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Check prices for these dates

Next weekend
15 Aug - 17 Aug
In two weeks
22 Aug - 24 Aug
In one month
5 Sept - 7 Sept
In two months
3 Oct - 5 Oct

Featured Villas in Middletown and around

NEW! Serenity house (3-Bedroom Villa) - Pets Allowed
Property grounds

NEW! Serenity house (3-Bedroom Villa) - Pets Allowed

10.0 out of 10, Exceptional, (1)
"One of the best properties I stayed at. My family lived it. The kiddos caught a few fishes. Only issue was the smoke alarm in the master bedroom would occasionally beep at night. My family will be returning"
NEW! Serenity house (3-Bedroom Villa) - Pets Allowed
Secluded Vineyard Estate Healdsburg
Terrace/patio

Secluded Vineyard Estate Healdsburg

9.8 out of 10, Exceptional, (120)
"Nice experience"
Secluded Vineyard Estate Healdsburg
Villa Terra Bella, by Vinifera Homes
Exterior

Villa Terra Bella, by Vinifera Homes

10.0 out of 10, Exceptional, (5)
Villa Terra Bella, by Vinifera Homes
Villa in French Chateau Estate in Napa Valley
Pool

Villa in French Chateau Estate in Napa Valley

9.2 out of 10, Wonderful, (5)
"Amazing property with an ideal location. "
Villa in French Chateau Estate in Napa Valley
Private 1+ acre, Bocce, New Heated Pool and Hot Tub
Exterior

Private 1+ acre, Bocce, New Heated Pool and Hot Tub

10.0 out of 10, Exceptional, (14)
"Everything was so great! The only recommendations I have are to put mirrors in every bedroom and some lighting outside by the pool and hot tub "
The price is €1,023
includes taxes & fees
1 Sept - 2 Sept
Private 1+ acre, Bocce, New Heated Pool and Hot Tub
Spacious 5-bedroom villa, with beautiful lake views in charming Lakeport.
Property grounds

Spacious 5-bedroom villa, with beautiful lake views in charming Lakeport.

Spacious 5-bedroom villa, with beautiful lake views in charming Lakeport.
Luxury Napa Estate With Pool/Hot-tub/Concierge
Exterior

Luxury Napa Estate With Pool/Hot-tub/Concierge

10.0 out of 10, Exceptional, (48)
"Exactly as described and pictured - beautiful property, clean, quiet, comfortable bedding, updated throughout. Gem!"
The price is €1,908
includes taxes & fees
2 Sept - 3 Sept
Luxury Napa Estate With Pool/Hot-tub/Concierge
Villa in French Chateau Estate in Napa Valley
Villa

Villa in French Chateau Estate in Napa Valley

2.0 star property
Villa in French Chateau Estate in Napa Valley
Heart of Sonoma County, Fountain Grove 4BR/4BA home, pool, spa, outdoor kitchen
Terrace/patio

Heart of Sonoma County, Fountain Grove 4BR/4BA home, pool, spa, outdoor kitchen

10.0 out of 10, Exceptional, (1)
"This was a perfect space to come back to after a full day of wine tasting and exploring the Valley. Very spacious, clean, and accommodating of all our needs. The host was prompt with any questions we had and the entire process was as seamless as could be. We will certainly be coming back! Just an amazing property."
Heart of Sonoma County, Fountain Grove 4BR/4BA home, pool, spa, outdoor kitchen
Calistoga Wine Ranch Estate
Exterior

Calistoga Wine Ranch Estate

10.0 out of 10, Exceptional, (83)
"Six couples stayed in the house extremely comfortably. The pool area was fantastic. We enjoyed utilizing the tennis and Pickleball courts and it was conveniently located close to the wineries we wanted to visit. Highly recommend the property and the owners."
Calistoga Wine Ranch Estate
Stunning Country Retreat, Pool, Hottub, Views, 92 Acres
Interior

