New Preston Vacation Rentals

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Check prices for these dates

In two weeks
Jul 10 - Jul 12
In two months
Aug 21 - Aug 23
In three months
Sep 18 - Sep 20
In four months
Oct 16 - Oct 18

Our top choices for New Preston vacation rentals

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.
The price is ￥17,771
￥33,262 total
includes taxes & fees
Jul 13 - Jul 14
Hoppy Hill Farm House
Terrace/patio

Enjoy a restful stay with fast internet, smart TV and the company of your pet.

Enjoy a restful stay with fast internet, smart TV and the company of your pet.
winsted
9.2 out of 10, Wonderful, (47 reviews)
"Fantastic hosts and great facilities would highly recommend"
United States
Steve
The price is ￥25,479
￥40,464 total
includes taxes & fees
Jul 2 - Jul 3
Enjoy a restful stay with fast internet, smart TV and the company of your pet.
Fridge, microwave, oven, stovetop

Private Apartment in Southbury 104

Private Apartment in Southbury 104
Southbury
The price is ￥19,251
￥42,158 total
includes taxes & fees
Jun 30 - Jul 1
Private Apartment in Southbury 104
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.
The price is ￥16,986
￥47,717 total
includes taxes & fees
Jul 21 - Jul 22
Cozy Attic 10 min to Llitchfield
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.
The price is ￥16,015
￥21,653 total
includes taxes & fees
Jul 1 - Jul 2
Private, Quiet, Cozy Studio Guesthouse with 75" TV WiFi etc. In Watertown.
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, (8 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.
The price is ￥12,958
￥21,614 total
includes taxes & fees
Jun 29 - Jun 30
Rare, peaceful glamping, hot shower, mini golf near appalachian trail
Smart TV, fireplace, books

Mid Century Modern Studio w/ Full Kitchen - Newly Built

Mid Century Modern Studio w/ Full Kitchen - Newly Built
Kent
9.8 out of 10, Exceptional, (16 reviews)
"We had a great stay, very cute town and close to our destination "
United States
Danielle F.
The price is ￥26,813
￥34,555 total
includes taxes & fees
Jun 28 - Jun 29
Mid Century Modern Studio w/ Full Kitchen - Newly Built
Dining

Art House 3 Beds Close to Warner Theater

Art House 3 Beds Close to Warner Theater
Torrington
10.0 out of 10, Exceptional, (2 reviews)
"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.
The price is ￥29,094
￥76,462 total
includes taxes & fees
Jul 14 - Jul 15
Art House 3 Beds Close to Warner Theater
Fridge, microwave, oven, stovetop

The Jefferson Guest House, Spacious, Special Views

The Jefferson Guest House, Spacious, Special Views
Litchfield
10.0 out of 10, Exceptional, (8 reviews)
"I stayed here for four nights, including one with my son, and it was fantastic.Everything is brand new, clean, and beautifully appointed, with every amenity you could want."
United States
Jennifer A.
The price is ￥47,108
￥61,001 total
includes taxes & fees
Jul 3 - Jul 4
The Jefferson Guest House, Spacious, Special Views
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.
The price is ￥17,795
￥23,700 total
includes taxes & fees
Jul 3 - Jul 4
Cozy 1-king size bedroom house in quiet Waterbury with 75" TV in your bedroom.
Private kitchen

Litchfield Retreat, Wineries, Foliage & Skiing

Litchfield Retreat, Wineries, Foliage & Skiing
Torrington
The price is ￥42,222
￥64,328 total
includes taxes & fees
Jul 7 - Jul 8
Litchfield Retreat, Wineries, Foliage & Skiing
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.
The price is ￥26,158
￥71,929 total
includes taxes & fees
Jul 14 - Jul 15
Cozy Modern Farmhouse Private Apt - 3 Beds
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, (3 reviews)
"Beautiful place. Very clean & welcoming "
United States
Chris
The price is ￥23,586
￥37,194 total
includes taxes & fees
Jun 30 - Jul 1
The Perch in the Purchase -- Cozy, unique, and private
Exterior

Charming 2-bedroom apartment on 2nd floor in Millbrook NY, right in the village

Charming 2-bedroom apartment on 2nd floor in Millbrook NY, right in the village
Millbrook
9.6 out of 10, Exceptional, (4 reviews)
"We had a wonderful time at this property. It was quaint and clean and right in the middle of town near everything. Thank you, Tanya."
United States
Laurie F.
The price is ￥51,766
￥79,422 total
includes taxes & fees
Jun 26 - Jun 27
Charming 2-bedroom apartment on 2nd floor in Millbrook NY, right in the village
Interior

The Tipsy Gypsy - Studio Apartment

The Tipsy Gypsy - Studio Apartment
Brewster
The price is ￥24,266
￥44,531 total
includes taxes & fees
Jun 28 - Jun 29
The Tipsy Gypsy - Studio Apartment
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)
The price is ￥38,873
￥101,256 total
includes taxes & fees
Jul 7 - Jul 8
"Country outside the city " 3 bedrooms 2 full bathrooms
Interior

Steps to the Delightful Village of Millbrook ☆ Fun Family Getaway

Steps to the Delightful Village of Millbrook ☆ Fun Family Getaway
Millbrook
10.0 out of 10, Exceptional, (6 reviews)
"This is a charming, historic, well-maintained home on a beautifully landscaped lot. The updates in the home balance a respect for tradition while also providing modernization. The village of Millbrook is a quintessential twee New England village. The house felt very comfortable and homey and the caretaker was attentive and accommodating. We enjoyed our stay!"
United States
Beth E.
The price is ￥64,708
￥135,973 total
includes taxes & fees
Jun 30 - Jul 1
Steps to the Delightful Village of Millbrook ☆ Fun Family Getaway
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.
The price is ￥16,177
￥37,976 total
includes taxes & fees
Jun 30 - Jul 1
Private Apartment in Southbury 103
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.
The price is ￥25,721
￥49,922 total
includes taxes & fees
Jul 21 - Jul 22
Private Apartment in Southbury 101
Cookware/dishes/utensils

Awesome Lake Home with tons of fun!

Awesome Lake Home with tons of fun!
New Fairfield
9.8 out of 10, Exceptional, (9 reviews)
"Great spot "
United States
Mike P.
The price is ￥65,517
￥114,736 total
includes taxes & fees
Jun 29 - Jun 30
Awesome Lake Home with tons of fun!
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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Top New Preston Hotel Reviews

Wyndham Southbury

Wyndham Southbury

8/10 Good
"Hotel staff very attentive, friendly and helpful. Toom service was excellent, but expensive- just order to go from the restaurant to save money. The outside of the property, pool area and furniture needs work and be updated. Just to clarify what needs to happen with the outside areas- the front of the building had the only outdoor seating available with benches or seating you didn’t have to bring out yourself. It was the smoking section, so there were smokers out and some left cigarettes ashes and butts outside of the recepticales, there were miscellaneous stains on the ground which could have easily been cleared with power washing. The pool area had seating inside, but the tables and chairs were outdated and rusty. There were tables outside behind the pool area but you have to bring the chairs out for yourself. The tables back there were very dated and rusty."
Valerie 14-night trip
Posted 3 hours ago
Wyndham Southbury

Find out more about New Preston

Search for holiday rentals in New Preston on Expedia! You can easily find your home rentals, villas, holiday apartments in New Preston using one of the methods below:

  • View our selection of featured holiday rentals in New Preston
  • Use the map to find apartments and other holiday homes in the New Preston neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in New Preston while they last

Look no further and take a look at our great range of rental properties in New Preston!

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 13 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 Tom 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.