The Milestone Inn

Hotel in Woodbury with free parking

Choose dates to view prices

Where to?

Dates

July 2025

August 2025

Relax in a spacious room with a large bed, two bedside tables, and a striped pattern on the walls.

Relax under the covered outdoor area, surrounded by lush greenery and a serene natural landscape.

Two single beds with white duvets and pillows, a nightstand with a lamp and telephone, and a window with curtains.

Enjoy freshly brewed coffee with the in-room coffee maker.

Relax in a serene space with a comfortable bed, bedside table, and convenient storage.

Overview
Rooms
Location
Policies

Popular amenities

Air conditioning
Parking included
Free WiFi

Explore the area

146 S Pomperaug Ave, Woodbury, CT, 06798

Glebe House Museum and The Gertrude Jekyll Garden
‪3 min drive‬
Quassy Amusement Park
‪7 min drive‬
Candlewood Lake
‪32 min drive‬
New Haven, CT (HVN-Tweed - New Haven Regional)
‪54 min drive‬

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Room options

Standard Room, 1 King Bed

Exceptional

Sleeps 2
1 King Bed

Standard Room, 2 Double Beds

Exceptional

301 sq ft
Sleeps 4
2 Double Beds

About the neighborhood

Woodbury

The Milestone Inn places you within a short walk of Hollow Park and within a mile (2 km) of Pilgrim Mall Shopping Center. This 10-room hotel has in-room conveniences like refrigerators, microwaves, and coffee makers.

What's nearby

Glebe House Museum and The Gertrude Jekyll Garden - 3 min drive - 2.2 miles
Quassy Amusement Park - 7 min drive - 4.7 miles
Southbury Dog Park - 8 min drive - 4.2 miles
Candlewood Lake - 32 min drive - 26.1 miles
Yale University - 47 min drive - 28.9 miles

Getting around

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

Restaurants

‪McDonald's - ‬6 min drive
‪Panera Bread - ‬5 min drive
‪Oriental Gourmet - ‬6 min drive
‪Woodbury Diner - ‬4 min drive
‪Julio's Wood Fired Pizza & Grill - ‬6 min drive

About this property

The Milestone Inn

Hotel in Woodbury with free parking

At The Milestone Inn, guests have access to free WiFi in public areas and express check-out. Free parking is included with your stay.

Guests can expect free WiFi and 40-inch TVs with cable channels. Bathrooms offer hair dryers and designer toiletries. Refrigerators, microwaves, and coffee makers are also standard.

Languages

English

Similar properties

Relax in our comfortable seating area with a sofa and armchairs, featuring a coffee table and ambient lighting.

Pool
Pet friendly
Parking included
Free WiFi

$93 nightly

Aug 5 - Aug 6

Total includes taxes and fees

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

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

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

This property doesn't allow pets

Property payment types

Important information

Optional extras

These fees and deposits will be charged at check-in, check-out, or the time of service.

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

This list may not be comprehensive. Fees and deposits might 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

Check-in: 4:00 PM—-8:00 PM
Check-out: 11:00 AM
Minimum check-in age: 25

Driving? This property offers free parking.

We should mention

Details about charges, deposits, or other important information:

This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession.
Charges for extra guests may apply and vary depending on the property's policy.
A cash deposit, credit card, or debit card for incidental charges, as well as a government-issued photo ID, may be required at check-in.
Special requests are subject to availability at the time of check-in and can't be guaranteed. Certain requests may come with additional charges.
This property accepts credit cards.
Onsite safety features include a fire extinguisher and a first aid kit.

Additional information about polices, regulations, and more:

There are no elevators.
No cribs or infant beds are available.
No rollaway or extra beds are available.

Property is also known as

Milestone Inn Woodbury

The Milestone Inn Hotel

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

Are free cancellation options available at The Milestone Inn?

The Milestone Inn provides free cancellation on select room rates. For additional details, take a look at the cancellation policy on Orbitz.

What's there to see around The Milestone Inn?

This hotel is located in Woodbury, a short 8-minute walk from Hollow Park and also 18 minutes on foot from Pilgrim Mall Shopping Center. You'll also find Quassy Amusement Park and Glebe House Museum and The Gertrude Jekyll Garden within a short drive.

Is there parking available at The Milestone Inn?

Yes, self parking is offered for free at the hotel. Accessible parking is also available for guests.

Does The Milestone Inn include a casino at the property?

No, The Milestone Inn doesn't have a casino.

Will I find an indoor pool at The Milestone Inn?

No, there is no indoor pool at this hotel.

Are there hot tubs at The Milestone Inn?

No, there isn't a spa tub at this hotel.

Does The Milestone Inn feature a restaurant that includes a breakfast menu?

No, The Milestone Inn doesn't have a restaurant that serves breakfast.

Will The Milestone Inn allow pets to stay free of charge?

No, pets aren't allowed at The Milestone Inn.

Are there connecting rooms at The Milestone Inn?

No, there aren't connecting guestrooms at this hotel.

How far is the airport from The Milestone Inn?

The closest major airport to The Milestone Inn is Oxford, CT (OXC-Waterbury - Oxford), which is 7.1 mi away (12 minutes by car). Another top airport is Danbury, CT (DXR-Danbury Municipal), which is located 23.3 mi away (26-minute drive).

Are there rooms with balconies at The Milestone Inn?

No, there aren't any guestrooms with balconies at The Milestone Inn.

The Milestone Inn 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

10/10 Excellent

DENIS, MT KISCO

Oct 27, 2024

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

Traveled with family

Jul 23, 2024

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

Lisa

Jun 3, 2024

Stayed 1 night in Jun 2024

10/10 Excellent

Emma K Griswold

Apr 1, 2024

Stayed 1 night in Mar 2024

10/10 Excellent

matt

Jan 12, 2024

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

Jan 7, 2024

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

Sean

Jan 2, 2024

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

Dale

Nov 24, 2023

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

Stayed 1 night in Nov 2023

10/10 Excellent

Jack

Traveled with family

Nov 11, 2023

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

Verified traveler

Nov 5, 2023

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

Stayed 1 night in Nov 2023

8/10 Good

Kathleen

Traveled with family

Oct 23, 2023

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

10/10 Excellent

Sherrie

Business traveler

Sep 27, 2023

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

10/10 Excellent

Michael

Traveled with family

Sep 26, 2023

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

Very efficient touchless system

Stayed 1 night in Sep 2023

10/10 Excellent

Greg

Traveled with partner

Sep 24, 2023

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

john

Sep 24, 2023

Stayed 2 nights in Sep 2023

10/10 Excellent

john

Sep 22, 2023

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

Stayed 1 night in Sep 2023

8/10 Good

Verified traveler

Sep 21, 2023

Liked: Cleanliness, staff & service, room comfort

Stayed 1 night in Sep 2023

8/10 Good

Verified traveler

Aug 30, 2023

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

Aug 23, 2023

Liked: Cleanliness, staff & service

All good!

Stayed 5 nights in Aug 2023

6/10 Okay

Donna

Traveled with family

Aug 20, 2023

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

4/10 Poor

carolynn

Aug 8, 2023

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

8/10 Good

WDavid

Jul 25, 2023

Stayed 2 nights in Jul 2023

8/10 Good

carolynn

Jul 20, 2023

Liked: Staff & service

Lovely

Stayed 1 night in Jul 2023

10/10 Excellent

Penny

Traveled with family

Jul 2, 2023

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

Traveled with family

Jun 27, 2023

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