Town of Olive Holidays

Book a Hotel + Flight or Car together to unlock savings

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    Save up to £750 when you book a flight and hotel together*

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    Packages with flights are ATOL protected

Your Town of Olive Holiday

Leave all the planning up to us with a Town of Olive holiday package. With everything arranged before you leave, the only thing you'll need to do is relax and experience this destination's culture and beauty. With so much to see and do on a trip to Town of Olive, it can be difficult to know where to begin. Kick off your travels in West Shokan at Catskill Mountains and Giant Ledge Trailhead — two popular attractions here. Another great city to add to your itinerary is Olivebridge. Be sure not to miss Woodstock Public Library and Woodstock Golf Club. Expedia has hotels, flights and whatever else you need to help you create your very own tailored Town of Olive holiday today.

Top Town of Olive Flight + Hotel Deals

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

Omni Berkshire Place

4 out of 5
Manhattan
Price was £2,440, price is now £1,322 per person
£1,322
per person
5 Jul - 8 Jul
found 24 hours ago
Return flight included
London (LON) to Newark Liberty Intl. Airport (EWR)
9.2/10 Wonderful! (2,170 reviews)
A very busy location . None friendly staff

Reviewed on 20 May 2026

Casa Francesca 6BR Villa & Heated Pool

Casa Francesca 6BR Villa & Heated Pool

3.5 out of 5
Save 100% on your flight
Price was £6,799, price is now £4,056 per person
£4,056
per person
5 Aug - 12 Aug
found 1 day ago
Return direct flight included
London (LGW) to Newark Liberty Intl. Airport (EWR)
No reviews
1 Hotel Central Park

1 Hotel Central Park

5 out of 5
Manhattan
Save 100% on your flight
Price was £4,958, price is now £3,094 per person
£3,094
per person
23 Jul - 2 Aug
found 1 day ago
Return flight included
London (LON) to New York (JFK)
9/10 Wonderful! (1,007 reviews)
Nice property great location

Reviewed on 21 May 2026

Loews Regency New York Hotel

Loews Regency New York Hotel

5 out of 5
Manhattan
Save 100% on your flight
Price was £3,386, price is now £2,250 per person
£2,250
per person
23 Jul - 2 Aug
found 1 day ago
Return flight included
London (LON) to New York (JFK)
9/10 Wonderful! (1,000 reviews)
This is the only hotel I stay in when I come to NYC. Everyone there is amazing!

Reviewed on 15 May 2026

Radio Hotel

Radio Hotel

4 out of 5
Manhattan
Price was £2,359, price is now £1,605 per person
£1,605
per person
31 Jul - 12 Aug
found 1 day ago
Return flight included
London (LON) to Newark Liberty Intl. Airport (EWR)
8.6/10 Excellent! (2,520 reviews)
Very clean and staff was nice.

Reviewed on 20 May 2026

Town of Olive Essential Information

Language
English
Currency
U.S dollars
Closest Airport
John F. Kennedy Intl. Airport (JFK)

Top hotels in Town of Olive

Relaxing Catskill Mountain Cottage.

Relaxing Catskill Mountain Cottage.

West Shokan NY
10/10 Exceptional! (65 reviews)
"What a great house and stay we had recently. Everything was as shown in photos. Kitchen had all we needed to prepare meals. Lots of coffee maker options. Wood burning stove heated up house so much we needed to open a couple of windows. 15-20 drive to Woodstock. Would rent again."

Reviewed on 5 May 2026

Get rates
Relaxing Catskill Mountain Cottage.
Best Western Plus Kingston Hotel And Conference Center

Best Western Plus Kingston Hotel And Conference Center

2.5 out of 5
503 Washington Ave Kingston NY
Fully refundableReserve now, pay when you stay
The price is £99 per night from 18 Jun to 19 Jun
£99
18 Jun - 19 Jun
includes taxes & fees
7.4/10 Good! (1,002 reviews)
"Kevin at the front desk was extremely helpful when we had a problem with the room. He moved us into another room, which was much better for us in order to sleep."

