See all properties

The Milestone Inn

Property class: 2.5

Choose dates to view prices

Photo gallery for The Milestone Inn

A hotel room with a large bed, two bedside tables with lamps, and a striped wall. - The Milestone Inn (Woodbury)
A Keurig coffee maker with a cup of coffee and several coffee pods on a tray. - The Milestone Inn (Woodbury)
A neatly made bed with white linens, a white bedside table with a lamp, and a telephone. - The Milestone Inn (Woodbury)
A covered porch with white columns and black hanging lanterns. - The Milestone Inn (Woodbury)
A hotel bathroom with a large mirror, a vanity with drawers, a sink, and a towel rack. - The Milestone Inn (Woodbury)
The Milestone Inn provides everything you need. Stay connected with free in-room WiFi.

Reviews

8.8 out of 10
Excellent

Popular amenities

  • Parking included
  • Free WiFi
  • Air conditioning

AARP members, discover the perfect stay for every budget with our fantastic hotel deals.

From charming, budget-friendly stays to premium, full-service hotels, find the perfect place to unwind—no matter your travel style or budget

Room options

Available filters for rooms
Showing 2 of 2 rooms

View all photos for Standard Room, 1 King Bed

A hotel room with a large bed, two bedside tables with lamps, and a striped wall.

Standard Room, 1 King Bed

8.0 out of 10
Very good
(8 reviews)
  • 1 bedroom
  • Sleeps 2
  • 1 King Bed

View all photos for Standard Room, 2 Double Beds

A hotel room with two beds, a nightstand with a lamp, and a window with curtains.

Standard Room, 2 Double Beds

9.8 out of 10
Exceptional
(11 reviews)
  • 28 sq m
  • 1 bedroom
  • Sleeps 2
  • 2 Double Beds

About the neighborhood

Woodbury is home to The Milestone Inn. Glebe House Museum and The Gertrude Jekyll Garden and Quassy Amusement Park are local attractions and those in the mood for shopping can visit Pilgrim Mall Shopping Center and Little Art Shop. Flanders Nature Center and Hollister House Garden are also worth visiting. Visit our Woodbury travel guide
Map
146 S Pomperaug Ave, Woodbury, CT, 06798

What's nearby

  • A large brick building with arched windows and domed towers, surrounded by a well-maintained lawn and a stone pathway.
    Yale University
    44 min drive - 30.6 miles
  • Hollow Park
    17 min walk - 1.0 mile
  • Pilgrim Mall Shopping Center
    2 min drive - 1.6 miles
  • Lake Quassapaug
    2 min drive - 2.0 miles
  • Glebe House Museum and The Gertrude Jekyll Garden
    3 min drive - 2.2 miles

Getting around

  • Oxford, CT (OXC-Waterbury - Oxford)
    16 min drive

Restaurants

  • McDonald's
    6 min drive
  • Panera Bread
    6 min drive
  • Oriental Gourmet
    6 min drive
  • Dunkin'
    5 min drive
  • Minami Sushi
    6 min drive

Similar properties

A breakfast buffet with various food items, including pastries, bread, and fruits.
Quality Inn Waterbury East
Waterbury
  • Breakfast included
  • Parking included
  • Free WiFi
  • Air conditioning
7.0 out of 10, Good, 1,001 reviews
Quality Inn Waterbury East
Compare similar properties

Property amenities

Internet

  • Available in all rooms: Free WiFi
  • Available in some public areas: Free WiFi

Parking and transportation

  • Free self parking on site
  • Wheelchair-accessible parking available

Family friendly

  • In-room microwave
  • In-room refrigerator

Accessibility

  • If you have requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking.
  • Low-height counter and sink
  • Low-height door lock
  • No elevator
  • Stair-free path to entrance
  • Well-lit path to entrance
  • Wheelchair accessibility
  • Wheelchair accessible (may have limitations)
  • Wheelchair-accessible parking
  • Wheelchair-accessible registration desk
  • Wheelchair-width doorways

More

  • 1 floor
  • Smoking not allowed

Room amenities

Bathroom

  • Designer toiletries
  • Hair dryer
  • Shower/bathtub combination

Entertainment

  • 40-inch TV with cable channels

Food and drink

  • Coffee/tea maker
  • Microwave
  • Refrigerator

More

  • Air conditioning
  • Desk
  • Heating
  • Iron/ironing board
  • Laptop workspace

Policies

Check-in

Check-in start time: 4:00 PM; Check-in end time: 8:00 PM
Early check-in subject to availability
Early check-in is available for a fee
Contactless check-in available
Minimum check-in age: 25

Check-out

Check-out before 11:00 AM
Contactless check-out available
A late check-out fee will be charged
Express check-out available

