Middlefield Holidays from £492

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Your Middlefield Holiday

Prepare to experience Middlefield on your terms with a custom Middlefield holiday package! Discovering the best parts of this captivating city is simple with a base in a neighbourhood such as Washington Street Historic District, which is great for history, among many other things. Wesleyan University, Powder Ridge Mountain Park and Resort and Brownstone Exploration & Discovery Park are just a few of the many sights you'll want to check out during your trip to Middlefield. No matter your travel plans or the size of your budget, organising your ultimate tailored Middlefield holiday is a cinch with Expedia.

The Latest Middlefield Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

2 out of 5
Saybrook Manor
per person
4 Sept - 8 Sept
found 23 hours ago
Return flight included
London (LGW) to New Haven (HVN)
7.8/10 Good! (974 reviews)
Property was clean buy outdated.

Reviewed on 23 Jun 2025

Saybrook Point Resort & Marina

Saybrook Point Resort & Marina

3.5 out of 5
Old Saybrook Center
per person
4 Sept - 8 Sept
found 23 hours ago
Return flight included
London (LGW) to New Haven (HVN)
9.4/10 Exceptional! (1,005 reviews)
Very nice large room with great views. However the white bathroom floor grout had visible stains (some dark brown) over the entire bathroom floor. Grout needs to be steam cleaned and re-sealed. Nozzles of tub jets were visibly dirty. Room 339

Reviewed on 22 Jun 2025

James Pharmacy Bed & Breakfast

James Pharmacy Bed & Breakfast

4 out of 5
Old Saybrook Center
per person
4 Sept - 8 Sept
found 23 hours ago
Return flight included
London (LGW) to New Haven (HVN)
9.4/10 Exceptional! (16 reviews)
We loved the convenient location and beautiful historic building, but we were very disappointed in the level of cleanliness (a layer of dust on shelves and fireplace, cobwebs under furniture). There were some other issues (loose shower head, broken coffee maker). There's no one on site to address in person. It's a lovely place, but needs some attention. For the price, it should be better! :(

Reviewed on 1 May 2025

The Captain Stannard

The Captain Stannard

3 out of 5
Westbrook Center
per person
4 Sept - 8 Sept
found 23 hours ago
Return flight included
London (LGW) to New Haven (HVN)
9.6/10 Exceptional! (227 reviews)
Very nice place and the owners are super people and treat their customers very well! I loved it here and would definitely stay here again!

Reviewed on 2 Jun 2025

The Niantic Inn

The Niantic Inn

2 out of 5
per person
4 Sept - 8 Sept
found 23 hours ago
Return flight included
London (LGW) to New Haven (HVN)
9.2/10 Wonderful! (96 reviews)
Everything was great .Location is perfect to shop and dine. Only issue was garbage was left in stairwells overnight

Reviewed on 2 May 2025

Middlefield Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Bradley Intl. Airport (BDL)
Max Temp Winter
2ºC
Max Temp Summer
27ºC
Top Sights
Toyota Presents Oakdale Theatre, Brownstone Exploration & Discovery Park and Dinosaur State Park

Our pick of the best Middlefield Hotel Deals

The Capitol Hotel
The Capitol Hotel
3 out of 5
440 Asylum St, Hartford, CT
Stay at this 3-star business-friendly hotel in Hartford. Enjoy free breakfast, free Wi-Fi and a 24-hour fitness centre. Our guests praise the breakfast and the ...
7.4/10 Good! (1,010 reviews)
"All was well, except the garage, which is in a really bad shape."

Reviewed on 22 Jun 2025

The Capitol Hotel
New Haven Hotel
New Haven Hotel
3.5 out of 5
229 George Street, New Haven, CT
Stay at this 3.5-star business-friendly hotel in New Haven. Enjoy free Wi-Fi, a fitness centre and parking (surcharge). Our guests praise the helpful staff and ...
8.8/10 Excellent! (1,609 reviews)
Great location
"Great location in downtown New Haven. Great lobby space and other amenities. Walking distance to many restaurants."

