Holiday rentals in Plymouth

4.99 out of 5 average rating, 114 reviews

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

5 out of 5 average rating, 111 reviews

Home in Ludlow

Stunning Okemo Views - 3BD 3BA on 10 Private Acres

Recently constructed on ten private acres with captivating views of Okemo. Three BR, three full bath, air conditioned modern chalet, just 1.5 miles from downtown and 3 miles from Okemo’s base areas. Epic views of Okemo and surrounding mountains from every room. Cozy around the fireplace in the living room or enjoy smores outside by the firepit, or unwind on the deck. Lower level has second living room great for kids with large TV, comfy couches, Pac Man arcade, foosball and board games.

Guest house in Wallingford

4.98 out of 5 average rating, 700 reviews

Vermont Home Central to Ski Areas-No Cleaning Fees

Comfortable guesthouse located conveniently on US Route 7 near ski areas. Half hour from Manchester Outlet Stores. Near Long Trail/Appalachian Trail, Weston and Dorset Playhouses and miles of scenic country roads. Close to Elfin Lake and White Rocks National Recreation Area.Great for couples, small families, solo adventurers, and business travelers. Queen size bed and full kitchen. Great for overnight stay or week-long vacation to enjoy the beauty of Vermont. No cleaning fees!

4.97 out of 5 average rating, 395 reviews

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.

4.98 out of 5 average rating, 126 reviews

Home in West Windsor

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.

4.98 out of 5 average rating, 246 reviews

Cabin in Mount Holly

Private Cabin/PetsOK/Minutes to Okemo/AC/Fast Wifi

Enjoy the beauty of Vermont at our private cabin. Situated on acres of woods next to a small creek, the cabin is 15 minutes to Okemo Mountain, excellent hiking on the Appalachian Trail and scenic Vermont towns for dining and shopping. With a queen bed loft, a double bed bedroom and a pull out sofa, the cabin sleeps up to 4 people. The kitchen is nicely equipped and there is a charcoal grill outside. High speed fiber optic internet will keep you connected. Max 2 pets allowed.

4.98 out of 5 average rating, 244 reviews

Guest house in Woodstock

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.

4.86 out of 5 average rating, 129 reviews

Cabin in Mount Holly

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.

4.9 out of 5 average rating, 122 reviews

Tiny home in Athens

LUXE Forest Retreat

Here you will experience a full sensory immersion in nature while simultaneously enjoying all the comforts of a custom built luxury home. The SY House derives its name from the Japanese expression Shinrin-yoku, which directly translates to "forest bathing... A practice of therapeutic relaxation where one spends time in a forest or natural atmosphere, focusing on sensory engagement to connect with nature." The essence of this house is nature.

4.91 out of 5 average rating, 168 reviews

Flat in Plymouth

Canyons Unit: 1 mile to F&W Summer Camp w/ HOT TUB

The Canyons Unit is a freshly renovated, 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 Killington’s Skyeship Gondola. 15 minutes to Killington’s main base area and 20 minutes to Okemo. If you would like to book multiple units, check out our other listings at this location called "the Moguls Unit", "The Ledges", and "The Glades".

4.96 out of 5 average rating, 613 reviews

Flat in Rutland

Your home away from home

Another glorious time of year in Vermont! Our house is close to the mountains (Killington, Pico, Okemo). You'll love our space for its central location to lakes, hiking, skiing, golf, restaurants and dining, downtown, art and culture, shopping and medical facilities.This first floor apartment with its home-like atmosphere has a separate entrance. It is good for couples, small families, solo adventurers, and business travelers.

