Vacation rentals with a kayak in Plymouth

The Grafton Chateau

Welcome to the Grafton Chateau, a gorgeous secluded and private country retreat for all of your family and friends. With six bedrooms and a den, four baths, two fireplaces, a sauna and a large private pond beautifully situated on 67 acres of woodlands, the Grafton Chateau is the perfect comfortable home base for ski trips, hiking, antiquing, or just enjoying the scenery while you sit around the fire pit. The garage has outdoor recreation gear, like snowshoes and sleds. The den has a variety of toys, and games for kids and adults. The whole house, sauna house, barn and all 67 acres are all yours! We are always available by phone, text, or email if you have any questions. Grafton is just about the most charming Vermont town you can find and is convenient to four ski mountains and every other outdoor activity you can imagine.

Outdoor spaces · Location · Sleep quality

Luxury Condo Tucked in the Heart of Killington

Welcome to our ❄newly renovated❄ Cozy Condo Located right off the "loop" walking trail on river road. Our end unit condo sits just 5 min from the base of Killington with easy access to night life/restaurants and much more. Whether you are skiing, hiking, biking, kayaking or just enjoying the fresh Vermont air, you'll love the comfort of our condo. Enjoy a space that is truly convenient, comfortable, child-friendly and fun for you to enjoy during your hard-earned vacation time in Killington!

Outdoor spaces · Value · Quiet

Escape to VT chalet between Okemo and Killington

Escape to private 3-bedroom cabin on 2 wooded acres between Okemo and Killington. Perfect for families, couples, friends and their dogs, Bigfoot Chalet gives the privacy of a secluded Vermont retreat while keeping you close to skiing, hiking, lakes and local attractions. Highlights: • Between Okemo (6 miles) & Killington Skyeship (12 miles) • Pet friendly • Fire pit and fire place • 2 private wooded acres • Deck • Fully equipped kitchen • Workspace Come for skiing, foliage, hiking or lakes.

Location · Outdoor spaces · Skiing

Ludlow Lake & Ski Cottage - Adventure Awaits!

Relax and unwind at our charming cottage directly on Lake Rescue in Ludlow, VT. Enjoy stunning lake views, direct access to water activities (kayaks and paddle boat included!), with close proximity to Okemo Mountain Resort (5 min), Fox Run Golf Club (5 min) and Killington Mountain Resort (15 min - Skyeship). Perfect for your family or a group of friends to take advantage of everything the area has to offer. Our cozy house offers everything you need for your relaxing (or adventurous) getaway!

Outdoor spaces · Location · Walkability

Close to Killington-Loaded with Amenities-Hot Tub

🚲 15 MINUTES to KILLINGTON 🛀🏼 PRIVATE HOT TUB 🔥 OUTDOOR SAUNA 🎥 Outdoor MOVIE PROJECTOR 🥃 SECRET BOOKCASE DOOR Hiding a large, well-equipped SPEAKEASY 🐕 PET FRIENDLY 🏌️‍♂️15 MINUTES to GOLF 🥾 Close to HIKING 🌲 Massive themed KIDS ROOM 🌱 2 MASTER BEDROOMS 🎱 THOUGHTFUL AMENITIES for large families seeking luxury and fun 💰 Cleaning Fee Reimbursement for stays >6 nights. See below! 👰🏻 < 20 minutes to MOUNTAINTOP 🔋EV CHARGER 🛌 INCREDIBLY COMFORTABLE beds and linens

Outdoor spaces · Value · Sleep quality

Cozy Cottage Lakefront

Cozy 3BR Lake home, enjoy year-round adventure & relaxation. Summer-enjoy swimming, paddling, and fishing right from the lake, or roast marshmallows at the fire pit under the stars. Winter, hit the slopes & come home to cozy up in a warm, inviting space. Explore nearby hiking trails, grab a bite at one of the many local restaurants, or plan a day trip to a charming VT town. Whether you're skiing, leaf-peeping, lake lounging, or just unwinding, this home is the ideal base for all-season fun.

Outdoor spaces · Value · Nearby

8-Acre Retreat Near Killington & Okemo, Sleeps 8

Escape to a private 8-acre retreat in Vermont's Green Mountains—just 7 min from Killington, and 15 from Okemo. This renovated home features a chef's kitchen, organic mattresses & hiking trails. Wake up to mountain views, explore pristine lakes nearby, dine at Long Trail Brewery & farm-to-table spots. Jump on the VAST trailsystem from our backyard. A classic Vermont country store sits across the street. Perfect for skiing, summer adventures & fall foliage. Your four-season basecamp awaits!

Location · Outdoor spaces · Comfort

Cozy Chic Resort Cabin! Hot-Tub Private Fire Pit

Sugar Maple Mountain Retreat is an intimate resort perfect for small groups. Our three light filled, cozy cabins are tucked deep into the Vermont woods—private, peaceful, and designed for guests who crave both comfort and the tranquil escape of nature. Enjoy the peace of a private 8-acre boutique resort, packed with comforts and amenities while still less than 20-minutes from local charming Vermont restaurants, attractions, and all the small‑town magic that makes this area unforgettable.

Location · Value · Cleanliness

Waterfront Vermont Lake House w/ Panoramic Sauna

Waterfront on Lake St. Catherine, with almost 100ft of private lake frontage and a view that's hard to beat. Watch the sunrise from the deck or from inside our new panoramic barrel sauna. Explore the lake by kayak or canoe — both included for guests. Keep an eye out for both bald eagles and loons. There's also a fire pit for evening s'mores — firewood included as well. Great for families — we've got a crib, a bunk room for the kids, and a bookshelf of board games for those rainy days.

Value · Location · Heating

VT Lakefront House, Lake Fun, Fall Foliage and Ski

Newly renovated, air conditioned, lake front home with a hot tub, fire pits and modern finishes. Tons of space, super comfortable beds. Plus TWO LARGE bonus rooms. Year-round fun; swim, kayak, golf and fish in the summer; hike and fall foliage in the fall and ski in the winter. 7 minutes from Okemo and 22 minutes from Killington. Cook with a stunning view of the lake, watch a movie by the fire or hottub. Outdoor shower, game room, movie room, screened porch and much more!

Outdoor spaces · Location · Family

Tranquil Ludlow Waterfront Retreat

Fully renovated in 2019, our four bedroom Ludlow, VT home has over 300' of river frontage on the west side of the Black River. Walk out to amazing fishing in one of Vermont's crystal clear rivers. Enjoy nature while your stress melts away or have some fun at the Okemo Resort boasting mountain biking, zip lining, and two 18-hole championship golf courses. Easy river access by kayak to Lake Rescue and a 2 min drive to the family-friendly beaches of Echo Lake.

Location · Value · River

Waterfront Cabin • Dock • Fire Pit • Kayaks & SUPs

Relax at this private Vermont lakefront getaway on North Bay. Unwind in a bright, comfortable space with a full kitchen, fast WiFi, and cozy bedrooms. Walk a few steps to the water front to enjoy morning coffee on the dock. Perfect for year-round escapes: -Summer (kayaks, SUPs, floating mat) -Fall (foliage, fire pit, hiking trails) -Winter (skiing, snowshoeing, ice fishing) -Spring (deck, hammock, fishing opener).

Location · Value · View