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 favourite
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, 122 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

Guest favourite
The historic Italianate home features a white exterior, with classic green shutters adorning tall windows. A spacious porch is supported by graceful columns, providing numerous seating options. The surrounding yard displays mature trees, enhancing the charm of the property set against a serene backdrop.
Apartment in Middletown Springs
4.9 out of 5 average rating, 268 reviews

Apartment in Vermont Historic Home

This lovely renovated 3-room apartment is attached to our 1885 Vermont italianate home, located is historic Middletown Springs, Vermont. We have been working on restoring this house, listed on Vermont's registry of historic homes, for a dozen years now. The apartment has its own entrance, full kitchen, and one spacious bedroom. The third room is a large sitting room with a shower and closet bath. Enjoy your morning coffee on the front porch, meet our chickens, and explore our garden.

Top guest favourite
A cozy living area features a mixture of seating options, including a tufted sofa and a vintage-style sofa adorned with decorative cushions. Natural wood floors enhance the warmth of the space, while artwork on the walls and a circular coffee table complete the inviting atmosphere.
Barn in Chester
4.99 out of 5 average rating, 699 reviews

Inviting studio apartment above barn in Vermont

This custom build apartment is located just 10 minutes from I91. In the winter you are 30 minutes away from some of the best skiing around. Located on 85 private acres with great views this is the perfect winter get away. In the summer you can relax by the firepit, hike in the woods, work in the gardens (just kidding), collect breakfast from the chickens or visit some of the local breweries. We are as close or as far away as you would like us to be with our house right next door.

Top guest favourite
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, 421 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 favourite
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
5 out of 5 average rating, 282 reviews

THE LOFT, stunning views from a timber framed barn

Welcome to "The Loft". The loft is a newly built apartment 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.

Top guest favourite
A modern kitchen features sleek white cabinetry and open shelving displaying glassware and kitchen essentials. A wooden dining table with black chairs provides a gathering space. Stainless steel appliances, including an oven and microwave, complement the stylish design, while a fresh plant adds a touch of greenery.
Apartment in Ludlow
4.95 out of 5 average rating, 104 reviews

Peaceful Ludlow Base 5 minutes to Okemo

Newly renovated, clean 1 BR apt. in historic house 2 blocks to town, 5 minute drive to Okemo, Buttermilk Falls, and 2 minute walk to the Ludlow Farmers Market. Enjoy complimentary coffee and local maple syrup while overlooking the town of Ludlow. Make yourself at home with a full kitchen/bath, wall-mounted flat screen TV, king bed, and comfortable futon. Free EV charging available. Kayaking, hiking, and golfing close by. We are dedicated to ensuring a top-notch experience!

Top guest favourite
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, 160 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.

Top guest favourite
A spacious living room features a comfortable sofa and armchair, enhancing relaxation. A large television is positioned in front, with decorative elements and artwork on the walls. Soft lighting from lamps and windows creates a welcoming ambiance in the well-designed space.
Guest suite in Clarendon
4.95 out of 5 average rating, 188 reviews

River House Apartment - Dog friendly

Entire downstairs of a house with one double bed. There is nice bathroom with shower. There is a microwave, coffee, massage chair, outdoor grill and picnic table. Internet and cable provided with fire stick for the TV. Fire pit and hot tub are shared by other guests. Up to three and all size dogs or pets are allowed and welcome. The three acres has a lovely place for them to run and has been sprayed for ticks and mosquitos. Please note: key replacement $30 if lost or taken

Top guest favourite
A cozy cabin is nestled among the trees, showcasing a rustic wooden exterior with large windows. It overlooks a gentle slope covered in green grass and wild plants, with sunlight filtering through the canopy above, creating a serene and inviting atmosphere.
Guesthouse in Woodstock
4.98 out of 5 average rating, 274 reviews

Cozy Little Spot (Self Check-in)

Contactless check-in. Cozy guest house, cabin-studio-getaway; enjoy the sounds of a stream outside the window (next to the bed). Views of a larger brook below. The"Cabin"is nestled in the trees giving a feeling of floating above the brook below. The interior is decorated w/family heirlooms gathered from around the country. Nothing fancy, just a cozy simple getaway. 3.25 mi from town. Choose from a variety of activities in town or hop on nearby trails. NO PETS ALLOWED.

Top guest favourite
The spacious interior of the yurt features a circular design with natural wood and fabric elements. Comfortable seating areas include a queen-sized futon and a wooden sofa. Large windows allow natural light to fill the space, while a wood stove provides warmth.
Guesthouse in Hartland
4.95 out of 5 average rating, 1,027 reviews

Yurt In The Woods - Private Refuge

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

Guest favourite
A cozy living area features a brick fireplace with a warm fire. A comfortable sofa adorned with decorative pillows is positioned nearby, accompanied by a wooden coffee table. Wall-mounted art and soft lighting enhance the welcoming ambiance.
Townhouse in Killington
4.96 out of 5 average rating, 128 reviews

Beautiful Spacious Condo at Killington Resort

This cozy and spacious Sunrise Mountain Village condo is perfectly situated to nearby mountain sports at Killington Ski Resort. It welcomes up to eight guests for an unforgettable stay in the Green Mountains! Exceptional access to year round outdoor activities, great community amenities, and a comfortable condo to come home to - what more could you ask for? Book Timberline K4 today for a thrilling Vermont getaway!

Guest favourite
A living room with a gas fireplace built into a brick facade provides warmth. A comfortable sectional couch faces the fireplace, complemented by a small coffee table. Large sliding glass doors open to a balcony, offering views of greenery outside.
Condo in Killington
4.98 out of 5 average rating, 136 reviews

Cozy Mountain Condo

Updated 1 Bdr Whiffletree condo in the heart of Killington minutes from everything. The condo is fully stocked with all of the essentials you will need for your Vermont get away. Ski locker for all your gear! Sleeps up to 4 with a king bed and queen pullout sofa. Shuttle in/out service available weekends (Dec–April), or ski home when conditions allow (check Killington trail status). Killington Reg #004858

Popular amenities for Plymouth vacation rentals

When is the best time to visit Plymouth?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price$554 CAD$624 CAD$502 CAD$373 CAD$416 CAD$400 CAD$435 CAD$395 CAD$390 CAD$424 CAD$423 CAD$538 CAD
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.

  • Do chalet rentals in Plymouth have a bbq area?

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

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

    Experience the best of Plymouth with our cabin rentals, starting at about $150 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Do chalet rentals in Plymouth have wifi?

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

  • Are there family-friendly chalet rentals in Plymouth?

    Plymouth has more than 10 family-friendly chalet rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

  • 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.

  • What are the most popular amenities for Cabin Rentals in Plymouth?

    Enhance your stay in our Cabin Rentals with the most popular amenities: over 10 homes with wifi, over 30 homes with a bbq area, and more. Indulge in the ultimate retreat, tailored to your preferences.

Quick stats about vacation rentals in Plymouth

  • Total vacation rentals

    Explore 140 vacation rentals in Plymouth

  • Nightly prices starting at

    Plymouth vacation rentals start at $99 CAD per night before taxes and fees

  • Verified guest reviews

    Over 5,350 verified reviews to help you choose

  • Family-friendly vacation rentals

    130 properties offer extra space and kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 60 rentals that welcome pets

  • Rentals with dedicated workspaces

    80 properties have a dedicated workspace

  • Wifi availability

    140 of Plymouth vacation rentals include wifi 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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