4.99 out of 5 average rating, 113 reviews

Apartment in Killington

Cozy Condo *AC & Pool *

Bright, updated 1-bedroom Whiffletree condo in the heart of Killington—just minutes from the bike park, adventure center, and golf! Cool off in the outdoor pool and enjoy air conditioning for those warm summer days. Fully stocked with all the essentials plus a gear locker. Sleeps up to 4 with a king bed and queen pullout sofa—your perfect summer getaway! Killington Reg #004858

Holiday rentals for every style

Get the amount of space that is right for you

Chalets

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Popular amenities for Plymouth holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Plymouth

4.75 out of 5 average rating, 215 reviews

Chalet in Plymouth

5BR Chalet in Historic Town bet Killington & Okemo

PamalaRating, 5 stars2 months ago

We had an issue with our previous rental and needed to find a place to stay that is pet friendly and available. Rad and Carol responded quickly to our reservation request. The house was made available to us early in the day and hot tub prepped last minute for us to enjoy! The Chalet is beautiful and spacious, the location is private and relaxing. The wood stove kept us warm and cozy while we enjoyed watching light snow fall. We would definitely stay there again and bring our family with us!

4.96 out of 5 average rating, 98 reviews

Cabin in Ludlow

Modern Okemo Smart Cabin - As Seen On DIY Channel

JonathanRating, 5 stars1 month ago

Aaron’s modern cabin in Ludlow was wonderful. Close to ludlow but nice and set back in the woods near town. Quiet and peaceful. The house is a newer build so it has all the creature comforts of home! My family had a great time and our 9 year old loved the loft space. Great to have a washer dryer and dishwasher in the Airbnb. Aaron was a responsive and helpful host with easy to follow rules. We enjoyed our time at the cabin and highly recommend. We will be back!

4.94 out of 5 average rating, 32 reviews

Cabin in Woodstock

Woodsy Retreat Minutes from Woodstock Village

CoryRating, 5 stars1 month ago

Fern Gully is magical, especially in Spring when we visited. Very private setting with breathtaking views of Vermont's landscape, but still easy to get into Woodstock. The place has everything you'd need and is tastefully decorated.

5 out of 5 average rating, 30 reviews

Guest house in Reading

Peace & quiet at Comet Farm

XiangchengRating, 5 stars3 months ago

This is an absolutely gorgeous place to stay in Vermont and we loved it!! The living room and bedrooms are all elegantly decorated and also very cozy. More importantly, Madeline and Parris are the best hosts we have ever had. We came to Vermont for a ski trip and ran into some snow-related issues on our first day. Madeline and Parris were very responsive and offered tremendous help to us. Overall, a beautiful house with great hosts for an amazing stay!

Cabin in Middletown Springs

5 out of 5 average rating, 4 reviews

Secluded Cabin: Studio Apartment

RivkahRating, 5 stars4 days ago

We had a great stay at Karen's place. We stayed in the studio apartment and it was clean and had a newly redone feeling. The scenery was beautiful and there's a nice waterfall within a 2 minute walk right on site. Karen was super responsive and helpful. Thank you!

4.92 out of 5 average rating, 71 reviews

Home in Reading

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

BrendaRating, 5 stars1 day ago

Wow! What a great find. Everything was perfect. We had plenty of room for all of us: 7 adults/1 baby. We've staying in a lot of Airbnb's and this place by far had the best amenities. Kitchen fully stocked with pots/pans, baking pans/sheet pans, loads of silverware and dishes, various bowls and storage containers, and epecially all the little things that you either forget or have to go out and buy. Reponsive hosts! Comfy beds:) Everything was very clean. Lots of seating. Large yard which was great for the dogs. Loved having the porch, which also had lots of seating, a gas grill, and the best was a built in gate for the stairs which was super handy for the dogs! (and the baby). The basement has a separate living area 2 sofa's and 2 twins beds (and a mini frig). The game room was fun and had a walkout to the area where the fire pit is. Very, very private area! We just loved it.

5 out of 5 average rating, 15 reviews

Flat in Killington

New Resort Condo Close to Lifts

TarekRating, 5 starstoday

The place was as described and Ryan was super responsive and very friendly. We enjoyed our stay