Guestling Vacations from $581

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Your Guestling Vacation

When a fun city getaway is calling, answer it with a vacation package to Guestling. The neighborhood of Winchelsea, which is great for nature, views and walking, makes an awesome base for your adventures. Like to explore? Blue Reef Aquarium, Hastings Castle and Hastings Pier are just three of the leading places to visit during your trip to Guestling. Browse Expedia's extensive range of travel options and book your perfect vacation to Guestling today.

The Latest Guestling vacation packages

Price found within the past 48 hours. Click for updated prices.
Trivelles Gatwick

Trivelles Gatwick

4 out of 5
Price was $607, price is now $581 per person
$581
per person
Feb 16 - Feb 19
found 1 day ago
Roundtrip flight included
New York (NYC) to London (LGW)
6.8/10 (650 reviews)
Firstly it was slightly confusing to have two hotels with the same name in the same locality. Eventually I found the correct one, room was nice but no bottled water except in the vending machine at airport prices. Fire doors squeaked loudly during the night, bedside shelf was drooping so I couldn’t rest anything on it safely and getting the shower to an acceptable temperature was very time consuming. Although this sounds very negative the room was nice and good value for money, so not overly disappointed but with a little more care it would have improved a lot!

Reviewed on Dec 21, 2025

Hurst Farm

Hurst Farm

3 out of 5
Price was $1,130, price is now $953 per person
$953
per person
Feb 13 - Feb 18
found 1 day ago
Roundtrip flight included
New York (NYC) to London (LGW)
9.6/10 Exceptional! (55 reviews)
Stayed one night Facilities good Cleanliness very good

Reviewed on Aug 16, 2025

Gothic House

Gothic House

3.5 out of 5
Price was $849, price is now $783 per person
$783
per person
Feb 13 - Feb 18
found 1 day ago
Roundtrip flight included
New York (NYC) to London (LGW)
8.6/10 Excellent! (92 reviews)
Well located to shops, restaurants, bus, and walking distance to the train station, but room was pretty basic. Many eateries in the area which serve when the in house catering is closed (open 10:00-3:00). Building is old, so not surprised by some minor plumbing issues. Staff friendly and helpful.

Reviewed on Dec 23, 2025

Little Foxes Hotel & Gatwick Airport Parking

Little Foxes Hotel & Gatwick Airport Parking

3 out of 5
Price was $719, price is now $680 per person
$680
per person
Feb 13 - Feb 18
found 1 day ago
Roundtrip flight included
New York (NYC) to London (LGW)
7.2/10 Good! (462 reviews)
Ok but bit noisy from person upstairs.

Reviewed on Dec 27, 2025

Holiday Inn Rochester Chatham by IHG

Holiday Inn Rochester Chatham by IHG

4 out of 5
Price was $685, price is now $653 per person
$653
per person
Feb 16 - Feb 19
found 1 day ago
Roundtrip flight included
New York (NYC) to London (LGW)
8.2/10 Very Good! (1,000 reviews)
Clean, spacious room Super friendly staff Great shower

Reviewed on Jan 8, 2026

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Discover the most popular places to visit in Guestling

Hastings Castle featuring heritage elements and a ruin

Hastings Castle

5/5(1 review)

Stir your imagination at the ruins of this once mighty clifftop fortress, built by William the Conqueror in the 11th century.

Hastings Castle
April 2014 A seemingly abandoned wheelchair sitting on Hastings beach in front of the burnt out remains of the town's pier. #BeachBound

Hastings Pier

After visiting Hastings Pier, make a plan to see the other sights and activities in Hastings. Wander the seaside and beautiful beaches in the area.

Hastings Pier
Hastings Country Park which includes a small town or village, general coastal views and a park

Hastings Country Park

Popular with dog walkers and exercisers, this expansive park provides a peaceful escape and coastal panoramas.

