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The Milestone Inn

2.5 star property
Hotel in Woodbury with free parking

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The Milestone Inn offers a genuine retreat where comfort meets practicality. Guests can stay connected with in-room WiFi while enjoying the time-saving convenience of express check-out. The property combines essential amenities with a restful atmosphere.

Reviews

8.8 out of 10
Excellent

Popular amenities

  • Parking included
  • Free WiFi
  • Air conditioning

Room options

Available filters for rooms
Showing 2 of 2 rooms

View all photos for Standard Room, 1 King Bed

Standard Room, 1 King Bed | Desk, laptop workspace, iron/ironing board, free WiFi

Standard Room, 1 King Bed

9.4 out of 10
Exceptional
(6 reviews)

Highlights

Air conditioning
Heating
Refrigerator
TV
Separate bedroom
Hair dryer
Designer toiletries
Private bathroom
  • 1 bedroom
  • Sleeps 2
  • 1 King Bed

View all photos for Standard Room, 2 Double Beds

Standard Room, 2 Double Beds | Desk, laptop workspace, iron/ironing board, free WiFi

Standard Room, 2 Double Beds

9.8 out of 10
Exceptional
(11 reviews)

Highlights

Air conditioning
Heating
Refrigerator
TV
Hair dryer
Designer toiletries
Private bathroom
Shower/tub combination
  • 28 sq m
  • Sleeps 4
  • 2 Double Beds
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About the neighborhood

Map
06798, CT, Woodbury, 146 S Pomperaug Ave

What's nearby

  • Hollow Park - 17 min walk - 1.5 km
  • Pilgrim Mall Shopping Center - 2 min drive - 2.5 km
  • Lake Quassapaug - 3 min drive - 3.2 km
  • Glebe House Museum and The Gertrude Jekyll Garden - 3 min drive - 3.6 km
  • Yale University - 38 min drive - 46.5 km

Getting around

  • Oxford, CT (OXC-Waterbury - Oxford) - 12 min drive

Restaurants

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

About this property

The Milestone Inn

Property highlights
The Milestone Inn provides everything you need. Stay connected with free in-room WiFi.
You'll also find perks like:
  • Free self parking
  • Express check-out and smoke-free premises
Room features
All guestrooms at The Milestone Inn have thoughtful touches such as laptop-friendly workspaces and air conditioning, as well as amenities like free WiFi.
More conveniences in all rooms include:
  • Designer toiletries, shower/tub combinations, and hair dryers
  • 40-inch TVs with cable channels
  • Refrigerators, microwaves, and coffee/tea makers

Similar properties

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Wyndham Southbury
  • Pool
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  • Parking included
  • Free WiFi
8.2 out of 10, Very Good, 1,022 reviews
The price is ￥14,319
￥16,467 total
includes taxes & fees
Dec 8 - Dec 9
Wyndham Southbury

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

Renovations and closures

This property is closed from July 21 2025 to July 17 2027 (dates subject to change).

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

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

Property is also known as

Milestone Inn Woodbury
The Milestone Inn Hotel
The Milestone Inn Woodbury
The Milestone Inn Woodbury
The Milestone Inn Hotel Woodbury
The Milestone Inn
The Milestone Inn Hotel
The Milestone Inn Woodbury
The Milestone Inn Hotel Woodbury

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).

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Reviews

The Milestone Inn Reviews

8.8

Excellent

9.2

Cleanliness

7.6

Location

8.4

Staff & service

8.4

Eco-friendliness

8.8

Property conditions & facilities
Rating 10 - Excellent. 113 out of 190 reviews
Rating 8 - Good. 49 out of 190 reviews
Rating 6 - Okay. 15 out of 190 reviews
Rating 4 - Poor. 8 out of 190 reviews
Rating 2 - Terrible. 5 out of 190 reviews

Reviews

10/10 Excellent

Jack

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

10/10 Excellent

Mark

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

10/10 Excellent

Greg

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

10/10 Excellent

Amy

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Cute little 10 room renovated motel. Perfect end for a day at the Litchfield county vineyards and can walk to many restaurants for dinner and breakfast.
Stayed 1 night in Oct 2022

