Rupert Holidays

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Top hotels in Rupert

Kimpton Taconic Hotel by IHG

Kimpton Taconic Hotel by IHG

4 out of 5
3835 Main St., Manchester, VT
Fully refundable
The price is S$337 per night from 27 Jul to 28 Jul
S$337
27 Jul - 28 Jul
includes taxes & fees
9.2/10 Wonderful! (779 reviews)
"I love that the hotel is dog friendly and have bikes and scooters available for guests. The room was comfortable and clean, nicely furnished. Staff was outstanding"

Reviewed on 15 Jul, 2025

Kimpton Taconic Hotel by IHG
The Equinox Golf Resort & Spa

The Equinox Golf Resort & Spa

4.5 out of 5
3567 Main Street Route 7A, Manchester, VT
Fully refundableReserve now, pay when you stay
The price is S$292 per night from 29 Jul to 30 Jul
S$292
29 Jul - 30 Jul
includes taxes & fees
7.2/10 Good! (494 reviews)
"The property was historic and very quaint and the common areas were nice. Coffee was good. For the price paid -carpet in halls & elevator needed replaced/woodwork repainted. Air conditioner was a window unit/room outdated."

Reviewed on 14 Jul, 2025

The Equinox Golf Resort & Spa
Hampton Inn and Suites Manchester

Hampton Inn and Suites Manchester

2.5 out of 5
4519 Main St, Manchester Center, VT
Fully refundableReserve now, pay when you stay
The price is S$215 per night from 3 Aug to 4 Aug
S$215
3 Aug - 4 Aug
includes taxes & fees
9.6/10 Exceptional! (1,004 reviews)
"2nd time here and we were extremely satisfied"

Reviewed on 19 Jul, 2025

Hampton Inn and Suites Manchester
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.

Frequently asked questions

How much does a Rupert holiday package cost?
You'll find cheap prices on Expedia for your Rupert getaway. However, factors like the hotel choice, length of stay and season will determine how much your holiday to Rupert costs.
What are the cheapest months to go to Rupert?
If you're hoping to snag a cheap Rupert holiday package, consider visiting in January, February and March. You'll typically find lower rates on flights and hotels during these quieter months — perfect for travellers wishing to save money.
How many days is enough for Rupert?
With a well-organised itinerary, you can easily hit the most popular Rupert attractions in a handful of days. But if you'd like to discover hidden gems or go on day trips, think about booking your Rupert holiday for longer.
How to find the best Rupert package deals?
Start your search for a Rupert package deal by entering your preferred trip dates and destination under our "Packages" tab. Then select some filters, like "Property type" and "Guest rating," to tailor the results to your exact needs. You can also sort by "Package discount" and discover offers that come with irresistible savings. If you don't find the perfect Rupert package deal right away, simply switch up your dates and search again. Remember that deals are only available for a limited time, so book early and get your Rupert escape underway.
Is it cheaper to book a Rupert holiday as a package?
Expedia holiday packages are designed to help you keep more cash in your pocket. Bundle your hotel, car rental and flight into one great-value price and you could save hundreds of dollars. You'll generally score a better deal than booking each component separately. And you'll still enjoy the flexibility to create a customised Rupert holiday by choosing your preferred type of stay, airline and car class.
When to book a holiday package to Rupert?
If you're considering a spur-of-the-moment Rupert holiday, check out our last-minute deals that can be booked up to a week before you go. Don't want to leave things to the last minute? You can find terrific deals on your hotels and flights by booking ahead.
How to plan a trip to Rupert?

  1. Pick your travel dates: What you'd like to do in Rupert and your favourite season can help you decide when to get away.
  2. Set your budget: Consider expenses like flights, food and transportation when calculating how much to set aside for your trip to Rupert. Then, select a property that fits your budget, whether that's a wallet-friendly stay or a lavish retreat.
  3. Work out your trip length: Consider how much time you want to spend discovering Rupert. Plan your itinerary so you can get to all the attractions and experiences you're interested in at a leisurely pace.
  4. Bundle your bookings: With your travel dates in order, you can combine your flights, car rental, hotels and more into a customised Rupert holiday package.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.