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The Milestone Inn

2.5 star property
Hotel in Woodbury

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Photo gallery for The Milestone Inn

Desk, laptop workspace, iron/ironing board, free WiFi
Desk, laptop workspace, iron/ironing board, free WiFi
Interior entrance
Desk, laptop workspace, iron/ironing board, free WiFi
Desk, laptop workspace, iron/ironing board, free WiFi
At The Milestone Inn, discover a haven of comfort and connection. Stay linked up with in-room WiFi and enjoy the ease of express check-out.

Reviews

8.8 out of 10
Excellent

Popular amenities

  • Non-smoking
  • Air conditioning
  • Free parking
  • Free WiFi

Main amenities (1)

  • Air conditioning

Feel at home (5)

  • Microwave
  • Cable/satellite TV service
  • Coffee/tea maker
  • Free self-parking
  • Hairdryer

Room options

Available filters for rooms
Showing 2 of 2 rooms

View all photos for 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
Fridge
TV
Separate bedroom
Designer toiletries
Hairdryer
Private bathroom
  • 1 bedroom
  • Sleeps 2
  • 1 King Bed

View all photos for 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
Fridge
TV
Designer toiletries
Hairdryer
Private bathroom
Shower/bath combination
  • 28 sq m
  • Sleeps 4
  • 2 Double Beds

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About the area

Map
146 S Pomperaug Ave, Woodbury, CT, 06798

What's nearby

  • Pilgrim Mall Shopping Center - 2 min drive - 2.5 km
  • Glebe House Museum and The Gertrude Jekyll Garden - 3 min drive - 3.6 km
  • Quassy Amusement Park - 7 min drive - 7.5 km
  • Candlewood Lake - 32 min drive - 42.0 km
  • Yale University - 47 min drive - 46.5 km

Getting around

  • Oxford, CT (OXC-Waterbury - Oxford) - 12 min drive
  • Danbury, CT (DXR-Danbury Municipal) - 26 min drive
  • Bridgeport, CT (BDR-Igor I. Sikorsky Memorial) - 45 min drive
  • New Haven, CT (HVN-Tweed - New Haven Regional) - 64 min drive

Restaurants

  • McDonald's
  • Panera Bread
  • Oriental Gourmet
  • ‪Constantine's Restaurant - ‬18 min walk
  • ‪San Remo - ‬4 min drive

About this property

The Milestone Inn

Enjoy your visit to Woodbury with a stay at The Milestone Inn. You'll have free perks such as WiFi and self-parking.

Languages

English

More about this property

VISIBILITY

At a glance

Hotel size

    • 10 rooms
    • Arranged over 1 level

Arriving/Leaving

    • Check-in start time: 4:00 PM; check-in end time: 8:00 PM
    • Contactless check-in and check-out are available
    • Express check-out available
    • Early check-in subject to availability
    • Minimum check-in age – 25
    • Check-out time is 11:00 AM
    • Contactless check-out

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

Required at check-in

    • Credit card, debit card or cash deposit required for incidental charges
    • Government-issued photo ID may be required
    • Minimum check-in age is 25

Children

    • No cots (infant beds)

Pets

    • Pets not allowed

Internet

    • Free WiFi in public areas
    • Free WiFi in rooms

Parking

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

Other information

    • Smoke-free property
LOB_HOTELS

Property amenities

Accessibility

  • Wheelchair-accessible
  • Wheelchair-accessible parking
  • Wheelchair-accessible registration desk
  • Closed-captioned TV
  • Lowered locks/deadbolt
  • Low-height worktop and sink
  • Wheelchair-width doorways
  • Well-lit path to entrance
  • Step-free path to entrance
ROOM

Room amenities

Be entertained

  • 40-inch TV
  • Cable TV channels

Home comfort

  • Air conditioning and heating
  • Coffee/tea maker
  • Iron/ironing board

Sleep well

  • Alarm clock

Freshen up

  • Shower/bath combination
  • Designer toiletries
  • Hairdryer

Stay connected

  • Desk
  • Free WiFi

Food and drink

  • Fridge
  • Microwave
MONETIZATION_ON

Fees & policies

Optional extras

  • Early check-in can be arranged for an extra charge (subject to availability)
  • Late check-out can be arranged for an extra charge

Renovations and closures

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

Policies

This property does not have lifts.
Guests can rest easy knowing that there's a fire extinguisher and a first aid kit on-site.
This property accepts credit cards.
Credit cards accepted: Visa, Mastercard, American Express, Discover

Also known as

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

Frequently asked questions

Is The Milestone Inn currently open?

