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Middletown Holiday Rentals

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Holiday Rentals in Middletown

Backyard Garden Oasis

3.0 star property
9.6 out of 10, Exceptional, (47)
"perfect place"
The price is AU$331
includes taxes & fees
13 July - 14 July
Backyard Garden Oasis

Pool & Deck: Wine Country Hideaway in Middletown!

Pool & Deck: Wine Country Hideaway in Middletown!

Clear Lake Cottages & Marina

2.5 star property
9.0 out of 10, Wonderful, (314)
"The cabin was very clean and it was in a nice and quiet location."
The price is AU$363
includes taxes & fees
22 July - 23 July
Clear Lake Cottages & Marina

The Ranch at Lake Sonoma

1.0 star property
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 !"
The price is AU$104
includes taxes & fees
13 July - 14 July
The Ranch at Lake Sonoma

Luxury 3-bedroom Estate surrounded by a 20-acre vineyard and 30-mile views.

10.0 out of 10, Exceptional, (5)
"We had a pleasant stay at the property over the Memorial Day weekend. It’s away from the crowds but yet 15 mins from Sonoma Lake for water sports and 30 mins from Healdsburg. Amazing view and great time in the pool. "
Luxury 3-bedroom Estate surrounded by a 20-acre vineyard and 30-mile views.

Escape to Wine County in your independant Cottage in Downtown Calistoga

9.8 out of 10, Exceptional, (19)
"We have stayed many times at the Cottage Grove Inn and it never disappoints. "
The price is AU$631
includes taxes & fees
14 July - 15 July
Escape to Wine County in your independant Cottage in Downtown Calistoga

Scenic and tranquil in the heart of Sonoma wine country.

10.0 out of 10, Exceptional, (94)
"Great location views and continently located. "
Scenic and tranquil in the heart of Sonoma wine country.

LAKEFRONT OASIS w/ BOAT DOCK FISHERMEN SPECIAL!

9.6 out of 10, Exceptional, (11)
"Right on the lake nice place to stay"
LAKEFRONT OASIS w/ BOAT DOCK FISHERMEN SPECIAL!

Charming Country Home Nestled In Kenwood Village the heart of the wine country.

10.0 out of 10, Exceptional, (197)
"Fun , lots of things todo nearby , fully equipped accommodation "
Charming Country Home Nestled In Kenwood Village the heart of the wine country.

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

10.0 out of 10, Exceptional, (232)
"Great stay with friends! Plenty of room to spread out. Home had all the amenities and lots of charm."
The price is AU$3,267
includes taxes & fees
14 July - 15 July
Beautiful Wine Country Vacation Home - St. Helena Short Term Permit PL-24-021

Calistoga Mid-Century-Modern w/Pool 4BD/4BA -- Sleeps 8

10.0 out of 10, Exceptional, (21)
"The host was very communicative before and during our stay. The property was very clean and exactly as shown in the pictures. Thanks for a great stay!"
Calistoga Mid-Century-Modern w/Pool 4BD/4BA -- Sleeps 8

The Lake Cottage on Soda Bay-Pet Friendly, Private Deck, Dock & Kayaks

10.0 out of 10, Exceptional, (62)
"Nice weekend by the lake Great fishing experience "
The Lake Cottage on Soda Bay-Pet Friendly, Private Deck, Dock & Kayaks

Cobb Mountain Chalet King Size Suite

9.8 out of 10, Exceptional, (18)
"Perfect place to stay, nice and cozy!"
The price is AU$223
includes taxes & fees
20 July - 21 July
Cobb Mountain Chalet King Size Suite

Wine Country Harvest Vacation Home

9.8 out of 10, Exceptional, (80)
"Clean and very nice back yard. Larger kitchen and dining area were great for group hanging. Location easy to access all the great vineyards!"
Wine Country Harvest Vacation Home

Mandala Springs Wellness Retreat Center

3.5 star property
8.6 out of 10, Excellent, (27)
"Beautiful quiet retreat "
The price is AU$386
includes taxes & fees
17 July - 18 July
Mandala Springs Wellness Retreat Center

Calistoga Vineyard House

10.0 out of 10, Exceptional, (47)
"Such a nice place. "
Calistoga Vineyard House

Experience Limerick Lane Cellars at our Vineyard Farmstay Retreat in Healdsburg

10.0 out of 10, Exceptional, (32)
"Absolutely wonderful stay. The house was beautiful and clean, with multiple spacious common areas for family time. The Limerick Lane team was also incredibly communicative and accommodating throughout. 100% recommend."
Experience Limerick Lane Cellars at our Vineyard Farmstay Retreat in Healdsburg

Beautiful Lake Front house with Spectacular view, new deck/private dock sleep 6

9.6 out of 10, Exceptional, (55)
"The deck is outstanding - we spent pretty much every moment, from morning coffee to evening cocktails, there. Super great communication with Martine, well-equipped kitchen, and all slept well. Didn't kayak (tho they were there and ready for us), but some of us went swimming and really enjoyed that. Well-appointed home, very comfortable and fun. Thank you, Martine"
The price is AU$718
includes taxes & fees
14 July - 15 July
Beautiful Lake Front house with Spectacular view, new deck/private dock sleep 6

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

10.0 out of 10, Exceptional, (61)
"Great stay, recommend in every way"
Awesome Hilltop Views, Pool, Vineyards, Olive Trees, 5 mins to Healdsburg

Rouge Cobb Mountain Cabins

2.0 star property
Rouge Cobb Mountain Cabins
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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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?

Scenic and tranquil in the heart of Sonoma wine country.: This holiday home rental outside of Middletown is located in a rural location, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a garden, 1 hot tub and a selection of books so that you can immerse yourself in your holiday.

How many holiday rentals are there in Middletown?

Expedia has 12 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 Rabbit Hill Preserve.

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.