The Towns

If you're looking to stay somewhere walking distance from restaurants, shops and cafés, you should definitely stay in either Northampton or Amherst. Northampton is a bit bigger and more fun, Amherst is smaller but more quaint. Northampton and Amherst are the only truly walkable towns. We will have a party bus leaving from Northampton and Amherst to head to the wedding venue.

NORTHAMPTON

Northampton is probably best described as "funky". The sign on the municipal parking lot reads "welcome to Northampton, where the coffee is strong and so are the women". It's the epicenter of rural hipsterdom, so you should not be surprised to see people riding around on fixed-gear bikes dressed as Huck Finn with a joint in one hand and a vat of home-made organic honey tucked under the other.

Northampton is also the nightlife hub of the area - there are a ton of great bars and restaurants, and it's also the musical capital of New England (Sonic Youth, Dinosaur Jr and other indie legends live here, and everyone touring New England stops in Northampton).

AMHERST

Amherst is extremely quaint. It's a quintessential New England town with wooden houses, fields, big old oak trees and the like. It's smaller than Northampton but still boasts a good number of quite excellent restaurants and bars, and is also closer to the wedding venue than Northampton. Amherst is also home to Amherst College, the fairest college in the land. [ED: Lil keeps changing "fairest" to "second-fairest"]

The nice hotel in the area (the Lord Jeffrey Inn) is nicer than the Northampton equivalent, despite being named for a murderous Englishman most famous for giving smallpox infected blankets to Native Americans.

Hotels

Below are a list of the best hotels in the area. For the Airbnb inclined, there are a lot of options in the area and if you're coming with friends, getting a house might be the best way to go.  We'd recommend staying in Amherst or Northampton if you're planning to take advantage of the surrounding area and spending the weekend here. If you're just coming in for the wedding, you'll probably want to be as close as possible to Montague.
 

The Hotel Northampton ($$)

6 King Street, Northampton
+1 413 584 3100

Located right in the center of downtown Northampton, this is the biggest hotel in the area, and the nicest in Northampton. Some of the rooms haven't been renovated as recently as the Lord Jeffrey Inn, but it's very nice and clean and a 3 minute walk from all the attractions of downtown Northampton. Mention the Smith/Alfandary wedding for a special rate!
 

The Holiday Inn Express ($)

400 Russell Street, Hadley
+1 413 582 0002

Located right on Route 9 in Hadley (between Northampton and Amherst). This isn't located in a walking-friendly location but is convenient by car to both Amherst and Northampton. Not that much to say about this place - it's clean and reasonable and it's a Holiday Inn. Mention the Smith/Alfandary for a special rate.
 

THE LORD JEFFERY INN ($$$)

30 Boltwood Avenue, Amherst
+1 413 256 8200

Probably the nicest hotel in the area, in downtown Amherst. It's a bit formal (and pretty stuffy), but it's the most comfortable and upmarket place around The town may not have as much to do as in Northampton (in terms of restaurants and entertainment), but the Lord Jeff and the Hotel Northampton are the only two hotels that are right in the town center, and within walking distance of restaurants and cafés.
 

The Amherst Inn ($)

257 Main Street, Amherst
+1 413 253 5000

A very unique (unique = a bit odd) bed and breakfast in Amherst. Not quite as close to the town center as the Lord Jeffrey Inn, but a 10 minute walk from the action.  Each room is uniquely decorated in a different style - from medieval (crocheted knights on the pillows) to Quaker rustic (husks of corn in the walls).
 

The Old Mill Inn ($$)

87 School St, Hatfield
+1 413 247-3301

Bed and breakfast in a quiet town, in a converted old grist mill. Affordable and nice place to stay but nothing walkable around there.

The Deerfield Inn ($$$)

Deerfield is pretty close to the wedding venue, but is a bit remote. It is extremely charming and picturesque, but there's basically nothing to do there. Deerfield = quaintest and least fun, Amherst = quaint and funish, Northampton = quaintish and funnest. 
 

The Autumn Inn ($)

259 Elm Street, Northampton
+1 413 584 7660

Located right across from Smith College Campus in Northampton, this is a small hotel and more affordable than the Hotel Northampton. It's about a 10-minute walk from downtown Northampton. It's not the nicest on the list, but it is well-situated Mention the Smith/Alfandary wedding for a special rate.