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Middletown Holiday Rentals

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Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Middletown holiday rentals

A fenced outdoor area with a red umbrella, a white building, and a natural landscape in the background.

1. Garden house with gas fireplace

Garden house with gas fireplace
Middletown
10.0 out of 10, Exceptional, (2 reviews)
"It was a quaint country house. The host was attentive, but also left us to ourselves. The house was clean. A/C worked well. It was very comfortable."
United States
Amy
The price is AU$291
includes taxes & fees
29 Oct - 30 Oct
Garden house with gas fireplace
A covered porch with two grey upholstered chairs and a small table, wooden railings, and a window with a curtain.

2. Tangerine Cottage spacious home

Tangerine Cottage spacious home
Middletown
The price is AU$419
includes taxes & fees
26 Oct - 27 Oct
Tangerine Cottage spacious home
A white building with a covered porch, potted plants, and a bicycle.

3. Mandala Springs Wellness Retreat Center

Mandala Springs Wellness Retreat Center
3.5 star property
Cobb
8.8 out of 10, Excellent, (38 reviews)
"Waterfront cabins were amazing. The location and wildlife were serene, fantastic place to stay."
United States
Carmino
The price is AU$212
includes taxes & fees
27 Oct - 28 Oct
Mandala Springs Wellness Retreat Center
A covered outdoor deck with a table and chairs, a grill, and a bottle of wine.

4. Cobb Mountain Chalet King Size Suite

Cobb Mountain Chalet King Size Suite
Cobb
9.2 out of 10, Wonderful, (31 reviews)
"Lovely place, very clean, in quiet surroundings."
United States
Brigid
The price is AU$266
includes taxes & fees
2 Nov - 3 Nov
Cobb Mountain Chalet King Size Suite
A cozy cabin with a loft bedroom, wooden exterior, and a small balcony.

5. Wildhaven Sonoma Glamping

Wildhaven Sonoma Glamping
1.0 star property
Healdsburg
9.2 out of 10, Wonderful, (136 reviews)
"Nice place to be in with your dog, very good for comfortable stay"
United States
NEERJA
The price is AU$159
includes taxes & fees
23 Nov - 24 Nov
Wildhaven Sonoma Glamping
A view from a window overlooking a lake with a dock and greenery.

6. Clear Lake Cottages & Marina

Clear Lake Cottages & Marina
2.5 star property
Clearlake
9.0 out of 10, Wonderful, (385 reviews)
"Clean, cozy and cute."
United States
Julian
The price is AU$218
includes taxes & fees
24 Nov - 25 Nov
Clear Lake Cottages & Marina
A wooden pier extending over calm water with mountains in the background.

7. Lake front unit #6 right by the water

Lake front unit #6 right by the water
Clearlake
8.6 out of 10, Excellent, (31 reviews)
"Mo the caretaker was so accommodating- we enjoyed a quiet, peaceful stay."
United States
Drew W.
The price is AU$177
includes taxes & fees
2 Nov - 3 Nov
Lake front unit #6 right by the water
A room with a brown sofa, two wicker chairs, a small table with a lamp, and a framed picture on the wall.

8. Hideaway Cottages

Hideaway Cottages
2.0 star property
Calistoga
The price is AU$282
includes taxes & fees
1 Nov - 2 Nov
Hideaway Cottages
A wooden deck leading to a building with a large window overlooking a lake and hills.

9. Bungalow on the lake

Bungalow on the lake
Clearlake
7.8 out of 10, Good, (8 reviews)
"Great little cottage for a good price. "
United States
Danielle C.
The price is AU$287
includes taxes & fees
25 Oct - 26 Oct
Bungalow on the lake
A view from a room with a large sliding glass door to a deck overlooking a lake.

