Middleton Vacation Packages

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    Save up to CA $1,096 when you book a flight and hotel together*
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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.

Top Middleton Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Staybridge Suites Boston Logan Airport - Revere by IHG

Staybridge Suites Boston Logan Airport - Revere by IHG

3 out of 5
Save 100% on your flight
per person
Aug 20 - Aug 24
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
8.8/10 Excellent! (553 reviews)
Staff were amazing! Room was great, didn’t care for the tv placement but other than that it was clean and quiet and plenty of places near to eat and shop. Also love the free shuttle to and from the airport!

Reviewed on Jul. 9, 2025

The Inn at Hastings Park, Relais & Chateaux - Boston

The Inn at Hastings Park, Relais & Chateaux - Boston

4 out of 5
Save 100% on your flight
per person
Aug 28 - Aug 31
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
9.6/10 Exceptional! (242 reviews)
Beautiful place. But floor in the bathroom was a little sticky. Yuck. When I checked in, I was shown a beautiful dining room where breakfast would be served. But then, instead, it was served in a much more shabby room. Also, the included breakfast was quite skimpy. Extra charge for a real breakfast. (Also, I may be wrong, but I don’t think the word “potatoes” appears anywhere on the menu. Of course, you do serve potatoes - with a delicious omelette that I enjoyed, for example.)

Reviewed on Jun. 6, 2025

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Save 100% on your flight
per person
Aug 12 - Aug 16
found 20 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Boston (BOS)
9.6/10 Exceptional! (118 reviews)
Beautiful facility and wonderful staff.

Reviewed on Jul. 10, 2025

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
per person
Aug 12 - Aug 16
found 20 hours ago
Roundtrip non-stop flight included
Hamilton (YHM) to Boston (BOS)
9.8/10 Exceptional! (1,005 reviews)
First class hotel with incredible staff and food onsite. Walk to anywhere downtown and the north end for great Italian food

Reviewed on Jul. 8, 2025

Encore Boston Harbor

Encore Boston Harbor

5 out of 5
Save 100% on your flight
per person
Aug 14 - Aug 17
found 16 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (3,076 reviews)
Place was beautiful well kept and very clean

Reviewed on Jul. 8, 2025

Ready to book your vacation to Middleton?

 

Choose your dates

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
The price is CA $156 per night from Jul 20 to Jul 21
CA $156
CA $169 total
Jul 20 - Jul 21
includes taxes & fees
7.6/10 Good! (1,001 reviews)
I would recommend this hotel
"Room we clean and spacious. Breakfast was included. Fast checkout."

Reviewed on Jul. 10, 2025

Best Western Plus Landmark Inn
Microtel Inn & Suites by Wyndham Dover
Microtel Inn & Suites by Wyndham Dover
2 out of 5
31 Webb Pl, Dover, NH
Fully refundableReserve now, pay when you stay
The price is CA $163 per night from Aug 4 to Aug 5
CA $163
CA $177 total
Aug 4 - Aug 5
includes taxes & fees
7.8/10 Good! (998 reviews)
"The hotel is fine except the room felt a little outdated. It was all kn good condition and clean, but it did not feel as up-to-date as some other chain hotel rooms. The bed was not overly comfortable, and all the mirrors made it a little cheesy, especially the ones around the jacuzzi. It was nice ..."

Reviewed on Jul. 6, 2025

Microtel Inn & Suites by Wyndham Dover
TownePlace Suites by Marriott Gilford
TownePlace Suites by Marriott Gilford
3 out of 5
14 Sawmill Road, Gilford, NH
The price is CA $208 per night from Jul 13 to Jul 14
CA $208
CA $226 total
Jul 13 - Jul 14
includes taxes & fees
9/10 Wonderful! (538 reviews)
"Fantastic front desk staff. Rooms are very cozy."

Reviewed on Jul. 5, 2025

TownePlace Suites by Marriott Gilford
See all 1,186 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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

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Frequently asked questions

How much does a Middleton vacation package cost?
You'll find cheap prices from CA $685 on Expedia for your Middleton escape. However, factors like the hotel choice, length of stay and season will determine how much your vacation to Middleton costs.
What are the cheapest months to go to Middleton?
You can usually find reduced prices and greater availability in January, February and March. Take a look at our cheap Middleton vacation packages and you could score some great off-season discounts.
How many days is enough for Middleton?
Usually, a handful of days is enough to tick off the major sights during your Middleton vacation. However, if you prefer to have time to rest or go on day tours, think about extending your trip.
How to find the best Middleton package deals?
Begin your search for a Middleton package deal by entering your travel dates and destination under our "Packages" tab. Then add some filters, like "Property type" and "Guest rating," to tailor the results to your exact style. You can also sort by "Package discount" and browse offers that come with unbeatable savings. If you don't find the ideal Middleton package deal straight away, simply tweak your dates and search again. Remember that deals are only available for a limited time, so book early and get your Middleton getaway off to a flying start.
Is it cheaper to book a Middleton vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your hotel, car rental and flight into one great-value price and enjoy significant savings. You'll generally snag a better deal than booking each component separately. And you'll still enjoy the freedom to create a tailored Middleton vacation by choosing your preferred airline, accommodation type and car class.
When to book a vacation package to Middleton?
If you're planning a spontaneous Middleton trip, check out our last-minute deals that can be booked up to a week before you go. Don't want to leave things to the last minute? You can land awesome deals on your hotels and flights by booking ahead.
How to plan a trip to Middleton?

  1. Choose when to travel: Check your calendar and pack your bags. Your preferred time of year and the activities available will also help you decide when to escape to Middleton.
  2. Budget wisely: As well as the price of your accommodations, you should consider other expenses. These include flights, food and transportation. Also, set aside some extra funds for unexpected costs that could crop up during your trip to Middleton.
  3. Decide how many days away: Start by compiling a list of the activities and attractions you want to experience in Middleton. Then, estimate how long you'll need at each, including any travel time.
  4. Combine your airfare and accommodations: Once you've nailed down your travel dates and duration, book the ideal Middleton vacation package for you.

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