Photo by Shannon Willitts

Search Vacation Homes in Middletown

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Compare 472 Vacation Homes in Middletown with updated reviews, rates, and availability.

1 Block To St. Helena Main Street Shops-Restaurants! Avail June 2-7, Aug 18-21
10.0 out of 10, Exceptional, (230)
"Beautiful home - extremely clean- the kitchen was well equipped and beautiful! Comfortable beds beds- nice sheets. Very private backyard- nice to sit out and visit and enjoy a bottle of wine. There were 4 of us- two couples. Close walking distance to restaurants and shops. Really enjoyed it. The only thing we would have liked was if there were TV’s in all the bedrooms- not just the Main bedroom. Perfect place to stay in St Helena! ❤️"
1 Block To St. Helena Main Street Shops-Restaurants! Avail June 2-7, Aug 18-21
Sunset Hideaway Lakefront Home w/3 bed/2 bath oasis
10.0 out of 10, Exceptional, (3)
"House was clean and smelled wonderful, great views, plenty of room, and the bonus part was the fish was biting right off our private dock in the backyard, the host Pamela was great"
Sunset Hideaway Lakefront Home w/3 bed/2 bath oasis
Lakefront Vacation Home, Private Beach, Dock, Pool Table, Fishing, Pet-Friendly!
8.8 out of 10, Excellent, (134)
"We were pleased with the home, the view and the grounds. Five adults, 2 kids and 2 dogs were very comfortable. Furniture was nice, there was plenty of dishes, silverware and pots and pans. The owners were super nice and very helpful. We would most definitely stay here again"
The price is AED 1,377
AED 2,641 total
includes taxes & fees
27 Jun - 28 Jun
Lakefront Vacation Home, Private Beach, Dock, Pool Table, Fishing, Pet-Friendly!
Save an average of 15% on thousands of hotels when you're signed in
Stunning retreat with private hot tub, firepit & 1 acre of country charm
9.2 out of 10, Wonderful, (64)
"Wonderful house and location. It was very private but easy access to wineries and restaurants. We did have a few small issues with things like the door entry system not functioning properly and the firepit gas running out, but overall it was a very nice rental!"
Stunning retreat with private hot tub, firepit & 1 acre of country charm
Charming Country Home Nestled In Kenwood Village the heart of the wine country.
10.0 out of 10, Exceptional, (159)
"We came here to enjoyed a quick getaway for my husband’s birthday. The property has a beautiful front garden and lots of outdoor space. The house was clean, well stocked and our host, Jackie, was very responsive. We will definitely stay here again!"
Charming Country Home Nestled In Kenwood Village the heart of the wine country.
Home near Sonoma & Calistoga in heart of Wine Country
9.6 out of 10, Exceptional, (22)
"Thank you for the clean, quiet place to land"
Home near Sonoma & Calistoga in heart of Wine Country
Healdsburg Villa on a Vineyard with Amazing Poolside Sunsets
10.0 out of 10, Exceptional, (68)
"We have visited Healdsburg for years, because of the house, this was our best trip. The home was incredibly comfortable and perfectly situated for wine tasting."
Healdsburg Villa on a Vineyard with Amazing Poolside Sunsets
The Lake Cottage on Soda Bay-Pet Friendly, Private Deck, Dock & Kayaks
10.0 out of 10, Exceptional, (49)
"We stayed here to attend a firefighter conference. After long days of physical training it was great to come back to such a relaxing and clean property!"
The price is AED 1,194
AED 2,124 total
includes taxes & fees
12 Jun - 13 Jun
The Lake Cottage on Soda Bay-Pet Friendly, Private Deck, Dock & Kayaks
Wine Country Backyard Escape
10.0 out of 10, Exceptional, (8)
"Plain house in a quiet neighborhood. The interior was fantastic! It completely remodeled with spacious modern kitchen and 4 beautifully comfortable bedrooms. The interior is very new and on trend. Perfect for 8 people. Backyard is large with jacuzzi outdoor seating, picnic table, barbecue, fire pit with seating ,bacci ball court,small mini golf course and swing set It has a covered patio with string lights throughout the backyard. It was perfect for our dog because the yard is completely fenced...
Wine Country Backyard Escape
Picturesque sunset views perfect for couples, families and fishermen
10.0 out of 10, Exceptional, (32)
"We had the opportunity to stay at this amazing house with my family and friends for our 4th annual fishing trip. The house had everything we needed to accommodate 5 adults and 3 kids. The location probably cannot get any better than that. It’s located right next to the opening of main lake access. Fish is jumping everywhere. We brought 4 bass boats and the house had parking for our truck and trailers as well as a big boat dock to fit all the boats too. Highly recommended and we hope to stay...
Picturesque sunset views perfect for couples, families and fishermen
Beautiful 4 bedroom home w/ luxurious furnishings
9.4 out of 10, Exceptional, (15)
"Very nice spacious house. Quiet neighborhood. Just what we all needed. Beds are SUPER comfy!"
Beautiful 4 bedroom home w/ luxurious furnishings