Stunning Country Retreat, Pool, Hottub, Views, 92 Acres

9.6 out of 10, Exceptional, (14)
"Nice space for a big group. We spent most of our time in the farm house because that is where the majority of the group slept. Pool house is very nice and spacious."
Stunning Country Retreat, Pool, Hottub, Views, 92 Acres
Year-Round Heated Pool | Hot Tub | Fire Pit | Huge Lawn | Vineyard Views
Exterior

Year-Round Heated Pool | Hot Tub | Fire Pit | Huge Lawn | Vineyard Views

10.0 out of 10, Exceptional, (39)
"Perfect place to tour Napa and Sonoma valley "
Year-Round Heated Pool | Hot Tub | Fire Pit | Huge Lawn | Vineyard Views
Calistoga Wine Ranch
Exterior

Calistoga Wine Ranch

10.0 out of 10, Exceptional, (1)
"Beautiful property in the hills of Calistoga. We had a party of six and there was ample room for everyone. The kitchen is well stocked, and every space is thoughtfully appointed. The outdoor spaces are also as lovely, with frequent deer and turkeys passing through the property grounds in evenings. Very serene and relaxing space."
Calistoga Wine Ranch
Calistoga Wine Ranch
Exterior

Calistoga Wine Ranch

4.0 star property
Calistoga Wine Ranch
Villa Colibri, by Vinifera Homes
Exterior

Villa Colibri, by Vinifera Homes

10.0 out of 10, Exceptional, (2)
"This is certainly a place I would love to go back. It would make more sense and enjoyable with a larger group in this property due to the size of it. I would definitely plan to be here longer and not just few days. "
Villa Colibri, by Vinifera Homes
Gorgeous Napa estate 15 mins to St Helena surrounded by vineyards. Permit 138485
Exterior

Gorgeous Napa estate 15 mins to St Helena surrounded by vineyards. Permit 138485

10.0 out of 10, Exceptional, (9)
"A wonderful large house in a beautiful location. Would love to come back."
Gorgeous Napa estate 15 mins to St Helena surrounded by vineyards. Permit 138485
Boutique Compound on Private Vineyard, Complete with Guest House
Terrace/patio

Boutique Compound on Private Vineyard, Complete with Guest House

10.0 out of 10, Exceptional, (83)
"Such a peaceful stay and the perfect get away for 3 ladies! We loved the home and outdoor setting! Can’t wait to return!"
Boutique Compound on Private Vineyard, Complete with Guest House
Stay surrounded by Fitch Mountain Park and Open Space Preserve.
Exterior

Stay surrounded by Fitch Mountain Park and Open Space Preserve.

9.4 out of 10, Exceptional, (24)
"Very clean and comfortable stay. "
Stay surrounded by Fitch Mountain Park and Open Space Preserve.
Exceptional Estate Vineyards in Healdsburg Sonoma County
Property grounds

Exceptional Estate Vineyards in Healdsburg Sonoma County

9.0 out of 10, Wonderful, (2)
"We enjoyed this home because of the large kitchen, huge dinning room table so we could have a meal with everyone sitting at the table. Extra perks... location to several wineries plus a hot tub. "
Exceptional Estate Vineyards in Healdsburg Sonoma County
Live like a vintner in the heart of California Wine Country
Exterior

Live like a vintner in the heart of California Wine Country

Live like a vintner in the heart of California Wine Country
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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Top Middletown Hotel Reviews

Golden Haven Hot Springs

Golden Haven Hot Springs

10/10 Excellent
"We loved our stay, the hotel was cute and it was a very calm and relaxing environment, not to mention the uniqueness of the springs!"
Shannon 1-night trip
Posted 1 day ago
Golden Haven Hot Springs

Frequently asked questions

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How can I find cheap villas in Middletown?
Expedia can help you easily locate cheap villas in Middletown. Simply use our handy filter tool to choose budget, star rating and amenities to refine your search and find a perfect stay in a few clicks.
What is there to do near my villa in Middletown?
The most useful travel accessory is a well-planned schedule. Beaver Creek Vineyards is a wonderful spot to begin your exploration of Middletown.