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

Does The Milestone Inn offer free cancellation for a full refund?

Yes, The Milestone Inn does have fully refundable room rates available to book on our site. If you’ve booked a fully refundable room rate, this can be cancelled up to a few days before check-in, depending on the property's cancellation policy. Just make sure that you check this property's cancellation policy for the exact terms and conditions.

Are pets allowed at The Milestone Inn?

Sorry, pets aren't allowed.

Is parking offered on site at The Milestone Inn?

Yes, there's free self parking.

What are the check-in and check-out times at The Milestone Inn?

Check-in start time: 4:00 PM; check-in end time: 8:00 PM. There's a charge for early check-in (subject to availability). Check-out time is 11:00 AM. Late check-out is available for a charge. Express check-out and contactless social distancing and check-out are available.

What's the area around The Milestone Inn like?

The Milestone Inn is a short 8-minute walk from Hollow Park and 18 minutes' walk from Pilgrim Mall Shopping Center.

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The Milestone Inn Reviews

Reviews

8.8

Excellent

9.2/10

Cleanliness

8.4/10

Staff & service

8.0/10

Amenities

8.8/10

Property conditions & facilities

8.4/10

Eco-friendliness

Popular mentions

Room
Bed
Bathroom
Restaurant
Amenities
Store
Microwave
Refrigerator
Service staff
Towns

Reviews

10/10 Excellent

Quiet and clean place to stay for one night.
Jack, 1-night trip

10/10 Excellent

Very nice…I’ve been two times and I’ll go back again!
Cynthia, 2-night trip

10/10 Excellent

Everything was great!
Mark, 1-night trip

10/10 Excellent

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.
Debra, 5-night trip

10/10 Excellent

Great place to stay. It is clean and cozy. Walking distance to several very good restaurants. Very responsive owners. Would definitely recommend.
Greg, 2-night trip

8/10 Good

Auto check in was novel Clean room and good bed!!!
Harold, 1-night trip

10/10 Excellent

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.
Amy, 1-night trip

10/10 Excellent

The Inn is a cute, clean spot. The bathroom was tiny but the bed was extremely comfortable. We needed an economical spot to rest for the night. This was perfect.
Charlotte, 1-night trip

8/10 Good

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.
Melinda, 1-night trip

10/10 Excellent

A hidden gem

Could not have been more pleased. Clean, quaint and in the heart of town.. Comfortable beds, high end linens and creamer with the coffee not the powdered stuff. Will be my new go to spot when visiting Woodbury.
Debra, 2-night trip

8/10 Good

Lovely
carolynn, 1-night trip

10/10 Excellent

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!
Eugene, 1-night trip

10/10 Excellent

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.
DENIS, 1-night trip

10/10 Excellent

Quiet. Very clean. Within walking distance to great dining, shops, breakfasts, delis, ice cream. Delightful staff.
Craig, 1-night trip

10/10 Excellent

Very efficient touchless system
Michael, 1-night trip

8/10 Good

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.
Sean, 1-night trip

10/10 Excellent

It was so quaint and charming! The room was very clean and generously sized, as was the bed. The fridge and microwave were nice added conveniences. Parking was extremely convenient. Check in was over the phone, which was incredibly easy and quick. I loved everything about the Milestone Inn and look forward to staying there again!
Elin, 2-night trip

10/10 Excellent

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.
Joshua, 1-night trip

10/10 Excellent

Very efficient and friendly. They responded very positively to a special request I made. Thank you!
Dosinda, 1-night trip

10/10 Excellent

Clean and Quaint

Room was clean and quaint. The wallpaper was peeling in the bathroom but we were just staying the night on our trip and the price was right. A refrigerator and a microwave were in the room.
Kimberley, 1-night trip

10/10 Excellent

Weekend trip!

The room was very clean, one thing I would say is the Water pressure was crazy! Kept on wetting the floor of the bathroom. So we just put a towel down when taking showers. But definitely booking here again!!
Susan, 3-night trip

8/10 Good

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
2-night trip

10/10 Excellent

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!!
Sherrie, 3-night trip

10/10 Excellent

Dropbox check in, with no front desk, is a new one on me. Not cheap at $148, but clean and in good shape. Zero amenities but no complaints beyond that.
P Thomas, 1-night trip

6/10 Okay

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.
Donna, 2-night trip