Photo by Shannon Willitts
Middletown Vacation Rentals
Change your mind
Book hotels with free cancellation
Be picky
Search almost a million properties worldwide
Check prices for these dates
Next weekend
In two weeks
In one month
In two months
Browse Select Middletown Vacation Homes

3 bd 2 ba Vineyard View Farmhouse close to downtown St. Helena Permit PL24-006
3 bd 2 ba Vineyard View Farmhouse close to downtown St. Helena Permit PL24-006
10.0 out of 10, Exceptional, (128)

Sonoma Wine Country Retreat: Scenic, tranquil, bucolic, Hot Tub
Sonoma Wine Country Retreat: Scenic, tranquil, bucolic, Hot Tub
10.0 out of 10, Exceptional, (96)

Casa Pavone, by Vinifera Homes
Casa Pavone, by Vinifera Homes
10.0 out of 10, Exceptional, (7)

Luxury 3-bedroom Estate surrounded by a 20-acre vineyard and 30-mile views.
Luxury 3-bedroom Estate surrounded by a 20-acre vineyard and 30-mile views.
10.0 out of 10, Exceptional, (6)

Charming Lake View house with WiFi, AC in tranquil Clearlake Oaks
Charming Lake View house with WiFi, AC in tranquil Clearlake Oaks

LAKEFRONT OASIS w/ BOAT DOCK FISHERMEN SPECIAL!
LAKEFRONT OASIS w/ BOAT DOCK FISHERMEN SPECIAL!
8.8 out of 10, Excellent, (13)

The Lake Cottage on Soda Bay-Pet Friendly, Private Deck, Dock & Kayaks
The Lake Cottage on Soda Bay-Pet Friendly, Private Deck, Dock & Kayaks
10.0 out of 10, Exceptional, (66)

Charming Country Home Nestled In Kenwood Village the heart of the wine country.
Charming Country Home Nestled In Kenwood Village the heart of the wine country.
10.0 out of 10, Exceptional, (200)
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.
Save an average of 15% on thousands of hotels when you're signed in
Top Middletown Hotel Reviews

Golden Haven Hot Springs
10/10 Excellent
Find out more about Middletown
Find out more about Middletown
Middletown Vacation Homes information
Number of reviews | 911 |
---|---|
Accommodation | 679 Vacation Homes |
Lowest Price | CA $74 |
Highest Price | CA $521 |
Explore a world of travel with Expedia
Explore a world of travel with Expedia
Top Vacation Homes in Other Destinations
- Vacation Homes in Los Angeles
- Vacation Homes in San Francisco
- Vacation Homes in Reno
- Vacation Homes in Sacramento
- Vacation Homes in Fresno
- Vacation Homes in Oakland
- Vacation Homes in Bakersfield
- Vacation Homes in Stockton
- Vacation Homes in Riverside
- Vacation Homes in San Bernardino
- Vacation Homes in Modesto
More Accommodation Types in Middletown
- Cottages in Middletown
- Apartments in Middletown
- Villas in Middletown
- Condo Rentals in Middletown
- B&B in Middletown
- Farmstay in Middletown
- Cabin Rentals in Middletown
- Motels in Middletown
- Resorts in Middletown
- Guest Houses in Middletown
- Aparthotels in Middletown
- RV Parks in Middletown
- Inns in Middletown
- Lodges in Middletown
- Holiday Park Resorts in Middletown
- Castles in Middletown
- Chalets in Middletown
- Safari Tentalow in Middletown
- Hotels
All Accommodation Types
Be inspired: Top Vacation Homes destinations in 2025
- Orlando Vacation Homes
- Florida Vacation Homes
- Kissimmee Vacation Homes
- Hawaii Vacation Homes
- Costa Rica Vacation Homes
- Walt Disney World® Vacation Homes
- Palm Springs Vacation Homes
- Naples Vacation Homes
- Victoria Vacation Homes
- Kelowna Vacation Homes
- Toronto Vacation Homes
- Las Vegas Vacation Homes
- Vancouver Vacation Homes
- Mexico Vacation Homes
- Phoenix Vacation Homes
- Fort Lauderdale Vacation Homes
- Davenport Vacation Homes
- Myrtle Beach Vacation Homes
- Los Angeles Vacation Homes
- Cape Coral Vacation Homes
More ways to book
Expedia's Latest Trends
Hotels
Flights
Vacation Rentals