A park with a large tree in autumn colors, a grassy field, and a forested hill in the background.

Plymouth Holiday Rentals

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Our top choices for Plymouth holiday rentals

1. RoundTop Chalet | Hot Tub, Fire Pit & Mountain Views near Killington & Okemo

RoundTop Chalet | Hot Tub, Fire Pit & Mountain Views near Killington & Okemo
Plymouth
8.8 out of 10, Excellent, (5 reviews)
"Everything about the property was beautiful and relaxing. We loved our stay .... We did however run into one issue, while we were enjoying the property, someone claiming to be there to service the hot tub decided to let themselves in with the lock code unannounced while we were undressed and stood there listening to us and only when the dog ran down there did he announce himself. Not sure if simple sent them or if they showed up on their own accord but boy did we get quite the scare and hope...
United States
Adam S.
The price is NZ$1,111
includes taxes & fees
8 Nov - 9 Nov
RoundTop Chalet | Hot Tub, Fire Pit & Mountain Views near Killington & Okemo

2. The Coolidge Barn | Game Room, Firepit & Mountain Views | Sleeps 6

The Coolidge Barn | Game Room, Firepit & Mountain Views | Sleeps 6
Plymouth
The price is NZ$1,065
includes taxes & fees
8 Nov - 9 Nov
The Coolidge Barn | Game Room, Firepit & Mountain Views | Sleeps 6

3. Brookside Cabin + Hot Tub | Woodstock & Killington

Brookside Cabin + Hot Tub | Woodstock & Killington
Bridgewater
10.0 out of 10, Exceptional, (10 reviews)
"Beautiful property on a nice quiet stream. House was super clean and had everything we needed. We took the dogs and they had fun with us around town and playing in the stream."
United States
tom b.
The price is NZ$1,473
includes taxes & fees
7 Nov - 8 Nov
Brookside Cabin + Hot Tub | Woodstock & Killington

4. Lodges at Sunrise 3BR Luxury Ski On Ski Off Condo. Pool. Hot Tub. Gym. Discounted Ski Rentals.

Lodges at Sunrise 3BR Luxury Ski On Ski Off Condo. Pool. Hot Tub. Gym. Discounted Ski Rentals.
Killington
9.8 out of 10, Exceptional, (20 reviews)
"Great stay! "
United States
Corey W.
Lodges at Sunrise 3BR Luxury Ski On Ski Off Condo. Pool. Hot Tub. Gym. Discounted Ski Rentals.

5. Bridgewater Living - Ben&Jerry Suite

Bridgewater Living - Ben&Jerry Suite
Bridgewater
10.0 out of 10, Exceptional, (1 review)
"Swati, my host, helped me when I had difficulties with tech issues and my stay was as smooth as silk. Thanks!"
United States
Sylvia F.
The price is NZ$360
includes taxes & fees
16 Nov - 17 Nov
Bridgewater Living - Ben&Jerry Suite

6. SunBear-Ski on Ski off, Pool, HotTub, Game Room!

SunBear-Ski on Ski off, Pool, HotTub, Game Room!
Killington
9.8 out of 10, Exceptional, (32 reviews)
"Very accommodating and helpful hosts"
United States
Sean W.
The price is NZ$1,022
includes taxes & fees
10 Nov - 11 Nov
SunBear-Ski on Ski off, Pool, HotTub, Game Room!

7. Topridge Style 3BR/4BA with Hot Tub, Ski On Ski Off, Mountain Views and Discounted Ski Rentals

Topridge Style 3BR/4BA with Hot Tub, Ski On Ski Off, Mountain Views and Discounted Ski Rentals
Killington
9.8 out of 10, Exceptional, (70 reviews)
"Excellent location and hosts would definitely recommend! House is perfect "
United States
Tim C.
Topridge Style 3BR/4BA with Hot Tub, Ski On Ski Off, Mountain Views and Discounted Ski Rentals

8. Charming 3BR/2BA Condo in Sunrise Village at Killington. Pool. Hot Tub. Sports Center.

Charming 3BR/2BA Condo in Sunrise Village at Killington. Pool. Hot Tub. Sports Center.
Killington
9.8 out of 10, Exceptional, (7 reviews)
"We had a special ski weekend with friends. "
United States
Adam C.
The price is NZ$1,167
includes taxes & fees
8 Nov - 9 Nov
Charming 3BR/2BA Condo in Sunrise Village at Killington. Pool. Hot Tub. Sports Center.

