Middleton Vacation Packages

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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.
Lakeside Inn

Lakeside Inn

2 out of 5
Save 100% on your flight
per person
Aug 26 - Sep 1
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
7.4/10 Good! (2,188 reviews)
Alway a good place to stay

Reviewed on Jul. 19, 2025

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Save 100% on your flight
per person
Oct 2 - Oct 5
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
9.6/10 Exceptional! (122 reviews)
Excellent, elegant, great service in every way possible. Friendly, helpful and responsive staff too.

Reviewed on Jul. 14, 2025

Maverick Suites at 245 Newbury St

Maverick Suites at 245 Newbury St

2 out of 5
Back Bay
Save 100% on your flight
per person
Sep 3 - Sep 9
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
8.2/10 Very Good! (135 reviews)
Nobody on property to talk to

Reviewed on May 20, 2025

The Cove At Salem

The Cove At Salem

3 out of 5
Save 100% on your flight
per person
Sep 18 - Sep 22
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Boston (BOS)
9.4/10 Exceptional! (595 reviews)
It was close to everything & really nice.

Reviewed on Jul. 19, 2025

Maverick Suites at 40 Temple St

Maverick Suites at 40 Temple St

2 out of 5
Beacon Hill
Save 100% on your flight
per person
Sep 3 - Sep 9
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Boston (BOS)
7.4/10 Good! (87 reviews)
Had a 4 night stay at the Maverick Suites on Temple Street. I mainly booked this room to be close to my daughter, who lives a couple of doors down. The room is a bit tight for two people, but my friend & I made it work by sleeping 90 degrees on the double bed to turn it into more of a "short king". Room was very clean, however the one suggestion I would make is to use less of the strong-smelling cleaner (Fabioso?) or a more natural cleaner. Otherwise, the property felt safe and clean. Beautiful hardwood floors, nice bathroom & small kitchen area. Staff is very responsive via TEXT (not by phone). We requested clean towels etc, and they were very accommodating. Temple St. is walkable to many sites you'll want to check out in Boston via a walk or to the Park St T station. I would recommend staying at the Maverick Suites!

Reviewed on Jun. 25, 2025

Ready to book your vacation to Middleton?

 

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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
The price is CA $162 per night from Aug 10 to Aug 11
CA $162
CA $176 total
Aug 10 - Aug 11
includes taxes & fees
7.6/10 Good! (1,005 reviews)
"Nice place"

Reviewed on Jul. 18, 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! (999 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
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
The price is CA $261 per night from Aug 10 to Aug 11
CA $261
CA $284 total
Aug 10 - Aug 11
includes taxes & fees
8.8/10 Excellent! (799 reviews)
"We had a lovely stay. The Inn is quaint, clean, and accessible."

Reviewed on Jul. 13, 2025

Fireside Inn & Suites Gilford
See all 1,189 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

Family Vacations

Frequently asked questions

How much does a Middleton vacation package cost?
You'll find cheap prices from CA $670 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.