Photo by Chris Kailher

Middlefield Holiday Rentals

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Holiday Rentals in Middlefield

Amazing Lakefront Property
9.8 out of 10, Exceptional, (23)
"Great views and a good central location for day trips 👌. "
Amazing Lakefront Property
New Haven Village Suites
3.0 star property
7.6 out of 10, Good, (1964)
"It is a great Apartment-hotel and the suites have the right amenities. One critic that I have would be that there would sometimes you could smell the cigarette smoke from other neighbours blowing into the furnace. Public transportation is limited and so it's best to have a car. Staff is super helpful and accommodating. "
The price is AU$175
includes taxes & fees
24 Nov - 25 Nov
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, (126)
"We stayed here for an anniversary weekend away and found the property and neighborhood to be amazing. We enjoyed the hot tub, pool and firepit and went kayaking in the afternoon. Enjoyed amazing sunsets from the deck; Adam gave us spot-on restaurant recommendations. I don't know if the supply of snacks is standard or an anniversary "special", but all in all this place was a wonderful find. Thank you!!"
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub
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
Year-Round Waterview 4 Beds, 2 Baths, Sleeps 13 with Linens & Towels Included
9.0 out of 10, Wonderful, (85)
"We liked the house which is ideal for a large group. But we were disappointed that the water views shown in the photo gallery did not exist as views from the house directly. "
Year-Round Waterview 4 Beds, 2 Baths, Sleeps 13 with Linens & Towels Included
Luxury Furnished Apartments by Hyatus Downtown at Yale
3.5 star property
9.8 out of 10, Exceptional, (34)
"So comfortable— just like home. I love having a full kitchen and living room with little homey touches. Nice luxury apartment in a great area. I stay here every time I’m in town."
Luxury Furnished Apartments by Hyatus Downtown at Yale
cozy 1 bedroom 3rd floor nice quiet and conveniently located next to everything.
The price is AU$179
includes taxes & fees
16 Nov - 17 Nov
cozy 1 bedroom 3rd floor nice quiet and conveniently located next to everything.
Beautiful cozy rooms near hospital and down town area
8.0 out of 10, Very good, (17)
"I will forever love coming here. The host was great, Parking was amazing, Rooms were so cleanly. "
The price is AU$386
includes taxes & fees
17 Nov - 18 Nov
Beautiful cozy rooms near hospital and down town area
gorgeous victorian direct ocean front single family six bedroom, ten rooms
10.0 out of 10, Exceptional, (58)
"Beautiful home with even more beautiful ocean view. "
gorgeous victorian direct ocean front single family six bedroom, ten rooms
Shalom Cottage with private beach rights.
9.0 out of 10, Wonderful, (17)
"Loved the overall stay and experience. The private beach access is a bonus"
The price is AU$259
includes taxes & fees
19 Nov - 20 Nov
Shalom Cottage with private beach rights.
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.
Waterfront Cottage in Branford
10.0 out of 10, Exceptional, (87)
"The house was perfect for our annual getaway. We are a group of nine women who have been friends for over 45 years. The large well stocked kitchen with amazing view of the water and fireplace made our Friendsgiving meal memorable! The outdoor hot tub, fire pit, and deck with comfy seating topped off the weekend. Great location, plenty of parking, responsive host. 5/5 stars! "
Waterfront Cottage in Branford
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.
Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape
10.0 out of 10, Exceptional, (26)
"We stayed at the property for 2 nights and it was just what we had hoped. We enjoyed the lake, the fall colors and the house thoroughly. Would love to come back someday. "
Enjoy Lakefront Sunsets in Cozy 2BR Cottage Escape
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!
Writer's Retreat & Explorer's Adventure, S of Rte. 1 Madison!
9.8 out of 10, Exceptional, (23)
"The Writer’s Retreat was perfect for a visit with my college roommate from 40 years ago!! We loved sitting and looking out on the river/marsh at any time of day. So peaceful. And so pretty in the Fall. The location was perfect too. Close to towns along Rt 1 and the beach! "
Writer's Retreat & Explorer's Adventure, S of Rte. 1 Madison!
Amazing Waterfront Home Private Beach 🏖+ Hot Tub
9.8 out of 10, Exceptional, (59)
"Overall the house was great. The beds were so so comfortable and the house has everything you need to cook and grill. Unfortunately weather wasn’t ideal but we still got to enjoy the hot tub and at least check out the private beach. The beach is across the street and it’s not too bad, just a lot of sharp shells so I’d rec wearing some sandals to and on the beach! The house is a lot bigger than we realized and beautiful views all around. Owner was great and responsive. The master was awesome and...
Amazing Waterfront Home Private Beach 🏖+ Hot Tub
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.
Don't see what you're looking for?
See all available properties in Middlefield
Save an average of 15% on thousands of hotels when you're signed in

Other types of properties in Middlefield you may be interested in

Best Western Hartford Hotel & Suites
2.5 star property
7.8 out of 10, Good, (1002)
"Good "
The price is AU$134
includes taxes & fees
16 Dec - 17 Dec
Best Western Hartford Hotel & Suites
New Haven Hotel
3.5 star property
8.8 out of 10, Excellent, (1380)
"The beds were very comfortable and the staff was lovely. "
The price is AU$264
includes taxes & fees
16 Dec - 17 Dec
New Haven Hotel
Red Roof Inn Meriden
2.0 star property
7.6 out of 10, Good, (1000)
"Everything was perfect except next room over the people were coughing and talking, two parents and a child, all night long. Felt like they were in our room, hard to sleep."
The price is AU$159
includes taxes & fees
16 Dec - 17 Dec
Red Roof Inn Meriden
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?

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.