Valley of the Moon by AvantStay | Tranquil Escape, Large Yard, Hot Tub, Fire Pit
Valley of the Moon by AvantStay | Tranquil Escape, Large Yard, Hot Tub, Fire Pit
Cottage home near the Russian River; county parks; numerous wineries
10.0 out of 10, Exceptional, (79)
"Our family had a wedding to attend in the area and the accommodations were perfect for us! Close to everything. We appreciated having some staples available too (coffee!). Would stay there again for sure!"
Cottage home near the Russian River; county parks; numerous wineries
Private Wine Country Estate with Panoramic Views, Tennis Court - TOT Cert 450N
10.0 out of 10, Exceptional, (200)
"There are no words for how stunning this property is. Everywhere you looked from floor to ceiling windows was just serene. We stayed for a weekend in May with family and friends and enjoyed every square footage. The pool, tennis courts, hot tub, outdoor BBQ/entertainment area- there was no reason to leave. We all enjoyed the peaceful fog covered mornings on the deck with our coffee, seeing if the wild turkeys were going to stop by! House was immaculate, felt like I was living in a show home....
Private Wine Country Estate with Panoramic Views, Tennis Court - TOT Cert 450N
3 bd 2 ba Vineyard View Farmhouse close to downtown St. Helena Permit PL24-006
10.0 out of 10, Exceptional, (96)
"Great location. Super clean. Super efficient. Super comfortable. Well appointed home. Smart and responsive host. Friendly and accommodating. We’ll be back!"
3 bd 2 ba Vineyard View Farmhouse close to downtown St. Helena Permit PL24-006
Lake Front Property With Million Dollar Views With Private Beach and Dock
9.8 out of 10, Exceptional, (54)
"Very nice property. From the instructions, it seems as if the renters had bad experiences in the past, which is really sad. The rental was very clean, location spectacular, truly million dollar views. We had a wonderful time. We hope that future renters can respect their property as their own so that the warnings don't have to seem so restrictive and negative. This is a lovely place and should be treated as such."
Lake Front Property With Million Dollar Views With Private Beach and Dock
Remodeled Lakefront House,Wrap around deck, Private ramp, dock-INCREDIBLE VIEWS!
8.0 out of 10, Very Good, (4)
"The house has a beautiful view from the living room & deck. It rained while we were here, but we all had an amazing time anyway because it was so cozy! The hot tub under the covered deck was fantastic as well!"
Remodeled Lakefront House,Wrap around deck, Private ramp, dock-INCREDIBLE VIEWS!
Pool/Spa Lakefront, Lakeport, Clearlake, King Ste W/dock for fishing or boating.
10.0 out of 10, Exceptional, (10)
"Beautiful home in a quiet neighborhood - we throughly enjoyed our stay! From catfishing, swimming, soaking up the sun & soaking in the hot tub to sitting by the fire pit, BBQing or simply watching various birds and enjoying all of the beauty nature has to offer at the lake. When the wind picked up or got too warm - my mom (91) could still enjoy the view from the living room through the big windows. Our host Steve, was very responsive & very kind - We look forward to coming back!!"
Pool/Spa Lakefront, Lakeport, Clearlake, King Ste W/dock for fishing or boating.
Majestic Rock House
9.8 out of 10, Exceptional, (19)
"The property is a gem. Immaculate and well stocked. Away from the hustle and noise. The views are beatiful and calm. We enjoyed identifying the birds but forgot our binoculars! Our host was helpful getting us settled in. Great stay!"
Majestic Rock House
2 BD/1 BA Home- Wine Country Getaway
9.8 out of 10, Exceptional, (21)
"Nice place, clean, well-maintained and managed, perfect location for us."
2 BD/1 BA Home- Wine Country Getaway
Don't see what you're looking for?
See all available properties in Middletown
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 Middletown

1 Block To St. Helena Main Street Shops-Restaurants! Avail June 2-7, Aug 18-21
10.0 out of 10, Exceptional, (230)
"Beautiful home - extremely clean- the kitchen was well equipped and beautiful! Comfortable beds beds- nice sheets. Very private backyard- nice to sit out and visit and enjoy a bottle of wine. There were 4 of us- two couples. Close walking distance to restaurants and shops. Really enjoyed it. The only thing we would have liked was if there were TV’s in all the bedrooms- not just the Main bedroom. Perfect place to stay in St Helena! ❤️"
1 Block To St. Helena Main Street Shops-Restaurants! Avail June 2-7, Aug 18-21
Safari West
2.0 star property
9.4 out of 10, Exceptional, (219)
"Incredible experience!"
The price is AED 1,745
AED 1,989 total
includes taxes & fees
2 Jun - 3 Jun
Safari West
Clear Lake Cottages & Marina
2.5 star property
9.0 out of 10, Wonderful, (272)
"Lovely lakefront cottage with a great kitchenette perfect for making breakfast in! The cottage was clean and well equipped! We wish we could have stayed longer! "
Clear Lake Cottages & Marina
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.

Recent reviews of Middletown hotels
Expedia verified reviews