Upton Holidays

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Top Flight + Hotel Deals in Upton

Price found within the past 48 hours. Click for updated prices.
Sunbird Cape Cod Resort

Sunbird Cape Cod Resort

2.5 out of 5
Price was €998, price is now €765 per person
€765
per person
7 Sept - 13 Sept
found 1 day ago
Return flight included
Dublin (DUB) to Boston (BOS)
7.8/10 Good! (551 reviews)
I loved to stayed at sunbird. The room is good The breakfast fast is great a lot option The pool is amazing too I really like. I can’t wait to come back

Reviewed on 30 Jun 2026

Sea Crest Beach Resort

Sea Crest Beach Resort

3.5 out of 5
Save 100% on your flight
Price was €2,994, price is now €2,018 per person
€2,018
per person
7 Sept - 13 Sept
found 1 day ago
Return flight included
Dublin (DUB) to Boston (BOS)
7.8/10 Good! (315 reviews)
Was looking for pet friendly on the beach for a long weekend on the Cape. I hadn’t been to SeaCrest in over a decade. Property was in great shape and looked like it was recently renovated. Fireplace studio was great with a view of Old Silver Beach. Beach service was quick and efficient. There were several events on the property and noise was never an issue. Meals were great. I wish the pizza place was open!

Reviewed on 28 Jun 2026

Sesuit Harbor House

Sesuit Harbor House

3 out of 5
Price was €1,664, price is now €1,238 per person
€1,238
per person
7 Sept - 13 Sept
found 1 day ago
Return flight included
Dublin (DUB) to Boston (BOS)
9.6/10 Exceptional! (179 reviews)
We had an amazing stay! Lots of great activities to entertain our 2 year old!

Reviewed on 28 Jun 2026

By the Sea Guests Bed & Breakfast & Suites

By the Sea Guests Bed & Breakfast & Suites

3.5 out of 5
Price was €1,230, price is now €933 per person
€933
per person
7 Sept - 13 Sept
found 1 day ago
Return flight included
Dublin (DUB) to Boston (BOS)
9.2/10 Wonderful! (189 reviews)
Nice property. A little parking issue due to limited parking. Only one space per room, I think some people didn't listen. But breakfast, the private beach, the staff, the amenities all awesome.

Reviewed on 25 Jun 2026

Bluebird Dennisport

Bluebird Dennisport

3 out of 5
Price was €1,285, price is now €1,007 per person
€1,007
per person
7 Sept - 13 Sept
found 1 day ago
Return flight included
Dublin (DUB) to Boston (BOS)
8.4/10 Very good! (222 reviews)
I would not recommend this property. Unfortunately, our experience was very disappointing. The staff were not particularly welcoming, and we found a cockroach in the bathroom. The TV in our room did not work, there was trash left under the bed, suggesting the room had not been properly cleaned, and we found hair in the shower upon arrival. Additionally, the peel-and-stick wallpaper was coming off the walls, making the room feel poorly maintained. Overall, the cleanliness and upkeep of the property fell well below expectations. Save yourself the hassle and consider staying elsewhere.

Reviewed on 28 Jun 2026

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 €105 per night from 4 Jul to 5 Jul
€105
4 Jul - 5 Jul
includes taxes & fees
8/10 Very good! (1,010 reviews)
"Gigantic centipede in the middle of the night. Called front desk, no one cared or showed up. Had to leave on the middle of the night traumatized."

Reviewed on 30 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 €109 per night from 19 Jul to 20 Jul
€109
19 Jul - 20 Jul
includes taxes & fees
8/10 Very good! (1,002 reviews)
"This was a very clean and inviting place to stay. The staff . . . . fantastic, especially the breakfast buffet staff. The best ! However, we had every expectation of using the pool and it was closed, for cleaning they said. Closed for the week ? ? But very disappointed and would have loved to have ..."

Reviewed on 30 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 €97 per night from 14 Jul to 15 Jul
€97
14 Jul - 15 Jul
includes taxes & fees
8.6/10 Excellent! (1,017 reviews)
"Very nice little property if you are attending a conference, a concert at XFinity or a game at Foxboro. Too far for a Boston trip though. Nice sports bar restaurant across the parking lot and other shopping nearby. Bar is a nice add and stays open late with friendly staff. Room was large and the ..."

Reviewed on 30 Jun 2026

Sonesta Select Boston Foxborough Mansfield
See all 626 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.

Stay near popular Upton attractions

Dean Pond

6.0/10 (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

How much does an Upton holiday package cost?
Offering great value package deals from €765 on Expedia, you'll be surprised at how little a holiday to Upton costs! Expedia's packages simplify travel planning and maximise your savings.
What are the cheapest months to go to Upton?
January, February and November are great times to search for cheap Upton holiday packages. Choosing to travel in less busy periods means you can typically find reduced prices on flights and accommodation.
How many days is enough for Upton?
With a well-organised travel plan, you can easily tick off the most popular Upton attractions in a handful of days. But if you'd like to venture off the beaten track or go on day tours, consider booking your Upton holiday for longer.
How to find the best Upton package deals?
Use Expedia's handy filters to help you find some unbeatable Upton package deals. When you start your search, simply set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your escape for midweek, or look for Upton package deals in the low season. Play around with your travel dates and you may land even better discounts. As a rule of thumb, it's usually best to lock in your holiday package as soon as possible.
Is it cheaper to book an Upton holiday as a package?
You can enjoy significant savings on your next Upton escape by booking a tailored holiday package. Click on the "Package" heading, then enter your destination and travel dates to browse some great airfares and hotel prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a holiday package to Upton?
Secure incredible bargains by booking your flights in advance with Expedia. If spontaneity is more your thing, snap up one of our last-minute deals for a spur-of-the-moment Upton adventure.
How to plan a trip to Upton?

  1. Pick your dates: What you want to do in Upton and your favourite season can help you decide when to travel.
  2. Budget wisely: In addition to the cost of your accommodation, you'll need to factor in other expenses. These include flights, food and transportation. Also, put aside some extra funds for unexpected expenses that may come up during your trip to Upton.
  3. Determine how many days away: Start by compiling a list of the activities and attractions you'd like to experience in Upton. Then, estimate how long you'll need for each, as well as any travel time.
  4. Bundle your bookings: With your travel dates in place, you can combine your flights, car rental, hotels and more into a tailored Upton holiday package.

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.