Greenfield Hill Vacations from $601

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Your Greenfield Hill Vacation

Reserving a Greenfield Hill vacation package is a good way to get to know this unique neighborhood. From its must-visit places to its little-known gems, you won't be short of adventures. Some leading nearby attractions to see during your trip to Greenfield Hill include Fairfield University, Fairfield Theater Company and Fairfield Museum and History Center. Expedia can help turn your ideal Greenfield Hill vacation into reality, whatever your budget or travel plans.

The Latest Greenfield Hill Vacation Packages

Price found within the past 48 hours. Click for updated prices.

Hyatus Luxury Residences City Crossing

The Hill

$601

per person

Nov 6 - Nov 8

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to New Haven (HVN)

9.4/10 Exceptional! (34 reviews)

The room was spacious and clean. Close to new haven union station, yale university and downtown. We enjoyed the pool, gym and the rooftop. Check in and check out process were very smooth. Sarah was very responsive to our questions. Would def stay here again.

Reviewed on Aug 10, 2026

Beechmont - Perfect for Family Retreat!

North End

Save 100% on your flight

$746

per person

Nov 6 - Nov 8

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to New Haven (HVN)

No reviews

Luxury Furnished Apartments by Hyatus Downtown at Yale

The Hill

$1,005

per person

Dec 29 - Jan 2

found 13 hours ago

Roundtrip flight included

Tampa (TPA) to New Haven (HVN)

9.6/10 Exceptional! (88 reviews)

Excellent value — a very thoughtfully decorated and well-maintained apartment, effective air conditioning, blackout curtains in every room — really helped the vacation to feel like a “treat”! I did feel their app / web portal had “quite a lot” baked in it which could feel intimidating at first — vs. a “easy button” version at the top for simple functions like lock/unlock door — but would absolutely consider other Hyatus properties in the future!

Reviewed on Sep 18, 2026

Landing Furnished Apartment Near Yale University

Downtown New Haven

$875

per person

Dec 29 - Jan 2

found 13 hours ago

Roundtrip flight included

Tampa (TPA) to New Haven (HVN)

2/10 (2 reviews)

Check in automated, but the key box was broken and it took me 30 on the phone with IT to get the keys. When I entered the apartment a water leak in the city had destroyed a chunk of the ceiling and there was a mess of drywall and dirty water on the floor. The firm tried to relocate me an hour away before promising to clean up and repair the problem while I was out, but maintenance never arrived. We had to book a hotel nearby. These people are incompetent

Reviewed on Sep 14, 2026

Landing Apartments Prospect Hill Historic District

Prospect Hill

$794

per person

Dec 29 - Jan 2

found 13 hours ago

Roundtrip flight included

Tampa (TPA) to New Haven (HVN)

6/10 (2 reviews)

The place was not cleaned beforehand. It looked like someone was sleeping in the bed before I got there. The sheets were not changed and had blood stains on them. They had to call someone to come clean the place while I was still staying because no cleaning was done before I arrived. There was leftover food on the stove. The cleaners took the comforter and did not replace it. Overall, terrible experience.

Reviewed on May 15, 2026

Where to stay in Greenfield Hill

Find the best Greenfield Hill areas and neighborhoods for the activities you enjoy most. Learn more about Greenfield Hill

A lighthouse at night with a full moon in the sky.

Fairfield Beach

3 out of top 10 points of interest in this area

If you're spending some time in Fairfield Beach, Penfield Beach and Fairfield Beach are top sights worth seeing.

Fairfield Center

1 out of top 10 points of interest in this area

While visiting Fairfield Center, you might make a stop by sights like Fairfield Theater Company and Connecticut Audubon Birdcraft Museum.

Grasmere

Grasmere might not have many top sights, but Jennings Beach and Fairfield Theater Company are two attractions nearby that you can check out.

A river winding through a forested area with houses along the banks.

Tunxis Hill

While there might not be top attractions in Tunxis Hill, you can explore the larger area and discover places like Lake Mohegan Beach and Lake Mohegan.

Sasco

1 out of top 10 points of interest in this area

While visiting Sasco, you might make a stop by sights like Country Club of Fairfield and South Pine Creek Beach.

Greenfield Hill Hotel Deals

Hotel Hi-Ho - Contactless Check-In

4180 Black Rock Turnpike Fairfield CT

Fully refundableReserve now, pay when you stay

$168 nightly

$193 total

Nov 1 - Nov 2

Total with taxes and fees

Amsterdam Hotel

19 Clarks Hill Ave Stamford CT

Fully refundableReserve now, pay when you stay

$105 nightly

$122 total

Nov 5 - Nov 6

Total with taxes and fees

8.4/10 Very Good! (1,802 reviews)

"My room was perfect, and the staff were very helpful and kind."

Reviewed on Oct 5, 2026

Hyatt Regency Greenwich

1800 E Putnam Avenue Old Greenwich CT

Fully refundableReserve now, pay when you stay

$178 nightly

$205 total

Oct 25 - Oct 26

Total with taxes and fees

8.8/10 Excellent! (1,172 reviews)

"Large and conveniently located. Showing some age. Outlet in the room didnt work, shower curtain needs replacement. Promised a rollaway but then said no and shrugged it off. Breakfast service slow and overpriced"

Reviewed on Oct 4, 2026

See all 1,094 properties in Greenfield Hill

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.