Upton Holidays from £1,021

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to £750 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Packages with flights are ATOL protected

Your Upton Holiday

When you book a holiday package to Upton, you can relax and enjoy your getaway knowing that all your travel plans are under control. Uncover the many charms of this amazing city while based in a neighbourhood like Blackstone, which is great for history. A trip to Upton is a wonderful opportunity to sightsee. Be sure to stop by well-known attractions like Hopkinton State Park, The Willard House & Clock Museum and Shining Rock Golf Club. Stop dreaming and start doing. Check out the wide range of options on Expedia today and finally put your Upton holiday plans in motion!

Top Upton Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
The Cove at Yarmouth by Westgate Resorts

The Cove at Yarmouth by Westgate Resorts

3 out of 5
Price was £1,441, price is now £1,021 per person
£1,021
per person
19 Sept - 26 Sept
found 21 hours ago
Return direct flight included
London (LON) to Boston (BOS)
9.2/10 Wonderful! (268 reviews)
P Indoor pool and hot tub loved and the outdoor Shack was great

Reviewed on 8 Jun 2026

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
Price was £2,999, price is now £1,840 per person
£1,840
per person
24 Aug - 30 Aug
found 1 day ago
Return flight included
Edinburgh (EDI) to Boston (BOS)
9.8/10 Exceptional! (1,002 reviews)
We were there for 5 days. It was impeccable. The location, service, ambiance everything was perfect! All small attentions that makes you feel comfortable. We took the water taxi from (and to) the airport directly to the hotel fastest way to get there. Easy to walk around and along the waterfront. Breakfast was excellent

Reviewed on 15 Jun 2026

Good Hotels Boston

Good Hotels Boston

2 out of 5
South End
Save 100% on your flight
Price was £1,718, price is now £1,122 per person
£1,122
per person
24 Sept - 28 Sept
found 1 day ago
Return direct flight included
London (LGW) to Boston (BOS)
8/10 Very good! (55 reviews)
This was a very clean and well-looked after property, and the staff went out of their way to check everything was in order.

Reviewed on 23 May 2026

The Atlas Hotel

The Atlas Hotel

4.5 out of 5
Allston
Price was £1,532, price is now £1,109 per person
£1,109
per person
24 Aug - 30 Aug
found 1 day ago
Return flight included
Edinburgh (EDI) to Boston (BOS)
9.4/10 Exceptional! (150 reviews)
The most impactful asset of this hotel is the staff. They were extremely accommodating and helpful, and made us feel very welcome. As a new hotel, they have a few tweaks to make: for example, it would be helpful to have a copy of the room service menu in each room. Based on the excellence of the staff, though, I am confident they will work out these minor issues.

Reviewed on 28 Jun 2026

InnSeason Resorts Surfside

InnSeason Resorts Surfside

3 out of 5
Price was £1,523, price is now £1,152 per person
£1,152
per person
19 Sept - 26 Sept
found 21 hours ago
Return direct flight included
London (LON) to Boston (BOS)
9.4/10 Exceptional! (424 reviews)
Gorgeous view

Reviewed on 13 Jun 2026

Upton Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Worcester Regional Airport (ORH)
Population
3,000
Max Temp Winter
2ºC
Max Temp Summer
27ºC
Top Sights
Southwicks Zoo, Apex Entertainment Centre and Worcester Art Museum

Top hotels in Upton

Sonesta Select Boston Milford

Sonesta Select Boston Milford

3 out of 5
10 Fortune Blvd Milford MA
Fully refundableReserve now, pay when you stay
The price is £90 per night from 5 Jul to 6 Jul
£90
5 Jul - 6 Jul
includes taxes & fees
8/10 Very good! (1,007 reviews)
"Its an ok property. Breakfast is not included and somehow I missed that when booking. There were missed cleaning opportunities, such as the walls in bathroom. For a two night stay we were only supplied with one towel each for the whole stay. There wasn't a freezer for ice packs, so had to use ice ..."

Reviewed on 28 Jun 2026

Sonesta Select Boston Milford
Best Western Royal Plaza Hotel & Trade Center

Best Western Royal Plaza Hotel & Trade Center

3 out of 5
181 Boston Post Rd W Marlborough MA
Fully refundableReserve now, pay when you stay
The price is £94 per night from 2 Jul to 3 Jul
£94
2 Jul - 3 Jul
includes taxes & fees
8/10 Very good! (1,022 reviews)
"Only complaint is the metal bedframe had slightly protruding metal near the feet. It was covered by a sheet but you could still easily hurt your foot if you banged into it. Otherwise everything was good. Good value."

