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
1 Block To St. Helena Main Street Shops-Restaurants! Avail June 2-7, Aug 18-21
10.0 out of 10, Exceptional, 231 reviews
"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 reviews
"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
Great Price! Sunset Beach House private beach, firepits, hottub, dock, & more!
10.0 out of 10, Exceptional, 98 reviews
"Everything was great!"
Great Price! Sunset Beach House private beach, firepits, hottub, dock, & more!
Save an average of 15% on thousands of hotels when you're signed in
Home near Sonoma & Calistoga in heart of Wine Country
9.6 out of 10, Exceptional, 22 reviews
"Thank you for the clean, quiet place to land"
Home near Sonoma & Calistoga in heart of Wine Country
Wooded Restful Retreat, with broad scenic views, outdoor dining
10.0 out of 10, Exceptional, 279 reviews
"Comfy and clean place to stay and relax"
Wooded Restful Retreat, with broad scenic views, outdoor dining
Lakefront Vacation Home, Private Beach, Dock, Pool Table, Fishing, Pet-Friendly!
8.8 out of 10, Excellent, 134 reviews
"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 HK$2,930
per night
10 Jun - 11 Jun
Lakefront Vacation Home, Private Beach, Dock, Pool Table, Fishing, Pet-Friendly!
Cottage home near the Russian River; county parks; numerous wineries
10.0 out of 10, Exceptional, 79 reviews
"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
Stunning retreat with private hot tub, firepit & 1 acre of country charm
9.2 out of 10, Wonderful, 65 reviews
"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, 160 reviews
"This cottage is perfectly located if you’re looking into exploring kenwood and all of the beautiful wineries around it. Very clean place. Its an older cottage but very specious . The host was very flexible and friendly. Thank you"
Charming Country Home Nestled In Kenwood Village the heart of the wine country.
The Lake Cottage on Soda Bay-Pet Friendly, Private Deck, Dock & Kayaks
10.0 out of 10, Exceptional, 49 reviews
"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 HK$2,539
per night
12 Jun - 13 Jun
The Lake Cottage on Soda Bay-Pet Friendly, Private Deck, Dock & Kayaks
Updated & Sunny Sonoma 1950s Ranch Near Santa Rosa & Wineries
9.8 out of 10, Exceptional, 90 reviews
"We were celebrating the anniversary of family members. The house is conveniently located, very attractive interior and backyard with nice amenities. On Day 2 the washer would not work despite multiple texts and phone calls to the property management company there was little to no response. We ended up taking our blotches snd the house towels to a laundry mat. Finally, on the day we were leaving we got a text back that s technician would be there next Tuesday (four days after we left). Beside...
Updated & Sunny Sonoma 1950s Ranch Near Santa Rosa & Wineries
Wine Country Backyard Escape
10.0 out of 10, Exceptional, 8 reviews
"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
E - Tiny Home, Big Feel - Just minutes from town and Sonoma County Airport!
8.8 out of 10, Excellent, 3 reviews
"Really nice private area on the property - for the review about the wifi - it worked wonderful - was gone during the day but relaxing and good vibe when I was there. Nice outside area as well."
The price is HK$1,164
per night
9 Jun - 10 Jun
E - Tiny Home, Big Feel - Just minutes from town and Sonoma County Airport!
Windsor home on golf course w/ hot tub
9.4 out of 10, Exceptional, 24 reviews
"We had 10 people and we all fit in the house comfortably! We loved the open layout in the kitchen. It allowed us all to really enjoy our time together."
Windsor home on golf course w/ hot tub
Picturesque sunset views perfect for couples, families and fishermen
10.0 out of 10, Exceptional, 32 reviews
"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 reviews
"Very nice spacious house. Quiet neighborhood. Just what we all needed. Beds are SUPER comfy!"
Beautiful 4 bedroom home w/ luxurious furnishings
Beautiful Wine Country Vacation Home - St. Helena Short Term Permit PL-24-021
10.0 out of 10, Exceptional, 199 reviews
"It was great and very spacious. It was hard to tell from the listing pictures on the two upper rooms on the third level that share a bathroom but we made it all work between 10 of us. The air conditioning was a little wonky the first day just getting it to stay on but once we figured it out it was totally fine!"
The price is HK$12,886
per night
10 Jun - 11 Jun
Beautiful Wine Country Vacation Home - St. Helena Short Term Permit PL-24-021
5BD/5BA Pool+Spa+Sonos+10beds: 12min Healdsburg & Alexander Valley
9.6 out of 10, Exceptional, 12 reviews
"We enjoyed the house very much! Backyard was great for cocktails and relaxing. The host was very responsive. Clean and well kept."
The price is HK$6,875
per night
16 Jun - 17 Jun
5BD/5BA Pool+Spa+Sonos+10beds: 12min Healdsburg & Alexander Valley
Healdsburg Villa on a Vineyard with Amazing Poolside Sunsets
10.0 out of 10, Exceptional, 68 reviews
"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
Majestic Rock House
9.8 out of 10, Exceptional, 19 reviews
"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
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

Safari West
2.0 star property
9.4 out of 10, Exceptional, 219 reviews
"Incredible experience!"
The price is HK$3,710
per night
10 Jun - 11 Jun
Safari West
Beautiful Wine Country Vacation Home - St. Helena Short Term Permit PL-24-021
10.0 out of 10, Exceptional, 199 reviews
"It was great and very spacious. It was hard to tell from the listing pictures on the two upper rooms on the third level that share a bathroom but we made it all work between 10 of us. The air conditioning was a little wonky the first day just getting it to stay on but once we figured it out it was totally fine!"
The price is HK$12,886
per night
10 Jun - 11 Jun
Beautiful Wine Country Vacation Home - St. Helena Short Term Permit PL-24-021
St Helena ~ Best Views Over Both Famous Valleys ~ Blair Spangler Design Group
10.0 out of 10, Exceptional, 15 reviews
"12 of us traveled to Napa for my 40th birthday and we had THE BEST trip ever. The accommodations were lovely, spacious, clean and luxurious. The concierge was so responsive and helpful. The chefs were fantastic. I'd highly recommend this property. As a frequent traveler, I've stayed in many luxury rentals and this was by far my favorite."
St Helena ~ Best Views Over Both Famous Valleys ~ Blair Spangler Design Group
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.

Middletown Vacation Homes information

Number of reviews
1,376
Accommodation
511 Vacation Homes
Lowest Price
HK$1,164
Highest Price
HK$12,886

Recent Hotel Reviews in Middletown
Expedia verified reviews