Family Stays: Middletown, CT

Middletown, Connecticut
$256 avg/night
Minimum Stay 1 Nights
Bed 4

Bed

Bath 2

Bath

Home Private Vacation Home

Property Type

Sleep 8

Max Sleeps

Night 1 nights

Min Stay

Centrally located and just 1.2 miles from Wesleyan University, this home offers comfort, convenience, and plenty of space for groups of all kinds. With four bedrooms across two floors, the layout gives everyone room to spread out. Bedrooms on separate levels create natural privacy, making it easy for guests to unwind while still enjoying the ease of staying together and sharing the comfort of one home.

Whether you're traveling with friends, children, extended family, or multiple couples, the two‑floor setup allows everyone to relax without feeling crowded. Ideal for multi‑generational stays and group getaways.

The space:
Bedrooms: 4 bedrooms across 2 floors.
- First Floor: Two queen bedrooms — great for parents, grandparents, or anyone avoiding stairs.
- Second Floor: One queen bedroom + two twin beds — perfect for a second family, teens, or younger kids.

Bathrooms: Full bathrooms on each floor.

Living Room: Ample space and a large Smart TV with Roku.

Kitchen: Well-equipped with appliances and cookware.

Dining Area: Seats 6 comfortably. Can accommodate up to 8 people with the table extension.

Climate Control: Mitsubishi Electric Split A/C units in bedrooms, living room, and dedicated workspace.

Laundry: Washer and dryer in the basement.

Family-Friendly: High chairs, toddler booster seat, Pack 'n Play, and playpen available for young guests. Shower chair is also available.

Outdoor Relaxation: Enclosed back porch and deck facing the backyard.

Guest access
- Enjoy the full use of the home, including a fenced backyard that borders the woods, providing an ideal space for children to play and run around.
- Self check-in key code entry.
- A 2-car garage and a spacious driveway for extra vehicles.

Other things to note.

Pricing Notice: Our minimum accommodation price covers up to three people. Any guests beyond the first three are charged according to our standard additional‑guest fee.

Maximum Guests: 8 adults.

Guest count:
The total number of guests, including the person making the reservation must match the number listed on the reservation to stay at the property. Bringing any undisclosed additional guest(s) will result in full additional‑guest charges for each night of the stay, plus a 50% penalty.

Safety Measures:
Our property features Ring security cameras. These cameras are external and outward-facing, ensuring privacy within interior spaces. They record video and sound when activated by motion.

Smoking Policy:
Smoking or vaping is not allowed inside the house. A $500 cleaning fee will be assessed for deep cleaning to remove any smoke odor before the next guest checks in. However, you’re welcome to smoke outside in the breezeway - an attached room by the garage. Please use the provided ashtray.

Location and neighborhood:
Our home is conveniently located near the downtown area and the recently updated Veterans Memorial Park swimming pool with a splash pad.
Abundant restaurants, grocery stores, and pharmacies are within easy walking distance.

The home is available for short-term rentals and mid-term stays.

Read More Expand
  • Feature Features
  • Map Map
  • School District Availability
  • Review Review

Feature Features

  • PETS

    No Pets Allowed
  • DINING

    Dining Table
  • SAFETY

    Carbon Monoxide Detector Installed (host Has Indicated There Is A Carbon Monoxide Detector On The Property) Deadbolt Lock Fire Extinguisher First Aid Kit Smoke Detector Installed (host Has Indicated There Is A Smoke Detector On The Property)
  • BEDROOM

    4 Bedrooms Bed Sheets Provided
  • GENERAL

    Recycling Uses Some LED Lighting
  • KITCHEN

    Coffee/tea Maker Cookware/dishes/utensils Dishwasher Electric Kettle Microwave Oven Paper Towels Refrigerator Stovetop
  • LAUNDRY