10. Overlooking Clearlake From The Living Room

Overlooking Clearlake From The Living Room
Clearlake
9.0 out of 10, Wonderful, (46 reviews)
"Tweeter ville,,,,the whole area is run down . I cried when we pulled in , run down old apartments. Bring your own towels and sheets maybe bedding , for half the price I could of stayed at the casino in lakeport,, lesson learned"
United States
Leighana
The price is AU$214
includes taxes & fees
2 Nov - 3 Nov
Overlooking Clearlake From The Living Room
A small, single-story house with a front porch, a chimney, and a door with a window above it.

11. Private Napa Valley Cottage, Peaceful, Pet Friendly, and Walkable to Downtown

Private Napa Valley Cottage, Peaceful, Pet Friendly, and Walkable to Downtown
Calistoga
9.6 out of 10, Exceptional, (47 reviews)
"We stayed here 15 years ago , same bedspreads and no new updates . We love it for its cozy feeling , and love the peacefulness of staying in Calistoga. We walked across the street for an awesome dinner at Sam’s Social club , walked down the street to shop and cruise around this quaint town . It’s a high price point , but we always enjoy our time there . I worry that if they ever remodel this place , the price point will be more than what it’s worth a night , for which I don’t believe would be...
United States
William
The price is AU$629
includes taxes & fees
26 Oct - 27 Oct
Private Napa Valley Cottage, Peaceful, Pet Friendly, and Walkable to Downtown
A lakeside cabin with a deck, outdoor seating, and a view of the lake.

12. Mount Konocti view

Mount Konocti view
Clearlake
8.2 out of 10, Very good, (10 reviews)
"The place was clean and well equipped and Mo was very responsive and made stay as pleasant as possible."
United States
Kayo
The price is AU$199
includes taxes & fees
27 Oct - 28 Oct
Mount Konocti view
A small, single-story house with a front porch, a chimney, and a door with a window above it.

13. Private Napa Valley Cottage, Peaceful, Walkable & Thoughtfully Designed

Private Napa Valley Cottage, Peaceful, Walkable & Thoughtfully Designed
Calistoga
10.0 out of 10, Exceptional, (5 reviews)
"Property is beautiful rooms are so clean. Service was incredible."
United States
Paul L.
The price is AU$573
includes taxes & fees
26 Oct - 27 Oct
Private Napa Valley Cottage, Peaceful, Walkable & Thoughtfully Designed
A hallway with wooden walls and a blue door, leading to a room with a bed and a table.

14. Cobb Mountain Chalet Main Floor

Cobb Mountain Chalet Main Floor
Cobb
9.4 out of 10, Exceptional, (22 reviews)
"Beautiful view from the deck! Wind was blowing the tree in the evening and it was so peaceful. House had everything you could need."
United States
tabatha p.
The price is AU$308
includes taxes & fees
27 Oct - 28 Oct
Cobb Mountain Chalet Main Floor
A house with a porch, a wooden door, and two rocking chairs. There are two suitcases and a table with bottles on the porch.

15. Escape to wine country in your independent cottage in downtown Calistoga

Escape to wine country in your independent cottage in downtown Calistoga
Calistoga
9.8 out of 10, Exceptional, (8 reviews)
"We absolutely loved our stay! The home was clean, quiet, private, and incredibly convenient. We were especially grateful that the hosts allowed our three dogs, which made this trip extra special. We spent a few days enjoying Calistoga and Napa before taking our sweet pup to UC Davis, and this was the perfect place for us. As empty nesters, we love traveling with our three dogs and hope to stay here again someday!"
United States
Jennifer G.
The price is AU$573
includes taxes & fees
26 Oct - 27 Oct
Escape to wine country in your independent cottage in downtown Calistoga
A wooden pathway leading to a house with a view of a lake and mountains.