Reviewed on 23 Jun 2025

New Haven Hotel
Clarion Inn
Clarion Inn
3 out of 5
201 Washington Avenue, North Haven, CT
Stay at this business-friendly hotel in North Haven. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the helpful staff ...
7.4/10 Good! (1,003 reviews)
"Elevator out of service closest to room. Not offered better directions to room felt like walked for miles. Halls do need upgrade but would return again"

Reviewed on 16 Jun 2025

Clarion Inn
See all 1,071 properties in Middlefield
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 Holidays

All Inclusive Holidays

Beach Holidays

Beach Holidays

Family Friendly Holidays

Family Friendly Holidays

Frequently asked questions

Why should I book my Middlefield holiday with Expedia?
Choose Expedia to organise your next big break with ease, all in one place. Our top tip for getting a fabulous deal on a Middlefield retreat? Bundle your accommodation, airfares and/or car hire into a package holiday. Then add a few fun tours and activities. Many bookings also come with flexible cancellation policies, so there's no need to panic if you have to switch up your travel agenda. Round-the-clock assistance with cancelling and amending your trip is on-hand via our Customer Service Portal link.
When is the best time of year to holiday in Middlefield?
Middlefield is a popular place in June, July and August. If you don't like big crowds and prefer a calmer pace, book your trip for December, January and February. To give you an idea of what type of weather you can experience, the daytime average temperature in January, the coolest month in Middlefield, is -1ºC. The warmest period here is July, when temperatures reach around 23ºC.
What is the top hotel for my holiday in Middlefield?
Offering many of the conveniences and comforts of home, The Inn at Mystic will make an ideal base for your Middlefield trip.
How do I get a cheap holiday to Middlefield?
Bundle your flight and hotel bookings, toss in extras such as tours, and save with a Middlefield holiday. You won't just score wonderful discounts on your escape --- you'll have loads of choice at your fingertips too. When you book with Expedia, you can select from more than 400 airlines and 321,000 properties worldwide. Your next grand adventure begins right here, right now! Learn more about how you can save money on your next holiday when you bundle your flight and hotel bookings with Expedia.
What should I do on my Middlefield holiday?
Ensure your holiday in Middlefield is an unforgettable one by taking in its best attractions. Wesleyan University, Toyota Oakdale Theatre, Choate Rosemary Hall and Powder Ridge Mountain Park and Resort are just a few of the things to put on your itinerary while you're in this city.
What is the best area to stay in when on holiday in Middlefield?
Middlefield has plenty of wonderful places to discover, such as Powder Ridge Mountain Park and Resort. Stay somewhere nearby and make sightseeing stress-free.
Do I need a visa for my Middlefield holiday?
Check the most up-to-date information on official government websites. Your nationality and whether you're travelling for business, leisure or study will determine if you require a visa for Middlefield. Find out about the application process, including the required documentation, fees and turnaround times. Start your application well in advance to allow plenty of time for processing. Some visas may take weeks or even months to go through, depending on the country.
What should I wear on my Middlefield holiday?
Do a little research into the types of clothing people in Middlefield wear, and maybe even check out fashion pages on social media for inspiration. Whatever your look, aim to create a versatile wardrobe full of pieces that suit your destination and show off your personal style. Pack your bags with confidence by checking the weather forecast in Middlefield. July brings the warmest temperatures, with daily averages of 23ºC, while January days average -1ºC, making it the coolest month.
What does an Expedia Middlefield holiday include?
Flights, hotels and car hires, or any combination of them --- it's your pick! Whether you're exploring Middlefield with the entire family or adventuring solo, there's a bundle to match your style and budget. Once you've made your booking, why not add on a few activities? Private holiday homes and cottages are two popular property types in Middlefield. No matter your holiday style or size of your group, you can rely on Expedia for the freedom and flexibility to customise your escape.
Does Expedia offer Book Now, Pay Later Middlefield holidays?
Expedia has partnered with online lender Klarna to make booking your next getaway a little easier on the wallet. Paying by instalment means you can spread the costs of your next dream escape, leaving you with more cash to splash while you're travelling. Klarna has several payment plans to pick from, so you're sure to find something that fits into your budget. Browse these flexible payment options:
  • Pay monthly holidays: If paying across multiple transactions is what works best for you, Klarna can help. Paying in convenient monthly instalments will make your getaway dreams come true.
  • No-deposit holidays: If no upfront fee for your trip makes pressing that "book now" button more stress-free, choose a no-deposit holiday plan with Klarna so that you can Book Now, Pay Later!

Can I choose my airline with a Middlefield Expedia holiday?
Expedia has access to more than 400 partner airlines globally, so you sure can! Simply pick your preferred carrier and create the perfect Middlefield trip.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.