Vacation rentals in Plymouth

4.99 out of 5 average rating, 170 reviews

Home in Woodstock

Cape Cod Home in Woodstock, Pet-Friendly & Wooded

Welcome to this charming 4-bedroom Cape Cod-style retreat in Woodstock, Vermont, a picture-perfect New England getaway set on a wooded hillside lot. With original wide-plank hardwood floors, a fully equipped chef's kitchen, and a spacious back deck with a 6-burner propane grill, this home offers the perfect blend of rustic character and modern comfort. Explore the covered bridges and artisan shops of Woodstock Village, or simply unwind in the peaceful garden setting. Please see: Other Things to

4.99 out of 5 average rating, 92 reviews

Cabin in Plymouth

Mountain Views, Hot tub, Trails, Pond, BBQ

Private Pond | Post & Beam | Nature Retreat | Hot Tub Sleeps up to 8 Welcome to your peaceful escape in the woods. This custom-built, post-and-beam home sits on 5 wooded acres with private frontage on a tranquil 6+ acre pond—perfect for nature lovers, quiet seekers, and family or friend groups looking to unwind. Highlights: * 4 bedrooms | 2.5 baths * 3 King beds & 1 Twin Bunk. All memory foam mattresses * 30-ft ceilings, reclaimed beams * Fully equipped kitchen * 75” TV, arcade, board games

4.99 out of 5 average rating, 131 reviews

The cabin entrance is framed by freshly fallen snow, with wooden siding that blends into the winter landscape. A lantern on the left provides a soft glow, illuminating the path. Tranquil trees surround the area, enhancing the serene atmosphere.

Cabin in Plymouth

~The ClubHaus~

Appreciate life at our peaceful home away from home in the Vermont Woods... Located a short drive from Killington and Okemo ski mountains, The ClubHaus is the perfect spot to unwind after enjoying four season New England activities. Breweries and great food are nearby in Woodstock, Manchester, and Dorset. Huge fireplace, hot tub, comfortable beds, and lots of thoughtful touches provided to welcome you to the ClubHaus family. Wifi, Netflix, and Disney+ included, no cable. @clubhausvt on IG

4.93 out of 5 average rating, 102 reviews

Home in Reading

Private, Large 4BR home | Pet friendly | 10 Acres

Okemo & Killington Ski House Large 4 bedroom 2.5 bath, 3,000+ sq ft home located close to Okemo Ski Resort and surrounded by 10 acres of land at the end of a private road! This recently renovated home features 3 levels, a large game room, 5 separate sleeping areas and a large covered porch! Enjoy ultimate privacy with proximity to multiple outdoor adventures including skiing, golfing, hiking and mountain biking. Just a short drive to downtown Ludlow and other surrounding stores in Cavendish.

4.99 out of 5 average rating, 72 reviews

Home in Ludlow

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!

A modern mountain retreat is set amidst a snowy landscape, showcasing a two-story green exterior. The gently sloping roof is adorned with a blanket of snow, while clear skies and distant trees complement the tranquil environment.

5.0 out of 5 average rating, 29 reviews

Mountain Home: Hot Tub & 9 Min to Skyeship Gondola

Escape to our family-friendly mountain retreat near Killington, Okemo, and Woodstock. Enjoy views, modern amenities, and a cozy atmosphere. Relax on the deck or in the hot tub. With 3 bedrooms and 2 baths, it's perfect for family getaways. Experience Vermont's beauty and adventure! NOTE: ON TOP OF CLEANING FEE FOR THE HOUSE, WE HAVE INCLUDED A FEE OF $209 TO SERVICE HOT TUB BETWEEN EACH GUEST'S USE. THIS IS TO ENSURE CLEAN WATER FOR YOU AND YOUR FAMILY/ GUESTS. THIS IS ACTUAL COST...

4.97 out of 5 average rating, 464 reviews

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

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.

