New Preston Vacation Rentals

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
May 22 - May 24
In two months
Jul 3 - Jul 5
In three months
Jul 31 - Aug 2
In four months
Aug 28 - Aug 30

Our top choices for New Preston vacation rentals

Cottage (3 Bedrooms) | Interior

Dainty New Preston Cottage w/ Dock & Lake Views!

Dainty New Preston Cottage w/ Dock & Lake Views!
3.0 star property
New Preston
$529 nightly
The price is $609
May 6 - May 7
Total with taxes and fees
Dainty New Preston Cottage w/ Dock & Lake Views!
Property grounds

Rare, peaceful glamping, hot shower, mini golf near appalachian trail

Rare, peaceful glamping, hot shower, mini golf near appalachian trail
Dover Plains
10.0 out of 10, Exceptional, (7 reviews)
"We thoroughly enjoyed our stay at this property, clean and spacious tents, impressive shower facility, and all the fun amenities you never thought you needed like an 18 hole putt putt course!"
United States
JoAnna S.
$118 nightly
The price is $134
May 11 - May 12
Total with taxes and fees
Rare, peaceful glamping, hot shower, mini golf near appalachian trail
Outdoor dining

Glamping, family fun, pet friendly

Glamping, family fun, pet friendly
Dover Plains
10.0 out of 10, Exceptional, (4 reviews)
"Great Glamping spot. The hosts were very responsive and the place provided many activities. "
United States
Gui
$118 nightly
The price is $134
May 11 - May 12
Total with taxes and fees
Glamping, family fun, pet friendly
Fridge, microwave, oven, stovetop

Private Apartment in Southbury 103

Private Apartment in Southbury 103
Southbury
10.0 out of 10, Exceptional, (3 reviews)
"Property management team was very quick to respond to any question or issue I had. Excellent location around eateries and activities "
United States
Dominick S.
$195 nightly
The price is $221
May 6 - May 7
Total with taxes and fees
Private Apartment in Southbury 103
Interior

Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.

Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.
Watertown
8.6 out of 10, Excellent, (10 reviews)
"Great night stay! Wonderful place would definitely recommend! "
United States
Laurie P.
$109 nightly
The price is $122
May 6 - May 7
Total with taxes and fees
Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.
Exterior

Cozy Attic 10 min to Llitchfield

Cozy Attic 10 min to Llitchfield
Torrington
9.2 out of 10, Wonderful, (5 reviews)
"A couple of the surfaces were not clean but mostly a clean comfy space. The bed was very comfortable and the bathroom was spacious and clean.The stairs are not for the faint of heart. A nice cozy place to stay once the luggage and groceries are up there."
United States
Rhonda H.
$227 nightly
The price is $270
May 6 - May 7
Total with taxes and fees
Cozy Attic 10 min to Llitchfield
Interior

Private Apartment in Southbury 101

Private Apartment in Southbury 101
Southbury
9.6 out of 10, Exceptional, (7 reviews)
"The apartment was nice, big area, loved this rental."
United States
Marissa G.
$206 nightly
The price is $234
May 6 - May 7
Total with taxes and fees
Private Apartment in Southbury 101
Exterior

Cozy One Bedroom Apartment Centrally Located in Southbury

Cozy One Bedroom Apartment Centrally Located in Southbury
Southbury
10.0 out of 10, Exceptional, (26 reviews)
"Excellent host."
United States
David
$110 nightly
The price is $124
May 10 - May 11
Total with taxes and fees
Cozy One Bedroom Apartment Centrally Located in Southbury
Exterior

Best Outdoors near the Berkshires

Best Outdoors near the Berkshires
Winchester
9.8 out of 10, Exceptional, (16 reviews)
"Great stay and wonderful house. "
United States
Rachel B.
$128 nightly
The price is $144
May 6 - May 7
Total with taxes and fees
Best Outdoors near the Berkshires
Smart TV, fireplace

Pristine Cozy Walkable Downtown 2BR Getaway

Pristine Cozy Walkable Downtown 2BR Getaway
Torrington
10.0 out of 10, Exceptional, (18 reviews)
"What a comfortable and welcoming place to stay! Great communication with the hosts, and the space had all the amenities we needed, as well as many thoughtful extra touches. Home was spotless, and tastefully decorated. Quiet neighborhood, and super easy access to downtown. Would absolutely stay here again!"
United States
Kathryn A.
$239 nightly
The price is $271
May 11 - May 12
Total with taxes and fees
Pristine Cozy Walkable Downtown 2BR Getaway
Property grounds

Hoppy Hill Farm House

Hoppy Hill Farm House
Dover Plains
9.8 out of 10, Exceptional, (6 reviews)
"Location was great. Accommodations were clean and comfortable. Host was accessible and responsive. Will stay here again if in the area again."
United States
Ken K.
$181 nightly
The price is $205
May 10 - May 11
Total with taxes and fees
Hoppy Hill Farm House
Fridge, microwave, oven, stovetop

Art House 3 Beds Close to Warner Theater

Art House 3 Beds Close to Warner Theater
Torrington
10.0 out of 10, Exceptional, (1 review)
"Place was perfectly located for where we needed to be. The host was amazing, would stay again. Unit was comfy and cozy with perfect little homey touches. "
United States
Brittany M.
$343 nightly
The price is $401
May 6 - May 7
Total with taxes and fees
Art House 3 Beds Close to Warner Theater
Interior

Cozy 1-king size bedroom house in quiet Waterbury with 75" TV in your bedroom.

