Sunday River. Don't go during MA school vacation week.

Summit Hotel at Sunday River hits all your asks, can usually find some decent prices if you're flexible on dates. They have a big outdoor heated pool too.

Sunday River has the Grand Summit and Grand Jordan hotels. Both are around the same price. The Grand Jordan is nicer, however its on the other side of the mountain. Both are ski in/out and have hot tubs If you want to enjoy the local nightlife it's a longer drive than staying at the Summit. The summit is outdated and tired. However if you complain they might toss in free lift tickets or take 10% off. Weekend skiing is god awful here, super crowded. If you are a fan of the beezlebubs lettuce there are pot shops all over the place.

Okemo has the Jackson Gore. The hotel itself is not bad, ski in/out is great, hot tubs cool, however when I stayed there for a wedding in January of 2021 they had a pillow shortage and were rationing 1 pillow per room. My pregnant wife was absolutely thrilled. (I broke into a linen closet and liberated a ton of pillows) I'd never stay there again because of that. But it's an option. Lines for Weekend Skiing were not horrible.

The Mountain Club on Loon. It's not bad, not amazing. Good indoor pool outdoor hot tub, a steam room full of naked old men who want to chat. My last trip was in the winter of 2020 right before the world went to shit and it was affordable. However weekend skiing is awful at loon.

Grand Hotel at Attitash. It's not bad, its affordable and a short drive to Conway where there is a ton of stuff to do. Mountains not bad either. You could also theoretically go night skiing down the street at Cranmore. But Cranmore is a terrible little mountain.

Check out Saddleback or Sugarloaf. Both are far enough away where the crowds shouldn't be too bad.

I always bring friends to Sunday River because I feel it's the biggest bang for your buck in terms of size for price paid. Yes it gets crowded on weekends but the mountain is big enough that they can be largely avoided, and overall having three lodges and multiple hotels spreads the crowds out better than other places. Everywhere will be crowded to a certain extent until the end of February. I tend to avoid Southern VT due to all the pushy and rude New Yorkers. Sugarloaf in Maine by far is the best and chillest vibe. You may have luck avoiding crowds at smaller areas but you may not get the bang for your buck.

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I'm not a big fan of Killington - the mountain is laborious and there are a lot of NJ/NY/CT types - but it's fun once in awhile and has everything you want and worth a mention. That being said. The Killington Grand is fairly good for what you are looking for (ski on / off, pool and hot tub, attached bar, nice apres scene, generally). What we did to really get our value for the $$ is you can book packages at the hotel that include your lift tickets. To really leverage the value, (I am the queen of cheap, sue me!) we rented the studio apartment option inside the hotel with kitchenette and brought some breakfasts and dinners to make ourselves to defray the costs.

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