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Vacation rentals in Cavendish

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Top-rated vacation rentals in Cavendish

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Guesthouse in Springfield

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.

Home in Cavendish

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.

Condo 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.

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.

Guesthouse in Wallingford

Vermont Home Central to Ski Areas-No Cleaning Fees

Comfortable guesthouse located conveniently on US Route 7 near ski areas. Half hour from Manchester Outlet Stores. Near Long Trail/Appalachian Trail, Weston and Dorset Playhouses and miles of scenic country roads. Close to Elfin Lake and White Rocks National Recreation Area.Great for couples, small families, solo adventurers, and business travelers. Queen size bed and full kitchen. Great for overnight stay or week-long vacation to enjoy the beauty of Vermont. No cleaning fees!

Rental unit 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.

Cabin in West Windsor

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.

Guest suite in Brownsville/West Windsor

Cozy Guest Suite in Charming Farmhouse

Your two story guest suite is attached to the (main house) with a private FRONT DOOR entry. Sorry there are no cooking elements available. Please take note that the antique stairs to the second floor are steep. You will find your very own first floor library/eating area with WiFi, mini fridge, coffee maker and 1/2 bath. Upstairs is a comfy bedroom suite with a private modern bathroom that includes a shower and Jacuzzi tub. None of these area are shared. It’s all yours!

Guesthouse in Cavendish

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!

Cottage in Ludlow

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.

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.

Condo in Ludlow

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.

Vacation rentals for every style

Get the amount of space that is right for you

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A space thats all yours, with room for everyone

Hotels

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Unique stays

Spaces that are more than just a place to sleep

Popular amenities for Cavendish vacation rentals

Free parking on premises

Air conditioning

Other great vacation rentals in Cavendish

Home in Ludlow

149 Upper Crossroad Unit A

Rental unit in Claremont

Beautiful 1 bedroom apartment with balcony

Cabin in West Windsor

Cowshed Cabin Farm & Stable

Farm stay in Baltimore

Hawk Mtn Farm's lovely one bedroom apartment!

Condo in Cavendish

Hotel Standard Condo Minutes from Okemo

Tiny home in Chester

Bearfoot Cottage: Tiny House w/ Hot Tub near Okemo

Cottage in Ludlow

The Little House

Guesthouse in Cavendish

Brand New Village home in Cavendish, VT

Quick stats about vacation 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
$30 before taxes and fees

Frequently Asked Questions

Do apartment rentals in Cavendish have a kitchen?
Absolutely! We offer over 10 apartment rentals with a kitchen in Cavendish. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Cavendish have free parking?
Absolutely! We offer over 50 house rentals with free parking in Cavendish. Enjoy a tailored experience with all the comforts you desire.
Do condo rentals in Cavendish have air conditioning?
Absolutely! We offer over 20 condo rentals with air conditioning in Cavendish. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly vacation rentals in Cavendish?
Cavendish has more than 90 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
Are there pet-friendly vacation rentals in Cavendish?
Four-legged friends are welcome in Cavendish. Choose from more than 40 vacation rentals for guests traveling with pets.
Do cabin rentals in Cavendish have wifi?
Absolutely! We offer over 10 cabin rentals with wifi in Cavendish. Enjoy a tailored experience with all the comforts you desire.
How much does it cost to stay in house rentals in Cavendish?
Experience the best of Cavendish with our house rentals, starting at about $60 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there vacation rentals with a dedicated workspace in Cavendish?
Yes! Work meets play with ease at over 70 vacation rentals in Cavendish featuring dedicated workspaces. Stay connected and productive in your home away from home.
What are the most popular amenities for House Rentals in Cavendish?
Enhance your stay in our House Rentals with the most popular amenities: over 50 homes with wifi, over 20 homes with air conditioning, over 50 homes with free parking, over 50 homes with a kitchen, and more. Indulge in the ultimate retreat, tailored to your preferences.
Are there Cavendish vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 40 vacation homes with pools in Cavendish, available on Airbnb. Make a splash and soak up the sun in style!

Destinations to explore