Middleton Vacations from $766

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Your Middleton Vacation

Book a custom vacation package to Middleton and get ready to experience this city however you like. Consider spending time in the neighborhood of Pine River Pond, which is great for fishing and much more. You'll want to do a little exploring during your trip to Middleton. Find time for popular attractions like Merrymeeting Lake, Sunrise Lake and Marchs Pond. Whoever you're taking time off with and whatever your budget, your dream Middleton vacation is just a few clicks away with Expedia.

The Latest Middleton vacation packages

Price found within the past 48 hours. Click for updated prices.
Meco Hotel - Hostel

Meco Hotel - Hostel

2 out of 5
West End
Save 100% on your flight
Price was $1,274, price is now $766 per person
$766
per person
Jul 30 - Aug 2
found 10 hours ago
Roundtrip flight included
Chicago (CHI) to Boston (BOS)
8.6/10 Excellent! (406 reviews)
1st time, felt safe. Towels were available. Bring your own lock. 1 block from train station. And good food and stores nearby

Reviewed on May 15, 2026

Sea Crest Beach Resort

Sea Crest Beach Resort

3.5 out of 5
Save 100% on your flight
Price was $4,091, price is now $2,498 per person
$2,498
per person
Jul 18 - Jul 25
found 2 hours ago
Roundtrip flight included
Chicago (CHI) to Boston (BOS)
8/10 Very Good! (269 reviews)
The room , was ok ! No super excellent clean !

Reviewed on May 11, 2026

The Onset Beach Compound-Cape Cod Beach Resort & Oceanic Habitat

The Onset Beach Compound-Cape Cod Beach Resort & Oceanic Habitat

3 out of 5
Save 100% on your flight
Price was $6,031, price is now $3,809 per person
$3,809
per person
Jul 4 - Jul 10
found 13 hours ago
Roundtrip flight included
Chicago (CHI) to Boston (BOS)
10/10 Exceptional! (9 reviews)
thanks u for very nice place and clean i really loved i will cominng back soon

Reviewed on May 8, 2025

Sunbird ANNEX Resort

Sunbird ANNEX Resort

2 out of 5
Save 100% on your flight
Price was $1,226, price is now $777 per person
$777
per person
Jul 18 - Jul 25
found 2 hours ago
Roundtrip flight included
Chicago (CHI) to Boston (BOS)
7.8/10 Good! (826 reviews)
Had a few bumps in my stay but overall was great! My son loves the playground and we were given 2 night stay for free in the future. Staff is always nice!

Reviewed on May 4, 2026

The Langham, Boston

The Langham, Boston

5 out of 5
Downtown Boston
Price was $1,448, price is now $920 per person
$920
per person
Jul 23 - Jul 26
found 1 day ago
Roundtrip flight included
Chicago (CHI) to Boston (BOS)
9.6/10 Exceptional! (1,007 reviews)
Right in heart of town

Reviewed on May 12, 2026

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Middleton Hotel Deals

Best Western Plus Landmark Inn

Best Western Plus Landmark Inn

2.5 out of 5
480 Main Street Laconia NH
Fully refundableReserve now, pay when you stay
$115 nightly
The price is $125 total per night from May 24 to May 25
$125 total
May 24 - May 25
Total with taxes and fees
7.8/10 Good! (1,005 reviews)
A solid choice for the value- comfortable room, great location, breakfast options hot and cold including Gluten Free and fresh fruit.

Reviewed on May 15, 2026

Best Western Plus Landmark Inn
Holiday Inn Express Hotel & Suites Rochester by IHG

Holiday Inn Express Hotel & Suites Rochester by IHG

2.5 out of 5
77 Farmington Rd Rochester NH
Fully refundable
$105 nightly
The price is $114 total per night from May 31 to Jun 1
$114 total
May 31 - Jun 1
Total with taxes and fees
8.8/10 Excellent! (1,003 reviews)
Nice stay

Reviewed on May 14, 2026

Holiday Inn Express Hotel & Suites Rochester by IHG
Homewood Suites by Hilton Dover

Homewood Suites by Hilton Dover

3 out of 5
21 Members Way Dover NH
Fully refundableReserve now, pay when you stay
$151 nightly
The price is $164 total per night from May 25 to May 26
$164 total
May 25 - May 26
Total with taxes and fees
9/10 Wonderful! (804 reviews)
Every thing was wonderful, the hot tub was not open yet. That’s the only bad thing I can say.

Reviewed on May 9, 2026

Homewood Suites by Hilton Dover
See all 1,252 properties in Middleton
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 Middleton Vacation Packages

Middleton Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Portsmouth Intl. Airport (PSM)
Top Sights
Merrymeeting Lake, Sunrise Lake and Stand Up Paddleboard NH

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Frequently asked questions

How much does a Middleton vacation package cost?
You'll find cheap prices from $766 on Expedia for your Middleton escape. However, a range of factors like the length of stay, hotel choice and season will determine how much your vacation to Middleton costs.
What are the cheapest months to go to Middleton?
January, September and October are great times to look for cheap Middleton vacation packages. Choosing to travel in less busy months means you can typically find better prices on flights and accommodations.
How many days is enough for Middleton?
The ideal length for your Middleton vacation depends on what you'd like to see and do. Generally, a few days to a week will give you plenty of time to check out all the leading sights and discover some hidden gems along the way.
How to find the best Middleton package deals?
Start your search for a Middleton package deal by entering your preferred travel dates and destination under our "Packages" tab. Then add a few filters, like "Property type" and "Amenities," to fine-tune the results to your exact style. You can also sort by "Package discount" and browse offers that come with big savings. If you don't find the ideal Middleton package deal right away, simply tweak your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Middleton escape off to a flying start.
Is it cheaper to book a Middleton vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your car rental, hotel and flight into one great-value price and enjoy significant savings. You'll generally get a better deal than booking each component individually. And you'll still enjoy the freedom to create a customized Middleton vacation by choosing your preferred accommodation type, airline and car class.
When to book a vacation package to Middleton?
Score incredible discounts by booking your flights in advance with Expedia. If spontaneity is more your style, take advantage of our last-minute deals for a spur-of-the-moment Middleton trip.
Does Expedia offer Book Now, Pay Later Middleton vacation packages?
If you're anything like us, you love going away but don't love the big price tag that can come with it. That's why we offer Book Now, Pay Later vacations. With the help of online lender Affirm, you can break down the cost of your Middleton vacation across 3, 6 or 12 months. There are also no hidden costs or late payment fees, so you can snap up cheap vacation packages with payment plans as soon as you see them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.