Photo by Chris Kailher

Middlefield Holiday Rentals

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Holiday Rentals in Middlefield

Smart TV, fireplace, offices
Amazing Lakefront Property
10.0 out of 10, Exceptional, (15)
"This was my second go round staying at this property. My family and I enjoyed it the first time. More so the second time with the upgrades. Being familiar with the area was a great help. This time we went in the lake and enjoyed ourselves. We are looking forward to returning back again. Thank you Raymond for letting us stay at your property. Richard and Joanne"
Amazing Lakefront Property
Aerial view
Family-Friendly Lakeside Cottage with Spectacular Sunset Views Pet-Friendly!
10.0 out of 10, Exceptional, (7)
"Adorable cottage with full kitchen, luxurious bathroom and comfiest beds!! Cutest cul de sac with friendly neighbors"
Family-Friendly Lakeside Cottage with Spectacular Sunset Views Pet-Friendly!
Property grounds
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub
10.0 out of 10, Exceptional, (110)
"I stayed at this amazing studio cottage with my girlfriend for 2 nights for her birthday. Our hosts, Liz and Adam were simply amazing. They allowed us an early check in and a late check out. Liz even brought out bicycles for us to use to tour around the neighborhood and ride along the shore line. Because it was my girlfriends birthday (or maybe they just do this), they had Prosecco and Orange Juice plus beer and cheese and other snacks for us when we arrived. The cottage is adorable, perfect...
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub
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Business centre
Luxury Furnished Apartments by Hyatus Downtown at Yale
3.5 star property
10.0 out of 10, Exceptional, (19)
"Everything was okay, the apartment was great, enough space for 3 people. During the nighttime no noise, silence, good for well sleeping and so on… 5 points!"
Luxury Furnished Apartments by Hyatus Downtown at Yale
Smart TV, fireplace
Patchogue River Retreat, 8 minute walk to West Beach
10.0 out of 10, Exceptional, (6)
"House was very nice. Location is great. Easy walk to beach and convenient to Westbrook center."
Patchogue River Retreat, 8 minute walk to West Beach
On the beach, beach towels
gorgeous victorian direct ocean front single family six bedroom, ten rooms
10.0 out of 10, Exceptional, (51)
"Wonderful host. Easy communication. Great house."
gorgeous victorian direct ocean front single family six bedroom, ten rooms
Property grounds
A TREETOPS Retreat! Upscale, Artsy 5 bedroom that sleeps 9-11, With POOL
10.0 out of 10, Exceptional, (15)
"By far the most unique architecture that we have ever stayed in. Every room is an adventure from its shape to the stunning artifacts from around the world. A gorgeous setting that was perfect for relaxing. Everything is first class-five star. So memorable that we are coming back next year."
A TREETOPS Retreat! Upscale, Artsy 5 bedroom that sleeps 9-11, With POOL
4 bedrooms, iron/ironing board, WiFi, bed sheets
Waterfront Cottage in Branford
10.0 out of 10, Exceptional, (80)
"The house is beautiful! Clean and organized. We had everything we needed and the view is incredible. We enjoyed the deck very much. So relaxing. My daughter (the bride) and her friends enjoyed getting ready there in the morning. I can’t say enough good things about this house."
Waterfront Cottage in Branford
Property grounds
Beautiful 4BR Beach House with Private Beach Access.
10.0 out of 10, Exceptional, (65)
"Small house a short walk from beach that well accommodated our party of five. Clean and comfortable, well laid out and equipped with everything you’d need."
Beautiful 4BR Beach House with Private Beach Access.
Property grounds
Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape
10.0 out of 10, Exceptional, (20)
"We had such a relaxing, wonderful stay at this lakefront oasis. The lake views from the upstairs living room & the downstairs kitchen and yard were lovely. The number of song birds was delightful to watch and hear. We counted 31 birds in <1 hour! We also saw turtles, fish, and a Bald Eagle."
Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape
Smart TV, books, stereo
Writer's Retreat & Explorer's Adventure, S of Rte. 1 Madison!
10.0 out of 10, Exceptional, (16)
"My month-long stay was absolutely wonderful. Hunter was an amazing, proactive host. The weather wasn't cooperative in the beginning of my stay, but Hunter went above and beyond to make sure whatever issues arose were taken care of and I couldn't be happier to have made this choice. I will definitely be back!"
Writer's Retreat & Explorer's Adventure, S of Rte. 1 Madison!
Aerial view
Private Island Compound with Large Cottage and Guest House
10.0 out of 10, Exceptional, (18)
"Beautiful property with a really cool history! Loved the water toys and little beach!"
Private Island Compound with Large Cottage and Guest House
Property grounds
The Dream Location for Your Perfect Vacation
9.8 out of 10, Exceptional, (15)
"The cottage has the most wonderful views! We loved our stay!"
The Dream Location for Your Perfect Vacation
Fridge, microwave, oven, stovetop
Amazing Waterfront, Private Sandy Beach 🏖Hot Tub, Gorgeous Sunsets
9.8 out of 10, Exceptional, (55)
"Everything was perfect!! House is amazing for family/friends gathering. Spacious, clean and great views. The home was everything we needed to celebrate the holiday. Thank you to host for communication and special touches throughout the home. Highly recommend"
The price is NZ$3,841
includes taxes & fees
22 Jun - 23 Jun
Amazing Waterfront, Private Sandy Beach 🏖Hot Tub, Gorgeous Sunsets
Property grounds
Waterfront Beach House
9.6 out of 10, Exceptional, (33)
"The cottage is a perfect cozy stay on the water - we stayed in the winter and still were able to enjoy the sand and the sunrises right outside the window. House is well-appointed and well-located within area with access to restaurants and shops in Clinton, Madison, Westbrook, Old Saybrook, etc."
Waterfront Beach House
Fridge, microwave, oven, stovetop
Beautiful Two Bedroom Home with Fireplace
9.6 out of 10, Exceptional, (8)
"Cozy, enjoyable stay at this house, added comforts and beautifully landscaped yard which adds peacefulness to the stay. I was able to relax, reflect and enjoy my time. The host accommodated my needs to make my trip what I needed for me. Definite return to this property in the future. Thank you"
The price is NZ$610
includes taxes & fees
23 May - 24 May
Beautiful Two Bedroom Home with Fireplace
Property grounds
Lake Front home, dock w/2 kayaks, firepit, grill, pedal boat. Lv2 EV charger
9.6 out of 10, Exceptional, (4)
"Super-clean and the kitchen cabinets and drawers were all labeled-a great convenience. The house is situated in a quiet and tranquil spot, perfect for unwinding and enjoying one’s companions. Not avlocation for people who need entertainment, but want tranquility and nature. Would be great if there could be access to the washer and dryer, especially when folks are in and out of the sweet lake. The owners are extremely king and helpful."
Lake Front home, dock w/2 kayaks, firepit, grill, pedal boat. Lv2 EV charger
Interior
Shalom Cottage with private beach rights.
9.4 out of 10, Exceptional, (8)
"Has everything you need for 2, for a Summer stay. (The portable heater didn't keep up with the December evenings)."
The price is NZ$348
includes taxes & fees
29 May - 30 May
Shalom Cottage with private beach rights.
TV, offices
Relaxing Coastal Escape: 3BR Haven
9.2 out of 10, Wonderful, (24)
"Lovely location near the beach/playground with views of wetlands. House was clean and beds comfortable. One mile walk to beautiful town green surrounded by shops and great restaurants. Excellent communication with host. We will stay there again!"
Relaxing Coastal Escape: 3BR Haven
Fridge, microwave, oven, stovetop
comfortable home away from home
9.2 out of 10, Wonderful, (5)
"This little house is tucked behind some bigger neighbors. It was comfortable and quiet! We had a ball watching the antics of a family of squirrels. It fit our needs perfectly!"
comfortable home away from home
Don't see what you're looking for?
See all available 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.

