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The Milestone Inn

2.5 star property
Travelers appreciate the perfect balance of modern connectivity and relaxation at this welcoming inn where every detail supports a smooth stay

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Photo gallery for The Milestone Inn

Standard Room, 1 King Bed | Desk, laptop workspace, iron/ironing board, free WiFi - The Milestone Inn (Woodbury)
Combined shower/tub, designer toiletries, hair dryer - The Milestone Inn (Woodbury)
Desk, laptop workspace, iron/ironing board, free WiFi - The Milestone Inn (Woodbury)
Interior entrance - The Milestone Inn (Woodbury)
Desk, laptop workspace, iron/ironing board, free WiFi - The Milestone Inn (Woodbury)
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)
  • 1 bedroom
  • Sleeps 2
  • 1 King Bed
  • Free WiFi

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)
  • 28 sq m
  • Sleeps 4
  • 2 Double Beds
  • Free WiFi

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

  • Yale university buildings in spring blue sky in New Haven, CT USA
    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
  • Minami Sushi
    6 min drive
  • Dunkin'
    5 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

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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

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

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.

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Reviews

The Milestone Inn Reviews

8.8

Excellent

9.2

Cleanliness

7.6

Location

8.4

Staff & service

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

Verified

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
Verified

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
Verified

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
Verified

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
Verified

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
Verified

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
Verified

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
Verified

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
Verified

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
Verified

10/10 Excellent

Anita

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

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
Verified

10/10 Excellent

Andrew

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

10/10 Excellent

Alan

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

10/10 Excellent

Cynthia

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

10/10 Excellent

Jaime

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

10/10 Excellent

Mark

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

8/10 Good

Harold

Liked: Cleanliness
Auto check in was novel Clean room and good bed!!!
Stayed 1 night in Aug 2022
Verified

10/10 Excellent

Jody

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
We absolutely loved our stay. Very clean, adorable room with all the amenities needed and staff was extremely pleasant . Will be staying again if ever up that way . Thank you
Stayed 1 night in Nov 2022
Verified

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
Verified

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
Verified

10/10 Excellent

Charlotte

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
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.
Stayed 1 night in Apr 2023
Verified

8/10 Good

Joan

Liked: Cleanliness, staff & service, amenities, property conditions & facilities
Small unassuming property with just about everything we needed at a decent price. Wish they had a little grab-and-go breakfast and that the vent and light were on separate switches in the bathroom. We'd stay there again.
Stayed 1 night in May 2023
Verified

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
Verified

10/10 Excellent

Debra

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

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.
Stayed 2 nights in May 2023
Verified

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