5.0 out of 5 average rating, 47 reviews

Cabin in Plymouth

Thundersnow | Woods • Mountains • Peaceful

Ideally located just 20 minutes to Killington via Bear Mountain and Skyeship, and 10 minutes to the quieter backside of Okemo. Thundersnow is a cozy year-round cabin tucked in the Green Mountains close to Woodstock and Ludlow’s great dining . With a classic stone fireplace, game room, and inviting spaces, it’s the perfect home base for four-season adventures—whether skiing, hiking, or simply relaxing with loved ones and soaking in the peaceful surroundings.

4.98 out of 5 average rating, 59 reviews

Charming pet-friendly retreat in the Vermont woods

Escape to this peaceful, pet-friendly retreat nestled in the heart of Vermont’s fall foliage. Spend your days exploring scenic forest trails, riding the chairlift to take in autumn views, biking through colorful woods or playing a round at Fox Run Golf Club. After a day surrounded by fall beauty gather around the fire pit under a star-filled sky. Whether you’re chasing peak foliage or looking for a peaceful escape, your Vermont getaway awaits.

4.93 out of 5 average rating, 45 reviews

Wooded Vermont Getaway 15 mi to Okemo & Killington

Fall in Vermont starts here. Escape to Plymouth, VT for crisp autumn days, colorful foliage, kayaking on Echo Lake, a small lakeside beach, and scenic biking and hiking trails - all from a peaceful home tucked in the woods. Spend your days exploring the brilliant fall colors, then return to unwind at Hawk Hill Lodge. Perfect for families and groups of friends looking for nature, comfort, and an unforgettable Vermont fall getaway.

Shipping container in Ludlow

Luxury Container Home with Sauna & Heated Pool

Escape to a luxury modern container retreat minutes from Okemo Mountain. Set on 3 private acres with mountain views, this unique getaway features a sauna, heated plunge pool and thoughtfully designed modern interiors. Perfect for skiing, hiking, fall foliage, or relaxing in nature, the home blends comfort, style, and privacy while still being close to restaurants, lakes, golf, and everything Ludlow has to offer year-round.

5.0 out of 5 average rating, 14 reviews

A wooden structure is set amidst lush greenery, with its sloped roof and chimney rising above the surrounding foliage. Stone steps lead to the entrance, which is framed by tall grass and shrubs, highlighting the property's natural setting.

4.99 out of 5 average rating, 90 reviews

Secluded 2600 sq ft home 15 min from Okemo+Killington

Welcome to the VT Treehouse in Plymouth, VT. Nestled in a serene mountain setting, this home offers both privacy and convenience. Located just 15 minutes from two of the largest ski resorts in New England—Killington and Okemo; you’ll have easy access to world-class skiing, snowboarding, and winter activities as well as hiking, mountain biking, and exploring nature’s beauty year-round.

Popular amenities for Plymouth vacation rentals

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Air conditioning

Other great vacation rentals in Plymouth

5.0 out of 5 average rating, 9 reviews

Home in Ludlow

Cozy Cottage Lakefront

4.74 out of 5 average rating, 19 reviews

Black Dog Lodge - Ski Chalet

4.95 out of 5 average rating, 42 reviews

A modern cabin stands surrounded by lush greenery, featuring a dark exterior that contrasts with the natural landscape. A spacious deck is supported by wooden beams, and large windows invite natural light. A stone wall borders the property, adding character to the setting.

Home in Killington

Skye Ridge Lodge: Private Hot Tub, Open Concept

5.0 out of 5 average rating, 9 reviews

8-Acre Retreat Near Killington & Okemo, Sleeps 8

Superhost

4.86 out of 5 average rating, 21 reviews

RoundTop Chalet | Hot Tub + Near Killington/Okemo

4.98 out of 5 average rating, 61 reviews

A warm, wooden exterior of a cabin-style home is highlighted, featuring a front porch with seating and a sloped roof. Surrounding trees reflect the changing colors of autumn, contributing to a serene outdoor setting.

Home in Mount Holly

Cozy 2 bedroom house, close to Okemo & Killington

An open living area features a cozy gray sofa facing a stone-accented wall with a mounted television and electric fireplace. Large windows allow natural light to fill the space, while a modern chandelier adds brightness. A dining table is situated nearby, enhancing functionality.

4.94 out of 5 average rating, 18 reviews

Snowledge II by Okemo/Killington