The Milestone Inn
A four-star stop in the Connecticut countryside, no pretense required.
A place to stay in Woodbury
The Milestone Inn is a four-star hotel in Woodbury, Connecticut, with an outdoor swimming pool, free private parking, and meeting space for business travelers. Rooms start at $199 per night across six room types, most running 36–37 m². The property sits within easy walking distance of several restaurants, a practical advantage in a town where dining options are spread out. With 48 guest reviews averaging 4.3/5, it draws a consistent if modest crowd of leisure and business visitors looking for a solid base in Litchfield County.
Who this stay suits
A well-maintained four-star hotel with reliable basics — pool, free parking, daily housekeeping — in a quieter Connecticut town that rewards having a car.
Best for
- Business travelers needing meeting facilities
- Couples visiting the Woodbury area
- Guests who need accessible parking
- Road trippers passing through Connecticut
Less suited to
- Travelers without a car
- Those wanting a wide choice of on-site dining
- Groups needing multi-room suites
The pool and outdoor space
The outdoor swimming pool is the centerpiece of the leisure side of the property. Sun umbrellas and outdoor furniture are available poolside, and pool towels are provided. The garden adds a bit of green to the setting without being manicured to the point of feeling artificial.
Room design and character
Most rooms run 36–37 m² and come with either a balcony or inner courtyard view. The Standard King and Standard Double rooms both include coffee machines, ensuite bathrooms, flat-screen TVs, and air conditioning — the kind of consistent setup that makes repeat stays predictable in a good way.
Business and meeting space
The business centre handles everyday needs including fax and photocopying. Meeting facilities make the property a workable choice for small corporate stays in the Woodbury area, where dedicated conference hotels are thin on the ground.
Rooms & suites
Standard King Room
36 m² · sleeps 2 · 1 extra-large double bed
- Balcony
- Inner courtyard view
- Air conditioning
- Ensuite bathroom
- Flat-screen TV
Standard Double Room
36 m² · sleeps 2 · 2 double beds
- Inner courtyard view
- Air conditioning
- Ensuite bathroom
- Flat-screen TV
- Coffee machine
Deluxe Double Room
36 m² · sleeps 2 · 2 double beds
- Inner courtyard view
- Air conditioning
- Ensuite bathroom
- Flat-screen TV
- Coffee machine
Standout features
Inside The Milestone Inn
Amenities at The Milestone Inn
Great for your stay
- Parking
- Free WiFi
- Free parking
- Non-smoking rooms
- Outdoor swimming pool
- Private parking
- Laundry
- Beach
Outdoors
- Outdoor furniture
- Garden
Internet
- Internet services
On-site parking
- Accessible parking
Transport
- Public transport tickets
Services
- Daily housekeeping
- Fax/photocopying
- Laundry
- Business centre
On the map
Things to do nearby
- In Memory of George Washington historic site 0.49 km
- Soldiers’ Monument historic site 1.67 km
Where to eat
- Dottie's Diner restaurant 0.12 km
- Al's Best Pizza restaurant 0.13 km
- Annoula's Taverna restaurant 0.24 km
- Carole Peck's Good News Cafe restaurant 0.41 km
- John's Cafe cafe 0.41 km
- Woodbury Pizza restaurant 0.46 km
Of 33 property-related comments, 28 were positive — the single strongest theme. Cleanliness scored 19 positives from 21 mentions. Service held up well at 12 out of 14. Sleep quality drew mostly favorable notes (9 of 11), and family stays were positive in 4 of 5 mentions. Bathroom feedback was more mixed, with 2 positives from 6 comments.
- Things to do3.5
- Restaurants4.2
- Public transit0
- Airport access3
Share of positive mentions per theme, from Google reviews.
Good to know
Frequently asked
Where exactly is The Milestone Inn located?
The hotel is in Woodbury, Connecticut. Woodbury is a small town in Litchfield County, best reached by car. Several restaurants are within walking distance, including Dottie's Diner about 120 meters away.
Is parking available, and does it cost extra?
Free private parking is available on-site, including accessible spaces. There is no charge for parking.
What room types are available?
There are six room types: Standard Double, Deluxe Double, Standard King, King Room, King Premium, and Two Queen Premium. Prices start at $199 for the Standard Double and go to $239 for the Premium tiers.
Do rooms have balconies or outdoor access?
The Standard King Room includes a balcony with an inner courtyard view. The King Room has outdoor furniture. Other room types have inner courtyard views rather than private outdoor space.
Is there Wi-Fi, and is it free?
Yes. Free Wi-Fi is available throughout the property.
Is there an outdoor pool?
Yes. The hotel has an outdoor swimming pool. Pool towels and sun umbrellas are provided.
Are there dining options nearby?
Several restaurants are within half a kilometer: Dottie's Diner (0.12 km), Al's Best Pizza (0.13 km), Annoula's Taverna (0.24 km), Carole Peck's Good News Cafe (0.41 km), John's Cafe (0.41 km), Woodbury Pizza (0.46 km), Carlito's of Woodbury (0.46 km), and Whole Egg (0.47 km).
Are there business or meeting facilities?
Yes. The hotel has a business centre with fax and photocopying, plus dedicated business and meeting facilities — useful for small corporate stays in the Woodbury area.
Is the property suitable for families?
Family stays drew positive feedback in 4 of 5 guest mentions. The Two Queen Premium room, with two large double beds, is the most practical option for families wanting extra sleeping space.
Is housekeeping included?
Yes. Daily housekeeping is provided as standard.
Is the hotel accessible?
Accessible parking is available on-site. Non-smoking rooms are standard throughout the property.
How do I book, and what is the lowest available rate?
Rooms start from $199 per night for the Standard Double Room. Bookings can be made directly with the hotel or through major travel platforms. Rates vary by date and room type.