Reviewed on 22 May 2026

Best Western Plus Kingston Hotel And Conference Center
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
The price is £118 per night from 4 Jun to 5 Jun
£118
4 Jun - 5 Jun
includes taxes & fees
9.2/10 Wonderful! (945 reviews)
"Clean room, beautiful property, outstanding staff….no elevator and no handicap access to rooms on ground level. Otherwise I would have stayed longer."

Reviewed on 19 May 2026

Hunter Lodge, a Bluebird by Lark
See all 2,207 properties in Town of Olive
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.
All Inclusive Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Frequently asked questions

How much does a Town of Olive travel package cost?
Starting from only £1,322, a travel package is your gateway to cheaper travel. Customize your Town of Olive trip by picking from our wide range of airfares, hotels and rental cars.
If I'm not able to travel, can I cancel my Town of Olive travel package?
Whether it's your hotel, flight or rental car, yes, you can cancel or amend it. Locked in your Town of Olive travel package in the last 24 hours? You may be able to make any changes for free. For older bookings, you may be charged a fee by your hotel, airline or car rental company. For more information, look up our Customer Service Portal. We're here to help you each step of the way.
How do I get a cheap travel package to Town of Olive?
It's easy. Just bundle everything together. Hotels, rental cars and flights — combine whatever you need into a Town of Olive travel package to save a pile of cash. Score even better deals when you add extras such as sightseeing tours to your booking. But that's not the only impressive part. You have the flexibility to customize your trip your own way. We offer more than 550 airlines and 1,000,000 hotel options worldwide, so that everyone has an opportunity to travel and live out those holiday dreams.
Does Expedia offer Book Now, Pay Later Town of Olive holidays?
Your bank balance shouldn't prevent you from escaping on holiday, so Expedia has come up with a solution to help. Now that we've teamed up with online lender Klarna, it's easier than ever to book a fabulous getaway without draining your savings. Klarna offers flexible payment options at checkout that take the worry out of budgeting for your break. Consider one of these flexible payment options:

  • Pay monthly holidays: Klarna offers convenient monthly payment plans that suit all budgets, so you can lock in that well-earned holiday sooner.
  • Pay in instalments holidays: Like the idea of paying off your holiday in multiple transactions? Then go for this Book Now, Pay Later option from Klarna.
  • Low deposit holidays: If paying a small percentage of your getaway (rather than the full total upfront) makes it easier to click that "book now" button, choose a low deposit holiday payment plan with Klarna.

What are the top hotels in Town of Olive?
Best Western Plus Kingston Hotel And Conference Centre and Howard Johnson by Wyndham Saugerties are a couple of the most popular properties in Town of Olive. Why not check out the facilities and amenities at each and then make a decision?
How far in advance should I book my Town of Olive holiday?
It can be hard to know exactly when is the ideal time to book your Town of Olive holiday. But usually the earlier you book, the more affordable the prices. Sometimes, you can book your flights and hotels up to 12 months before your departure date. If you're eager to escape on a last-minute getaway, no need to fret! There are terrific deals popping up on Expedia every day.
What does an Expedia Town of Olive travel package include?
With Expedia, you can choose any combination of hotels, car rentals and flights to build your perfect Town of Olive package. Once you've made your booking, you can add on the fun stuff like tours and activities. Don't forget, the more you bundle, the more you'll save!
What should I know before booking a Town of Olive travel package?
You can save a tidy sum by bundling your flights, hotels and rental cars. Once you've created your package, add on fun stuff like tours and activities. Your next unforgettable adventure is only a couple of clicks away.
Can I choose my airline with a Town of Olive Expedia travel package?
You can, and with over 550 airlines to select from all over the world, you're not short on choice. Look through the available options and find out which airline suits your budget and needs.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.