Reviewed on 29 Jun 2026

Best Western Royal Plaza Hotel & Trade Center
Sonesta Select Boston Foxborough Mansfield

Sonesta Select Boston Foxborough Mansfield

3 out of 5
35 Foxborough Boulevard Foxborough MA
Fully refundableReserve now, pay when you stay
The price is £83 per night from 14 Jul to 15 Jul
£83
14 Jul - 15 Jul
includes taxes & fees
8.6/10 Excellent! (1,011 reviews)
"We had a great stay at this hotel. It was clean, well-maintained, and in a great location. The staff was friendly and helpful. Our room was comfortable and had everything we needed. The beds were cozy, and the common areas were inviting. We appreciated the attention to detail and excellent service. ..."

Reviewed on 29 Jun 2026

Sonesta Select Boston Foxborough Mansfield
See all 628 properties in Upton
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.
All Inclusive Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Stay near popular Upton attractions

Dean Pond

6.0/5 (1 review)
Commune with nature and explore the great outdoors at Dean Pond during your travels in Upton. Discover the lively bars and great live music in this family-friendly area.
See properties

Frequently asked questions

Why should I book my Upton holiday with Expedia?
Expedia has your back for all aspects of your Upton trip. You'll always get the best prices around, but when you bundle your accommodation, airfares and/or hire car into a holiday package, you'll get even more savings. Looking to really make the most of your break? Add a few fun tours and activities to your package. Expedia offers flexible cancellation policies on almost all bookings, so you won't need to worry if your plans change. Visit our Customer Service Portal link to discover more.
When is the best time of year to holiday in Upton?
If you love the excitement that comes with peak season, head to Upton in June, July and August. If you prefer a calmer vibe, November, December and January will suit you better. With daytime average temperatures of -2ºC, January is the coolest month in Upton. The warmest time of year is July, when you can experience average temperatures of 22ºC during the day. Whatever the weather conditions, you'll discover plenty of things to keep you occupied here.
What is the top hotel for my holiday in Upton?
Relax in comfort in Upton by choosing Boston Park Plaza as your gateway to fun and adventure.
How do I get a cheap holiday to Upton?
Our Upton holidays offer plenty of savings for the savvy explorer. For the best deal, simply bundle your flights, hotels and extras (including tours). But great bargains are just the beginning of your next amazing adventure. Book with Expedia and you'll have more than 400 airlines and 321,000 hotel options globally to choose from. Whatever your budget, there's a holiday here just for you. Learn more about how you can save money on your holiday when you bundle your flight and hotel bookings with Expedia.
What should I do on my Upton holiday?
Ensure your holiday in Upton is one to remember by visiting its well-known attractions. Southwicks Zoo, Hopkinton State Park, New England Baseball Complex and Cummings School of Veterinary Medicine at Tufts University are just a few of the things worth seeing while you're in the area.
Do I need a visa for my Upton holiday?
Visa requirements for Upton vary depending on your nationality and reason for your visit. We recommend checking official government websites to determine if you need a visa for your trip. This is also a good place to find the most up-to-date information, including details about application procedures or any supporting documentation you might need. Research your visa requirements in advance to ensure a travel experience that's hassle free. Also make sure your passport is valid for at least six months from your date of return.
What should I wear on my Upton holiday?
First, think about the types of things you'll be doing during your trip to Upton and travel with pieces that you can easily mix and match. For fashion inspiration or even information on dress codes, look up style blogs or social media accounts. Have a look at the weather forecast so you can pack your bags accordingly. The warmest time of year in Upton is July, with average daytime temperatures of 22ºC. If you're visiting in the coolest month of January, the mercury hovers around -2ºC during the day.
What does an Expedia Upton holiday include?
Expedia has everything you need to arrange your Upton getaway, but what your package looks like is totally up to you. Choose from any combination of hotels, hire cars and flights. In search of some experiences or tours to keep you busy? Once you've made your booking, you can add them on too. No matter your style or budget, there's a holiday package to suit your needs. Apartments and private holiday homes are a couple of the most popular property types in Upton. Whatever your holiday style or size of your group, you can rely on Expedia for the flexibility and freedom to personalise your dream escape.
Does Expedia offer Book Now, Pay Later Upton holidays?
Expedia has partnered with online lender Klarna to make your next getaway a bit easier on the wallet. Paying by instalment means you can spread the costs of your dream holiday, leaving you with more money to spend while you're away. Klarna has several payment plans to choose from, so you're sure to find one that fits your budget. Take a look at these flexible payment options:

  • Pay monthly holidays: Klarna offers payments in multiple transactions that fit all budgets, so you can lock in that well-deserved holiday now.
  • No-deposit holidays: Hitting the "book now" button is easier with this plan. With no deposit required for your getaway, you can Book Now, Pay Later and get on your way.

Can I choose my airline with an Upton Expedia holiday?
Definitely. Expedia has more than 400 airline partners to pick from around the world. With all that choice at your fingertips, finding the ideal carrier to fly you to Upton shouldn't be hard.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.