The Milestone Inn

Hotel · Woodbury

The Milestone Inn

Hotel · Woodbury

1

146 S Pomperaug Ave, Woodbury, CT 06798

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The Milestone Inn by null
The Milestone Inn by null
The Milestone Inn by null
The Milestone Inn by null
The Milestone Inn by null
The Milestone Inn by null
The Milestone Inn by null
The Milestone Inn by null
The Milestone Inn by null
The Milestone Inn by null
The Milestone Inn by null
The Milestone Inn by null
The Milestone Inn by null
The Milestone Inn by null
The Milestone Inn by null
The Milestone Inn by null
The Milestone Inn by null
The Milestone Inn by null
The Milestone Inn by null
The Milestone Inn by null
The Milestone Inn by null
The Milestone Inn by null
The Milestone Inn by null
The Milestone Inn by null
The Milestone Inn by null

Highlights

Comfy beds, clean rooms, quiet stay, easy check-in  

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146 S Pomperaug Ave, Woodbury, CT 06798 Get directions

milestoneinnct.com

$

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146 S Pomperaug Ave, Woodbury, CT 06798 Get directions

+1 203 405 6261
milestoneinnct.com

$

Features

Last updated

Aug 14, 2025

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What a Hotel Concierge Is, And What They Can Do For You - AFAR

"Offers a dedicated pet concierge that coordinates bespoke services for traveling animals, including custom bedding, leashes, tailored menus, and even arranging a portrait session with the hotel's resident artist, catering to guests traveling with pets." - Sarah Khan

https://www.afar.com/magazine/what-a-hotel-concierge-is-and-what-they-can-do-for-you
View Postcard for The Milestone Inn

N1263DQjanaw

Google
Great Place to stay in quaint Woodbury CT , rooms are clean , beds are amazingly comfortable . Very quiet yet close to great places to eat , antiques, brewery and vineyards. Check in is like how you would for an AirBNB , access codes and things to know through text or email as there are no attendants onsite . Very responsive and friendly. I recently made my third reservation .

ma onh

Google
We arrived at the "inn" after asking for an early check in, since we had an appointment to get to. when I called the number, no- one answered the phone, and there wasn't anyone there to help. After several phone calls, we were able to get someone to give us the lock box number so we could get the key. The room was a good size, but that's the only good thing. The bulbs in the fixtures were burned out, the bathroom was falling apart, (tub fixtures, pealing wall paper, a rusty towel rack), then to top it all off, the place was almost completely empty, but they put the only other guest in the next room who player their TV all night extremely loudly, and the walls were extremely thin. I could hear everything. There was no one to talk to about it in the middle of the night. Don't stay here. Pay a couple of bucks more and stay somewhere decent.

Donovan Williams

Google
This motor hotel is a decent value and surprisingly quiet and well kept for a drive-up and park joint. The room was nice, not especially elegant but not trashed, exactly what you'd want for a budget place to rest your bones. The down- side for our stay was that check in is entirely via phone and electronic keypad. No staff on desk duty. If everything goes smoothly, that works fine. But if there's an issue like we had with a mis-labelled reservation, youre on your own. In fairness, the hotel was efficient about how they responded once the problem was fixed and it wasn't their fault, it was a glitch in the third-party dot-com reservation, but we had to do all the back-and-forth calling. Zero help from the motel itself and a mostly indifferent attitude over the phone. If you want no frills rest, this place is definitely better than Motel 6, but don't look for pampering.

michaellS5404FL

Google
This place was clean and easily accessible. There are no hotel in the area but you don’t need a lot of choices when you have availability here. It’s very basic but has everything we needed. They do not have breakfast had daily cleaning of the room and there is a wonderful cafe across the street. It my go-to in the area.

Marf

Google
My wife and I stayed here this past week and found the Milestone Inn to be totally charming. The room was neat, clean and enjoyable. The beds and bedding were very comfortable, too. The owners are really customer-focused and were very accommodating. They couldn't have been nicer. My wife and I are Woodbury residents and needed a place to stay for one night. We're happy we stayed at the Milestone. We will stay there again, as needed, and plan to have relatives stay there. Really happy we stayed at The Milestone.

Andrew P

Google
Beautiful and homely rooms. Customer service was top notch. Owners were incredible to work with and very accommodating and helpful. Recommend 10/10.

A Jewell

Google
I can't get over how clean it was! It is quiet... you hear no doors slamming all night, no flushing toilets or shower noise, no kids loudly carrying on running up and down halls or stairs. It is simple and peaceful. Coffee pot and fridge worked great and there were plenty of towels. I work at an upscale Inn in NYS and it is habit to go into a room looking at everything. The sheets were tight and clean, no hairs anywhere, bed was comfy, and no dust on anything. We travel alot and this will be our new place to stay. Late check in was easy and the woman who helped us by phone was very friendly.Thank you!

