Vacation rentals in Plymouth

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Top-rated vacation rentals in Plymouth

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite
Treehouse in Brookline
4.98 out of 5 average rating, 257 reviews

Glamping Cabin with Hot Tub on Flower Farm

<b>Vermont's Most Wish Listed</b> ﹏﹏﹏ Nestled in a wooded grove on Tanglebloom Flower Farm, this unforgettable glamping-inspired farm stay invites you to escape the everyday & immerse yourself in nature - comfortably. Designed with a clear roof looking up to the trees and screened sides to let in the breeze, the handmade tiny cabin invites you to slow down. Explore southern Vermont's hikes, farmer's markets & swimming holes or stay put. Perfect for a romantic couples retreat or solo getaway.

Guest favorite
A large hot tub is positioned under a wooden structure, offering a view of the snow-covered building in the background. The exterior is characterized by dark accents against white walls, and natural scenery is visible through the open roof.
Apartment in Plymouth
4.93 out of 5 average rating, 194 reviews

Moguls Unit: Skyeship Gondola 2 miles w/ HOT TUB

The Mogul's Unit is a recently updated, fully separate, ground level, 2 bedroom/ 1 bathroom apartment in our four-family French Chalet. Located 1 mile to lakes and summer camps and 2 miles from Skyship Gondola. 15 minutes to Killington’s main base area and 20 minutes to Okemo or Woodstock. If you would like to book multiple units, check out our other listings by clicking my Host Profile Picture below. The units at this location are called "the Canyons Unit", "The Ledges", and "The Glades".

Guest favorite
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
4.99 out of 5 average rating, 129 reviews

~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

Top guest favorite
The uniquely shaped house, adorned with shingles, is surrounded by lush greenery. Large windows reflect the vibrant foliage, allowing natural light to illuminate the structure. The natural stone wall complements the rustic aesthetic, creating a harmonious blend with the wooded landscape.
Home in Fairlee
4.96 out of 5 average rating, 580 reviews

Cozy Bow House Perched in Trees w/ Hot Tub & View

The cozy Bow House is perched up above a lovely valley and boasts large south facing windows, a unique bowed loft and a warm, inviting space to relax. Up a charming dirt road past Brushwood & Fairlee Forests with hiking, biking and ATV trails nearby. Lake Fairlee is a scenic 10 min drive; 15 min to Lake Morey & I-91 and 30 min to Dartmouth College. Enjoy the glow of the rising sun and beautiful views above the fog, unwind in the hot tub surrounded by the magical woods and wildlife of Vermont.

Top guest favorite
A unique treehouse is seen perched among tall trees, with a blend of rustic wood siding and large windows that reflect the surrounding greenery. The structure stands elevated from the ground, supported by slender pillars, blending harmoniously with the natural forest environment.
Treehouse in Hancock
4.98 out of 5 average rating, 171 reviews

Weasley's Enchanted Treehouse @ Vermont ReTREEt

Welcome to our enchanting treehouse! We crafted this unique and magic inspired dwelling for any admirer of a beloved wizarding world, or anyone who appreciates isolation in a fun space. As you cross the elevated walkways, you'll feel like you're entering a wizards treehome in the forest. The 1,100 sqft treehouse is nestled in and among trees, providing a magical and secluded escape from life. Have a question or hesitations? reach out check out our other listings for glamping style treehouses

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 kitchen area features a large island with seating and modern appliances. Natural wood paneling complements the high cathedral ceiling. Glass doors open to a scenic view of the surrounding hills, providing ample natural light and a connection to the outdoors.
Barn in Woodstock
4.99 out of 5 average rating, 305 reviews

THE LOFT, stunning views from a timber framed barn

Welcome to "The Loft". A lofted space on the top floor of a timber framed barn. The owners are designer/builders who have combined the elements of old world craftsmanship with high tech efficiency to create a living space that is bright, airy and yet cozy. Powered by solar, this attached carriage barn is located on a quiet back road 3.5 miles from Woodstock Village and 3 miles from GMHA. The Loft has its own private entrance, parking and a sunset balcony. For more go to @theloft.vt

Top guest favorite
The rustic cabin, surrounded by lush trees, features a porch with a picnic table. The wooden structure is designed with a gabled roof and large windows, providing a welcoming entrance. Flower boxes adorn the front, enhancing the natural setting.
Cabin in West Windsor
4.96 out of 5 average rating, 278 reviews

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!

