Vacation rentals in Cavendish

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Top-rated vacation rentals in Cavendish

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Top guest favorite
An open-concept kitchen and living area are highlighted by high ceilings and large windows, allowing natural light to fill the space. A central island with a dark countertop complements the cabinetry, while a cozy seating area is visible through expansive glass doors opening to the outdoors.
Home in Windsor
4.98 out of 5 average rating, 129 reviews

Stylish Vermont Cabin | Views · Trails · Luxe

Combining sweeping views of distant hills with complete privacy and wraparound porches on two sides, the Red House is a custom cabin built for couples and smaller families. Surrounded by working farms and within easy reach of trailheads to hike or bike Mt Ascutney, or to visit Woodstock, Hanover, Ludlow and the Upper Valley, the Red House sits among some of the best restaurants in Vermont and awaits the discerning traveler who has earned the right to do absolutely nothing and experience it all.

Guest favorite
The inviting living room features a modern wood-burning stove against a backdrop of light wooden walls. A comfortable dark sofa is arranged around a round wooden coffee table, complemented by a decorative plant. Natural light filters through the windows, enhancing the cozy atmosphere.
Cabin in Londonderry
4.95 out of 5 average rating, 252 reviews

Summit View Cottage:Ski | Hot tub|Fireplace3bd 2ba

Summit view cottage boasts 3 acres in the beautiful green mountains, we are 1,700 feet up in elevation . At this brand newly built PET FRIENDLY cabin you will have 3 bedrooms and 2 full bathrooms, which will sleep 7 comfortably. We have a brand new 6 person HOT TUB! You will find yourself within 15 minutes to the world famous Stratton mtn, 15 minutes from Bromley mtn and a close 4 minutes to the local Magic mtn.Very close proximity to the town of Manchester, which has great shops and restaurants

Top guest favorite
A log cabin is set amidst a snowy landscape, featuring a large wrap-around deck that offers outdoor seating. Snow blankets the ground and the roof, while evergreen trees frame the property, enhancing the secluded ambiance. The stone chimney rises from the cabin, suggesting warmth inside.
Cabin in Cavendish
4.97 out of 5 average rating, 108 reviews

Pine Ridge Log Cabin Minutes to Okemo & Killington

Get away to Pine Ridge Cabin! A secluded quintessential Vermont log cabin nestled below a pine filled ridge. Have your morning coffee on the large wrap around deck overlooking Elm Brook before your day hiking, brewery hopping, or hitting the slopes! The cabin provides open floor plans centered around the large stone face fireplace, the perfect space for gatherings of family, friends, or a couples retreat! Pine Ridge Cabin is only a few minutes to town, shopping, restaurants, bars, and spa!

Top guest favorite
Tiny home in Wilmington
4.99 out of 5 average rating, 377 reviews

Beautiful Timber Frame Retreat

This cabin retreat is situated on a natural clearing in the beautiful Green Mt. Forrest. Surrounded by a dense grove of spruce trees gives you complete privacy. It's only a quick 5 minute drive to great restaurants, breweries, and shops in downtown Wilmington. It's also less than 20 minutes to Mt. Snow. There's great hiking at Molly Stark State Park right across the street and amazing lakes all within a 10 minute drive! No WIFI and cell service is not great so it is a great place to unplug!

Top guest favorite
A mid-century modern home set among lush greenery features a stone foundation and large windows. A brick chimney rises above the roofline, while several wooden Adirondack chairs are positioned on a stone patio, providing a relaxing outdoor space to enjoy the surrounding nature.
Home in Cavendish
5 out of 5 average rating, 128 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.

Top guest favorite
The private guest house is surrounded by lush greenery, featuring a covered porch with a chimney and hanging planters. A well-maintained lawn leads to the house, while a backdrop of rolling hills enhances the tranquil setting.
Cottage in Windsor
4.97 out of 5 average rating, 449 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. Please note not handicapped accesible.