Rebecca Gaconnet

Google
We chose this inn last spring because it was conveniently located for the family event we had come for. Four of us shared a room and were comfortable for our single overnight. The accommodations were clean, well-provisioned, and quiet. The atmosphere was really very pleasant for an outside stroll at the edge of the woods in the evening. It's not a resort; it's not a luxury hotel. It's a good place to stay for a night or two. We plan to return this spring.
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Marie C.

Yelp
The room was supposed to be non-smoking, however, it reeked of cigarettes. There were cigarette butts strewn about outside the door and another guest was smoking outside the door. The shower curtain had mildew and the beds were very uncomfortable. The wallpaper was peeling and the worst part was that there were cameras installed above the television directed at the bed. The front desk was deserted and we had to call a number listed on the door for instructions to get into the room.
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Pamela F.

Yelp
I stayed 2 nights for Gilmore Girls Fan Festival this weekend. I have to say I was VERY concerned about the mixed reviews I was reading both here and on another sites, but my entire stay was seamless. The rooms are quite nice, of that of a good quality hotel, and appear to be renovated recently. The room itself was clean and the bed was comfy. The area was safe. Check in was a breeze and check out as well. Conveniently located close to Washington Depot and the I84, along with stores across the street and gas station close by. Don't listen to those other reviews, this place is very nice and modern. It isn't much from the outside, but I felt relieved when I walked inside. I also think the outside is typical of others in the area. Don't be afraid to stay here! I would do so again, especially during this time of year.
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Chris M.

Yelp
We made an online reservation for one night in May 2015, which I even confirmed over the phone the day before. Upon arriving, we were told that there was no room for us and that our reservation could not be honored. By the flustered demeanor the manager had, we could tell that this was a common problem with this establishment. We drove 3.5 hours only to have to scramble on a Saturday night at 7pm to find another hotel during graduation weekend. The massive inconvenience and additional stress was completely unnecessary. I would not suggest you stay at this hotel, as you certainly run a similar risk.
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Monica T.

Yelp
Comfy looking place with nice rooms, cleanliness and a fridge in the room. Definitely a quiet place & feels like a hidden gem.

Henry N.

Yelp
We had a fantastic experience with the Milestone Inn. We were contacted by the owner the day before our stay to ensure we were familer with check in process. As the Inn's front desk has limited hours, we made arrangements for a late check in. Later in the evening we were notified that there was an issue with our two bed accommodation and if we were ok with moving to another room with a king and rollaway. For our party that was 100% fine. When we arrived the room was perfect...but no rollaway. We contacted owner who advised he would be over immediately as there was a miscommunication in regards to rollaway. Moments later he called us back and said the room next to ours was available and it was ok for our grown daughter stay in the empty / available room. Again...Fantastic! We appreciate your customer service and for taking care of our family. The rooms were very beautiful and homey...all white accessories with huge comfortable beds that just made you melt. Thank you! We will totally return in the future if we are lucky enough to make it back this way! Two thumbs up!!

Alex C.

Yelp
SERVICE: That's the most important feature in the hospitality industry. My husband was stranded during the most recent snow storm. Frank, the Manager went above and beyond his pay grade to help us out. If everyone took their work as seriously, it would be a more perfect travel world. Kudos to Frank and I can't emphasize enough what a valued employee the Milestone Inn is lucky enough to have on staff. Thank you Frank. To the owner: don't lose this one - you would be hard pressed to find another Frank.

Dana F.

Yelp
Came in from Missouri for a week to visit relatives, stayed at the Milestone Inn and was so glad we did. The room was super clean ,the sheets were the freshest I've seen in a motel in a long time. The manager Frank was there to assist at every turn, after it snowed I came out to leave and there was Frank cleaning off my car for me! Perfect location in Woodbury with any kind of food you would want right across the street. Very quiet and the mattresses are new and wonderful! Thank you Frank for taking such good care of us, we so appreciate all you did! We will definitely recommend the Milestone Inn to all friends and family!

Melissa F.

Yelp
I stayed a night at the Milestone while taking a road trip with a friend. The room was clean and very comfortable. The Inn manager (Frank) was incredibly accommodating and made a wonderful recommendation for breakfast the next day. I highly recommend this place.

Jill J.

Yelp
This inn, which looks more like a unprepossessing motel, is in an very convenient location near all local attractions including some excellent restaurants. Though rather basic, this inn is clean, quiet and comfortable. This seems to be a mom and pop operation, so make sure you follow the instructions on the website and call in advance with your arrival time, so someone can be available to provide a key to your room.