Photo by Chris Kailher

Middlefield Holiday Rentals

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Holiday Rentals in Middlefield

Amazing Lakefront Property

9.8 out of 10, Exceptional, (24)
"Absolutely beautiful house! Super clean! Superb setting! Very comfortable! Amazing view! Many amenities! Host very responsive and kind! The property manager quickly responded to our needs. My family and friends loved the spectacular experience and would definitely comeback! "
Amazing Lakefront Property

New Haven Village Suites

3.0 star property
7.6 out of 10, Good, (1985)
"One of our favorites"
The price is AU$181
includes taxes & fees
30 Dec - 31 Dec
New Haven Village Suites

Family-Friendly Lakeside Cottage with Spectacular Sunset Views Pet-Friendly!

10.0 out of 10, Exceptional, (13)
"This was a great spot to stay with my wife, another couple, and my dog! The house is small - especially downstairs. But it is extremely well thought out and space is used as effectively as can be. Upstairs had 2 good sized bedrooms with king beds and a nicely renovated bathroom with a great shower. The house is located in a small, cute, and a bit of an unusual neighborhood. Very quiet. Very safe feel. But not too good for much dog walking and parking is super tight. Owner was very good with...
Family-Friendly Lakeside Cottage with Spectacular Sunset Views Pet-Friendly!

Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub

10.0 out of 10, Exceptional, (127)
"Although I went went it is cold the view and location were excellant. I can definately see taking advantage of this place during the summer. The host was responsive and available. "
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub

Luxury Furnished Apartments by Hyatus Downtown at Yale

3.5 star property
9.8 out of 10, Exceptional, (37)
"I was completely satisfied with my stay. Apartment had wonderful amenities and an amazing view. Great location near downtown restaurants too."
Luxury Furnished Apartments by Hyatus Downtown at Yale

Patchogue River Retreat, 8 minute walk to West Beach

10.0 out of 10, Exceptional, (8)
"My staff and I stayed here for a horse show. It was clean and very comfortable. We wished we had time to actual enjoy the house!!!"
Patchogue River Retreat, 8 minute walk to West Beach

Spacious 5-bedroom, 6 bath vacation home just 5 min drive to Connecticut River

10.0 out of 10, Exceptional, (32)
"We stayed for our annual Columbus Day weekend away with a group of 9 friends. The house was very comfortable and we had plenty of space. We really enjoyed the game room in the evenings - all the games were in excellent condition and everything was in working order (which has not usually been the case at other vacation rentals we have been to). We were lucky enough to have beatiful fall weather all weekend, so we could enjoy the lovely back yard. We made use of the gas grill, watch a playoff game...
Spacious 5-bedroom, 6 bath vacation home just 5 min drive to Connecticut River

Year-Round Waterview 4 Beds, 2 Baths, Sleeps 13 with Linens & Towels Included

9.0 out of 10, Wonderful, (86)
"Very cute ranch in a lovely neighborhood. Good location for access to area sites like Hammonasset Beach, Chamard Vineyard, and the Water's Edge. Not truly a "water's view", but the house had all the amenities needed for a fun stay! "
Year-Round Waterview 4 Beds, 2 Baths, Sleeps 13 with Linens & Towels Included

cozy 1 bedroom 3rd floor nice quiet and conveniently located next to everything.

The price is AU$187
includes taxes & fees
30 Dec - 31 Dec
cozy 1 bedroom 3rd floor nice quiet and conveniently located next to everything.

Beautiful cozy rooms near hospital and down town area

7.8 out of 10, Good, (18)
"I will forever love coming here. The host was great, Parking was amazing, Rooms were so cleanly. "
The price is AU$407
includes taxes & fees
6 Jan - 7 Jan 2025
Beautiful cozy rooms near hospital and down town area

A TREETOPS Retreat! Sleeps 10-12, perfect for large gatherings. Seasonal POOL!

10.0 out of 10, Exceptional, (24)
"The house is an architectural gem with plenty of space for the family. We enjoyed the fireplace in the evenings."
A TREETOPS Retreat! Sleeps 10-12, perfect for large gatherings. Seasonal POOL!