10/10 Excellent

Eugene

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

Highly Recommend

Was only there for one night, but it was a nice comfortable hotel. Room was very clean. Hotel is located in a nice area. Only contact with staff was on the phone or by text, but it was very professional. Highly recommend for a basic hotel!
Stayed 1 night in Jul 2022

10/10 Excellent

Michael

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Very efficient touchless system
Stayed 1 night in Sep 2023

10/10 Excellent

Joshua

Liked: Cleanliness, staff & service, amenities
There's a small lockbox beside the door that you'll need to type your code to access the keys. Once we figured that out, it was a very pleasant stay.
Stayed 1 night in Feb 2023

8/10 Good

Sean

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

10/10 Excellent

Dosinda

Liked: Cleanliness, staff & service, property conditions & facilities
Very efficient and friendly. They responded very positively to a special request I made. Thank you!
Stayed 1 night in Sep 2022

10/10 Excellent

Sherrie

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

6/10 Okay

Sarah

Liked: Staff & service
Good Location, Room 7 however needs to be updated. Wallpaper is peeling all over the room and what looks like mold on the ceiling in the bathroom.. everything needs to be cleaned really well. The shower curtain had mold on the bottom of the curtain and the tub didnt drain. When you showered by the end of it your in a full bath.

4/10 Poor

carolynn

Liked: Amenities, property conditions & facilities
Very dissapointed this time. Room was dirty! Two dirty towels, food on floor, terrible smell of mold, and AC didn’t work properly - not adjustable
Stayed 2 nights in Aug 2023

6/10 Okay

Michael

Liked: Cleanliness, staff & service

Charming place

Our stay was decent and seems like it's run by some nice people. It's located in a nice town with really good restaurants and was quiet. However, my only reason for writing this review is so you are aware of what you're getting. If you like antiquated, then this your place. We were in room 4 and it's dim lit, had a swivel armchair at the desk (keep this in mind if you are on business), and the bed was way too soft. And they really need to invest in heavier shower curtains because they billow horribly. In their defense, they did reach out to me and offered an office chair and a box of tissues, which we didn't have in the room. Despite all that, I grew up nearby and would consider staying here again.
Stayed 2 nights in Dec 2022

10/10 Excellent

DENIS

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

4/10 Poor

Jenita

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

10/10 Excellent

matt

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

Great value clean quiet

Really nice little motel that is reasonably priced in an time when every chain hotel is 200-300 bucks
Stayed 1 night in Jan 2024

10/10 Excellent

Debra

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

8/10 Good

Kathleen

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

8/10 Good

Verified traveler

Liked: Cleanliness, staff & service, property conditions & facilities, room comfort
Love staying at milestone inn. I stay in 3 rooms. Room 4 and 5 beautiful clean ann cozy. Was disappointed with room 6. Wall paper peeling off the walls and long cowwebs were hanging off the ceiling. But besides that it was all good
Stayed 2 nights in Aug 2023

10/10 Excellent

Henrik

Liked: Cleanliness, staff & service
All good!
Stayed 5 nights in Aug 2023

6/10 Okay

Donna

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

8/10 Good

carolynn

Liked: Staff & service
Lovely
Stayed 1 night in Jul 2023

10/10 Excellent

Penny

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

6/10 Okay

Sheryl

Liked: Staff & service, room comfort

It worked for us

The online and phone communication was incredible; responses took 5 or less minutes. Very accommodating and friendly. The room had a musty smell, so we ran the bathroom fan most of the time. The beds were comfortable, the pillows not as much, at least for me. We were gone all of the time except for sleeping, so it worked for us. Nice breakfast restaurant right across the street, amazing French bakery just up the road.
Stayed 3 nights in Jun 2023

8/10 Good

Melinda

Liked: Cleanliness, staff & service, property conditions & facilities
It was a bit awkward that the bathroom sink was located outside of the bathroom, but it was tastefully done. The room was attractive and the bed was cozy. Great value.
Stayed 1 night in Jun 2023