Middleton Holidays

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Top Flight + Hotel Deals in Middleton

Price found within the past 48 hours. Click for updated prices.
YOTEL Boston

YOTEL Boston

4 out of 5
Seaport District
Save 100% on your flight
per person
10 Sept - 13 Sept
found 1 day ago
Return flight included
Chicago (ORD) to Boston (BOS)
8.6/10 Excellent! (2,098 reviews)
Located in a new neighborhood with lots of dining options and easy access to public transportation.

Reviewed on 28 Jul 2025

Boston Harbor Hotel

Boston Harbor Hotel

5 out of 5
North End
Save 100% on your flight
per person
10 Sept - 13 Sept
found 1 day ago
Return flight included
Chicago (ORD) to Boston (BOS)
9.8/10 Exceptional! (1,018 reviews)
I would say this is one of the best hotel I've stayed in my life!! The room had an amazing harbor view and nice chair, comfortable bed and best amenities!! The stuff was super nice too. Definitely 5 stars!!!

Reviewed on 28 Jul 2025

Raffles Boston

Raffles Boston

5 out of 5
Back Bay
Save 100% on your flight
per person
10 Sept - 13 Sept
found 1 day ago
Return flight included
Chicago (ORD) 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 14 Jul 2025

The Colonnade Hotel Back Bay

The Colonnade Hotel Back Bay

4 out of 5
Back Bay
Save 100% on your flight
per person
10 Sept - 13 Sept
found 1 day ago
Return flight included
Chicago (ORD) to Boston (BOS)
9/10 Wonderful! (1,964 reviews)
Great location. Easy access to the City.

Reviewed on 29 Jul 2025

Encore Boston Harbor

Encore Boston Harbor

5 out of 5
Save 100% on your flight
per person
10 Sept - 13 Sept
found 1 day ago
Return flight included
Chicago (ORD) to Boston (BOS)
9.6/10 Exceptional! (3,076 reviews)
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Reviewed on 28 Jul 2025

Top hotels in Middleton

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 €115 per night from 10 Aug to 11 Aug
€115
10 Aug - 11 Aug
includes taxes & fees
7.6/10 Good! (1,022 reviews)
"Big parking lot which would be helpful for larger vehicles or towing something; 15 minute walk to a beach and the WOW bike trail but what really impressed me most was the staff. Super helpful with directions for things in the area"

Reviewed on 25 Jul 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 €111 per night from 3 Aug to 4 Aug
€111
3 Aug - 4 Aug
includes taxes & fees
7.8/10 Good! (1,008 reviews)
"Great location"

Reviewed on 27 Jul 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 €178 per night from 10 Aug to 11 Aug
€178
10 Aug - 11 Aug
includes taxes & fees
8.8/10 Excellent! (817 reviews)
"Great property, clean and spacious"

Reviewed on 27 Jul 2025

Fireside Inn & Suites Gilford
See all 1,184 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.

Frequently asked questions

How much does a Middleton holiday package cost?
You'll find cheap prices from €546 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 holiday to Middleton costs.
What are the cheapest months to go to Middleton?
You can usually find lower prices and greater availability in January, February and March. Take a look at our cheap Middleton holiday packages and you could land some great off-season discounts.
How many days is enough for Middleton?
The ideal length of your Middleton holiday depends on what you'd like to see. Usually, a few days to a week will give you enough time to visit all the major sights and explore some hidden treasures 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 holiday as a package?
Expedia holiday 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 customised Middleton holiday by choosing your preferred accommodation type, airline and car class.
When to book a holiday 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.
How to plan a trip to Middleton?

  1. Pick your dates: What you want to do in Middleton and your favourite season will help you decide when to travel.
  2. Figure out your budget: Ensure you have enough money to cover everything from transportation and food to airfares and activities. Your hotel will likely be the largest expense during your trip to Middleton.
  3. Decide your trip length: Consider how much time you'd like to spend discovering Middleton. Plan your itinerary so you can get to all the attractions and experiences you're interested in at a comfortable pace.
  4. Combine your flights and hotel: Epic destination, check. Length of stay, check. Now all that's left is to find a Middleton holiday package that brings all your bookings together.

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