New Preston Vacations from $404

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Your New Preston Vacation

A great way to experience this city is with a custom-made New Preston vacation package. Stay in the neighborhood of Washington, which is good for nature, history and views or choose someplace else — our package deals are all about you. Any trip to New Preston needs a well-thought-out itinerary. Fill yours with leading attractions like Lake Waramaug, Lake Waramaug State Park and Steep Rock Preserve. Whoever you're heading away with and whatever you plan to spend, your ultimate New Preston vacation is just clicks away with Expedia.

The Latest New Preston vacation packages

Price found within the past 48 hours. Click for updated prices.
Days Inn by Wyndham Ridgefield

Days Inn by Wyndham Ridgefield

2 out of 5
Save 100% on your flight
per person
Sep 19 - Sep 25
found 16 hours ago
Roundtrip flight included
Atlanta (ATL) to New Haven (HVN)
5.8/10 (859 reviews)
All good except for the breakfast.

Reviewed on Aug 6, 2025

Holiday Inn Express Southington by IHG

Holiday Inn Express Southington by IHG

2.5 out of 5
per person
Oct 9 - Oct 14
found 13 hours ago
Roundtrip flight included
San Juan (SJU) to New Haven (HVN)
8.8/10 Excellent! (1,052 reviews)
It was walking distance to Thompson’s point where the music festival I went to see was being held. The staff from the front desk to cleaning staff, were all very friendly. More hooks and/or towel bars in the bathroom. Other than the shelf/rack that all the towels were stored on that is IN THE SHOWER (i.e. not practical to keep your towels on while you’re staying for a few days) there was 1 hook with 2 prongs on the door. It was a pain enough for me, and I stayed in the room by myself. I can’t imagine how aggravating it would be for a couple or a family.

Reviewed on Aug 15, 2025

Courtyard by Marriott Southington

Courtyard by Marriott Southington

3 out of 5
per person
Oct 9 - Oct 14
found 13 hours ago
Roundtrip flight included
San Juan (SJU) to New Haven (HVN)
8.8/10 Excellent! (423 reviews)
Everything was good

Reviewed on Jul 25, 2025

Hilton Garden Inn Milford

Hilton Garden Inn Milford

3 out of 5
Save 100% on your flight
per person
Sep 19 - Sep 25
found 16 hours ago
Roundtrip flight included
Atlanta (ATL) to New Haven (HVN)
8.2/10 Very Good! (1,001 reviews)
What I did not like is the fact that they resubmitted an incidental fee to my bank card which they have not returned as of today. Watch your funds, people!

Reviewed on Aug 16, 2025

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Discover the most popular places to visit in New Preston

Out of the two wineries in the area, we preferred Hopkins Vineyard.

Lake Waramaug

Commune with nature and explore the great outdoors at Lake Waramaug during your travels in New Preston. Wander the parks and beaches while you're in the area.

Lake Waramaug

Hopkins Vineyard

You can enjoy a tasting or tour at Hopkins Vineyard during your travels to Warren. While you're in the area, wander around the natural setting.

Hopkins Vineyard

New Preston Hotel Deals

Wyndham Southbury

Wyndham Southbury

3 out of 5
1284 Strongtown Road, Southbury, CT
Fully refundableReserve now, pay when you stay
$93 nightly
The price is $107 total per night from Aug 24 to Aug 25
$107 total
Aug 24 - Aug 25
Total includes taxes and fees
8/10 Very Good! (1,004 reviews)
Thumbs up
"Nice hotel, would stay again. Bartender Anthony was great."

Reviewed on Aug 13, 2025

Wyndham Southbury
Courtyard by Marriott Waterbury Downtown

Courtyard by Marriott Waterbury Downtown

3 out of 5
63 Grand St, Waterbury, CT
Fully refundableReserve now, pay when you stay
$89 nightly
The price is $102 total per night from Sep 2 to Sep 3
$102 total
Sep 2 - Sep 3
Total includes taxes and fees
8.4/10 Very Good! (1,002 reviews)
"Everything was great except the toilet having to be flushed multiple times and loud air conditioner. I would still stay there again because of the staff and cleanliness of the rooms."

Reviewed on Aug 14, 2025

Courtyard by Marriott Waterbury Downtown
La Quinta Inn & Suites by Wyndham Danbury

La Quinta Inn & Suites by Wyndham Danbury

3 out of 5
116 Newtown Road, Danbury, CT
Fully refundableReserve now, pay when you stay
$87 nightly
The price is $100 total per night from Aug 24 to Aug 25
$100 total
Aug 24 - Aug 25
Total includes taxes and fees
8.2/10 Very Good! (1,009 reviews)
"NO"

Reviewed on Aug 14, 2025

La Quinta Inn & Suites by Wyndham Danbury
See all 642 properties in New Preston
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.

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Frequently asked questions

How much does a New Preston vacation package cost?
Offering excellent value package deals from $404 on Expedia, you'll be pleasantly surprised at how much a vacation to New Preston costs! Our packages mean less travel planning for you and greater savings.
What are the cheapest months to go to New Preston?
You can usually find lower rates and better availability in December, January and February. Browse our cheap New Preston vacation packages and you could get some great off-season discounts.
How many days is enough for New Preston?
When planning your New Preston vacation, a handful of days will be enough to tour the top spots. Be sure to check out Lake Waramaug — it's one of the top attractions in this destination. If you're after more adventure, think about basing yourself here and setting off on some day trips from New Preston.
Is it worth booking a vacation package to New Preston?
Boasting a host of highlights starting with its amazing nature, New Preston is a good vacation destination. Whether you'd like to explore attractions such as Lake Waramaug and Mount Bushnell State Park or venture off the beaten track, you'll have plenty to keep you busy during your New Preston vacation.
How to find the best New Preston package deals?
Use Expedia's filters to find some terrific New Preston package deals. When you begin your search, just set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your trip for midweek, or search for New Preston package deals in the low season. Play around with your travel dates and you may land even bigger discounts. As a rule of thumb, it's typically best to book your vacation package as soon as possible.
Is it cheaper to book a New Preston vacation as a package?
You can enjoy significant savings on your New Preston break by booking a tailored vacation package. Click on the "Package" heading, then enter your destination and travel dates to view the best flight and hotel prices. Bundling can save travelers hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a vacation package to New Preston?
Enjoy amazing discounts by booking your flights in advance with Expedia. If spontaneity is more your thing, snap up one of our last-minute deals for an impromptu New Preston adventure.
Does Expedia offer Book Now, Pay Later New Preston vacation packages?
Your New Preston trip should be a relaxing escape from your busy life, not a reason for money-related stress. So to give you that extra flexibility, we've partnered with online lender Affirm to offer you our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and spread the total cost over 3, 6 or 12 months. Plus, there are no hidden or late payment fees to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.