Top guest favorite
A well-appointed bedroom showcases a spacious bed dressed in white linens, complemented by decorative pillows. A wooden bench is situated at the foot of the bed. A large mirror and artful wall decor enhance the serene atmosphere, while natural light enters through a large window.
Home in West Windsor
4.98 out of 5 average rating, 181 reviews

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.

Guest favorite
A modern two-story cabin, featuring a rich red exterior, is nestled among autumn trees. Large windows allow natural light to fill the interior. A seating area with dark chairs is positioned around a fire pit, accentuating the outdoor space surrounded by colorful fall foliage.
Cabin in Cavendish
4.95 out of 5 average rating, 110 reviews

Luxury Cabin#1 Hot Tub Fire Pit Kayak Paddle Board

Escape in a beautiful light-filled upscale cabin deep in the woods at Sugar Maple Mountain Retreat. Relax at the end of the day in our hot tub which is shared between our 3 cabins. Steps away from two picturesque lakes, enjoy complimentary seasonal use of our kayaks, paddle boards and snow shoes. Go fishing, biking, hike country roads or trails on the 1275 acres of surrounding preserved land. In winter hop on the VAST trail nearby. 4 WD Required Dec 1- April 15th

Superhost
A modern cabin features a contrasting black exterior and wooden accents, nestled among lush trees. A wide deck with railing leads to the entrance, offering a welcoming space to enjoy the surrounding nature. Large windows provide ample natural light and views of the forest.
Tiny home in Athens
4.86 out of 5 average rating, 179 reviews

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.

Guest favorite
The exterior of the renovated schoolhouse is illuminated at dusk, showcasing large windows that reflect a warm glow from within. The distinctive architectural features are highlighted against a twilight sky, with trees positioned in the background.
Home in Cavendish
4.94 out of 5 average rating, 111 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.

Guest favorite
Guesthouse in Cavendish
4.96 out of 5 average rating, 184 reviews

Charming Cavendish Guesthouse w/ Sauna!

Cavendish Cottage Guest House! Freshly renovated with designer touches, this charming guest house blends style, comfort, and Vermont charm. Enjoy free access to our traditional sauna — shared with two other units and your host. Robes robes provided so you can unwind after skiing or hiking, then cozy up by the pellet stove. 10 minutes to Okemo, 2 minutes to groceries, and super comfy vibe await!

Top guest favorite
A patio area is visible, featuring a stone fire pit with colorful glass accents. Comfortable seating is arranged around the fire pit, with a large umbrella providing shade. The expansive green landscape stretches in the background, offering a view of distant mountains under a cloudy sky.
Apartment in Weathersfield
4.97 out of 5 average rating, 152 reviews

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.

Popular amenities for Cavendish vacation rentals

When is the best time to visit Cavendish?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$65,487 GYDG$66,742 GYDG$53,770 GYDG$39,752 GYDG$39,752 GYDG$44,983 GYDG$43,100 GYDG$42,472 GYDG$40,589 GYDG$44,564 GYDG$46,029 GYDG$61,302 GYD
Avg. temp-5°C-4°C1°C8°C14°C18°C21°C20°C16°C9°C4°C-2°C

Frequently Asked Questions

  • What are the best places to stay in Cavendish?

    Stays near Cavendish Village or close to the river are often recommended for easy access to local dining, trails, and community events. Cabins, historic homes, and modern cottages provide a variety of atmospheres.

  • What are the best things to do in Cavendish with kids?

    Families often explore nature trails, picnic by the river, or visit nearby farms to experience seasonal activities like apple picking or maple sugaring. Outdoor parks and small museums also provide hands-on activities for children.

  • What are some of the best things to do in Cavendish?

    Hiking forested trails, experiencing local heritage sites, and attending community events are frequently suggested in Cavendish. Outdoor enthusiasts also enjoy birdwatching, fishing, and seasonal adventures along riverbanks.

  • How is the weather in Cavendish?

    Cavendish has cold snowy winters near 13–32°F (-11–0°C), and warm summers around 57–81°F (14–27°C), with the wettest months in mid to late summer. Layered clothing and rain gear are useful throughout the year.

