Middlefield Cottages

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Find holiday rentals that suit your style

Check prices for these dates

Next weekend

In two weeks

In one month

In two months

Our top choices for Middlefield cottages

A small single-story house with a front porch, a potted plant, and two Adirondack chairs.

1. 1-bedroom cottage with Grove Beach 🏖️ access.

Clinton

JM B.

includes taxes & fees

12 Nov - 13 Nov

A two-story house with a porch, a mailbox, and a lawn.

2. Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!

Madison

Samantha D.

includes taxes & fees

8 Nov - 9 Nov

A white cottage with a front door, a garage, and a small porch with a potted plant.

3. The gardners Cottage 1 mile from long Island Sound - pet friendly

Clinton

Wink V.

includes taxes & fees

8 Nov - 9 Nov

A two-story house with a covered porch, a front door, and a small outdoor seating area with a table and chairs.

4. Cozy Home near private beach , close to New Haven area colleges Hospitals

Branford

Vincent

includes taxes & fees

17 Nov - 18 Nov

A two-story brick house with a white garage door, surrounded by a well-maintained lawn and a tree.

5. Watertown Home w/ Yard: 1 Mi to Echo Lake Park!

Oakville

includes taxes & fees

7 Nov - 8 Nov

View all properties

Learn more about Middlefield

Lyman Orchards invites visitors to pick seasonal fruits and navigate its famous corn maze during autumn festivities. Powder Ridge Mountain Park offers skiing in winter and mountain biking in summer, while nearby Wadsworth Falls State Park features refreshing swimming holes locals can direct you to.

See all hotels in Middlefield