Photo by Chris Kailher

Search Vacation Homes in Middlefield

June 2025

SundayMondayTuesdayWednesdayThursdayFridaySaturday

July 2025

SundayMondayTuesdayWednesdayThursdayFridaySaturday
    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

Next weekend
27 Jun - 29 Jun
In two weeks
4 Jul - 6 Jul
In one month
18 Jul - 20 Jul
In two months
15 Aug - 17 Aug

Vacation Homes in Middlefield

Blue Back Bungalow
Exterior

Blue Back Bungalow

2.0 star property
9.6 out of 10, Exceptional, (12)
"Seamless check in, beautiful quaint home with excellent water pressure and hot water!Location is excellent, thank you to our hosts "
The price is AED 367
AED 1,315 total
includes taxes & fees
17 Jun - 18 Jun
Blue Back Bungalow
🌾Welcoming Tiny Home! Downtown & Beachy☀️
Terrace/patio

🌾Welcoming Tiny Home! Downtown & Beachy☀️

8.8 out of 10, Excellent, (6)
"The property had a beautiful secluded outdoor space that complemented the tiny home."
🌾Welcoming Tiny Home! Downtown & Beachy☀️
Relax by the River | Branford Waterfront Home
Fridge, microwave, oven, stovetop

Relax by the River | Branford Waterfront Home

10.0 out of 10, Exceptional, (2)
"Clean, family friendly, and fun."
Relax by the River | Branford Waterfront Home
Grammy's Lake House w/ Private Waterfront Access
Interior

Grammy's Lake House w/ Private Waterfront Access

9.4 out of 10, Exceptional, (12)
"Enjoyable stay, nice property and great views. The home is aged, but the location is amazing! We had a nice weekend excursion to enjoy New England in October. "
Grammy's Lake House w/ Private Waterfront Access
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, (130)
"My husband and I had a wonderful time at this idyllic cottage on the water in Branford. Great location and hosts. Beautiful community for long walks, restaurants nearby. Highly recommend! "
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub
Charming 3BR Hilltop House, Newly Remodeled with Arcade
Interior

Charming 3BR Hilltop House, Newly Remodeled with Arcade

10.0 out of 10, Exceptional, (21)
"Clean, Cozy and Comfortable "
Charming 3BR Hilltop House, Newly Remodeled with Arcade
Charming beach home, complete with pool & cozy guest house!
Interior

Charming beach home, complete with pool & cozy guest house!

9.6 out of 10, Exceptional, (25)
"Wonderful property. Plenty of room for 7 adults. Would definitely stay there again. "
Charming beach home, complete with pool & cozy guest house!
2 Mi to Dtwn: 2-Acre Retreat w/ Large Yard!
Fridge, microwave, oven, stovetop

2 Mi to Dtwn: 2-Acre Retreat w/ Large Yard!

10.0 out of 10, Exceptional, (1)
"My family are former Madison residents and were visiting friends over the Holidays. This location was everything we were looking for. Highly recommend. "
2 Mi to Dtwn: 2-Acre Retreat w/ Large Yard!
Shoreline Oasis
Exterior

Shoreline Oasis

6.0 out of 10, (1)
"So the listing said house number 26 but it's really 25. So we circled the block a few times. Then the key was not in the key safe. Called the owner who apologized profusely. Had to wait a half hour for the key. Not ideal. Otherwise ok. "
The price is AED 657
AED 957 total
includes taxes & fees
11 Jul - 12 Jul
Shoreline Oasis
Cozy 3 bedroom minutes from Yale and the beach
Private kitchen

Cozy 3 bedroom minutes from Yale and the beach

Cozy 3 bedroom minutes from Yale and the beach
Spacious 5-bedroom, 6 bath vacation home just 30 min drive to beaches and casino
Outdoor pool

