Photo by Matthew Walls

Middletown Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
19 Dec - 21 Dec
In two months
30 Jan - 1 Feb
In three months
27 Feb - 1 Mar
In four months
27 Mar - 29 Mar

Holiday Rentals in Middletown

Property grounds
Backyard Garden Oasis

Backyard Garden Oasis

3.0 star property
Middletown
9.6 out of 10, Exceptional, (51)
"Cute garden area, quiet, nice all inclusive spot"
United States
Jodi
The price is HK$1,510
HK$1,684 total
includes taxes & fees
4 Dec - 5 Dec
Backyard Garden Oasis
View from property
Clear Lake Cottages & Marina

Clear Lake Cottages & Marina

2.5 star property
Clearlake
9.0 out of 10, Wonderful, (326)
"Great stay!"
United States
Andrey and Irina
The price is HK$1,225
HK$1,366 total
includes taxes & fees
4 Dec - 5 Dec
Clear Lake Cottages & Marina
Interior
Beautiful Wine Country Vacation Home - St. Helena Short Term Permit PL-24-021

Beautiful Wine Country Vacation Home - St. Helena Short Term Permit PL-24-021

St Helena
10.0 out of 10, Exceptional, (252)
"Wonderful home, perfect place for a family of all ages! "
United States
Anonymous traveller
The price is HK$12,066
HK$15,534 total
includes taxes & fees
4 Dec - 5 Dec
Beautiful Wine Country Vacation Home - St. Helena Short Term Permit PL-24-021
Front of property
The Ranch at Lake Sonoma

The Ranch at Lake Sonoma

1.0 star property
Geyserville
10.0 out of 10, Exceptional, (1)
"The location is fantastic, with a spectacular view on the lake if you choose a lakeview. A very genuine welcome from The Ranch team, with all detailed explanations, a map to help you to navigate around. For our first time going camping, we want definitely to come back there !"
United States
Tamara
The price is HK$462
HK$527 total
includes taxes & fees
4 Dec - 5 Dec
The Ranch at Lake Sonoma
Outdoor dining
Private Wine Country Estate with Panoramic Views, Tennis Court - TOT Cert 450N

Private Wine Country Estate with Panoramic Views, Tennis Court - TOT Cert 450N

Kenwood
10.0 out of 10, Exceptional, (243)
"Absolutely beautiful and fun getaway with family and friends. We can't wait to come back next year. "
United States
Judy W.
The price is HK$12,455
HK$18,915 total
includes taxes & fees
29 Dec - 30 Dec
Private Wine Country Estate with Panoramic Views, Tennis Court - TOT Cert 450N
Outdoor dining
Casa Bella Estate in Wine Country w/ New Pool!

Casa Bella Estate in Wine Country w/ New Pool!

Kenwood
9.6 out of 10, Exceptional, (136)
"Lovely property. Pool was perfect for families with small children. Outdoor amenities are first rate. Comfortable bedding, well-equipped kitchen. Perfect setting for a large family gathering."
United States
Nita R.
Casa Bella Estate in Wine Country w/ New Pool!
Terrace/patio
Escape to Wine County in your independant Cottage in Downtown Calistoga

Escape to Wine County in your independant Cottage in Downtown Calistoga

Calistoga
9.6 out of 10, Exceptional, (30)
"Great place! Clean, and very close to everything!"
United States
Levi J.
The price is HK$2,328
HK$3,193 total
includes taxes & fees
4 Dec - 5 Dec
Escape to Wine County in your independant Cottage in Downtown Calistoga
Meeting facility
Mandala Springs Wellness Retreat Center

Mandala Springs Wellness Retreat Center

3.5 star property
Kelseyville
8.6 out of 10, Excellent, (27)
"Beautiful quiet retreat "
United States
Belwadi
The price is HK$1,254
HK$1,963 total
includes taxes & fees
4 Dec - 5 Dec
Mandala Springs Wellness Retreat Center
Terrace/patio
Calistoga Dream Inn

Calistoga Dream Inn

Calistoga
9.8 out of 10, Exceptional, (21)
"Convenient location. Within walking distance of the Main Street in Calistoga, including coffee shops, shopping, restaurants, and grocery store. Central location for wineries.Home was clean and bright, with a modern upscale kitchen, lounge area and a nice back yard.Most importantly the host is very responsive throughout the stay."
United States
Anonymous traveller
Calistoga Dream Inn
Exterior
Luxury Napa Estate With Pool/Hot-tub/Concierge

Luxury Napa Estate With Pool/Hot-tub/Concierge

Calistoga
10.0 out of 10, Exceptional, (50)
"Perfect location for a wine weekend. "
United States
John W.
The price is HK$10,217
HK$16,913 total
includes taxes & fees
9 Dec - 10 Dec
Luxury Napa Estate With Pool/Hot-tub/Concierge
Outdoor spa tub
Casa Loma - Luxury estate with the Best Napa Valley Views - 35 acres

Casa Loma - Luxury estate with the Best Napa Valley Views - 35 acres

Sonoma County
10.0 out of 10, Exceptional, (141)
"Stunning property in a perfect location in Napa Valley! House and amenities were amazing, owner was incredibly thoughtful and responsive, and the setting is unbeatable. Will absolutely stay again."
United States
Jonathan B.
Casa Loma - Luxury estate with the Best Napa Valley Views - 35 acres
Dining
Modern Bennett Valley Home with Privacy and Views

Modern Bennett Valley Home with Privacy and Views

Santa Rosa
10.0 out of 10, Exceptional, (67)
"We really enjoyed our stay. The house & farm were an amazing escape from the noise of the city. We will definitely be coming back if available. "
United States
James T.
Modern Bennett Valley Home with Privacy and Views
Outdoor pool
Luxury Vineyard Guest House with Amazing Views, Pool, Pickle Ball & Tennis!

