Middleton Vacations from $899

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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.
By the Sea Guests Bed & Breakfast & Suites

By the Sea Guests Bed & Breakfast & Suites

3.5 out of 5
Price was $1,235, price is now $899 per person
$899
per person
Jun 22 - Jun 26
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Boston (BOS)
9.2/10 Wonderful! (185 reviews)
Our room had an wonderful Ocean View. The room was excellent and meals were awesome. Staff were very helpful. We will be going back next year!

Reviewed on Sep 20, 2025

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
Price was $2,429, price is now $1,657 per person
$1,657
per person
Jun 5 - Jun 8
found 24 hours ago
Roundtrip flight included
Dallas (DAL) to Boston (BOS)
9.8/10 Exceptional! (1,001 reviews)
Everything was great, however the pool itself was not heated, it was cold and no one really stayed in it for that reason. Thankfully there was a hot tub.

Reviewed on Mar 23, 2026

Beachside Village Resort

Beachside Village Resort

3 out of 5
Save 100% on your flight
Price was $1,682, price is now $1,195 per person
$1,195
per person
Jun 3 - Jun 6
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
9.4/10 Exceptional! (101 reviews)
Very clean and quiet place to relax. Very friendly and professional! We will come back!

Reviewed on Nov 10, 2025

Centerboard

Centerboard

2 out of 5
Nantucket Town
Save 100% on your flight
Price was $3,519, price is now $2,547 per person
$2,547
per person
Jun 13 - Jun 19
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Boston (BOS)
9.8/10 Exceptional! (105 reviews)
There was hair on our bed, I ask for late due to getting dress for my wedding and I was told

Reviewed on Mar 20, 2026

The Wylie Inn and Conference Center at Endicott College

The Wylie Inn and Conference Center at Endicott College

3.5 out of 5
Price was $1,474, price is now $1,098 per person
$1,098
per person
Jun 22 - Jun 26
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Boston (BOS)
9.2/10 Wonderful! (1,174 reviews)
Parking was easy. Staff friendly. Room was nice. Breakfast was fair. Nice location

Reviewed on Mar 30, 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
$101 nightly
The price is $110 total per night from Apr 5 to Apr 6
$110 total
Apr 5 - Apr 6
Total with taxes and fees
7.8/10 Good! (1,003 reviews)
Really great location and a nicely remodeled place. Could use modernized tv’s or other tech, and a warmer pool, but overall the price was great and I can tell the folks that own it take pride in their business. Cleanliness was top tier in rooms, lobby and pool as far as I could tell. Will absolutely ...

Reviewed on Mar 29, 2026

Best Western Plus Landmark Inn
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
$127 nightly
The price is $138 total per night from Apr 8 to Apr 9
$138 total
Apr 8 - Apr 9
Total with taxes and fees
9/10 Wonderful! (783 reviews)
Even though the hotel was undergoing some rennovations, we never heard anything. Our room was newly renovated, clean, spacious and very comfortable. The pool was clean and we enjoyed the hot tub immensely. Definitely will return when visiting the area again.

Reviewed on Mar 31, 2026

Homewood Suites by Hilton Dover
Fireside Inn & Suites Gilford

Fireside Inn & Suites Gilford

2.5 out of 5
17 Harris Shore Road Gilford NH
Fully refundableReserve now, pay when you stay
$130 nightly
The price is $141 total per night from Apr 1 to Apr 2
$141 total
Apr 1 - Apr 2
Total with taxes and fees
8.8/10 Excellent! (962 reviews)
It was the perfect choice for our family, pool and hot tub were awesome.

Reviewed on Mar 22, 2026

Fireside Inn & Suites Gilford
See all 1,196 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 $899 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.