Wife and I recently stayed at The Wentworth in Jackson, NH. Very cozy with nice spa. Dining at the hotel was great, too. We found it to be reasonably priced back in November. https://www.thewentworth.com/

Maybe too fancy or too far, but I always enjoy Cliff House in Maine. I go when they're cheapest - usually February - and their cheapest is luckily the most I'd ever spend on a hotel. Took my mom there who has some mobility issues, it was nice to not have to go far for food/spa/nature.

Cranwell Spa in Lenox

Mirbeau in Plymouth - even in cold weather! There’s lots amenities indoor and outdoors. Restaurant, hot tub, solarium. I’ve sat outside in the hot tub or in the glass solarium in snow or sun!

My advice is book one or two services with a lunch reservation in between. You can eat lunch in your spa bathrobe, and there is so much to do that is complementary to spa guests that you can still have a full day even with one treatment. I found it a lot harder at Chatham bars Inn to do that because there aren’t many amenities after your service is done, especially in the winter.

Mirabeau in Plymouth

newbury has some nice spaces. Rooftop restaurant is great and bar/library for guests is very cozy. Rooms so so. Four seasons dalton great rooms with big windows and views and quiet! sushi restaurant is part of a chain but excellent.

both locations are great for walking or taking the T anywhere

I stayed at one dalton recently (and scored an epic upgrade and cookie plate thanks to Alex!) the spa was great, unbearable location and good food

Raffles butler was not that useful AND they really made us wait for our room even though we tried to check in at 3

Haven't stayed there, but i would lean to the Raffles as its a new hotel, and they appear to be really ontop of things service wise. Mandarin seems a bit outdated at this point.

Four seasons Boylston is lovely and amazing service.

Racebrook Lodge in Sheffield MA may not be as luxury as you're seeking but they have a sauna and nice restaurant on site, and great hiking right off the property. Gedney Farm is right around corner from Old Inn on Green and has great dining (not sure about hot tub). You could also try Tourists Welcome in North Adams, which has a heated pool I believe and a restaurant on site.

Happy to provide food and hiking recs if you come to the Berkshires!

Private outdoor hot tubs (not just jetted tubs in the bathroom) at the Wentworth in NH: https://www.thewentworth.com/accommodations/rooms/arden-sunnyside-hot-tub/

Hotel Northampton is beautiful.

Wheatleigh, Blantyre, The Old Inn on the Green, or the Reluctant Panther.

The Equinox Resort. Great dining at the resort (and plenty more in the town of Manchester). Easy access to skiing and hiking. Lots of shopping in the area if that's your thing. And they do have hot tubs.

Western Mass. Last spring my wife and I went to The Norman Rockwell Museum, The Mass MOCA, and spent two days in North Hampton. It was cheap, the scenery was beautiful, and it was close.

I love Western MA, particularly the area around Williamstown/North Adams. If you’re interested in art, the MassMoCA can’t be missed, and there are lots of interesting natural areas around there, plus the Berkshires are beautiful.

Portland Maine, airbnbs are reasonable and it’s a fun spot to bounce around.

You could do a getaway midweek. It’s a tiny house cabin in the NH area.

The Mohawk Trail through the Berkshires is a good bet. I actually stayed in the Berkshires last spring and it was affordable and got some really good and quiet hikes in because people in MA don't seem to go hiking in early spring. The cape will be grey and closed in March, the islands are not affordable.

Just came back from a weekend at the Boston Harbor Hotel - absolutely stunning views and the staff couldn’t have been more welcoming

We stayed there last April. It’s ok. Nothing special. Limited on site dining options. Bathrooms are small even at the suite level. I would try a different hotel. It’s not a good value for the price.

Its been our first choice for 5-6 years now.

Wonderful location: we usually take Amtrak - 2 blocks from South Station. Subways are right there as well.

Get a room overlooking the harbor. Just beautiful. Sometimes you can see the planes landing at Logan. There is also a room with a large balcony which is also great, especially having breakfast their.

The rooms are beautiful! Wonderful staff, extremely quite, beautiful bathrooms and the rooms are a nice size. Ferries from LOG drop you off right into the hotel. Pretty cool.

The only thing they don't have is an upscale restaurant, like the MO. The Dark Bar is beautiful and Rowes Wharf Sea Grille is fine all day.

If the Boston Harbor is full, the MO is our second choice.

Outstanding hotel

For the price, I'd pick Langham. The rooms are much nicer, if that matters to you.

Newbury St in the spring and summer, and the Seaport area for flashy cars and hotels

This is new england, it's just not that showy

If you want shopping, newberry st though

Villas? This is Boston. We have brownstones.

Rodeo drive is like that because money talks and wealth whispers. Boston is old money were not very flashy. Go to Nantucket or MV and some of the most expensive houses have basic range rovers or even just newer toyotas in the driveways. I think the last time I saw a huge amount of extremely expensive sports car in Boston was when the goldRush rally came to boston a few years back.

Boston isn’t really about “flash”. The rich people here don’t show it off, but Beacon Hill is a very pricy neighborhood. Seconding Newbury Street.

Lots of stuff, I miss my state. Walking around the backstreets of Cambridge is cool..but try not to sprain your ankle. The Butterfly Place in Chelmsford. If ya haven't seen the cliffs on Martha's Vineyard in Aquinna, hurry up.

Take a nice walk in the woods.

Seriously. We have some absolutely stunning forest and thankfully we’ve managed to hold of the worst of the invasive species in many areas unlike the Midwest and southern central US which being overrun rapidly.

jerk off

Start a revolution

Go to the native plant botanical garden (Garden in The Woods) in Framingham, especially in late May/June when the native azaleas and mountain laurel are in full bloom. It’s really inspiring to see what can be done with native plants here in the Northeast.

Wow, that's beautiful. Maybe one day I'll get a sick upgrade like that.

We've stayed at this hotel a couple of times. The service here was always top-notch.

Our last stay had that exact view but several floors down.

Nice!

That is a lot of towels

I stayed at this hotel as an explorist and I loved it. The hotel is clean, modern and has great staff. I was there on a sold out night so no upgrades sadly. But that suite looks amazing!

Where in CT is the wedding?

Well, you aren’t near it, but my favorite spot maybe anywhere in New England is the Flume in the White Mountains of New Hampshire. And the (even more inconvenient to CT) coast of Maine.

Boston.

Ooo lots of options…

I’ll get started with the obvious one: Mystic Seaport, Mystic Aquarium, and all of the shops around the aquarium.

For food, if you want some classic (ish) New England seafood… I can recommend Lenny and Joe’s. If you want something perhaps slightly more upscale (but not crazy over the top), Old Saybrook Inn has a decent restaurant right on the ocean.

There is also the Essex Steam Train and Gillette Castle nearby. Both are lots of fun but admittedly kinda touristy. If you’re looking for a cool day hike, Devil’s Hopyard is a favorite of mine. That’s slightly more inland, but not crazy far from the shore.

If you want to go for a boat ride, there are numerous ferries that run from southern Connecticut & Rhode Island to Long Island, Martha’s Vineyard, Block Island, etc.

I could come up with more, especially if I go to other places in New England (Cape Cod, for example) but there’s a few random choices around southern Connecticut.

Well New Haven has the best pizza in America. Frank Pepe Pizzeria Napoletana 📍 Modern Apizza 📍 Sally's Apizza If you are going to the ocean house watch hill? They have a great view and awesome beach to walk on that will give you a classic New England feel Mystic is a great visit. https://mysticseaport.org. This is an 18th century whaling village.