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Middletown Holiday Rentals

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Check prices for these dates

Tonight
13 Jul - 14 Jul
Tomorrow
14 Jul - 15 Jul
Next weekend
18 Jul - 20 Jul
In two weeks
25 Jul - 27 Jul

Holiday Rentals in Middletown

Backyard Garden Oasis
Stroll through a serene garden with mature trees and a variety of shrubs.

Backyard Garden Oasis

3.0 star property
9.6 out of 10, Exceptional, (47)
"perfect place"
The price is HK$1,523
HK$1,698 total
includes taxes & fees
14 Jul - 15 Jul
Backyard Garden Oasis
Pool & Deck: Wine Country Hideaway in Middletown!
Relax by the pool surrounded by lush greenery and shaded by two umbrellas.

Pool & Deck: Wine Country Hideaway in Middletown!

Pool & Deck: Wine Country Hideaway in Middletown!
Clear Lake Cottages & Marina
Enjoy a serene lakeside view from this balcony overlooking a peaceful lake and lush surroundings.

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 HK$1,690
HK$1,885 total
includes taxes & fees
3 Aug - 4 Aug
Clear Lake Cottages & Marina
The Ranch at Lake Sonoma
Enjoy dining or events in this charming barn-style building with a large open entrance and outdoor seating area.

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 HK$466
HK$532 total
includes taxes & fees
14 Jul - 15 Jul
The Ranch at Lake Sonoma
Luxury 3-bedroom Estate surrounded by a 20-acre vineyard and 30-mile views.
Enjoy expansive views of the surrounding landscape from the large windows in this stylish living area.

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

10.0 out of 10, Exceptional, (6)
"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
Stroll along the paved pathway to a charming entrance, surrounded by lush gardens and a large tree.

Escape to Wine County in your independant Cottage in Downtown Calistoga

9.8 out of 10, Exceptional, (20)
"We have stayed many times at the Cottage Grove Inn and it never disappoints. "
The price is HK$2,347
HK$3,204 total
includes taxes & fees
14 Jul - 15 Jul
Escape to Wine County in your independant Cottage in Downtown Calistoga
Scenic and tranquil in the heart of Sonoma wine country.
Relax on the deck with a serene mountain view, surrounded by lush plants and a comfortable seating area.

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!
Enjoy casual dining on the water with a round table set amidst a serene outdoor seating area.

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.
Relax in the hot tub on the deck, surrounded by a fence.

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
Classic hallway with ornate door, framed artwork, and comfortable seating area.

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

10.0 out of 10, Exceptional, (233)
"Wonderful accommodations for a family weekend in the wine country!"
The price is HK$12,952
HK$16,598 total
includes taxes & fees
14 Jul - 15 Jul
Beautiful Wine Country Vacation Home - St. Helena Short Term Permit PL-24-021
Calistoga Mid-Century-Modern w/Pool 4BD/4BA -- Sleeps 8
Surrounded by lush greenery and mountains, this pool area offers a serene escape.

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
Relax by the water's edge in this serene outdoor seating area, complete with a picnic table and kayaks for a leisurely paddle.

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
Cozy living space with a dining area, sofa, and TV, perfect for relaxing and enjoying meals together.

Cobb Mountain Chalet King Size Suite

9.8 out of 10, Exceptional, (18)
"Perfect place to stay, nice and cozy!"
The price is HK$403
HK$1,131 total
includes taxes & fees
20 Jul - 21 Jul
Cobb Mountain Chalet King Size Suite
Awesome Hilltop Views, Pool, Vineyards, Olive Trees, 5 mins to Healdsburg
Enjoy cooking in this well-equipped kitchen with a central island, gas stove, and ample counter space.

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
Mandala Springs Wellness Retreat Center
Guests can enjoy a charming porch surrounded by lush greenery and beautiful planters.

Mandala Springs Wellness Retreat Center

3.5 star property
8.6 out of 10, Excellent, (27)
"Beautiful quiet retreat "
The price is HK$1,265
HK$1,979 total
includes taxes & fees
27 Jul - 28 Jul
Mandala Springs Wellness Retreat Center
Experience Limerick Lane Cellars at our Vineyard Farmstay Retreat in Healdsburg
Enjoy a backyard with a swimming pool surrounded by lush landscaping and a shaded pergola.

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
Enjoy a serene lakeside retreat with a deck, table, and chairs.

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 HK$1,678
HK$3,645 total
includes taxes & fees
14 Jul - 15 Jul
Beautiful Lake Front house with Spectacular view, new deck/private dock sleep 6
Comfort and Style in Our Queen Cottage
Enter a serene bedroom with a comfortable bed, bedside table, and wall-mounted lamp.

Comfort and Style in Our Queen Cottage

9.8 out of 10, Exceptional, (48)
"Nice location and space was very comfortable"
The price is HK$1,405
HK$1,897 total
includes taxes & fees
14 Jul - 15 Jul
Comfort and Style in Our Queen Cottage
Rouge Cobb Mountain Cabins
Guest house nestled among trees, offering a peaceful retreat.

Rouge Cobb Mountain Cabins

2.0 star property
Rouge Cobb Mountain Cabins
Escape to Paradise: A Stunning Tuscany-Style Home with Views of Vineyards
Relax in a tranquil outdoor space with a hot tub and pool surrounded by a deck and a scenic mountain view.

Escape to Paradise: A Stunning Tuscany-Style Home with Views of Vineyards

10.0 out of 10, Exceptional, (20)
"Amazing location and charming home."
Escape to Paradise: A Stunning Tuscany-Style Home with Views of Vineyards
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?

Luxury 3-bedroom Estate surrounded by a 20-acre vineyard and 30-mile views.: This holiday home rental outside of Middletown offers an outdoor pool, a patio and a BBQ to help you feel perfectly comfortable 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.