Photo by Chris Kailher

Middlefield Vacation Rentals

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Check prices for these dates

Next weekend
Jan 24 - Jan 26
In two weeks
Jan 31 - Feb 2
In one month
Feb 14 - Feb 16
In two months
Mar 14 - Mar 16

Browse Select Middlefield Vacation Homes

McAngel Haven: 5 mins from Yale
Fridge, microwave, oven, stovetop

McAngel Haven: 5 mins from Yale

9.8 out of 10, Exceptional, (9)
"Excellent to had a nice house like that "
The price is CA $369
CA $823 total
includes taxes & fees
Jan 20 - Jan 21
McAngel Haven: 5 mins from Yale
The Santiago in Science Park at Yale New Haven
Exterior detail

The Santiago in Science Park at Yale New Haven

8.0 out of 10, Very good, (5)
"Stay was great. You are within a longish walk or very short drive of all the good stuff in and around New Haven. We had a little mix up with the bedding left by the laundry service but hosts fixed it right away. Unique unit with some fun character. Would stay there again. "
The price is CA $138
CA $253 total
includes taxes & fees
Feb 3 - Feb 4
The Santiago in Science Park at Yale New Haven
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
7.0 out of 10, Good, (2)
"We stay in rental all the time. This was definitely the worst that we have ever seen. There was no booklet of information left to give you instructions for the house. There were no labels on switches, instructions on how to use the fireplace, photograph of the supplies in the kitchen were not the same as what you Experienced. Made it very difficult to cook, so we just didn’t. The pots and pans were old and scratched, and not the kind of thing that anybody should be using and they should be...
The price is CA $190
CA $431 total
includes taxes & fees
Feb 3 - Feb 4
15mins to Hartford, Home in Manchester w/ King Bed
Spacious 5-bedroom, 6 bath vacation home just 30 min drive to casinos
Outdoor pool

Spacious 5-bedroom, 6 bath vacation home just 30 min drive to casinos

10.0 out of 10, Exceptional, (33)
"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 casinos
Amazing Lakefront Property
Dining

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 modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (9)
"My friends and I have stayed twice now at this house and have had the best time both times! It has everything we could need in the house and we can’t wait to be back again!"
The price is CA $869
CA $1,235 total
includes taxes & fees
Jan 20 - Jan 21
New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.
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
Enjoy a taste of New England in Historic Guilford Ct
Beach nearby

Enjoy a taste of New England in Historic Guilford Ct

10.0 out of 10, Exceptional, (9)
"Wonderful property combining original details with modern amenities. Well located near the town green and shops. We would definitely stay here again."
Enjoy a taste of New England in Historic Guilford Ct
Steps to beach! Custom-built house with panoramic ocean views, wrap-around deck.
Beach nearby, sun loungers, beach towels

Steps to beach! Custom-built house with panoramic ocean views, wrap-around deck.

10.0 out of 10, Exceptional, (42)
"This property is beautiful and the house is spacious and well equipped for a wonderful stay. The host was attentive and easy to contact when it was necessary. Such a fantastic choice for a stay in a delightful town. "
Steps to beach! Custom-built house with panoramic ocean views, wrap-around deck.
Ranch style living at its best with country garden & patio!
Exterior

Ranch style living at its best with country garden & patio!

9.6 out of 10, Exceptional, (8)
"Host worked with me due to larger dog. Very accurate instructions and all amenities were very good. Will stay here again"
Ranch style living at its best with country garden & patio!
Near Yale with Game Room
Fridge, microwave, oven, stovetop

Near Yale with Game Room

The price is CA $776
CA $1,657 total
includes taxes & fees
Jan 20 - Jan 21
Near Yale with Game Room
Walk to Beaches: Sunny East Haven Home w/ Grill
Beach nearby

Walk to Beaches: Sunny East Haven Home w/ Grill

2.0 star property
10.0 out of 10, Exceptional, (3)
"6 of us stayed here for a music festival. The location, fantastic! Ocean views, check. The bedding, the furniture, kitchen supplies....no amenity was overlooked. Happened to meet owner when were checking in. He was great. Couldn't have been more accomodating. Great great place for a few nights or longer. Wush we were here longer. "
Walk to Beaches: Sunny East Haven Home w/ Grill
Beautiful 3BR, Rare Find, Clean & Guest Favorite
Fridge, microwave, oven, stovetop

Beautiful 3BR, Rare Find, Clean & Guest Favorite

2.0 star property
10.0 out of 10, Exceptional, (2)
"Nice clean 3 bedroom that was as described. It was a short drive to downtown West Hartford."
The price is CA $190
CA $431 total
includes taxes & fees
Jan 20 - Jan 21
Beautiful 3BR, Rare Find, Clean & Guest Favorite
Spacious, quiet suburban getaway in Madison. 15 min from beach & hiking trails!
Outdoor dining

Spacious, quiet suburban getaway in Madison. 15 min from beach & hiking trails!

2.0 star property
10.0 out of 10, Exceptional, (6)
"We had an absolute fantastic time staying at this place. My son was got married at the Beech Tree Cottages (also was the perfect wedding venue) in Madison, Ct. about 15 minutes from the house which worked out perfectly for staying here. From start to finish, everything exceeded our expectations. The communication with Chase was smooth and prompt, making the booking process hassle free. Upon our arrival we were greeted with a welcome gift. The space was clean, modern and beautifully...
Spacious, quiet suburban getaway in Madison. 15 min from beach & hiking trails!
Family Stays: Middletown, CT
Fridge, microwave, oven, stovetop

Family Stays: Middletown, CT

10.0 out of 10, Exceptional, (1)
"Our experience with this facility, from online service to exiting the residence, was the most pleasurable experience, for staying in accommodations when traveling!!The owner was a complete gentleman and it was absolutely wonderful experience to meet and talk with him."
The price is CA $159
CA $287 total
includes taxes & fees
Jan 22 - Jan 23
Family Stays: Middletown, CT
A TREETOPS Retreat! Sleeps 10-12, perfect for large gatherings. Seasonal POOL!
Outdoor pool, a heated pool

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!
Waterfront Beach House
Terrace/patio

Waterfront Beach House

9.6 out of 10, Exceptional, (42)
"The property is nicely located on the water and convenient to many attractions. "
Waterfront Beach House
Charming Coastal Retreat Steps from the Beach!
Smart TV, fireplace, books, stereo

Charming Coastal Retreat Steps from the Beach!

9.8 out of 10, Exceptional, (31)
"The house was perfect for our multi generation gathering, spacious enough for all. The kitchen was well equipped for our cooking needs. The beds very comfortable. Would highly recommend it!"
Charming Coastal Retreat Steps from the Beach!
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, (23)
"Wonderful property. Plenty of room for 7 adults. Would definitely stay there again. "
Charming beach home, complete with pool & cozy guest house!
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
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, (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
Fridge, microwave, coffee/tea maker, cookware/dishes/utensils

New Haven Village Suites

3.0 star property
7.6 out of 10, Good, (1994)
"One of our favorites"
The price is CA $143
CA $165 total
includes taxes & fees
Jan 27 - Jan 28
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.