea provided. Fast wifi.

9–16 Dec

€ 111 per night

Holiday rentals for every style

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Popular amenities for Cavendish holiday rentals

Free parking on premises

Air conditioning

Stay near Cavendish's top sights

The Pointe at Castle Hill3 locals recommend

Castle Hill Resort and Spa17 locals recommend

Singleton's General Store81 locals recommend

Neal's Restaurant20 locals recommend

Vermont Apple Pies Breakfast Bakery Restaurant10 locals recommend

Crows Bakery & Opera House Cafe24 locals recommend

Other great holiday rentals in Cavendish

Guest favourite

Home in Cavendish

5.0 out of 5 average rating, 99 reviews

Midcentury Hillside Retreat - Summer Paradise

7–14 Jun

€ 398 per night

Guest favourite

Cabin in Cavendish

4.89 out of 5 average rating, 18 reviews

Caretaker’s Cottage

5–12 Jul

€ 48 per night

Guest favourite

Farm stay in Baltimore

4.92 out of 5 average rating, 96 reviews

Hawk Mtn Farm's lovely one bedroom apartment!

25 Jun – 2 Jul

€ 126 per night

Apartment in Cavendish

4.78 out of 5 average rating, 45 reviews

Hotel Standard Condo Minutes from Okemo

23–30 Jul

€ 131 per night

Guest favourite

Home in Cavendish

5.0 out of 5 average rating, 9 reviews

VT Cabin close to Okemo and Killington

10–17 Aug

€ 530 per night

Guest favourite

Cabin in Cavendish

5.0 out of 5 average rating, 37 reviews

Pine Ridge ~Cozy Log Cabin Near Okemo & Killington

21–28 Jun

€ 332 per night

Guest favourite

Cottage in Ludlow

5.0 out of 5 average rating, 13 reviews

The Little House

10–17 Jul

€ 135 per night

Guest favourite

Home in Cavendish

5.0 out of 5 average rating, 8 reviews

The Carol

12–19 Jun

€ 190 per night

Quick stats about holiday rentals in Cavendish

Total rentals
130 properties
Rentals with a pool
40 properties have a pool
Pet-friendly rentals
40 properties allow pets
Family-friendly rentals
90 properties are a good fit for families
Total number of reviews
4.2K reviews
Nightly prices starting at
€ 28 before taxes and fees

Destinations to explore