Photo by Stephanie Sutton

Search Guest Houses in Middletown

Plan, book, stay with confidence

Be picky

Search almost a million properties worldwide

Treat yourself

Change your mind

Book hotels with free cancellation

Check prices for these dates

Next weekend

In two weeks

In one month

In two months

Compare 6 Guest Houses in Middletown with updated reviews, rates, and availability.

Premier Villa, 1 King Bed, Mountain View | Terrace/patio

"Perfect location and stay to combine with dinner at the Inn at Little Washington."

AED 1,382 total

includes taxes & fees

24 Apr - 25 Apr

"Convenient location in Winchester though the property made it feel like you are in the country. Check in time must be precise as the owner needs to explain a couple things and let you in. This was good as my husband had a couple questions. Toaster oven was missing its tray so it was not easy to use the appliance. Coffee maker and refrigerator work great, bathroom facilities work. The house is in great condition and a neat place to stay."

"We are so glad we stumbled upon this gem! Looking to find a place to celebrate our anniversary & get away (long overdue), I found Ramana’s garden paradise. It is a quaint 1920’s carriage house with beautiful hardwood floors, a pedestal tub, fully stocked kitchen & large screened in porch for relaxing on those gorgeous evenings! Upon arrival, Ramana greeted us with our keys & a tour of the whole property, including where we would be staying, showing us where we could find organic veggies & herbs...

"We had a lovely stay! If the weather had been better, I know we would have taken advantage of all the outdoor amenities -- big porch and fire pit. Ferhan was very responisve to any questions we had. "

"This is the perfect couple's heaven. Beautifully decorated, art in every corner. Comfortable bed, relaxing tub and cozy living room couch. The property is gorgeous and very quiet. 10min away from nice restaurants, bakery and more than a dozen wineries. The national park is just 5min away with great trails and breath taking views. Stephen is very attentive and you can add many services to your stay. My husband and I had the most amazing time and can't wait to be back. "

"Had a great time arching the sun rise and set over the blue ridge mountains "

AED 1,163 total

includes taxes & fees

6 May - 7 May

Save an average of 15% on thousands of hotels when you're signed in

Other property types in Middletown

"This lovely cabin was exactly what we were looking for. It's cozy with a spectacular view and the river access was perfectly scenic. "

"This beautiful cabin has everything you need for a wonderful stay. My husband and I stayed here for our 44th anniversary while visiting local wineries. It was a perfect location."

"It was very rustic and supplies were plentiful. The cleaner went above and beyond to help me and checked on me after a bad storm. The only hassle was the security gate, but I understand the need to keep unauthorized persons off the property. It was just getting the key out opening and closing and relocking every trip out. It’s all ok. I do suggest that candles are available as the power was out one night for 3 hours and I was alone and not scared but just in darkness except for moonlight. Loved...