  • When is the best time to visit Cavendish?

    Late spring through early autumn is often recommended for milder temperatures, blooming wildflowers, and colorful foliage. Winter is popular for snow sports, but travelers should prepare for cold and snowy conditions.

  • What are the best places to visit in Cavendish?

    Explore the historic Cavendish Village green, pop into local farmstands, or wander the natural trails near the Black River. The Old Stone Church is often recommended for those interested in local history.

  • What are some hiking trails in Cavendish?

    Cavendish has forested trails winding through woodlands and along the Black River, with some paths featuring gentle slopes suitable for a range of abilities. Trailheads near the village green are frequently suggested starting points.

  • What are some family activities we can do in Cavendish?

    Families often explore nature trails, join in maple sugaring or apple picking when in season, or picnic by local rivers. Small museums and playgrounds are also available for younger children.

  • What are some of the best day trip ideas from Cavendish?

    Explore covered bridges, visit nearby mountain resorts for seasonal recreation, or browse the shops in small local towns. Popular ideas also include touring sugarhouses or checking out art galleries in the region.

  • Are there any pet friendly accommodations available in Cavendish?

    Many accommodations in Cavendish welcome pets, especially homes with yards or nearby access to trails. Parks and outdoor spaces make it easy to include pets in your daily routine.

  • What are some local tips for visiting Cavendish?

    Pack for varied weather, bring reusable water bottles, and check local boards for updates on seasonal activities or road conditions. Early mornings provide quiet time for walks, and small shops frequently feature local crafts worth exploring.

  • What is Cavendish known for?

    Cavendish is known for its scenic rural landscape, New England architecture, and connection to classic Vermont traditions like maple production. The quiet natural setting is often highlighted by visitors.

  • What are the best hidden gems to explore in Cavendish?

    Seek out the lesser-known hiking paths along shaded brooks, or discover small community gardens maintained by locals. The Cavendish Historical Society often shares stories connecting sites to unique regional history.

  • What are the best foods to try in Cavendish?

    Cavendish has a tradition of classic Vermont flavors—try local maple syrup, artisan cheeses, and apple cider pressed nearby. Seasonal farm-to-table menus are frequently suggested, especially in autumn when harvest produce is abundant.

  • What should I bring for a trip to Cavendish?

    Bring layers for fluctuating temperatures, comfortable shoes for outdoor exploring, and rain gear, as weather can shift quickly. In autumn and winter, warmer clothing is important, with snow boots suggested during the coldest months.

  • What is the nightlife in Cavendish like?

    Nightlife in Cavendish is low-key, centering around cozy taverns, local gathering spots, and live folk or acoustic music events. Visitors often enjoy evenings sampling Vermont ciders or relaxing by a fire.

  • What are the most popular events or festivals in Cavendish?

    Cavendish has community gatherings featuring local crafts, music, and traditional Vermont foods, often around late summer and during autumn foliage. Nearby, agricultural fairs and maple festivals are frequently suggested seasonal highlights.

  • Are there family friendly vacation rentals in Cavendish?

    Many vacation rentals in Cavendish include space for families, with options near parks, rivers, and walking trails. Look for homes with common spaces, kitchens, and outdoor areas for a relaxed family getaway.

Quick stats about vacation rentals in Cavendish

  • Total vacation rentals

    Explore 120 vacation rentals in Cavendish

  • Nightly prices starting at

    Cavendish vacation rentals start at G$8,369 GYD per night before taxes and fees

  • Verified guest reviews

    Over 5,830 verified reviews to help you choose

  • Family-friendly vacation rentals

    80 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 30 rentals that welcome pets

  • Vacation rentals with a pool

    30 properties feature pools

  • Rentals with dedicated workspaces

    70 properties have a dedicated workspace

  • Wi-Fi availability

    120 of Cavendish vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Cavendish rentals

  • 4.8 Average rating

    Cavendish stays are highly rated by guests—averaging 4.8 out of 5!

  1. Airbnb
  2. United States
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  4. Windsor County
  5. Cavendish