Pet-friendly holiday rentals in Cavendish

Boulder House - Extraordinary Luxury in the Woods!

From its unique interior wall of huge boulders to the soaring post and beam construction, Boulder House is bolder in every way. It's a rare combination of peace, solitude, and luxury in a beautiful and secluded setting within the 250-acre Lakefalls estate. The very private deck overlooks "Chandler Meadow" and 11,000 acres of conserved land and water, with stunning views from the sunken tub and outdoor shower. The interior appointments and amenities provide extraordinary comfort and aesthetics.

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

Fat Cat Barn - Close Okemo & Magic, Vermont

Welcome to Fat Cat Barn! This is an incredibly unique, family oriented 1850's Mennonite built Post & Beam barn on 10+ acres in the pastoral hills of Andover, VT. We are wedged between the wonderful villages of Weston, Ludlow & Chester. Just 15 minutes from Okemo and Magic ski mountains with Stratton, Bromley & Killington all within 40 minutes. This is a wonderful four season property with plenty of options for fun right outside our door step. The Stratton mountain views and sunsets are stunning

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!

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

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 minutes from Mt. Ascutney's hiking/biking trails and in the middle of fantastic cycling country. Near local race including the VT100, Vt overland, VT50. Sunset Cabin is a marvelous spot for enjoying fall foliage and exploring VT!

Modern Okemo Smart Cabin - As Seen On DIY Channel

This is a brand new modern timber frame smart cabin in Ludlow (~5 min from Okemo). The house was recently featured on DIY / Discovery’s acclaimed TV show, Building Off The Grid. Warm up after a day of skiing or riding with heated floors and a walk-in shower. Charge up your electric vehicle in the private garage. Directly access the VAST snowmobile trail from the backyard or sit back on the porch and soak up the views. Message host about renting for next winter season!

Yurt In The Woods - Come to the Yurt.

The Yurt In The Woods is 30 ft in diameter - 700 spacious sq. ft. It's surrounded by trees and has a yard. 2 night stays required for Weekends. October 6th and 12th are currently vacant if you want a fall foliage trip. There is a "one" night stay fee of $50 Allowed 2 dogs with the agreement to my animal policy & $50 fee WiFi 1,000 megabits per second a fiber network Outdoor Gas Grill , Outdoor Fire Circle, and Outdoor Shower available May - October

VT Retreat: Hot tub | pool table | 70” TV | bbq

Come and stay in this extraordinary Cavendish home filled with historical charm yet fully updated with all the modern amenities you have come to expect. Our home has everything you need for your getaway. Gourmet kitchen, BBQ, Hot Tub, 2 master suites, games room, pool table, 70" TV, and window A/C's in all the bedrooms. Located just a short drive to many of Vermont's summer and winter attractions.

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.

5 miles from Woodstock-Dog Friendly w/FIOS

Just 5 miles from Woodstock, the Cottage at StillwoodVT is a bright and cozy two-story home set on a peaceful 20-acre oasis of woods, pasture, and hill views. Two bedrooms (queen upstairs, full downstairs), one bath with shower, and open kitchen/living/dining area. Private, quiet, and surrounded by nature. One-bedroom use receives 10% back after checkout (not combinable with other discounts).

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!