Preston Hollow Vacations from $492

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The Latest Preston Hollow vacation packages

Price found within the past 48 hours. Click for updated prices.
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

4.5 out of 5
Save 100% on your flight
Price was $829, price is now $492 per person
$492
per person
Jan 16 - Jan 19
found 1 day ago
Roundtrip flight included
Tampa (TPA) to Albany (ALB)
18.4/10 Exceptional! (110 reviews)
It’s nice to come to this lovely setting and to be greeted by such a welcoming, smiling host! You cannot beat the ambiance, and the breakfast was marvelous. The entire cast and crew presented their masterpiece!!!

Reviewed on Oct 27, 2025

Wilder House Berkshires

Wilder House Berkshires

2 out of 5
Save 100% on your flight
Price was $734, price is now $530 per person
$530
per person
Jan 16 - Jan 19
found 1 day ago
Roundtrip flight included
Tampa (TPA) to Albany (ALB)
19.6/10 Exceptional! (38 reviews)
Wilder House is warm and charming. I’ve stayed many times and it always feels like home. I had a lovely breakfast and a great stay. Thank you!

Reviewed on Nov 10, 2025

Pocketbook Hotel and Bath

Pocketbook Hotel and Bath

2 out of 5
Price was $693, price is now $520 per person
$520
per person
Dec 26 - Dec 28
found 18 hours ago
Roundtrip flight included
New York (NYC) to Albany (ALB)
17.6/10 Exceptional! (3 reviews)
The room was nice and clean, but the hotel itself was still under construction and it took 45 minutes for us to get in our room for check-in I was able to ask for extended check out and we got two complementary drinks from the bar but overall they should have waited to open

Reviewed on Nov 12, 2025

Pondfront Gem Minutes From Hudsons Best Shops & Cafes The Stillwater House

Pondfront Gem Minutes From Hudsons Best Shops & Cafes The Stillwater House

3 out of 5
Save 100% on your flight
Price was $1,012, price is now $791 per person
$791
per person
Jan 16 - Jan 19
found 1 day ago
Roundtrip flight included
Tampa (TPA) to Albany (ALB)
12/10 Exceptional! (1 review)
The location of the house was very near for food and supplies,yet very private. The inside was very clean and well kept. We enjoyed the quietness and surrounding grounds with views of local wild life. The things that we did not like was the musty - moldy smell when we first got there. Every time you used the water it smelled. Red light on fridge for changing filter. Bought spring water to use for drinking, coffee, and cooking. All reported to host upon departure.

Reviewed on Aug 23, 2025

The Haüs Windham

The Haüs Windham

2 out of 5
Price was $1,214, price is now $996 per person
$996
per person
Dec 26 - Dec 28
found 18 hours ago
Roundtrip flight included
New York (NYC) to Hudson (HCC)
17.2/10 Exceptional! (17 reviews)
Hot tub could have been cleaner but all in all. Beautiful and amazing views! Great service with the front desk calls and extra towels provided no problem!

Reviewed on Sep 15, 2025

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Preston Hollow Hotel Deals

Hunter Lodge, a Bluebird by Lark

Hunter Lodge, a Bluebird by Lark

3 out of 5
7433 Main St Hunter NY
Fully refundableReserve now, pay when you stay
$138 nightly
The price is $149 total per night from Nov 30 to Dec 1
$149 total
Nov 30 - Dec 1
Total with taxes and fees
9.2/10 Wonderful! (810 reviews)
Easy and quick transaction

Reviewed on Nov 13, 2025

Hunter Lodge, a Bluebird by Lark
Hotel Vienna

Hotel Vienna

2.5 out of 5
107 State Route 296 Windham NY
$112 nightly
The price is $121 total per night from Nov 25 to Nov 26
$121 total
Nov 25 - Nov 26
Total with taxes and fees
9.2/10 Wonderful! (705 reviews)
We enjoyed our stay which included our continental breakfasts, great coffee (machine offered several variations), pool, sauna fresh air and a quiet room. The room did lack clothes dressers or a place to put our clothes.

Reviewed on Nov 21, 2025

Hotel Vienna
Kaatskill Mountain Club at Hunter Mountain

Kaatskill Mountain Club at Hunter Mountain

2 out of 5
61 LIFTSIDE DR Hunter NY
Fully refundableReserve now, pay when you stay
$218 nightly
The price is $235 total per night from Dec 2 to Dec 3
$235 total
Dec 2 - Dec 3
Total with taxes and fees
9.2/10 Wonderful! (314 reviews)
228

Reviewed on Nov 11, 2025

Kaatskill Mountain Club at Hunter Mountain
See all 1,327 properties in Preston Hollow
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.

Find the Best Preston Hollow Vacation Packages

Preston Hollow Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Albany Intl. Airport (ALB)

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Frequently asked questions

How much does a Preston Hollow vacation package cost?
You'll find cheap prices from $492 on Expedia for your Preston Hollow getaway. However, a range of factors like your choice of hotel, the season and length of stay will influence how much your vacation to Preston Hollow costs.
What are the cheapest months to go to Preston Hollow?
If you're looking to snag a cheap Preston Hollow vacation package, consider planning a trip in November, December and January. You'll generally find lower prices on flights and accommodations during these months — perfect for travelers wishing to save money.
How many days is enough for Preston Hollow?
The ideal length for your Preston Hollow vacation depends on what you'd like to do and see. Usually, a handful of days to a week will give you enough time to tick off all the top attractions and discover some hidden treasures along the way.
How to find the best Preston Hollow package deals?
Start your search for a Preston Hollow package deal by entering your destination and preferred travel dates under our "Packages" tab. Then add a few filters, like "Property type" and "Amenities," to fine-tune the results to your exact needs. You can also sort by "Package discount" and browse offers that come with irresistible savings. If you don't find the ideal Preston Hollow package deal right away, just tweak your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Preston Hollow escape underway.
Is it cheaper to book a Preston Hollow vacation as a package?
Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your hotel, car rental and flight into one great-value price and you could save hundreds of dollars. You'll typically land a better deal than booking each component individually. And you'll still have the flexibility to create a personalized Preston Hollow vacation by choosing your preferred accommodation type, airline and car class.
When to book a vacation package to Preston Hollow?
Enjoy incredible bargains by reserving your flights in advance with Expedia. If spontaneity is more your thing, take advantage of our last-minute deals for an impromptu Preston Hollow adventure.
Does Expedia offer Book Now, Pay Later Preston Hollow vacation packages?
Your Preston Hollow getaway should be an escape from your busy life, not a source of money worries. So to give you that extra flexibility, we've teamed up with online lender Affirm to bring you our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and spread the total cost over 3, 6 or 12 months. Plus, there aren't any hidden costs 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.