    Laundry Facilities Near Laundromat Washing Machine And Dryer
  • PARKING

    Onsite Parking Onsite Parking Options Include A Garage
  • INTERNET

    Free WiFi
  • OUTDOORS

    Barbecue Grill Fenced Yard Garden Outdoor Furniture Patio
  • BATHROOMS

    2 Bathrooms Bathtub Or Shower Hair Dryer Shampoo Soap Toilet Paper Towels Provided
  • WORKSPACES

    Computer Monitor Desk Desk Chair
  • LANGS SPOKEN

    English
  • THINGS TO DO

    Fitness Facilities Nearby Swimming Nearby
  • ENTERTAINMENT

    Games Smart TV
  • CLIMATE CONTROL

    Air Conditioning Heating
  • FAMILY FRIENDLY

    Children's Books Children's Dinnerware Highchair Playground Travel Crib
  • LOCATION HIGHLIGHTS

    Near A Hospital
  • SERVICES AND CONVENIENCES

    Iron/ironing Board
  • SUITABILITY/ACCESSIBILITY

    Handrails In Stairways If You Have Requests For Specific Accessibility Needs, Please Contact The Property Using The Information On The Reservation Confirmation Received After Booking. No Elevators Smoke-free Property Well-lit Path To Entrance

CheckIn Check-in : 04:00 PM CheckOut Check-out : 11:00 AM
No Wheelchair No smoking No pets Children allowed
Occupancy Max occupancy : 8

Map Map

School District Availability

Review Review

  • George

    Submitted Apr 7, 2025

    Stayed Apr 4, 2025

    House was extremely clean, plenty of room, and provided all the comforts of home. Owner provided snacks, water, sodas, etc. Everything was perfect. Wouldn't change a thing!

  • Lucy L.

    Submitted Jun 2, 2026

    Stayed May 29, 2026

    Property is very Clean and organized. Host is very nice.

  • Wayne L.

    Submitted May 4, 2026

    Stayed May 1, 2026

    This is a fantastic property; perhaps the most well run, stocked, equipped, and prepared VRBO or the like that I've ever stayed in. House is extremely well kept and organized. The recliners everywhere approach to the living room is a bit hilarious, but no complaints! Very nice grounds, easy to get to, complete and clear communication from the host. Just lovely.

  • Jennifer L.

    Submitted Apr 27, 2026

    Stayed Apr 24, 2026

    Everything about this home is amazing and the host was very friendly and accommodating being in contact with us before coming to stay in the house and during. The house is beautiful and very clean so much room, We had a lot of fun staying here and would definitely recommend anyone to come and stay! 10/10

  • Trisha T.

    Submitted Apr 15, 2026

    Stayed Apr 11, 2026

    Clean, fully equipped kitchen, family friendly

  • Kristin O.

    Submitted Apr 9, 2026

    Stayed Apr 7, 2026

    Gilbert and Mary are excellent hosts. Gilbert communicated a lot of information before we arrived so we were well prepared for our visit. This was probably the best stocked kitchen in any house that I’ve rented. We were not lacking for anything… pots, pans, equipment were all in great shape and the house had everything we needed . Gilbert and Mary very generously left some snacks and drinks and the kitchen had a well stocked spice cabinet. The living room was comfortable and had enough seating for our whole group to hang out together. The beds were really comfortable and the bedrooms were spacious. The bathrooms were very clean and the towels were really nice too! Gilbert and Mary also generously stock the bathrooms with soap, shampoo, conditioner and many other items ‘just in case.’ I can’t say enough good things about the house and the hosts!

  • DANIEL M.

    Submitted Mar 17, 2026

    Stayed Mar 12, 2026

    Everything was perfect. Not much more else to say.

  • Diana C.

    Submitted Mar 1, 2026

    Stayed Feb 28, 2026

    House is immaculate and the hosts were great! Made is feel very welcome. Would definitely stay again!

  • Michelle P.

    Submitted Feb 17, 2026

    Stayed Feb 12, 2026

    The property was clean and welcoming. The hosts included many special touches. Would definitely stay again.