Cozy 1-king size bedroom house in quiet Waterbury with 75" TV in your bedroom.
Waterbury
8.0 out of 10, Very Good, (1 review)
"I had an emergency and was only able to stay one night, but enjoyed my stay "
United States
Dirk N.
$119 nightly
The price is $134
May 6 - May 7
Total with taxes and fees
Cozy 1-king size bedroom house in quiet Waterbury with 75" TV in your bedroom.
Interior

Private Apartment in Southbury 102

Private Apartment in Southbury 102
Southbury
9.2 out of 10, Wonderful, (5 reviews)
"Over all a great place. Nice to have everything on one floor. Dogs loved it. Some businesses in the building and everyone is friendly!"
United States
Debbie P.
$217 nightly
The price is $246
May 11 - May 12
Total with taxes and fees
Private Apartment in Southbury 102
Outdoor dining

The Perch in the Purchase -- Cozy, unique, and private

The Perch in the Purchase -- Cozy, unique, and private
Southbury
10.0 out of 10, Exceptional, (1 review)
"Beautiful place. Very clean & welcoming "
United States
Chris
$196 nightly
The price is $223
May 11 - May 12
Total with taxes and fees
The Perch in the Purchase -- Cozy, unique, and private
Private kitchen

Litchfield Retreat, Wineries, Foliage & Skiing

Litchfield Retreat, Wineries, Foliage & Skiing
Torrington
$349 nightly
The price is $396
May 6 - May 7
Total with taxes and fees
Litchfield Retreat, Wineries, Foliage & Skiing
Smart TV, fireplace, books

Mid Century Modern Studio w/ Full Kitchen - Newly Built

Mid Century Modern Studio w/ Full Kitchen - Newly Built
Kent
10.0 out of 10, Exceptional, (11 reviews)
"We had a great stay, very cute town and close to our destination "
United States
Danielle F.
$188 nightly
The price is $213
May 6 - May 7
Total with taxes and fees
Mid Century Modern Studio w/ Full Kitchen - Newly Built
Fridge, microwave, oven, stovetop

Private Apartment in Southbury 104

Private Apartment in Southbury 104
Southbury
$211 nightly
The price is $239
May 6 - May 7
Total with taxes and fees
Private Apartment in Southbury 104
Fridge, microwave, oven, stovetop

"Country outside the city " 3 bedrooms 2 full bathrooms

"Country outside the city " 3 bedrooms 2 full bathrooms
Holmes
9.6 out of 10, Exceptional, (4 reviews)
"Great house! We had a fantastic weekend!! Thank you so much "
United States
pamela w.
$561 nightly
The price is $635
May 11 - May 12
Total with taxes and fees
"Country outside the city " 3 bedrooms 2 full bathrooms
Exterior

Cozy Modern Farmhouse Private Apt - 3 Beds

Cozy Modern Farmhouse Private Apt - 3 Beds
Torrington
10.0 out of 10, Exceptional, (4 reviews)
"My husband and I came down from Boston for Christmas to see family and couldn’t find one decent hotel in the area. We were relieved to find this place. Cute, comfortable, clean environment and just what we needed. "
United Kingdom
Louisa A.
$366 nightly
The price is $423
May 6 - May 7
Total with taxes and fees
Cozy Modern Farmhouse Private Apt - 3 Beds
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top New Preston Hotel Reviews

Comfort Inn & Suites Danbury-Bethel

Comfort Inn & Suites Danbury-Bethel

10/10 Excellent
"I always enjoy staying at the comfort Inn. Front desk staff were beet kind & friendly each time I entered and exited the property and when i needed assistance they were accommodating."
Isaac 2-night trip
Posted 1 hour ago
Comfort Inn & Suites Danbury-Bethel

Find out more about New Preston

Everything you need to know about New Preston vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the New Preston vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect New Preston vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

New Preston vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in New Preston. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit New Preston in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $124 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on New Preston rentals

At Expedia, we put the best New Preston vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top New Preston rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream New Preston vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around New Preston. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

Frequently asked questions

Are there vacation rentals in New Preston?

Yes, we give you a choice of vacation rentals close to popular sights in New Preston, or you can go with a more secluded option if you're looking for relaxation. New Preston is known for its wineries and parks. Make sure you have time to check out the beaches while you're in the area.

What's the top vacation rental in New Preston?

Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed: This vacation home rental outside of New Preston offers a fireplace, a patio, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

How many vacation rentals are there in New Preston?

With 12 Expedia vacation rentals, you're sure to find just the right place for your New Preston stay.

What can I see and do in New Preston?

Lake Waramaug and Lake Waramaug State Park are a couple of lovely local spots to get outside and enjoy nature. Hopkins Vineyard and Mount Bushnell State Park are other places to visit while you're in town.

What are vacation rentals like in New Preston?

Vacation rentals are private accommodations you can book for several days or longer in New Preston. Vacation rentals provide amenities such as kitchens and laundry facilities so your stay will be comfortable. If you're concerned about a clean environment, vacation rentals can provide a sense of safety away from shared hotel elevators and busy concierge desks while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a standard hotel, which makes a vacation rental a great option for family gatherings.