Plan your trip
Check prices for these dates, December 15 – 16, 2026
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.
The best area to stay in Cheltenham is the area immediately surrounding The Promenade, particularly for those seeking convenience and quality.
This central area is characterized by its wide, tree-lined avenue, The Promenade, which is home to many upscale shops, restaurants, and elegant Regency architecture. It's very walkable, with the Imperial Gardens at one end and the central shopping district extending from the other.
Couples will find this location ideal for a sophisticated getaway. You'll be within easy walking distance of quality dining, theaters, and boutique shopping. The tranquil Imperial Gardens offer a pleasant spot for a stroll, and the overall ambiance is refined and relaxed.
For solo travelers looking for a comfortable and easy experience, staying near The Promenade offers excellent access to local amenities and attractions.
The best time to go to Cheltenham is during the dry season, from December to May, when you'll experience pleasant temperatures and minimal rainfall.
During these months, the weather is consistently sunny with average temperatures ranging from the mid-70s to low 80s Fahrenheit (24-28 degrees Celsius), making it ideal for outdoor activities like hiking and exploring the island's natural beauty. The waters are calm and clear, great for snorkeling, diving, and sailing.
The shoulder months of November and June also offer good weather with fewer crowds and potentially lower prices on accommodations and activities.
You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if canceled within 24-48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to "My Trips", and selecting your reservation. To find flexible deals, filter your search by "Fully refundable property" for hotels in Cheltenham.
Prices for hotels in Cheltenham often vary, but you can find a great deal from $92 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. Find the best deals by being flexible with your dates, and sort search results by "Price: low to high" for the cheapest rate.