Other types of properties in Middlefield you may be interested in

Exterior detail
New Haven Hotel
3.5 star property
8.8 out of 10, Excellent, (1232)
"Great! "
The price is NZ$281
includes taxes & fees
26 May - 27 May
New Haven Hotel
Exterior
Holiday Inn Express Southington, an IHG Hotel
2.5 star property
8.4 out of 10, Very good, (1001)
"Everything was clean and staff was friendly. The bedding and pillows were very comfortable and fluffy. Very nice stay."
The price is NZ$217
includes taxes & fees
26 May - 27 May
Holiday Inn Express Southington, an IHG Hotel
Lobby
Best Western Hartford Hotel & Suites
2.5 star property
8.0 out of 10, Very good, (999)
"Great breakfast and attentive associates "
The price is NZ$190
includes taxes & fees
3 Jun - 4 Jun
Best Western Hartford Hotel & Suites
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Middlefield holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Middlefield. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Middlefield. Seeing all the best attractions is bound to make you fall in love with Middlefield. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Middlefield short-term rentals, that won’t be hard to do.

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?

Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub : This holiday home rental outside of Middlefield is located on the beach, and has an outdoor pool, a balcony and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave. Kick off your shoes and enjoy yourself with a garden and 1 hot tub.

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.

Recent reviews of Middlefield properties
Expedia verified reviews