Hastings Country Park

What to do in Guestling

Sussex Heritage Coast - Online Self Guided Road Trip Plan

Sussex Heritage Coast - Online Self Guided Road Trip Plan

$18
per traveler
Sussex Heritage Coast - Online Self Guided Road Trip Plan
Battle Abbey Gatehouse

1066 Battle of Hastings Guided Tour

$202
per adult
1066 Battle of Hastings Guided Tour
See all activities in Guestling

Guestling Hotel Deals

Guestling Hall Hotel

Guestling Hall Hotel

3.5 out of 5
Guestling Hall Hastings England
Fully refundableReserve now, pay when you stay
$79 nightly
The price is $95 total per night from Jan 15 to Jan 16
$95 total
Jan 15 - Jan 16
Total with taxes and fees
9/10 Wonderful! (496 reviews)
Beautiful hotel, secluded, run by lovely staff, and a relaxed feeling overall. The room was wonderful and many little touches.

Reviewed on Jan 3, 2026

Guestling Hall Hotel
The View Hotel

The View Hotel

3 out of 5
Grand Parade Eastbourne England
Fully refundableReserve now, pay when you stay
$82 nightly
The price is $98 total per night from Jan 25 to Jan 26
$98 total
Jan 25 - Jan 26
Total with taxes and fees
9.2/10 Wonderful! (1,012 reviews)
Breakfast was very well organised and the food was to a very good standard - the plate warmer actually works in this hotel - well done for this.

Reviewed on Jan 5, 2026

The View Hotel
The Burlington Hotel

The Burlington Hotel

3 out of 5
Grand Parade Eastbourne England
Fully refundableReserve now, pay when you stay
$44 nightly
The price is $53 total per night from Jan 23 to Jan 24
$53 total
Jan 23 - Jan 24
Total with taxes and fees
7.6/10 Good! (1,470 reviews)
The staff are friendly and very helpful. The hotel has a relaxed feeling. It offers free entertainment. The food is excellent value.

Reviewed on Jan 6, 2026

The Burlington Hotel
See all 1,917 properties in Guestling
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 Guestling Vacation Packages

Guestling Essential Information

Language
English
Currency
British pounds sterling
Max Temp Winter
45ºF
Max Temp Summer
65ºF
Top Sights
Carr Taylor Vineyard, Hastings Museum and Art Gallery and Blue Reef Aquarium

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Frequently asked questions

How much does a Guestling vacation package cost?
You can grab a vacation package to this destination from $581 on Expedia. However, how much your vacation to Guestling costs will depend on factors like your hotel choice, season and length of stay.
What are the cheapest months to go to Guestling?
If you'd like to score a cheap Guestling vacation package, consider planning a trip in February, September and December. You're likely to find better rates on airfares and hotels during these months — perfect for travelers wishing to save money.
How many days is enough for Guestling?
The ideal length of your Guestling vacation depends on what you'd like to do. Typically, a handful of days to a week will give you enough time to visit all the major sights and discover some hidden spots along the way.
How to find the best Guestling package deals?
Use Expedia's filter tool to find some unbeatable Guestling package deals. When you start your search, just set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your break for midweek, or look for Guestling package deals in the off-peak season. Switch up your travel dates and you may score even bigger discounts. As a rule of thumb, it's typically best to lock in your vacation package well in advance.
Is it cheaper to book a Guestling vacation as a package?
Expedia vacation packages are designed to make your money go further. Bundle your car rental, flight and hotel into one great-value price and you could save hundreds of dollars. You'll typically snag a better deal than booking each component separately. And you'll still get the flexibility to create a personalized Guestling vacation by choosing your favorite airline, accommodation type and car class.
When to book a vacation package to Guestling?
If you're planning an impromptu Guestling getaway, check out our last-minute deals that can be booked up to a week before you take off. Prefer not to wait until the last minute? You can land amazing deals on your hotels and flights by booking well in advance.
Does Expedia offer Book Now, Pay Later Guestling vacation packages?
Set off on your perfect trip to Guestling with Expedia's Book Now, Pay Later vacations. There's no need to scrimp and save or hold off until your next paycheck — we've teamed up with online lender Affirm to give you financial flexibility. Our vacation packages with payment plans let you spread the total cost over 3, 6 or 12 months. With no late payment fees or extra charges, it's easy to budget for your trip and snap up cheap deals before they disappear.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.