343 Main Street East, Picton
The Merrill Inn is a beautiful old Inn located in Picton with a wonderful restaurant as well (we are standing in front of it above!). The staff are warm and very helpful and the rooms are supposed to be quite charming and comfortable and it is undergoing a major renovation for 2019. It is in a great location as well.
2274 County Road 1, Bloomfield
We stayed at the Huff Estates a few years ago and it was a great experience. There are 21 suites right on their vineyards. The room we had was spacious, and the location is great, it is very central.
396 Sandy Hook Road, Between Picton and Bloomfield
We stayed here quite some time ago and enjoyed it. The location is about as central as you can get! There are two restaurants including The Barley Pub right on the premises, and they also offer recreational cooking classes.
433 Main Street, Bloomfield
We have not stayed here, but friends have and they love it and return each year. We also recently had a tour of the hotel. It is a super quaint Inn (there are elegant rooms in the main building which is a historic century home as well as newly renovated rooms in an adjacent building on the lot that looks like the coolest motel you have ever seen). The rooms are classicly modern and feature stunning wallpaper created by local PEC artist Kate Golding. They also have a wonderful restaurant and an adjacent pub called The Hub that we love.
10 Chapel Street, Picton
I hear this is quite a lovely Inn with a swinning pool and modern amenities. It is in a great location as well and also has high ratings on Trip Advisor.
24 Wharf Street, Wellington
This gorgeous hotel opened in the fall of 2014 and it really is quite beautiful. We had stayed in the hotel before the folks at The Drake in Toronto purchased it and the renovations are spectacular. We have also had lunch at their restaurant and it was delicious, the service was great and the view is just unbeatable. We have also spoken to a few people who have stayed there and they have all loved it.
There are A LOT of B&Bs all over the county. I can vouch for a couple and have listed them below. If B&Bs are your thing and you wish to explore more, I have included a link below. You can also check out airbnb for rentals in the area.
166 County Road #18, Cherry Valley
This is a very quaint and beautiful B&B has been highly recommended by friends of ours from Toronto who have stayed there a number of times, and it's easy to see why. The website is fantastic and will give you a great feel for what to expect. Their number is: (613) 476-2554.
Formerly a gallery owned by County-based artist Stewart Jones and his wife Rebecca Hunt - owner/operator of the wonderful Picnic food truck, this has been converted to a B&B. We were in the building when it was a gallery and it was quite nice. They did a gorgeous job converting it into a B&B , and it seems the owners are very hosptitable. It's in a great location, close to all of the wineries and great restaurants.
The Garden Suite (in the Hand Works Gallery/Store)
246 Main Street, Bloomfield
This is a beautiful room with adjoining washroom (so it is private) and is located in the heart of beautiful Bloomfield. The room is part of Tammy Love's Hand Works Gallery/store. For reservations, you can book through airbnb.com (Search for The Garden Suite, Bloomfield ON for the dates you wish to stay) or you can call Tammy at 613-393-3888.
Just before we took the plunge and bought our own little piece of heaven here, we rented a cottage for a week holiday. We found the cottage on this link below and it is a GREAT way to really explore the area - you can sample some restaurants but also stay in and cook some of the fresh produce you have picked up in your daily travels :) It was SO easy to fill that week with great things to do - PEC is a perfect vacation spot.
OTHER RESOURCES FOR B&Bs
We haven't stayed in a hotel or B&B here since putting down our own roots, but we had stayed in a few places before doing so. Below are some hotels and B&Bs that I can personally vouch for, and others that I know are nice from very reliable sources! There are MANY more options though, and I've included a link below so you can research more if you wish. For B&Bs, you can visit BBCanada.com and airbnb is also also good resource. Or, you can do what we did and buy a place of your own!