  • Erin

    Submitted Jan 16, 2026

    Stayed Jan 10, 2026

    What stood out most was how beautifully maintained the space was and how genuinely warm and welcoming it felt from the moment we arrived. The host clearly put a lot of care into the details, with thoughtful touches like water and extra toiletries in case something was forgotten, which made us feel right at home. There were plenty of towels and sheets, and the space was comfortable and roomy, making it an easy, relaxing, and enjoyable stay overall. Will definitely return and recommend to anyone visiting the area.

  • Betty-Jean R.

    Submitted Dec 15, 2025

    Stayed Dec 12, 2025

    This was the perfect house to stay in for our family wedding. Gilbert was the perfect host and thought of every amenity we could have asked for. The house was spotless, very nicely decorated, had very comfortable beds and the bath towels were luxurious. The dining table had ample seating for our card playing crowd. From his greeting at arrival to looking out for our well being throughout the stay, Gilbert was a fantastic host.The house was close to our wedding venue and had ample off street parking. If it hadn't been cold and snowing, the backyard and deck looked very appealing. We would love to stay there again.

  • Paula R.

    Submitted Nov 7, 2025

    Stayed Nov 1, 2025

    We had a wonderful stay. My sister and I came down from NH & ME along with our cousin who flew up from NC to attend a family wedding. The home was cozy and inviting with snacks, coffee, tea & bottled water in the fridge. Everything that we could potentially need was thought of; plenty of towels, toiletries, games, books & magazines even a drawer of items that you might have forgotten. We could walk to the pastry shop or drugstore and my sister was able to get her daily run in a neighborhood that was safe.

  • Debbi O.

    Submitted Nov 1, 2025

    Stayed Oct 30, 2025

    We all agree this is our best VRBO experience. Clear communication, everything we needed plus more. We felt welcome and cared about. We had a great visit with family and attended a wedding nearby.

  • Jessica S.

    Submitted Oct 14, 2025

    Stayed Oct 10, 2025

    Gilbert and Mary were wonderful hosts. The house was immaculate and organized. They left snacks and drinks for us upon our arrival to the property which was very much appreciated by kids and adults alike. The house is in a great location; we were close to all the shops and restaurants! The baby loved roaming the fenced in backyard while our 11 year old loved having his own room upstairs to play his video games!

  • Harmony R.

    Submitted Oct 7, 2025

    Stayed Oct 1, 2025

    A truly wonderful experience! The host and home were amazing and we’ll definitely be staying here again!

  • ronald c.

    Submitted Oct 1, 2025

    Stayed Sep 25, 2025

    The location worked well for our needs. The house was super clean. The host supplied everything that you would hope to have and then went above and beyond.Would not hesitate to stay again. Thanks Gilbert for a wonderful stay!

  • Jason C.

    Submitted Sep 19, 2025

    Stayed Sep 14, 2025

    Gilbert was an outstanding host! We loved the house- it was clean, cozy and everything was in excellent condition. Having all the drawers and lighting labeled was very helpful. We really appreciated all the drinks, snacks and extra items when we arrived. The backyard is huge and we loved sitting out on the deck at night. Our kids enjoyed the books and games in the basement. If we ever return to New England for another vacation, we will definitely stay here again!

  • Kimbal G.

    Submitted Aug 26, 2025

    Stayed Aug 19, 2025

    Our family was here for our son and now daughter in laws wedding. We loved the house - perfect location close to the wedding venue , other family homes, and restaurants . Gilbert is the consummate host , polite , great communication , every amenity you could think of provided , balloons and congrats signs, and so clean. The topper were the cotton tail rabbits and woodchuck in the backyard ! Thank you Gilbert for a fantastic stay.

  • Joann W.

    Submitted Aug 17, 2025

    Stayed Aug 15, 2025

    Very nice house. The place was immaculate and the snacks were great. And the grounds were so secure. Every place you walked in the back yard a light would come on for safe walking. The communication was excellent! Would definitely recommend and stay there again.

  • Michelle S.