16. Watefront Getaway w/ Mtn Views & Dock in Clearlake

Watefront Getaway w/ Mtn Views & Dock in Clearlake
3.0 star property
Clearlake
4.0 out of 10, (1 review)
"If it weren’t for the kindness of the host, who accommodated us for an early check-in and late checkout, I would’ve given this zero stars. It’s totally rundown, looks like it hasn’t been power washed in 20 years, as soon as you walk up it smells like mold. The listing doesn’t tell you that it’s on a main street. The inside has rotting walls with actual holes, you can smell the mold and in one of the bedrooms it smelled so toxic like cat urine and chemicals - no one could sleep in there. The...
United States
Jennifer
The price is AU$390
includes taxes & fees
25 Oct - 26 Oct
Watefront Getaway w/ Mtn Views & Dock in Clearlake
A wooden pathway leading to a house with a view of a lake and mountains.

17. Watefront Getaway w/ Mtn Views & Dock in Clearlake

Watefront Getaway w/ Mtn Views & Dock in Clearlake
Clearlake
8.0 out of 10, Very good, (4 reviews)
"We had a wonderful one-night stay at this waterfront home. The location is unbeatable: right on the lake with mountain views and a private dock, and it made a perfect home base for a show at Cache Creek Winery. The host was excellent, quick to respond with clear check-in instructions, and the place was spotless when we arrived. Comfortable beds, everything we needed for the weekend, and easy to find. We would happily stay here again and recommend it to anyone visiting Clear Lake."
United States
Alison
The price is AU$389
includes taxes & fees
25 Oct - 26 Oct
Watefront Getaway w/ Mtn Views & Dock in Clearlake
A modern living room with a built-in bench, a wooden coffee table, and a dining area with chairs.

18. Fully furnished apartment tucked away on-site at UpValley Inn & Hot Springs

Fully furnished apartment tucked away on-site at UpValley Inn & Hot Springs
Calistoga
9.6 out of 10, Exceptional, (12 reviews)
"Enjoyed our stay and everything was as described. Very friendly staff. "
United States
Mete Y.
The price is AU$616
includes taxes & fees
2 Nov - 3 Nov
Fully furnished apartment tucked away on-site at UpValley Inn & Hot Springs
A hot tub with a blue light, surrounded by a wooden fence and string lights.

19. Hot tub lake wine Cottage State Park 4 mins away

Hot tub lake wine Cottage State Park 4 mins away
Kelseyville
10.0 out of 10, Exceptional, (5 reviews)
"10/10 stay!"
United States
Janneth M.
The price is AU$367
includes taxes & fees
3 Nov - 4 Nov
Hot tub lake wine Cottage State Park 4 mins away
A modern building with a metal exterior, a wooden door, and a small window on the side.

20. Country Carriage House in Downtown Geyserville, Vineyard Views

Country Carriage House in Downtown Geyserville, Vineyard Views
Geyserville
10.0 out of 10, Exceptional, (5 reviews)
"Cozy, rustic, and with all great amenities."
United States
Gina I.
The price is AU$558
includes taxes & fees
29 Oct - 30 Oct
Country Carriage House in Downtown Geyserville, Vineyard Views
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

The Sandman Santa Rosa Sonoma, an Ascend Collection Hotel

The Sandman Santa Rosa Sonoma, an Ascend Collection Hotel

10/10 Excellent
"Very easy access from 101. Room was spacious and clean. Bed very comfortable. It was handy having fridge microwave and toaster oven. Great price"
Barbara 1-night trip
Posted less than an hour ago
The Sandman Santa Rosa Sonoma, an Ascend Collection Hotel

Find out more about Middletown

Everything you need to know about Middletown holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Middletown holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Middletown holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Middletown holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Middletown. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Middletown holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Middletown holiday rentals we have selected for you start as low as AU$128 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Middletown rentals

At Expedia, we put the best Middletown holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Middletown rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Middletown holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Middletown. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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?

Beautiful Wine Country Vacation Home - St. Helena Short Term Permit PL-24-021: This holiday home rental outside of Middletown is located in the city centre, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 6 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Make the most of games in this rental home to help you unwind.

How many holiday rentals are there in Middletown?

Expedia has 10 holiday rentals for your stay in Middletown.

What can I see and do in Middletown?

Explore the area and family-friendly sights such as Calistoga Spit N' Cycle, 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.