Spacious 5-bedroom, 6 bath vacation home just 30 min drive to beaches and casino

10.0 out of 10, Exceptional, (35)
"Spacious, full stocked, amenity filled home with enough room for family members to gather and/or spread out.The game room is perfect for all ages with a variety of choices for your competitive play. Grocery/liquor store and Gillette Castle State Park are minutes away.Beautiful area. "
Spacious 5-bedroom, 6 bath vacation home just 30 min drive to beaches and casino
Historical Blvd. Cheney Bros HillTop Mansion
Fridge, microwave, oven, stovetop

Historical Blvd. Cheney Bros HillTop Mansion

9.2 out of 10, Wonderful, (14)
"We enjoyed our stay, everything as described."
Historical Blvd. Cheney Bros HillTop Mansion
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, (2)
"A group of us stayed there for a work trip and it was the perfect situation for us. The beds were SO comfortable! The decor was vibe! Supplies were plenty. Towels were top quality. The fire pit was so fun to use on our last night in town. Very close to a beach so we could dip our toes in the ocean.There is an airport runway behind the property but the noise wasn’t terrible. "
The price is AED 911
AED 2,072 total
includes taxes & fees
29 Jun - 30 Jun
The Jewel of The Cove - Historic Coastal Retreat
Direct Waterfront Private Beach Escape
Outdoor dining

Direct Waterfront Private Beach Escape

9.8 out of 10, Exceptional, (13)
"The house was great! Beautiful ocean front property with beachy vibes all throughout the neighborhood and interior of the home. The host was extremely clear on directions and provided amazing instructions. Very comfortable stay! "
Direct Waterfront Private Beach Escape
Old Avon Village
Private kitchen

Old Avon Village

2.0 star property
6.0 out of 10, (4)
"We had a nice stay while visiting our son at AOF. There were a couple of small issues which the owner remedied IMMEDIATELY. Things happen in life which are unforeseen, we appreciated the owner jumping on the issues quickly."
The price is AED 404
AED 1,226 total
includes taxes & fees
23 Jun - 24 Jun
Old Avon Village
Heavenly Home in New Haven /5 mins drive from Yale

Heavenly Home in New Haven /5 mins drive from Yale

8.8 out of 10, Excellent, (18)
"The property was prepared well and we enjoyed our stay. Thanks"
The price is AED 3,239
AED 4,459 total
includes taxes & fees
22 Jun - 23 Jun
Heavenly Home in New Haven /5 mins drive from Yale
McAngel Haven: 5 mins from Yale
Fridge, microwave, oven, stovetop

McAngel Haven: 5 mins from Yale

9.8 out of 10, Exceptional, (10)
"Had a wonderful but short stay in New Haven. Home.of PEZ and PIZZA . "
The price is AED 843
AED 1,909 total
includes taxes & fees
17 Jun - 18 Jun
McAngel Haven: 5 mins from Yale
Charming 3-Bedroom Home with Modern Comforts in West Hartford
Fridge, microwave, oven, stovetop

Charming 3-Bedroom Home with Modern Comforts in West Hartford

2.0 star property
9.0 out of 10, Wonderful, (4)
"Great house in a safe neighborhood with a fenced in yard. Amenities provided. "
The price is AED 744
AED 1,418 total
includes taxes & fees
22 Jun - 23 Jun
Charming 3-Bedroom Home with Modern Comforts in West Hartford
New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.
Smart TV, fireplace, video games

New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.

10.0 out of 10, Exceptional, (14)
"perfect location beautiful house"
The price is AED 1,983
AED 2,850 total
includes taxes & fees
22 Jun - 23 Jun
New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.
7Mins to Yale I ENTIRE HOUSE I Large fenced yard I King bed I 3BR I Group Gather
Fridge, microwave, oven, stovetop

7Mins to Yale I ENTIRE HOUSE I Large fenced yard I King bed I 3BR I Group Gather

10.0 out of 10, Exceptional, (11)
"Is a great location given minutes from Yale. We were able to make a nice meal to celebrate our son’s success. Nice place!"
7Mins to Yale I ENTIRE HOUSE I Large fenced yard I King bed I 3BR I Group Gather
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free