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Compare 243 Vacation Homes in Middlefield with updated reviews, rates, and availability.

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
Beautiful 4BR Beach House with Private Beach Access.
10.0 out of 10, Exceptional, (65)
"Visited family back in CT and this was the perfect place to stay. Kind of like a Tardis, it was bigger on the inside! Thank you!"
Beautiful 4BR Beach House with Private Beach Access.
Magnificent Riverfront home, completely private. BOOK 7 NIGHTS GET 10% OFF
9.8 out of 10, Exceptional, (107)
"A number of friends and I stayed here to be nearby our friends wake and memorial service. It was a really nice homely, quiet space that had plenty of room for everyone and the view over the river is gorgeous. Would love to come back sometime for more uplifting circumstances"
Magnificent Riverfront home, completely private. BOOK 7 NIGHTS GET 10% OFF
Save an average of 15% on thousands of hotels when you're signed in
New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.
10.0 out of 10, Exceptional, (2)
"Beautiful new home and property! Would one back for sure!"
The price is $600
$853 total
includes taxes & fees
Jun 14 - Jun 15
New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub
10.0 out of 10, Exceptional, (113)
"Was looking for a coastal retreat to enjoy a couple days with my daughter who lives near this location. This property had everything from a super clean, cozy studio with fridge and counters filled with surprising treats, incredible hot tub with lights in the trees, pool to cool off and little private beach to launch a paddlleboard and kayak, or hang out at night with a burn pit. If you are just a beach person and want toes in the sand and to swim in the ocean, this area is not for you....
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub
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
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
Direct Waterfront Private Beach Escape
9.8 out of 10, Exceptional, (9)
"Thank you so Much, the family had a great time. Found some good seaglass"
Direct Waterfront Private Beach Escape
Cozy Modern Home
9.6 out of 10, Exceptional, (26)
"Very nice place, stay there for a couple of nights for a get together, plenty of room. Only problem was some of the cleaning supplies where locked away where we couldn’t access it so we had to bring a mop and other supplies."
Cozy Modern Home
McAngel Haven: 5 mins from Yale
9.0 out of 10, Wonderful, (2)
"The location was good for our needs and the place well maintained. There were scent devices in many outlets and two of our guests are allergic. We had to unplug them and air out the home. It would be good to alert guests to those devices and allow them to choose to have them not present."
The price is $219
$525 total
includes taxes & fees
Jul 14 - Jul 15
McAngel Haven: 5 mins from Yale
Trout Brook Trail 2 · Sprawling Classic New England Home
10.0 out of 10, Exceptional, (11)
"In town for our daughters graduation. The home was perfect in every way! Clean, all rooms are a good size, nicely situated kitchen, beautiful deck for socializing, our guests did not feel like we were on top of each other. Plenty of blankets, towels, kitchen supplies. Everything in good working condition. The home has antique charm with updated benefits. The host Mark was easy to communicate with. We walked to town and loved every part of our weekend! Its a must! Thank you Mark for sharing Trout...
The price is $316
$529 total
includes taxes & fees
Jun 16 - Jun 17
Trout Brook Trail 2 · Sprawling Classic New England Home
Family Friendly Lake House: Lake Pocotopaug, Fire-pit, Kayaks, Canoe. Sunsets.
10.0 out of 10, Exceptional, (13)
"This is a beautiful house on a lovely lake. It made a wonderful home base for our long weekend while we were in the area for our son's college graduation. Kris and Alan are fabulous hosts and they were readily available when a couple of questions popped up. There were so many amenities included in the house plus loads of extras like the makings for s'mores. Everything was labeled, so it was easy to feel at home. The lake is gorgeous, and there are kayaks and a canoe that guests can use, as well...
Family Friendly Lake House: Lake Pocotopaug, Fire-pit, Kayaks, Canoe. Sunsets.
Near Yale 8 beds Gaming Room
Near Yale 8 beds Gaming Room
Year-Round Waterview 4 Beds, 2 Baths, Sleeps 13 with Linens & Towels Included
9.0 out of 10, Wonderful, (69)
"We very much enjoyed our stay and the host had everything prepared for us. The check in/out process was very easy as well!"
The price is $290
$614 total
includes taxes & fees
Jun 16 - Jun 17
Year-Round Waterview 4 Beds, 2 Baths, Sleeps 13 with Linens & Towels Included
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
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
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
Ennis Cottage - A holiday by the sea!
9.8 out of 10, Exceptional, (14)
"Branford is home to our family and this spot was a perfect place to drop the bags! Quient place, clean with all you need for 2 people"
Ennis Cottage - A holiday by the sea!
Historic Essex Home w/ Large Yard Near Downtown!
10.0 out of 10, Exceptional, (32)
"We absolutely loved our stay here. It was very peaceful. The hosts were easy to contact and replied quickly"
Historic Essex Home w/ Large Yard Near Downtown!
Beachside Retreat
9.4 out of 10, Exceptional, (3)
"Old world charm meets modern amenities, beach views are calming and relaxing. Exceptional communication with host."
Beachside Retreat
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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 property types in Middlefield

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
New Haven Village Suites
3.0 star property
7.6 out of 10, Good, (1843)
"Comfortable beds and clean for the most part. Rooms are good size. More like a studio apartment. Will stay again sometime 👍 👍 ✌️. "
The price is $99
$114 total
includes taxes & fees
Jul 1 - Jul 2
New Haven Village Suites
Family-Friendly Lakeside Cottage with Spectacular Sunset Views Pet-Friendly!
10.0 out of 10, Exceptional, (8)
"We were there for a family event in Glastonbury for just a couple of days, and so we didn't go to the lake. However, the cottage was perfect for our needs -- quiet, allowed for contemplation, and privacy that we needed. We hope to perhaps and experience the beautiful lake."
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.

Middlefield Vacation Homes information

Number of reviews
521
Accommodation
243 Vacation Homes
Lowest Price
$219
Highest Price
$600

Recent reviews of Middlefield hotels
Expedia verified reviews