Middlefield Holiday Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Middlefield holiday rentals

9.6 out of 10, Exceptional, (121 reviews)
"Staff was sooo helpful that stood out the most honestly I loved it I’ll book again definitely "
United States
Aliah
The price is AU$243
includes taxes & fees
5 Mar - 6 Mar
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

Apartment in East Haddam

Walk To Goodspeed Opera House!
9.4 out of 10, Exceptional, (34 reviews)
"Place was clean, beds were comfortable. We were only there one night but was well worth it."
United States
Annette L.
The price is AU$258
includes taxes & fees
5 Mar - 6 Mar
Walk To Goodspeed Opera House!
9.6 out of 10, Exceptional, (37 reviews)
"Many local restaurants near by. Christy's for breakfast was very good. "
United States
Benjamin H.
The price is AU$259
includes taxes & fees
5 Mar - 6 Mar
1-bedroom cottage with Grove Beach 🏖️ access.
10.0 out of 10, Exceptional, (28 reviews)
"Wonderful home"
United States
Glenna M.
The price is AU$363
includes taxes & fees
4 Apr - 5 Apr
Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown
9.0 out of 10, Wonderful, (13 reviews)
"Excellent option for a short stay near the heart of it all in Wallingford."
United States
Jeanette W.
The price is AU$430
includes taxes & fees
8 Mar - 9 Mar
Once the old Schools house now a newly furnished Apartment
10.0 out of 10, Exceptional, (55 reviews)
"Amazing property, we loved everything about it, highly recommended, will stay again "
United States
Rick
The price is AU$1,133
includes taxes & fees
5 Mar - 6 Mar
COZY Maple Tree Cabin - Situated on 6 private acres- Enjoy nature
9.8 out of 10, Exceptional, (8 reviews)
"Place was just as advertised. It was clean, comfy, nice neighborhood. Check in and out was easy with no issues. "
United States
Ryan A.
The price is AU$491
includes taxes & fees
9 Mar - 10 Mar
#23 *COMFORT & LUXURY* 3 BR/2 BA House

Apartment in Manchester Center

Humble Abode #2
10.0 out of 10, Exceptional, (1 review)
"the place was clean bed was nice"
United States
Jonathan
The price is AU$227
includes taxes & fees
5 Mar - 6 Mar
Humble Abode #2

Apartment in Wallingford Center

All New 1BR with tons of Charm
9.8 out of 10, Exceptional, (8 reviews)
"Charming, unique, and very comfortable. Would surely stay again. "
United States
David S.
The price is AU$430
includes taxes & fees
8 Mar - 9 Mar
All New 1BR with tons of Charm
10.0 out of 10, Exceptional, (6 reviews)
"Quiet place with spacious living room perfect for movie nights. Also just a 10-minute drive from the beach and multiple dining options. Host was very accommodating and communicative. Would stay here again."
United States
Veronica
The price is AU$467
includes taxes & fees
5 Mar - 6 Mar
Angelica’s safe haven @ west haven
9.6 out of 10, Exceptional, (15 reviews)
"Had a really nice stay, enjoyed this open airy space with comfortable beds and beautiful light with a view of the river. Very nice time, would stay again."
United States
Brian B.
The price is AU$459
includes taxes & fees
9 Mar - 10 Mar
Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit.
10.0 out of 10, Exceptional, (7 reviews)
"Cute, comfortable, quiet accommodation. It was perfect for our visit to Hartford. "
United States
Diana V.
The price is AU$265
includes taxes & fees
15 Mar - 16 Mar
Cozy 1-bedroom with WiFi, central air, in unit laundry in enjoyable Manchester

Holiday Home in Middletown

Cozy Guest Suite in Historic Home
10.0 out of 10, Exceptional, (1 review)
"Perfect for a single traveler. Clean, roomy, quaint room. "
United States
Brooke
The price is AU$304
includes taxes & fees
8 Mar - 9 Mar
Cozy Guest Suite in Historic Home
10.0 out of 10, Exceptional, (1 review)
"Super great communication and help getting situated in the room!"
United States
Glenn
The price is AU$220
includes taxes & fees
4 Apr - 5 Apr
Cozy Room in charming New Haven near Yale/Hospitals!

Holiday Home in West Haven

McAngel Haven: 5 mins from Yale
9.6 out of 10, Exceptional, (20 reviews)
"Excellent location Clean and spacious Comfortable beds "
United States
Joseph T.
The price is AU$747
includes taxes & fees
5 Mar - 6 Mar
McAngel Haven: 5 mins from Yale
9.8 out of 10, Exceptional, (7 reviews)
"loved it so much, beautiful property 100 % would stay again "
United States
Leilani R.
The price is AU$729
includes taxes & fees
11 Mar - 12 Mar
The Jewel of The Cove - Historic Coastal Retreat
9.8 out of 10, Exceptional, (10 reviews)
"Beautiful and spacious home in lovely neighbourhood. We so enjoyed our brief stay. "
Australia
Nina
The price is AU$600
includes taxes & fees
22 Mar - 23 Mar
Casa Soleada in Heart of East Rock 3BR | Cozy King Bed | Near DT/Yale
9.2 out of 10, Wonderful, (20 reviews)
"Great value very close to university. "
United States
Lawrence
The price is AU$320
includes taxes & fees
5 Mar - 6 Mar
Stocked home close to Yale, in Heart of New Haven
9.6 out of 10, Exceptional, (19 reviews)
"House was great & close to where we needed to be. "
United States
Erica M.
The price is AU$402
includes taxes & fees
9 Mar - 10 Mar
Modern ~ 3 Bedroom House ~ Sleeps 8 ~ 11 mins to Hartford
The price is AU$293
includes taxes & fees
19 Mar - 20 Mar
One bedroom apartment in United States of America, New Haven
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.

The Annual Holiday Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.
Save an average of 15% on thousands of hotels when you're signed in

Top Middlefield Hotel Reviews

Find out more about Middlefield

Everything you need to know about Middlefield holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Middlefield holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Middlefield holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Middlefield holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Middlefield. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Middlefield holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Middlefield holiday rentals we have selected for you start as low as AU$243 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Middlefield rentals

At Expedia, we put the best Middlefield holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Middlefield rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Middlefield holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Middlefield. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Can I find a holiday rental in Middlefield?

Yes, there are holiday rentals close to the most popular sights in Middlefield, or you can select a more secluded option if you're looking for a relaxing stay. Middlefield is known for its golf courses and waterfalls. Make sure you have time to check out the ski areas and restaurants during your trip.

What are some of the best holiday rentals that Middlefield has to offer?

A spacious TREETOPS Reunion/ Retreat/Event venue! Sleeps 10-12. Seasonal POOL!: This holiday home rental outside of Middlefield is located in the city centre, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a balcony, a garden and a selection of books so that you can immerse yourself in your holiday.

How many holiday rentals are there in Middlefield?

With 6 Expedia holiday rentals, you're guaranteed to find just the right place for your Middlefield stay.

What’s there to see and do in Middlefield?

Lake Beseck Beach and Wadsworth Falls State Park are a couple of lovely local spots to get outside and enjoy nature. Other places in town to visit include Lyman Orchards and Powder Ridge Mountain Park and Resort.

What’s a holiday rental in Middlefield like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Middlefield. Holiday rentals provide amenities like WiFi and washers and dryers so you'll have a home away from home. If you're concerned about cleanliness, holiday rentals can offer a sense of privacy away from public hotel lifts and lobbies bustling with people while still allowing you the experience of travel. You'll also have more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a popular choice for small groups.