Luxury Vineyard Guest House with Amazing Views, Pool, Pickle Ball & Tennis!

Calistoga
10.0 out of 10, Exceptional, (89)
"This was our second visit and it was as lovely as we had remembered. It's remote enough to feel like an oasis of calm yet clonvenient to all the sites Napa has to offer. The house is well-appointed and the property is beautiful."
United States
Lois P.
Luxury Vineyard Guest House with Amazing Views, Pool, Pickle Ball & Tennis!
Smart TV, fireplace, DVD player, books
Wine Country Getaway with Panoramic Views-5 min from downtown Healdsburg

Wine Country Getaway with Panoramic Views-5 min from downtown Healdsburg

Healdsburg
10.0 out of 10, Exceptional, (267)
"This is a beautiful home with a fantastic view. Plenty of room for multiple couples, and it has everything you need. "
United States
Michelle B.
Wine Country Getaway with Panoramic Views-5 min from downtown Healdsburg
Terrace/patio
Scenic and tranquil in the heart of Sonoma wine country.

Scenic and tranquil in the heart of Sonoma wine country.

Riebli-Wallace Neighborhood Group
9.8 out of 10, Exceptional, (103)
"We had a wonderful stay. Everything was as described and expected. Thank you, would stay again. "
United States
JEFF H.
Scenic and tranquil in the heart of Sonoma wine country.
Exterior
Luxury Napa Valley Estate Surrounded by Vineyards

Luxury Napa Valley Estate Surrounded by Vineyards

Calistoga
9.8 out of 10, Exceptional, (33)
"Amazing home and property. Suited for all ages.Quiet, comfortable, convenient to all Napa area.We loved it‼"
United States
Mary Ann D.
Luxury Napa Valley Estate Surrounded by Vineyards
Outdoor dining
Wine Country Harvest Vacation Home

Wine Country Harvest Vacation Home

Scenic Brush Creek
9.8 out of 10, Exceptional, (88)
"Very clean and beautiful place. "
United States
Kevin K.
The price is HK$2,574
HK$5,281 total
includes taxes & fees
5 Dec - 6 Dec
Wine Country Harvest Vacation Home
A heated pool
Farpoint: Heated Infinity Pool, Mountain Views

Farpoint: Heated Infinity Pool, Mountain Views

Santa Rosa
9.8 out of 10, Exceptional, (7)
"Great location with lots of amenities. Very calming atmosphere. Very attentive staff. Can’t wait to go back."
United States
Christy
The price is HK$3,503
HK$7,333 total
includes taxes & fees
14 Dec - 15 Dec
Farpoint: Heated Infinity Pool, Mountain Views
Fridge, microwave, oven, stovetop
Awesome Hilltop Views, Pool, Vineyards, Olive Trees, 5 mins to Healdsburg

Awesome Hilltop Views, Pool, Vineyards, Olive Trees, 5 mins to Healdsburg

Healdsburg
10.0 out of 10, Exceptional, (66)
"This place was beautiful and we had such a lovely stay. Would recommend and also stay here again! Hosts were communicative and Andy at the property’s winery (Limerick) was an absolute gem! 🥹"
United States
Alex D.
Awesome Hilltop Views, Pool, Vineyards, Olive Trees, 5 mins to Healdsburg
Outdoor spa tub
Private Vineyard Estate | Sleeps 10

Private Vineyard Estate | Sleeps 10

Windsor
9.4 out of 10, Exceptional, (3)
"Stayed here for a wedding "
United States
Lanna E.
The price is HK$3,456
HK$7,802 total
includes taxes & fees
7 Dec - 8 Dec
Private Vineyard Estate | Sleeps 10
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Middletown Hotel Reviews

Hotel La Rose

Hotel La Rose

10/10 Excellent
"A convenient, comfortable, and historic place to spend a get-a-way to Sonoma County!"
Michael 3-night trip
Posted 21 hours ago
Hotel La Rose

Find out more about Middletown

Search for holiday rentals in Middletown on Expedia! You can easily find your home rentals, villas, holiday apartments in Middletown using one of the methods below:

  • View our selection of featured holiday rentals in Middletown
  • Use the map to find apartments and other holiday homes in the Middletown neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Middletown while they last

Look no further and take a look at our great range of rental properties in Middletown!

Frequently asked questions

Can I find holiday rentals in Middletown?

Yes, there are holiday rentals close to the most popular sights in Middletown, or you can select a more secluded option if you're looking for a relaxing stay. Middletown is known for its hot springs and wineries. Make sure you have time to check out the spas and casinos during your trip.

What are some of the best holiday rentals that Middletown has to offer?

Casa Bella Estate in Wine Country w/ New Pool!: This holiday home rental outside of Middletown is located in a rural location, and has a fireplace, 1 hot tub and a BBQ to put you at ease in your new surroundings. It has 10 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

How many holiday rentals are there in Middletown?

Expedia has 11 holiday rentals for your stay in Middletown.

What can I see and do in Middletown?

Explore the area and family-friendly sights such as SingleThread Farm at Dry Creek, or get out into nature at a spot like Boggs Mountain Demonstration State Forest. Other places in town to visit include Twin Pine Casino and Robert Louis Stevenson State Park.

What are holiday rentals like in Middletown?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Middletown. Holiday rentals offer amenities such as patios, hot tubs and fire pits so you'll feel just like you're at home. If you're concerned about cleanliness, holiday rentals can provide a sense of security away from shared hotel lifts and busy lobbies while still allowing you the enjoyment of travel. You'll also find more space in a holiday rental than in a hotel, which makes a holiday rental an attractive option for family trips.