Special check-in instructions

There is no front desk at this property
Guests must contact the property in advance for check-in instructions and lockbox information; access will be through a private entrance
This property doesn't offer after-hours check-in
To make arrangements for check-in please contact the property at least 24 hours before arrival using the information on the booking confirmation
Information provided by the property may be translated using automated translation tools

Access methods

Lockbox, private entrance

Pets

Pets not allowed

Children and extra beds

Children are welcome
Rollaway/extra beds are not available
Cribs (infant beds) are not available

Property payment types

  • American Express
  • Discover
  • Mastercard
  • Visa

Important information

Optional extras

  • Early check-in is available for a fee (subject to availability)
  • A late check-out fee will be charged

The above list may not be comprehensive. Fees and deposits may not include tax and are subject to change.

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card, or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
This property accepts credit cards
Safety features at this property include a fire extinguisher and a first aid kit

We should mention

This property does not have elevators

Frequently asked questions

Is The Milestone Inn pet-friendly?

No, pets are not allowed at this property.

How much is parking?

Self parking is free at this property.

What time is check-in at The Milestone Inn?

Check-in start time: 4:00 PM; Check-in end time: 8:00 PM. A fee applies for early check-in (subject to availability). After-hours check-in is not available.

What time is check-out at The Milestone Inn?

Check-out is at 11:00 AM. Late check-out is available for a fee.

Where is The Milestone Inn located?

Situated in Woodbury, this hotel is within 1 mi (2 km) of Hollow Park, Pilgrim Mall Shopping Center, and Glebe House Museum and The Gertrude Jekyll Garden. Lake Quassapaug and Southbury Dog Park are also within 3 mi (5 km).

Can I cancel my reservation for free and receive a full refund?

Yes, this property offers free cancellation on select room rates, because flexibility matters! Please refer to the property cancellation policy on our site for more details about any exclusions or requirements.

Have a question?

AI iconBeta

Get instant answers with AI powered search of property information and reviews.

Reviews

The Milestone Inn Reviews

8.8

Excellent

9.2

Cleanliness

7.6

Location

8.6

Staff & service

8.8

Property conditions & facilities
Rating 10 - Excellent. 121 out of 204 reviews
Rating 8 - Good. 53 out of 204 reviews
Rating 6 - Okay. 17 out of 204 reviews
Rating 4 - Poor. 8 out of 204 reviews
Rating 2 - Terrible. 5 out of 204 reviews

Reviews

Verified review

8/10 Good

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Perfect location for our visit to Hogpen Sculpture Farm and the surrounding area. Check in was very easy
Stayed 1 night in Oct 2026
Verified review

8/10 Good

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Check in was very easy
Stayed 2 nights in Oct 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Very comfortable simple place to stay. Thank you very affordable
Stayed 1 night in Sep 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
The service was great, Kiki was very prompt with her responses to any and all questions my fiancé had
Stayed 1 night in Sep 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
We had a wonderful overnight stay at the Milestone Inn! Our room was clean, spacious, and had plenty of lighting. Everything worked well, and having a mini refrigerator, coffee maker and microwave was a nice convenience. The inn itself is small, quaint, and cozy, with a very comfortable bed and pillows. It’s conveniently located near stores and restaurants, yet our stay was quiet and relaxing, with plenty of parking. I also really appreciated the contact-free check-in—it was very easy. You simply call the number provided and your room card is waiting for you in a lockbox. One of the nicest touches was the customer service: I accidentally left my glasses behind when we checked out, and even though I was already in the next town, I called and they had them ready for me to pick up. The only thing I wish they had was a vending machine or some way to purchase drinks on-site. Overall, a very comfortable, convenient, and charming place to stay. I would definitely stay here again!
Stayed 1 night in Oct 2026
Verified review

6/10 Okay

Liked: Cleanliness
Disliked: Amenities
We were going to Hogpen Hill Farms and the property was conveniently located to it and fairly priced. The room was clean and well decorated; there was a refrigerator and coffeemaker. The bed was comfortable. There are plenty of restaurants and shops nearby. We liked Dottie's, just across the street so much we went for breakfast two days in a row. It was a bit strange that there was no person to check in with, it was done by phone, which worked fine; it was just unusual. We didn't see an ice or vending machine, but didn't go looking too hard. There is a deli just in front of the Inn (it closes at 3 PM, I think) are stores within a short distance if truly needed. There were a few maintenance items that needed some attention; I brought them to the attention of the contact at the property.
Stayed 2 nights in Sep 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, property conditions & facilities
Quiet and clean place to stay for one night.
Stayed 1 night in Nov 2023
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort

