Roxbury Holidays

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    Better together
    Save up to S$134 when you book a flight and hotel together*
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    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Plan, book, and manage your trip all in one place

Top hotels in Roxbury

Middlebury Inn
Middlebury Inn
3 out of 5
14 Court Square, Middlebury, VT
Fully refundableReserve now, pay when you stay
The price is S$227 per night from 8 Jul to 9 Jul
S$227
8 Jul - 9 Jul
includes taxes & fees
8.8/10 Excellent! (1,001 reviews)
"Wonderful place to stay in quaint Middlebury. Historic inn and very nice, clean rooms. Love the rocking chairs on the front porch."

Reviewed on 18 Jun, 2025

Middlebury Inn
Best Western Plus Waterbury - Stowe
Best Western Plus Waterbury - Stowe
3 out of 5
45 Blush Hill Rd, Waterbury, VT
Fully refundableReserve now, pay when you stay
The price is S$179 per night from 29 Jun to 30 Jun
S$179
29 Jun - 30 Jun
includes taxes & fees
9.4/10 Exceptional! (1,001 reviews)
"Breakfast was amazing! Prepared well and numerous choices."

Reviewed on 19 Jun, 2025

Best Western Plus Waterbury - Stowe
Comfort Inn & Suites Montpelier-Berlin
Comfort Inn & Suites Montpelier-Berlin
2.5 out of 5
213 Paine Turnpike N, Berlin, Montpelier, VT
Fully refundableReserve now, pay when you stay
The price is S$231 per night from 29 Jun to 30 Jun
S$231
29 Jun - 30 Jun
includes taxes & fees
9.4/10 Exceptional! (1,002 reviews)
"Very clean, staff attentive and friendly. Complimentary fresh baked cookies. If room is near dining area, waffle maker sounds like a fire alarm. Overall good experience."

Reviewed on 18 Jun, 2025

Comfort Inn & Suites Montpelier-Berlin
See all 878 properties in Roxbury
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 Roxbury holiday package cost?
Offering excellent value package deals on Expedia, you'll be thrilled with how little a holiday to Roxbury costs! Expedia's packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Roxbury?
To pick up cheap Roxbury holiday packages, organise your getaway outside of busy periods like public holidays and major events. You'll generally find lower prices and better availability in the off-season or when it's less busy.
How many days is enough for Roxbury?
Generally, a handful of days is enough to go to the major attractions during your Roxbury holiday. However, if you'd like to have more time to kick back or go on day tours, think about extending your trip.
How to find the best Roxbury package deals?
Use Expedia's handy filters to help you find some unbeatable Roxbury package deals. When you begin your search, simply set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your break for midweek, or search for Roxbury package deals in the off-season. Switch up your travel dates and you may land even better discounts. As a rule of thumb, it's typically best to lock in your holiday package as early as possible.
Is it cheaper to book a Roxbury holiday as a package?
Expedia holiday 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 generally snag a better deal than booking each component separately. And you'll still have the flexibility to create a customised Roxbury holiday by choosing your favourite type of stay, airline and car class.
When to book a holiday package to Roxbury?
If you're considering an impromptu Roxbury getaway, 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 find incredible deals on your hotels and flights by booking ahead.
How to plan a trip to Roxbury?

  1. Choose your travel dates: What you plan to do in Roxbury and your favourite season will help you decide when to travel.
  2. Budget wisely: Besides the cost of your stay, you should factor in other expenses too. These include flights, transportation and food. Also, set aside some extra funds for unexpected expenses that could crop up during your trip to Roxbury.
  3. Set the duration of your trip: Start by listing all the attractions you'd like to get to in Roxbury. Then, estimate how long you'll need at each, as well as any travel time.
  4. Bundle your hotel and flights: Awesome destination, check. Length of stay, check. Now all that's left is to choose a Roxbury holiday package that brings all your bookings together.

* 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.