Upton Vacations from $626

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The Latest Upton vacation packages

Price found within the past 48 hours. Click for updated prices.
Bluebird Ocean Point Inn

Bluebird Ocean Point Inn

3 out of 5
Ocean Point
Save 100% on your flight
Price was $875, price is now $626 per person
$626
per person
Jul 24 - Jul 27
found 15 hours ago
Roundtrip flight included
Chicago (CHI) to Augusta (AUG)
8.8/10 Excellent! (556 reviews)
Thank you for another great stay, 37 years and counting! Clean updated rooms, friendly staff, morning coffee and the most amazing key lime pie on the planet.

Reviewed on Oct 23, 2025

Topside Inn

Topside Inn

3 out of 5
Save 100% on your flight
Price was $1,588, price is now $1,094 per person
$1,094
per person
Jul 24 - Jul 27
found 15 hours ago
Roundtrip flight included
Chicago (CHI) to Augusta (AUG)
10/10 Exceptional! (88 reviews)
The staff at Topside are the best-attentive, helpful and kind. The Inn and grounds are beautiful and the breakfast is the best ever. We will definitely return!

Reviewed on May 4, 2026

Greenleaf Inn

Greenleaf Inn

2 out of 5
Save 100% on your flight
Price was $1,001, price is now $759 per person
$759
per person
Jul 24 - Jul 27
found 15 hours ago
Roundtrip flight included
Chicago (CHI) to Augusta (AUG)
9.2/10 Wonderful! (15 reviews)
Our host is the best! Such a beautiful property.

Reviewed on Nov 16, 2025

OneSixtyFive

OneSixtyFive

3 out of 5
Price was $1,230, price is now $959 per person
$959
per person
Jun 27 - Jul 3
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Augusta (AUG)
9.4/10 Exceptional! (149 reviews)
Wonderful property, quiet comfortable rooms, friendly staff, great location in Brunswick, definitely worth staying for the delicious breakfast too,

Reviewed on Mar 12, 2026

Newly Renovated Acadia Apartment Maple Street

Newly Renovated Acadia Apartment Maple Street

3 out of 5
Save 100% on your flight
Price was $1,567, price is now $1,225 per person
$1,225
per person
Jun 27 - Jul 3
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Augusta (AUG)
10/10 Exceptional! (3 reviews)
The inside apartment was clean new. The first look of the house was old in appearance. The heating was not good in the BR off the kitchen. Bigger BR was toasty. Overall I would return in a minute. Biggest issue was only finding decafe coffee in the cupbord. :(

Reviewed on Oct 19, 2025

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Discover the most popular places to visit in Upton

Sunday Covered Bridge in Newry Maine it Spans the Sunday River. It is one of the Most Painted and Photographed Covered Bridges in Maine

Sunday River

Hit the slopes in Newry with a visit to Sunday River. Stroll along this relaxing area's riverfront, or simply enjoy its bars.

Sunday River
Grafton Notch State Park

Grafton Notch State Park

Walk along a piece of the Appalachian Trail and enjoy stunning views from atop Old Speck in Newry’s mountainous patch of wilderness.

Grafton Notch State Park

Sunday River Golf Club

Enjoy a round of golf in Newry at Sunday River Golf Club. Amble around this relaxing area's riverfront, or seek out the ski slopes.

Sunday River Golf Club

Upton Hotel Deals

Jordan Hotel

Jordan Hotel

3 out of 5
27 Grand Circle Newry ME
$142 nightly
The price is $154 total per night from May 17 to May 18
$154 total
May 17 - May 18
Total with taxes and fees
8.8/10 Excellent! (534 reviews)
Rooms need updating and sliders needs a complete overhaul, but the updates to the main lobby and the staff plus amenities were great.

Reviewed on Apr 30, 2026

Jordan Hotel
Grand Summit Hotel

Grand Summit Hotel

3 out of 5
97 Summit Road Newry ME
$154 nightly
The price is $167 total per night from Jun 2 to Jun 3
$167 total
Jun 2 - Jun 3
Total with taxes and fees
8.4/10 Very Good! (373 reviews)
Slope easily accessible. Helpful, Friendly staff

Reviewed on Apr 16, 2026

Grand Summit Hotel
The Inn at the Rostay

The Inn at the Rostay

2 out of 5
186 Mayville Road Bethel ME
Fully refundableReserve now, pay when you stay
$125 nightly
The price is $136 total per night from May 7 to May 8
$136 total
May 7 - May 8
Total with taxes and fees
9/10 Wonderful! (473 reviews)
Needed a place to stay at the last minute. Even though there were no staff, we were able to make a reservation and get a room quickly and easily. Simple accommodations but it was a great stay!

Reviewed on Apr 28, 2026

The Inn at the Rostay
See all 860 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.

Find the Best Upton Vacation Packages

Upton Essential Information

Language
English
Currency
U.S dollars
Top Sights
Grafton Notch State Park, Grafton Notch Trailhead and Speck Pond

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Frequently asked questions

How much does an Upton vacation package cost?
Offering excellent value package deals from $626 on Expedia, you'll be pleasantly surprised at how much a vacation to Upton costs! Expedia's packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Upton?
You can usually find lower prices and greater availability in April, June and November. Browse our cheap Upton vacation packages and you could land some great off-season discounts.
How many days is enough for Upton?
With a well-planned itinerary, you can easily visit the main Upton sights in a handful of days. But if you prefer to discover hidden gems or take day trips, think about booking your Upton vacation for longer.
How to find the best Upton package deals?
Start your search for an Upton package deal by entering your destination and travel dates under our "Packages" tab. Then add a few filters, like "Guest rating" and "Property type," to fine-tune the results to your exact needs. You can also sort by "Package discount" and discover offers that come with huge savings. If you don't find the perfect Upton package deal straight away, simply play around with your dates and search again. Keep in mind that deals are only available for a limited time, so book early and get your Upton adventure off to a flying start.
Is it cheaper to book an Upton vacation as a package?
You can enjoy significant savings on your next Upton break by booking a tailored vacation package. Click on the "Package" heading, then select your travel dates and destination to browse some great airfares and hotel prices. Bundling can save travelers hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a vacation package to Upton?
If you're considering a spontaneous Upton trip, 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 terrific deals on your hotels and flights by booking well in advance.
Does Expedia offer Book Now, Pay Later Upton vacation packages?
If you're like us, you love exploring new places but don't love the price tag that can come with it. That's why we've created Book Now, Pay Later vacations. With the help of online lender Affirm, you can spread the overall cost of your Upton break over 3, 6 or 12 months. There are also no hidden or late payment fees, so you can secure cheap vacation packages with payment plans as soon as you spot them.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.