9. Trailside Village #8: Slopeside 3BR w/ Hot Tub and Sauna. Ski In/Out with Discounted Ski Rentals

Trailside Village #8: Slopeside 3BR w/ Hot Tub and Sauna. Ski In/Out with Discounted Ski Rentals
Killington
9.4 out of 10, Exceptional, (31 reviews)
"The condo was great. Clean, well appointed, and location was fantastic. No complaints, would stay here again. "
United States
Andrew F.
Trailside Village #8: Slopeside 3BR w/ Hot Tub and Sauna. Ski In/Out with Discounted Ski Rentals

10. Pet Friendly | Game Room | Minutes to Woodstock and Killington

Pet Friendly | Game Room | Minutes to Woodstock and Killington
Bridgewater
10.0 out of 10, Exceptional, (4 reviews)
"We loved the farmhouse. It was very charming and cozy. Plenty of space for us and exactly as advertised. We would definitely stay here again. Thank you"
United States
Lisa G.
The price is NZ$917
includes taxes & fees
11 Nov - 12 Nov
Pet Friendly | Game Room | Minutes to Woodstock and Killington

11. Trail Creek Killington Condos #18: Ski Home Trail. Bus. Hot Tub. Pool.

Trail Creek Killington Condos #18: Ski Home Trail. Bus. Hot Tub. Pool.
Killington
9.8 out of 10, Exceptional, (14 reviews)
"Great Location"
United States
Brian B.
Trail Creek Killington Condos #18: Ski Home Trail. Bus. Hot Tub. Pool.

12. NEW Cozy 4-bedroom cabin with AC, WiFi, Hot Tub and Fire Place!

NEW Cozy 4-bedroom cabin with AC, WiFi, Hot Tub and Fire Place!
Killington
10.0 out of 10, Exceptional, (4 reviews)
"Location near gondola was clutch (short 1 min drive). Super clean and layout of cabin was perfect for our group. We had a fair amount of snow and icy weather and our host kept the road and driveway clear."
United States
Jeremy F.
The price is NZ$2,082
includes taxes & fees
16 Nov - 17 Nov
NEW Cozy 4-bedroom cabin with AC, WiFi, Hot Tub and Fire Place!

13. Whiffletree Cozy Condo: 2-Bedroom Condo in Killington, VT with Garden View and Ski Rental Deals

Whiffletree Cozy Condo: 2-Bedroom Condo in Killington, VT with Garden View and Ski Rental Deals
Killington
10.0 out of 10, Exceptional, (1 review)
"The property was a great location. Close enough for a daily drive to stowe or woodstock. I would highly recommend this place. The only thing I wish I would have known is there are a few flights of stairs to go up and down with luggage. Thanks for a great stay"
United States
Brandy
The price is NZ$672
includes taxes & fees
8 Nov - 9 Nov
Whiffletree Cozy Condo: 2-Bedroom Condo in Killington, VT with Garden View and Ski Rental Deals

14. Fat Sheep Farm & Cabins

Fat Sheep Farm & Cabins
3.0 star property
Windsor
9.8 out of 10, Exceptional, (15 reviews)
"This property was extremely beautiful and peaceful. Loved being able to walk around the farm and say hi to the animals. The views of the mountains from the cabin or gorgeous, we enjoyed having our coffee on the porch each morning. Having fresh eggs and scones in our cabin upon arrival was a very nice surprise. Will definitely be staying there again."
United States
Brenda
The price is NZ$317
includes taxes & fees
17 Nov - 18 Nov
Fat Sheep Farm & Cabins

15. Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore

Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore
Mt Holly
9.8 out of 10, Exceptional, (42 reviews)
"This house has great hang out space and plenty of space for a big family!"
United States
Cheri V.
The price is NZ$833
includes taxes & fees
15 Nov - 16 Nov
Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore

16. Trail Creek: 1 BR with Loft. Ski Home Trail. Bus. Hot Tub. Pool. #64

Trail Creek: 1 BR with Loft. Ski Home Trail. Bus. Hot Tub. Pool. #64
Killington
7.0 out of 10, Good, (2 reviews)
"it was okay a bit misrepresented"
Canada
Ian P.
The price is NZ$738
includes taxes & fees
8 Nov - 9 Nov
Trail Creek: 1 BR with Loft. Ski Home Trail. Bus. Hot Tub. Pool. #64

17. Mountain Green ground-floor condo with private yard off the patio

Mountain Green ground-floor condo with private yard off the patio
Killington
The price is NZ$496
includes taxes & fees
14 Nov - 15 Nov
Mountain Green ground-floor condo with private yard off the patio

18. Newly Renovated Studio! Amazing Views/Location 3F9. Pool. Hot Tub, Shuttle.

Newly Renovated Studio! Amazing Views/Location 3F9. Pool. Hot Tub, Shuttle.
Killington
10.0 out of 10, Exceptional, (15 reviews)
"A wonderful up to date property a short walk to the lifts! Would definitely stay here again."
United States
Mike B.
The price is NZ$568
includes taxes & fees
8 Nov - 9 Nov
Newly Renovated Studio! Amazing Views/Location 3F9. Pool. Hot Tub, Shuttle.

19. New Luxury Home in Killington with Hot Tub, Sauna and Fireplace

New Luxury Home in Killington with Hot Tub, Sauna and Fireplace
Killington
10.0 out of 10, Exceptional, (4 reviews)
"We had a fabulous time enjoying this lovely property! The host, Erin, was super responsive and helpful, we will definitely be returning for future visits! "
United States
jeannie g.
The price is NZ$1,608
includes taxes & fees
9 Nov - 10 Nov
New Luxury Home in Killington with Hot Tub, Sauna and Fireplace

20. Wade`s World Ski Home Shuttle location

Wade`s World Ski Home Shuttle location
Killington
9.6 out of 10, Exceptional, (7 reviews)
"Gorgeous little spot. Slept for comfortably had a fantastic vacation weekend. Great snow first class owners. Perfect for a ski weekend."
United States
Michael K.
The price is NZ$749
includes taxes & fees
8 Nov - 9 Nov
Wade`s World Ski Home Shuttle location
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Plymouth Hotel Reviews

Find out more about Plymouth

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Plymouth holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Plymouth. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Plymouth. Seeing all the best attractions is bound to make you fall in love with Plymouth. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Plymouth short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find a holiday rental in Plymouth?

Yes, there are holiday rentals close to the most popular sights in Plymouth, or you can select a more secluded option if you're looking for a relaxing stay. Plymouth is known for its churches and ski areas.

What are some of the best holiday rentals that Plymouth has to offer?

Traveling with kids? Try this secluded & updated 3-bedroom home close to Okemo: This holiday home rental outside of Plymouth is located on a lake, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games.

How many holiday rentals are there in Plymouth?

Choose from 48 Expedia holiday rentals in Plymouth for a memorable holiday.

What can I see and do in Plymouth?

Amherst Lake and Echo Lake are a couple of lovely local spots to get outside and enjoy nature. Calvin Coolidge Historic Site and Coolidge State Park are other places to visit while you're in town.

What are holiday rentals like in Plymouth?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Plymouth. Holiday rentals provide amenities such as kitchens and laundry facilities so you'll be comfy for your stay. If you're concerned about a clean environment, a holiday rental can provide a sense of seclusion away from shared hotel lifts and busy lobbies while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a standard hotel, which makes a holiday rental a great option for a small group gathering.