Photo by Chris Kailher

Holiday Homes in Middlefield

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Featured Holiday Homes in Middlefield

Charming 2-bedroom townhome
Fridge, microwave, oven, stovetop
Charming 2-bedroom townhome
2.0 star property
9.6 out of 10, Exceptional, (5)
"The home was beautiful and I would stay there again."
The price is AU$344
includes taxes & fees
20 Nov - 21 Nov
Charming 2-bedroom townhome
Waterfront Beach House
Terrace/patio
Waterfront Beach House
9.6 out of 10, Exceptional, (39)
"This was perfect for us. We had a family funeral and this was a nice retreat. We would stay again for sure. "
Waterfront Beach House
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub
Outdoor pool, a heated pool
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
Year-Round Waterview 4 Beds, 2 Baths, Sleeps 13 with Linens & Towels Included
Beach nearby, sun-loungers, beach towels
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
Historic Essex Home w/ Large Yard Near Downtown!
TV
Historic Essex Home w/ Large Yard Near Downtown!
9.8 out of 10, Exceptional, (40)
"All bedrooms up were difficult with luggage. Fully equipped for an extended stay would be convenient. Very close to marina and shopping."
Historic Essex Home w/ Large Yard Near Downtown!
15mins to Hartford, Home in Manchester w/ King Bed
Fridge, microwave, oven, cookware/dishes/utensils
15mins to Hartford, Home in Manchester w/ King Bed
2.0 star property
10.0 out of 10, Exceptional, (1)
"Very spacious location. Ideal fit for our plans. "
The price is AU$575
includes taxes & fees
21 Nov - 22 Nov
15mins to Hartford, Home in Manchester w/ King Bed
Amazing Lakefront Property
Dining
Amazing Lakefront Property
9.8 out of 10, Exceptional, (23)
"Great views and a good central location for day trips 👌. "
Amazing Lakefront Property
Lakefront Home, Close to Mt Southington!
Fridge, microwave, stovetop, dishwasher
Lakefront Home, Close to Mt Southington!
10.0 out of 10, Exceptional, (13)
"Staff very much enjoyed the atmosphere after long days of work. Wonderful Ownership. Thank you so much Susan!"
Lakefront Home, Close to Mt Southington!
Summer at the Haddam House
Property grounds
Summer at the Haddam House
10.0 out of 10, Exceptional, (49)
"Hands down , Very nice property , highly recommend staying at this location . You won’t be let down . "
Summer at the Haddam House
Cozy Modern Home
Fridge, microwave, oven, stovetop
Cozy Modern Home
9.6 out of 10, Exceptional, (29)
"I gave the property listing all five stars because all aspects of the property were as described in the listing. The only suggestion l have for improvement of the property would be for hand railings to be installed on the wall side of the stairs to the 2nd floor, as the stairs are very steep and hard to navigate for an older person. "
Cozy Modern Home
Charming 3BR Hilltop House, Newly Remodeled with Arcade
Interior
Charming 3BR Hilltop House, Newly Remodeled with Arcade
10.0 out of 10, Exceptional, (18)
"So glad we found this property to accommodate our family of six for the weekend. It was cozy, updated and immaculately clean. The owners seem to have thought of everything and clearly care about providing an exceptional experience. Highly recommend!"
Charming 3BR Hilltop House, Newly Remodeled with Arcade
BEACH BUM CARRIAGE HOUSE with kayaks - steps to beach, park, marinas & brewery!
Beach nearby
BEACH BUM CARRIAGE HOUSE with kayaks - steps to beach, park, marinas & brewery!
10.0 out of 10, Exceptional, (2)
"Started with Kristine greeting us as we drove in. Was accommodating to our requests and was very quick to reply to our few messages. Clothes dryer is very small. Short walk to a great park and beach."
BEACH BUM CARRIAGE HOUSE with kayaks - steps to beach, park, marinas & brewery!
Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit.
Smart TV
Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit.
9.6 out of 10, Exceptional, (11)
"Very nice and clean family was visiting my daughter at the University of New Haven was also very close "
The price is AU$432
includes taxes & fees
16 Dec - 17 Dec
Gorgeous Waterfront 3 Bedroom, 1.5 Bathroom Unit.
McAngel Haven: 5 mins from Yale
Fridge, microwave, oven, stovetop
McAngel Haven: 5 mins from Yale
9.6 out of 10, Exceptional, (5)
"The house was perfect for a family of 4 and a couple! It’s a fairly quiet neighborhood so it was a good place to come back to relax each day. Parking for 2 cars was helpful and the coded entry was very easy. Nice setup and thoughtful features. Angela was very responsive and friendly! Definitely recommend!"
The price is AU$829
includes taxes & fees
21 Nov - 22 Nov
McAngel Haven: 5 mins from Yale
Home on the sound
Beach
Home on the sound
8.6 out of 10, Excellent, (7)
"This was a greay stay and the property was really cute and cozy. It is an upstairs portion of a duplex "
Home on the sound
Cozy 2 bedroom home located minutes from downtown
Interior
Cozy 2 bedroom home located minutes from downtown
9.6 out of 10, Exceptional, (23)
"We found this house to be the perfect spot just outside downtown New Haven. We did need a car, but the location was great. We had easy access to main roads, downtown, and there was sufficient local restaurants and stores for stocking the house. The unit was as it appeared and the host was responsive and helpful when needed."
Cozy 2 bedroom home located minutes from downtown
Guilford home -self check in, off-street parking
Outdoor dining
Guilford home -self check in, off-street parking
9.4 out of 10, Exceptional, (8)
"The property was nice, clean and comfortable. "
Guilford home -self check in, off-street parking
Near Yale 8 beds Gaming Room
Fridge, microwave, oven, stovetop
Near Yale 8 beds Gaming Room
The price is AU$1,721
includes taxes & fees
20 Nov - 21 Nov
Near Yale 8 beds Gaming Room
NEW-Another Fun Downtown Location 1st floor
Interior
NEW-Another Fun Downtown Location 1st floor
2.0 star property
10.0 out of 10, Exceptional, (6)
"This was our second stay at this VRBO and hope to stay again on return trips to the area."
NEW-Another Fun Downtown Location 1st floor
The Jewel of The Cove - Historic Coastal Retreat
Beach nearby
The Jewel of The Cove - Historic Coastal Retreat
2.0 star property
10.0 out of 10, Exceptional, (1)
The price is AU$762
includes taxes & fees
8 Dec - 9 Dec
The Jewel of The Cove - Historic Coastal Retreat
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 property types in Middlefield

Amazing Lakefront Property
Dining
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
Fridge, microwave, coffee/tea maker, cookware/dishes/utensils
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!
Miscellaneous
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!
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.