Gorgeous Victorian direct ocean front single family six bedroom, ten rooms

10.0 out of 10, Exceptional, (58)
"Great"
Gorgeous Victorian direct ocean front single family six bedroom, ten rooms

1-bedroom cottage just 6 minutes from Clinton Crossing Premium Outlets

9.0 out of 10, Wonderful, (20)
"Spent a weekend in this cottage while attending an event for my daughter. Very cozy and comfortable. Host was great, with excellent communication. Renovations are taking place in adjacent units, however it did not impact my stay. Highly recommend. "
The price is AU$311
includes taxes & fees
3 Jan - 4 Jan 2025
1-bedroom cottage just 6 minutes from Clinton Crossing Premium Outlets

Waterfront Cottage in Branford

10.0 out of 10, Exceptional, (89)
"House is beautiful and the view even better. On the waters edge and very quiet grandkids were occupied and very happy "
Waterfront Cottage in Branford

lakefront estate

3.8 out of 10, (8)
"Overall do not stay in this house! They are scamming people! They say they are military family yet took advantage of one!! Still owe me my refund and refuse to answer VRBO to give the okay to refund my money! This place was not clean it was very unsanitary and there were drug paraphernalia in the backyard! Towels wet and dirty on the bathroom floor and one of the bedrooms the sheets were dirty in the floor claimed that the house keeper cleaned it! The pool was disgusting!! I have videos pictures...
lakefront estate

Grace Island. Private Island! Vacations, Getaways, Weddings & Special Events.

Grace Island. Private Island! Vacations, Getaways, Weddings & Special Events.

Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape

10.0 out of 10, Exceptional, (27)
"This was a great get away for Thanksgiving. The listing is very accurate and the house is very well equipped especially as far as the kitchen and supplies. The space is very well thought out as well. "
Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape

The Dream Location for Your Perfect Vacation

9.8 out of 10, Exceptional, (16)
"beautiful quiet spot on the beach, great place to stay."
The Dream Location for Your Perfect Vacation

Beautiful 4BR Beach House with Private Beach Access.

9.8 out of 10, Exceptional, (69)
"our annual girls (5) trip took us to Branford, CT this year. It was awesome to have a private beach access even though we couldn’t get in the water, but it was great for strolls and shell collecting. Would definitely do better with a second bathroom, but we managed just fine. Overall, it’s a nice little place to stay for a getaway. My only issue is not with the hosts or place, but with one of the fees and the checkout process. However, it does not take away from our stay. "
Beautiful 4BR Beach House with Private Beach Access.

New Haven Gem w/ Private Pool, Walk to Beach!

9.6 out of 10, Exceptional, (4)
"In town for college visits we were able to stay and use the home as “base” giving everyone space - inside and out to decompress. Kitchen was great and outdoor space is lovely. Beautiful walk to Lighthouse Point Park!"
New Haven Gem w/ Private Pool, Walk to Beach!
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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Other types of properties in Middlefield you may be interested in

New Haven Hotel

3.5 star property
8.8 out of 10, Excellent, (1385)
"Great stay! "
The price is AU$203
includes taxes & fees
5 Jan - 6 Jan 2025
New Haven Hotel

The Capitol Hotel, Ascend Hotel Collection

3.0 star property
7.4 out of 10, Good, (969)
"Asani was amazing at check in. Very hospitable and knowledgeable of the area, offering recommendations for a meal. Would recommend this hotel to anyone and will go back. "
The price is AU$157
includes taxes & fees
5 Jan - 6 Jan 2025
The Capitol Hotel, Ascend Hotel Collection

Best Western Hartford Hotel & Suites

2.5 star property
7.8 out of 10, Good, (1001)
"WItnessed staff cleaning the interior building,elevators and even the exterior landscaping "
The price is AU$187
includes taxes & fees
12 Jan - 13 Jan 2025
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.

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?

Spacious 5-bedroom, 6 bath vacation home just 5 min drive to Connecticut River: This holiday home rental outside of Middlefield is located on a river, 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 patio, a garden and a selection of games 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.