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, 446 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
The living area features a spacious sofa and armchair, framed by large windows that provide ample natural light. Exposed wooden beams run along the ceiling. A decorative rug adds color to the hardwood floor, and a mantelpiece serves as a focal point in the room.
Home in Tinmouth
5 out of 5 average rating, 101 reviews

Charming Vermont Schoolhouse

Kick back and relax in this calm, stylish space. A beautifully restored schoolhouse circa 1860 welcomes you. Situated on a quiet country road this adorable home on one wooded acre has lovely mountain views and a peaceful setting. Nearby you will find skiing, hiking trails and quaint Vermont towns with shops and restaurants. Manchester and Rutland are 30 min. drives, Dorset is just 20 min. Granville NY has a large grocery store and other shops and is only a 15 min. drive.

Guest favorite
An A-frame cabin is nestled among trees with autumn leaves in vibrant shades. A large deck extends from the cabin, featuring a hot tub and outdoor dining area. A barrel sauna is positioned nearby, completing the inviting outdoor space.
Cabin in Mount Holly
4.87 out of 5 average rating, 164 reviews

Okemo A-Frame - Floor Hammock, Sauna & Hot Tub

Welcome to the Okemo A-Frame! With an oversized deck, featuring outdoor dining, a barrel sauna, and hot tub you'll enjoy the outdoors year round. Enter into an open-concept dining area, kitchen, and living room with stylish mid-century malm fireplace. Take your rest in one of the three bedrooms or cozy up on the indoor floor hammock. Located 10 minutes from Okemo Mountain Resort and the town of Ludlow enjoy skiing, shopping, dining, and all that Vermont has to offer.

Top guest favorite
The Kingsley Grist Mill is positioned alongside a flowing river, surrounded by trees showcasing autumn colors. A historic covered bridge is visible in the distance, enhancing the landscape. The building features multiple stories with varying textures and roof styles, reflecting its rich history.
Castle in Clarendon
4.98 out of 5 average rating, 501 reviews

Kingsley Grist Mill Waterfall & Private Beach OMG

One of the "World's Most Amazing Vacation Rentals " as seen on the exciting NetFlix series, s.2, ep.7 and on HGTV's "You Live in What?, s.2, ep.1. Join us this season for the romance, the history, the breakfast, the natural mineral spring tap water, the concert, the rafting, the architecture and the legacy of the KGM, Vermont's Wright-esque falling water masterpiece. No cleaning fees added. Come make history with us ! Near Killington & Okemo Mtns.

Popular amenities for Plymouth vacation rentals

When is the best time to visit Plymouth?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$94,122 GYDG$104,580 GYDG$78,017 GYDG$55,428 GYDG$61,702 GYDG$59,402 GYDG$64,631 GYDG$58,565 GYDG$57,937 GYDG$67,559 GYDG$58,983 GYDG$88,266 GYD
Avg. temp-7°C-6°C0°C7°C14°C18°C21°C20°C15°C9°C3°C-3°C

Frequently Asked Questions

  • Are there pet-friendly vacation rentals in Plymouth?

    Four-legged friends are welcome in Plymouth. Choose from more than 60 vacation rentals for guests traveling with pets.

  • Are there vacation rentals with a dedicated workspace in Plymouth?

    Yes! Work meets play with ease at over 80 vacation rentals in Plymouth featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there family-friendly vacation rentals in Plymouth?

    Plymouth has more than 140 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • How much does it cost to stay in cabin rentals in Plymouth?

    Experience the best of Plymouth with our cabin rentals, starting at about $170 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do house rentals in Plymouth have air conditioning?

    Absolutely! We offer over 40 house rentals with air conditioning in Plymouth. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Plymouth have wifi?

    Absolutely! We offer over 80 house rentals with wifi in Plymouth. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Plymouth have a bbq area?

    Absolutely! We offer over 50 house rentals with a bbq area in Plymouth. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Plymouth have a gym?

    Absolutely! We offer over 10 house rentals with a gym in Plymouth. Enjoy a tailored experience with all the comforts you desire.

Quick stats about vacation rentals in Plymouth

  • Total vacation rentals

    Explore 150 vacation rentals in Plymouth

  • Nightly prices starting at

    Plymouth vacation rentals start at G$16,733 GYD per night before taxes and fees

  • Verified guest reviews

    Over 5,860 verified reviews to help you choose

  • Family-friendly vacation rentals

    140 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 60 rentals that welcome pets

  • Rentals with dedicated workspaces

    80 properties have a dedicated workspace

  • Wi-Fi availability

    150 of Plymouth vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Gym, BBQ grill, and Laptop-friendly workspace across Plymouth rentals

  • 4.8 Average rating

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

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