A waterfall in a forested area with a rocky ledge and a calm pool at the base.

Middlefield Vacation Rentals

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Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Middlefield vacation rentals

A compact kitchen with wooden walls, a window with a view of greenery, a built-in dishwasher, and a sink.

1. Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
2.5 star property
East Haddam
9.4 out of 10, Exceptional, (191 reviews)
"Beautiful cabin! Will def go again!"
United States
Morainny
$189 nightly
The price is $217
Sep 28 - Sep 29
Total with taxes and fees
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
A modern kitchen with a central island, bar stools, and pendant lighting.

2. New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.

New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.
Durham
10.0 out of 10, Exceptional, (32 reviews)
"This was an amazing home that exceeded our expectations- it was clean, comfortable, and in such a beautiful setting! A great place for our family to stay together during a college graduation trip! We would certainly come back again!"
United States
Iris F.
$912 nightly
The price is $1,032
Sep 25 - Sep 26
Total with taxes and fees
New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.
A wooden deck with chairs overlooking a calm lake surrounded by autumn foliage.

3. #24 Serenity A Lakefront Cottage Retreat

#24 Serenity A Lakefront Cottage Retreat
Middletown
9.8 out of 10, Exceptional, (25 reviews)
"It was great "
United States
Rodrigo C.
$317 nightly
The price is $341
Sep 28 - Sep 29
Total with taxes and fees
#24 Serenity A Lakefront Cottage Retreat

4. Family Stays: Middletown, CT

Family Stays: Middletown, CT
Middletown
10.0 out of 10, Exceptional, (30 reviews)
"Clean, fully equipped kitchen, family friendly"
United States
Trisha T.
$224 nightly
The price is $255
Sep 29 - Sep 30
Total with taxes and fees
Family Stays: Middletown, CT
A two-story house with a front porch, a garage, and a well-maintained lawn.

5. Home away from home Hot Tub and Pool in Middletown home of Wesleyan university

Home away from home Hot Tub and Pool in Middletown home of Wesleyan university
Middletown
9.6 out of 10, Exceptional, (19 reviews)
"The house was exactly what we were looking for, for a weekend away. Will surely book again, thank you!"
United States
Lee S.
$742 nightly
The price is $840
Sep 28 - Sep 29
Total with taxes and fees
Home away from home Hot Tub and Pool in Middletown home of Wesleyan university
A compact kitchen with modern appliances, a dining area with a glass table and black chairs, and a geometric pendant light.

6. 2BR Apartment Near Wesleyan 102

2BR Apartment Near Wesleyan 102
Washington Street Historic District
9.0 out of 10, Wonderful, (6 reviews)
"Excellent beds and clean."
United States
DANIEL M.
$291 nightly
The price is $330
Sep 27 - Sep 28
Total with taxes and fees
2BR Apartment Near Wesleyan 102
A living room with a grey sofa, red and yellow cushions, a wooden coffee table, and a TV on a wooden cabinet.

7. Newly Remodeled 1-BR Close to Everything yet Very Private

Newly Remodeled 1-BR Close to Everything yet Very Private
Wallingford
10.0 out of 10, Exceptional, (10 reviews)
"Very Clean with everything I needed. I will stay here again."
United States
David M.
$276 nightly
The price is $294
Oct 5 - Oct 6
Total with taxes and fees
Newly Remodeled 1-BR Close to Everything yet Very Private
A bedroom with a bed, a painting of birds, a window with shutters, and a patterned rug.

8. The Cottage by the Woods -private getaway to relax

The Cottage by the Woods -private getaway to relax
Meriden
$562 nightly
The price is $636
Sep 25 - Sep 26
Total with taxes and fees
The Cottage by the Woods -private getaway to relax
A living room with a grey sofa, yellow cushions, a wooden coffee table, a TV on a stand, and a lamp on a side table.

9. Newly Remodeled with deck. Close to town center

Newly Remodeled with deck. Close to town center
Wallingford
10.0 out of 10, Exceptional, (2 reviews)
"The apartment was perfect - size, location, furnishings and price. Will definitely return when I visit friends and family."
United States
Karen F.
$274 nightly
The price is $292
Sep 25 - Sep 26
Total with taxes and fees
Newly Remodeled with deck. Close to town center
A modern living room with a sofa, a dining table, and a massage chair.

10. #29 - Modern 5 Bedroom/2 Bath

#29 - Modern 5 Bedroom/2 Bath
Middletown
9.0 out of 10, Wonderful, (7 reviews)
"Great place! "
United States
Gail R.
$468 nightly
The price is $501
Oct 7 - Oct 8
Total with taxes and fees
#29 - Modern 5 Bedroom/2 Bath
A modern living room with a sofa, coffee table, and a TV mounted on the wall.

11. Once the old Schools house now a newly furnished Apartment

Once the old Schools house now a newly furnished Apartment
Wallingford Center
9.0 out of 10, Wonderful, (14 reviews)
"This apartment was wonderful - clean, well stocked, and cute. Aside from the proximity to the train tracks (although earplugs were thoughtfully provided), the location was great - close to the highway and more importantly Dairy Queen."
United States
Becky P.
$274 nightly
The price is $292
Sep 27 - Sep 28
Total with taxes and fees
Once the old Schools house now a newly furnished Apartment

12. All New 1BR with tons of Charm

All New 1BR with tons of Charm
Wallingford Center
10.0 out of 10, Exceptional, (11 reviews)
"Bigger than expected! Very nice and lovely little amenities provided."
United States
Hannah Z.
$274 nightly
The price is $292
Oct 12 - Oct 13
Total with taxes and fees
All New 1BR with tons of Charm
A spacious living area with a wooden floor, a dining table with chairs, a sofa, and a coffee table. There is a kitchen in the background with white cabinets and a wooden countertop.

13. Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown

Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown
Haddam
10.0 out of 10, Exceptional, (37 reviews)
"We had a great stay, very clean and cozy! Our host was very nice and responsive. Great location, would definitely recommend!!!"
United States
Kristy C.
$236 nightly
The price is $267
Oct 20 - Oct 21
Total with taxes and fees
Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown
A living room with a sofa, a coffee table, and a kitchen area with a brick wall and white appliances.

14. All New Private and Cozy in great location

All New Private and Cozy in great location
Wallingford
8.8 out of 10, Excellent, (6 reviews)
"The pictures must have been old. Very deceiving. Expected it to be more spacious. Hard to get in and out because of the busy road"
United States
ROBERT P.
$263 nightly
The price is $281
Sep 30 - Oct 1
Total with taxes and fees
All New Private and Cozy in great location
A two-story building with a dark blue facade, a central arched entrance, and a number '43' plaque.

15. All New Studio apartment in center of town

All New Studio apartment in center of town
Wallingford Center
10.0 out of 10, Exceptional, (2 reviews)
"I had the most amazing stay. The apartment is decorated beautifully. The bed was comfortable. It was spotless, clean the towels were soft. It was perfect."
United States
Nadine C.
$274 nightly
The price is $292
Sep 29 - Sep 30
Total with taxes and fees
All New Studio apartment in center of town
A spacious living area with a sofa, a dining table, and a kitchen in the background.

16. #43- Modern Luxury Log Cabin Retreat - Fire Pit

#43- Modern Luxury Log Cabin Retreat - Fire Pit
Prospect
9.4 out of 10, Exceptional, (3 reviews)
"3.5 rounding up to 4. We had a good stay overall. I travel fairly often and tend to reserve 5 stars for places where every detail of the guest experience feels really thoughtfully considered. This home was comfortable and worked fine for our trip, but it felt a bit more basic compared to some other rentals I’ve stayed in."
United States
Lauren P.
$503 nightly
The price is $543
Oct 6 - Oct 7
Total with taxes and fees
#43- Modern Luxury Log Cabin Retreat - Fire Pit
A modern living room with a blue sofa, a coffee table, and a dining area with a kitchen in the background.

17. #23 COMFORT & LUXURY 3 BR/2 BA House

#23 COMFORT & LUXURY 3 BR/2 BA House
Southington
9.8 out of 10, Exceptional, (9 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.
$348 nightly
The price is $374
Oct 7 - Oct 8
Total with taxes and fees
#23 COMFORT & LUXURY 3 BR/2 BA House

18. Private Apartment in Berlin

Private Apartment in Berlin
Berlin
9.0 out of 10, Wonderful, (7 reviews)
"Clean, convenient, and great location."
United States
Shaun L.
$230 nightly
The price is $261
Sep 30 - Oct 1
Total with taxes and fees
Private Apartment in Berlin
A loft-style room with a sloped ceiling, a wooden beam, a TV, a white entertainment unit, a black chair, a small table, and a lamp.

19. Bristol Condo Near Espn HQ & Lake Compounce!

Bristol Condo Near Espn HQ & Lake Compounce!
3.5 star property
Bristol
$273 nightly
The price is $314
Sep 27 - Sep 28
Total with taxes and fees
Bristol Condo Near Espn HQ & Lake Compounce!
A covered porch with white rocking chairs and a table, a blue ceiling, and a view of the garden.

20. Charming New England Home in West Hartford Center

Charming New England Home in West Hartford Center
West Hartford
10.0 out of 10, Exceptional, (32 reviews)
"Great location. Beautiful, comfortable home."
United States
karen
$544 nightly
The price is $592
Sep 27 - Sep 28
Total with taxes and fees
Charming New England Home in West Hartford Center
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.
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Top Middlefield Hotel Reviews

New Haven Hotel

New Haven Hotel

8/10 Good
"The room was clean and the hotel staff was OK. Parking is extra and located across the street. The downtown area that it situated down is nice and has some amenities. I wouldn’t stay here for a vacation but for a business trip it’s OK and serve the purpose Nicely as a business traveler looks for 9+ properties. This one fits at a nine."
Chris 1-night trip
Posted 4 hours ago
New Haven Hotel

Find out more about Middlefield

Everything you need to know about Middlefield vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Middlefield vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Middlefield vacation 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 low season months. For more hustle and bustle, you may prefer to visit Middlefield in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $217 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Middlefield rentals

At Expedia, we put the best Middlefield vacation 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 vacation.

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.

Explore a world of travel with Expedia

Frequently asked questions

Can I find a vacation rental in Middlefield?

Yes, there are vacation rentals in Middlefield close to Lyman Orchards Corn Maze, or you can select a more remote option if you're looking for extra privacy while you relax. 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 vacation rentals in Middlefield?

New Madison beach house - Ocean front- Great views- booking Summer 2026: This vacation home rental outside of Middlefield is located on the beach and has a balcony, a barbecue grill, and air-conditioning to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

How many vacation rentals are there in Middlefield?

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

What’s there to see and do in Middlefield?

Lake Beseck Beach and Beseck Lake 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 vacation rental in Middlefield like?

A vacation rental is a private property you can book for a couple of days or more in Middlefield. Vacation rentals provide amenities like kitchens and laundry facilities so you'll have all the conveniences of home. If you're concerned about a clean environment, vacation rentals can offer a sense of security away from public hotel elevators and busy front desks while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a great choice for family trips or small group gatherings.