    Submitted Aug 15, 2025

    Stayed Aug 8, 2025

    We had a wonderful weekend stay. Everything was clean and very clearly marked.The home had everything you could think of and more. Felt like our home for the weekend! Gilbert was wonderful and had the perfect amount of communication. Would certainly stay again in the future if we are in the area. Thanks again Gilbert!

  • Christina M.

    Submitted Jun 7, 2025

    Stayed Jun 2, 2025

    This property is exactly as listed. Bonus is a large beautiful private backyard with a lighted patio and seating (along with several very cute woodland visitors). This home is impeccably kept inside and out. It's fully stocked with everything you might need, including things you may have forgotten. It is a full home. It's like staying with family without the annoying family. The host has thought of absolutely everything you might need. It's centrally located in Middletown in a very nice neighborhood. An Aldi and CVS are within walking distance if needed. It's not far from the major highways, but still in a quiet neighborhood. We were easily able to visit attractions in 4 states within our few days here and come back to the property at night. The owner truly cares about the guests and this home. This is our first time using a vacation rental over a hotel and we might now be hooked. This property and the owner get 5 stars in every possible category.

  • Cari M.

    Submitted May 25, 2025

    Stayed May 23, 2025

    The house was great, the welcome snacks and balloons were thoughtful and the kitchen coffee, etc, was much appreciated. This was an excellent stay and I highly recommend it!

  • Katie W.

    Submitted May 6, 2025

    Stayed May 1, 2025

    There is so much space in this house and yard that we could do things together or have our own place to be. The house is stocked with so much so anything we forgot, they had. We were able to cook every meal, enjoy a big pot of coffee every day, kids had hot cocoa, sit on the enclosed porch and read, eat on the back deck, play catch in the backyard, watch tv and retreat to our own bedrooms at night. It felt like our home. Everything is labeled so we were able to use things without fear we would break it trying to figure out how. The light switch labels were also helpful so we didn't have to guess which switch controlled which lights. There are also a few grocery stores really close to make a last minute stop easy. My daughter was especially excited about the airplane comforters! We have stayed at quite a few places and this may be the best one!

  • Jon N.

    Submitted Apr 29, 2025

    Stayed Apr 27, 2025

    My colleague and I recently had a short two night stay here and we enjoyed it in every way. The house was spotless, perfectly organized and very comfortable. But what really made the trip was the very thoughtful and friendly host. He provided us with tons of useful information for the stay. Gilbert is a true professional and it shows!

  • Elizabeth D.

    Submitted Mar 6, 2025

    Stayed Feb 28, 2025

    We came to the area for a long weekend event at Wesleyan University. I had never booked through VRBO and was not familiar with the process. From my first communication with Gilbert I felt like I was going to visit family. He was amazing to communicate with provided information about the area and the process and was super accommodating when he learned our flight was arriving early. From the moment we stepped through the door we knew our stay would be special. The home is beautiful, beds comfortable but the attention to detail was beyond what I had expected. We were delighted to have some nice treats and drinks in the refrigerator after a long flight. The owners thought of every detail had anything we could have imagined. I only wish I had meet them a few years ago when I began traveling to the area. I would have stayed with them every time. Gilbert thank you for making our stay extra special. Thank you for making us feel at home we really enjoyed your property and your hospitality and hope to see you again soon. If you have a chance to stay at this property take it because it was fantastic and convenient to the area.

  • Sarah T.

    Submitted Jan 21, 2025

    Stayed Jan 19, 2025

    We came to stay at Gilbert’s for a quick ski weekend at Powder Ridge. Gilbert was incredibly gracious and accommodating. He was very easy to communicate with, and really went out of his way to make us feel at home. The location is a little loud at night/early morning, as it is very close to a main road. But the property itself was exactly as described. Clean, comfortable, and very welcoming.

  • Michael H.

    Submitted Jan 10, 2025

    Stayed Jan 7, 2025

    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.

Your dates are Available!

Total

Includes taxes and fees
$255+
View details