Cute spot

Cute motel with friendly owners. Had housekeeping every day which seems to be a rarity these days. Perfect spot for us when visiting family.
Stayed 5 nights in Dec 2023
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Great place to stay. It is clean and cozy. Walking distance to several very good restaurants. Very responsive owners. Would definitely recommend.
Stayed 2 nights in Sep 2023
Verified review

8/10 Good

Liked: Cleanliness, staff & service, property conditions & facilities
Everything was just fine. A bit expensive for what you get, but that's the market. Very basic simple clean and quiet and comfortable room. I slept well.
Stayed 1 night in Dec 2023
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
I really enjoyed my stay at The Milestone Inn. It was just what I was going for! Staff were awesome and prompt and professional with their communications. I was pleasantly surprised that housekeeping took care of me each and every day. For some reason i did not expect housekeeping but it was so nice to come home to a nicely made bed with everything replenished. This experience, was a good one. Highly recommend!!
Stayed 3 nights in Sep 2023
Verified review

10/10 Excellent

Liked: Cleanliness, property conditions & facilities
The Milestone Inn is a comfortable, clean and well appointed motel room. The motel uses a contactless checkin with no staff on site which was a new experience for us. There was a local phone problem which rendered contacting the inn difficult prior to the stay. Rinal from the motel contacted us the day prior to the stay and walked us through the check in process and took care of any final questions including providing us with and alternate contact number.
Stayed 1 night in Oct 2024
Verified review

6/10 Okay

Disliked: Amenities
This is a good option if you are looking for a relatively inexpensive property but the amenities are sparse. The room was relatively clean, however there was an overwhelming musty scent. There wasn't anyone onsite so if there was an issue you had to make contact via phone. It is in a good location for shopping and eating.
Stayed 2 nights in Aug 2023
Verified review

4/10 Poor

Liked: Cleanliness, staff & service
Disliked: Property conditions & facilities
It was a quiet clean property good price however no hot water they claimed the boiler just broke before pir arrival & there were spiders & bugs in our room. I was offered half off my stay & still haven't received anything not even a receipt that i asked to be sent to me. Staff that I meant was very nice & did apologize
Stayed 1 night in Jul 2024
Verified review

8/10 Good

Liked: Cleanliness, staff & service, property conditions & facilities
Milestone Inn as a "turn-key" motel was certainly adequate for our brief stay (2 nights). It was clean and accessible to visiting family in Washington, CT. Only one glitch was the room had not been cleaned on Sunday - we called and our only request was not for the beds to be made or towels replenished, but for more coffee for this morning! We called the (203) # and a nice gal arrived promptly with coffee in hand yay! A couple of thoughts for the owners: the lighting, especially over the sink, is dim and not conducive to two 60-something year old women getting gussied up with some make-up. Also maybe some seating (like Adirondack chairs) outside might be nice to allow us to sit out and enjoy our coffee or wine. My son runs The Mayflower Inn in Washington, CT, and I am by no means comparing the two properties but just making a gentle suggestion. Also, a little basket of gift certificates to or samples from some of the local purveyors (coffee shops, restaurants, a nearby bakery, Salon Bella, etc.) might be another way that guests can leave with a favorable impression. Other than that, we were satisfied with the room and experience. Thank you. P.S. An invoice for our stay via email would be appreciated.
Stayed 2 nights in Oct 2023
Verified review

8/10 Good

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Our room was clean and they staff was helpful, but the room smelled like mildew and it was unpleasant.
Stayed 1 night in Sep 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Overall it is a great place.. the unique process of having to call to get a code to unlock room and having no staff on site is a bit weird and when we tried to call we couldn't get through first , second or third call... the cell service is very dodgy in the area. Location is prime , I like the small motel drive up vibe and would stay here again when in the area. Room was clean and all we needed was there but had a bit of a odor to it.. as old rooms do.. I checked the air filter on the AC and that was likely to be the issue.
Stayed 1 night in Aug 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Nice
Stayed 1 night in Sep 2026
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, property conditions & facilities
We would definitely stay here again!
Stayed 1 night in May 2023
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Nice, clean hotel. Great location, nice staff.
Stayed 2 nights in Jun 2023
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, property conditions & facilities
Clean and quiet. Great place to stay when in the area for a great price.
Stayed 1 night in Feb 2023
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Clean, comfortable, spacious and quiet. I would stay here again…
Stayed 1 night in Apr 2023
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Very nice…I’ve been two times and I’ll go back again!
Stayed 2 nights in Dec 2022
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort

Beautiful

The inn was extremely clean. Very nice place to stay. We will be back for a longer stay.
Stayed 1 night in Oct 2022
Verified review

10/10 Excellent

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Everything was great!
Stayed 1 night in Mar 2023