Chichester Vacations from $502
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Your Chichester Vacation
Lock in a Chichester vacation package and get ready for a thrilling adventure. With a reputation for its rich history and coastal scenery, there's plenty to keep you on the go in this fascinating city. Make your trip to Chichester even more fun and exciting by including some sightseeing. Copperhood Retreat & Spa, Mount Tremper Arts and Empire State Railway Museum are some of the popular attractions you'll want to explore. A couple of quick clicks is all it takes to put together your dream Chichester vacation on Expedia.
The Latest Chichester Vacation Packages
- AutoCamp Catskills
Jan 12 - Jan 14AutoCamp Catskills + Flight
Saugerties2 nights5.0 star property9.0/10 - Wonderful (595 reviews)Roundtrip • Miami (MIA) - Poughkeepsie (POU)MIA - LGA • Nonstop EWR - MIA • 1 stop$537$502found 5 hours agoper traveler - Woodstock Way Hotel
Jan 12 - Jan 14Woodstock Way Hotel + Flight
Woodstock2 nights4.0 star property9.6/10 - Exceptional (327 reviews)"We had an amazing time and would highly recommend this beautiful hotel to anyone who’s looking for a retreat like atmosphere and lovely amenities. We will definitely be back."Reviewed November 10, 2026Roundtrip • Miami (MIA) - Poughkeepsie (POU)MIA - LGA • Nonstop EWR - MIA • 1 stop$708$618found 5 hours agoper traveler - Inn at Pine Plains
Jan 12 - Jan 14Inn at Pine Plains + Flight
Pine Plains2 nights3.5 star property9.8/10 - Exceptional (318 reviews)"good location/ walkable to down town !"Reviewed October 1, 2026Roundtrip • Miami (MIA) - Poughkeepsie (POU)MIA - LGA • Nonstop EWR - MIA • 1 stop$651$585found 5 hours agoper traveler - the Alander
Dec 25 - Dec 29the Alander + Flight
Copake4 nights2.5 star property9.0/10 - Wonderful (292 reviews)Roundtrip • Miami (MIA) - Poughkeepsie (POU)MIA - BDL • Nonstop BDL - MIA • Nonstop$955$884found 1 day agoper traveler - The Millerton Inn
Jan 12 - Jan 14The Millerton Inn + Flight
Millerton2 nights2.0 star property8.4/10 - Very good (53 reviews)Roundtrip • Miami (MIA) - Poughkeepsie (POU)MIA - LGA • Nonstop EWR - MIA • 1 stop$544$514found 5 hours agoper traveler
Where to stay near Chichester
Woodstock
Discover Woodstock, a vibrant destination perfect for travelers seeking a weekend getaway immersed in nature, art, and culture. With stunning attractions like the Bethel Woods Museum, the historic Bard College, and the breathtaking Kaaterskill Falls, visitors can enjoy a rich blend of outdoor adventure and scenic beauty. Located about 16 miles by car from Chichester, Woodstock offers easy access to its captivating landscapes and cultural experiences, making it a smart choice for your next vacation.
Hunter
Experience the charm of Hunter, a delightful hub for adventure seekers and families looking for a nature-filled getaway. With stunning attractions like Kaaterskill Falls, the expansive Catskill State Park, and the breathtaking Catskill Mountains, Hunter offers year-round outdoor activities, particularly thriving from December to February for ski enthusiasts. Located about 14 miles by car from Chichester, this city is an ideal choice for travelers eager to immerse themselves in the beauty of the great outdoors.
Phoenicia
Make the most of your visit by staying in Phoenicia, a haven for nature enthusiasts and adventure seekers thanks to its stunning scenery and outdoor activities. Enjoy the breathtaking Catskill Mountains and explore the nearby Catskill State Park, perfect for hiking and family outings. Don’t miss the unique Emerson Place Kaleidoscope, adding a touch of creativity to your trip. Phoenicia is about a 2-mile drive from Chichester, making it an ideal choice for a memorable getaway.
Big Indian
Immerse yourself in Big Indian, where adventure seekers and nature lovers can easily access the stunning Catskill Mountains, the serene Belleayre Beach, and the expansive Catskill State Park. This charming city is a family-friendly destination that offers a blend of outdoor activities year-round, with peak visitor seasons in April to May and July. Located about 10 miles by car from Chichester, Big Indian is an ideal choice for travelers looking for a memorable getaway.
Mount Tremper
Travelers visiting the area often choose Mount Tremper, especially those seeking a weekend getaway filled with nature and adventure. Surrounded by the stunning Catskill Mountains and close to attractions like Catskill State Park and the Emerson Place Kaleidoscope, this destination offers a wealth of outdoor activities year-round, including skiing in the winter. Located about 4 miles by car from Chichester, Mount Tremper is an ideal base for your vacation, ensuring a refreshing escape into the great outdoors.
Chichester Hotel Deals
"Beautiful Inn. Every detail was so well thought out!"
"Lovely setting, room was clean and comfortable. We ate dinner and breakfast at the hotel restaurant and enjoyed both meals."
Hunter Lodge, a Bluebird by Lark
Hunter Lodge, a Bluebird by Lark"The room was clean and comfortable; however, the lighting was very dim. There was a need for more or brighter lights. The breakfast was good but could have been better. There needed to be more food choices available. The staff was pleasant and helpful."
"A very nice experience, the Howland House is a very charming guesthouse with cozy, rooms, an excellent restaurant, Oliver’s, right downstairs and a really welcoming atmosphere. Staff were helpful and friendly, really couldn’t have asked for a nicer stay. We had a standard room with a shared bathroom, but the way it was setup made it totally comfortable. Highly recommended place if you’re in the area and we’ll almost certainly return."
Frequently Asked Questions
How much does a Chichester vacation package cost?
You'll find cheap prices from $502 on Expedia for your Chichester break. However, a range of factors like the season, choice of hotel and length of stay will influence how much your vacation to Chichester costs.
What are the cheapest months to go to Chichester?
You're likely to find lower rates and better availability in November, December and January. Browse our cheap Chichester vacation packages and you could get some great off-season discounts.
How many days is enough for Chichester?
With a well-organized schedule, you can easily visit the main Chichester attractions in a few days. But if you want to venture off the beaten track or take day trips, think about booking your Chichester vacation for longer.
How to find the best Chichester package deals?
Use Expedia's handy filters to find some great Chichester package deals. When you begin your search, simply set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your adventure for midweek, or look for Chichester package deals in the off-peak season. Play around with your travel dates and you may land even bigger discounts. As a rule of thumb, it's usually best to book your vacation package as soon as possible.
Is it cheaper to book a Chichester vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your hotel, flight and car rental into one great-value price and you could save hundreds of dollars. You'll usually land a better deal than booking each component individually. And you'll still have the freedom to create a tailored Chichester vacation by choosing your favorite type of stay, airline and car class.
When to book a vacation package to Chichester?
If you're planning a spontaneous Chichester vacation, browse our last-minute deals that can be booked up to a week before you take off. Don't want to leave things to the last minute? You can land sensational deals on your flights and hotels by booking well in advance.
Does Expedia offer Book Now, Pay Later Chichester vacation packages?
Set off on your dream trip to Chichester with help from Expedia's Book Now, Pay Later vacations. No need to scrimp and save or wait until payday — we've teamed up with online lender Affirm to offer you financial flexibility. Our vacation packages with payment plans mean you can split the cost over 3, 6 or 12 months. With no hidden or late payment fees, it's easy to stay on budget and snap up bargains while they last.