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Middletown Vacation Rentals

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Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Middletown vacation 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 ￥17,242
￥33,693 total
includes taxes & fees
Oct 11 - Oct 12
Garden house with gas fireplace
A kitchen counter with a coffee maker, toaster, and a decorative tray with condiments.

2. Tangerine Cottage spacious home

Tangerine Cottage spacious home
Middletown
The price is ￥25,108
￥48,005 total
includes taxes & fees
Oct 8 - Oct 9
Tangerine Cottage spacious home
A view from a window overlooking a lake with a dock and greenery.

3. Clear Lake Cottages & Marina

Clear Lake Cottages & Marina
2.5 star property
Clearlake
9.0 out of 10, Wonderful, (378 reviews)
"I loved staying there! Amazing hospitality. I will absolutely recommend the cabins to family and friends. The front desk lady was friendly and helpful! The cabin was so adorable , SUPER clean and well equipped."
United States
Tomessa
The price is ￥20,825
￥23,220 total
includes taxes & fees
Oct 13 - Oct 14
Clear Lake Cottages & Marina
A white building with a covered porch, potted plants, and a bicycle.

4. 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 ￥21,877
￥24,393 total
includes taxes & fees
Oct 15 - Oct 16
Mandala Springs Wellness Retreat Center
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, (134 reviews)
"Nice place to be in with your dog, very good for comfortable stay"
United States
NEERJA
The price is ￥16,742
￥19,086 total
includes taxes & fees
Oct 25 - Oct 26
Wildhaven Sonoma Glamping
A covered outdoor deck with a table and chairs, a grill, and a bottle of wine.

6. Cobb Mountain Chalet King Size Suite

Cobb Mountain Chalet King Size Suite
Cobb
9.2 out of 10, Wonderful, (30 reviews)
"My husband and I cannot stop talking about this beautiful, serene gem. Each room was immaculate. The sofas were so cozy and plenty of soft blankets! The market is equipped with everything & just a few minutes away. We are house hunting & can’t wait to return to the chalet!"
United States
Roberta F.
The price is ￥10,943
￥27,685 total
includes taxes & fees
Oct 20 - Oct 21
Cobb Mountain Chalet King Size Suite
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, (30 reviews)
"Mo the caretaker was so accommodating- we enjoyed a quiet, peaceful stay."
United States
Drew W.
The price is ￥9,238
￥19,366 total
includes taxes & fees
Oct 17 - Oct 18
Lake front unit #6 right by the water
A small, single-story house with a front porch, a chimney, and a door with a window above it.

8. 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, (45 reviews)
"Host, amenities, location….all excellent. "
United States
Amy B.
The price is ￥55,205
￥75,379 total
includes taxes & fees
Oct 12 - Oct 13
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.

9. 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 ￥11,370
￥21,723 total
includes taxes & fees
Oct 18 - Oct 19
Mount Konocti view
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, (45 reviews)
"Maureen was lovely and the sunset and sunrise were beautiful!"
United States
Steven W.
The price is ￥11,104
￥23,501 total
includes taxes & fees
Oct 14 - Oct 15
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, 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 ￥53,531
￥73,153 total
includes taxes & fees
Oct 12 - Oct 13
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.

12. Cobb Mountain Chalet Main Floor

Cobb Mountain Chalet Main Floor
Cobb
9.4 out of 10, Exceptional, (21 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 ￥13,382
￥33,392 total
includes taxes & fees
Oct 12 - Oct 13
Cobb Mountain Chalet Main Floor
A wooden deck leading to a building with a large window overlooking a lake and hills.

13. 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 ￥21,070
￥31,350 total
includes taxes & fees
Oct 8 - Oct 9
Bungalow on the lake
A house with a porch, a wooden door, and two rocking chairs. There are two suitcases and a table with bottles on the porch.

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

Escape to wine country in your independent cottage in downtown Calistoga
Calistoga
10.0 out of 10, Exceptional, (6 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 ￥53,531
￥73,153 total
includes taxes & fees
Oct 12 - Oct 13
Escape to wine country in your independent cottage in downtown Calistoga
An outdoor seating area with a table, candles, and a potted plant.

15. Comfort and Style in Our Queen Cottage

Comfort and Style in Our Queen Cottage
Calistoga
9.8 out of 10, Exceptional, (49 reviews)
"Great place to stay. Clean and well appointed and in a great location for access to sites, vineyards, and restaurants "
United States
Robert
The price is ￥29,845
￥38,112 total
includes taxes & fees
Nov 1 - Nov 2
Comfort and Style in Our Queen Cottage
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
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 ￥20,528
￥43,491 total
includes taxes & fees
Oct 12 - Oct 13
Watefront Getaway w/ Mtn Views & Dock in Clearlake
A kitchen with a stainless steel faucet, a microwave, and an oven.

17. Suites On Main

Suites On Main
2.0 star property
Kelseyville
9.0 out of 10, Wonderful, (4 reviews)
"Staff is great! They were right there to answer any questions or to assist with our needs. Our suite was very spacious, clean and great ambiance. Great restaurant the Saw Shop a block away and coffee & pastries across the street. We very much enjoyed our stay and will stay again."
United States
Margaret
The price is ￥30,792
￥45,388 total
includes taxes & fees
Oct 9 - Oct 10
Suites On Main
A hot tub with a blue light, surrounded by a wooden fence and string lights.

18. 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, (3 reviews)
"10/10 stay!"
United States
Janneth M.
The price is ￥19,581
￥41,238 total
includes taxes & fees
Oct 12 - Oct 13
Hot tub lake wine Cottage State Park 4 mins away
A single-story cabin with a small porch, situated on a hillside overlooking a body of water and mountains.

19. The Ranch at Lake Sonoma

The Ranch at Lake Sonoma
1.0 star property
Geyserville
9.8 out of 10, Exceptional, (6 reviews)
"Nice camping spot "
United States
Evelyn
The price is ￥12,506
￥14,257 total
includes taxes & fees
Oct 8 - Oct 9
The Ranch at Lake Sonoma
A small, single-story house with a porch, a red door, and two bicycles parked outside.

20. Charming King Cottage

Charming King Cottage
Calistoga
9.8 out of 10, Exceptional, (11 reviews)
"Nice comfortable cottage."
United States
Michael E. S.
The price is ￥33,003
￥42,217 total
includes taxes & fees
Nov 2 - Nov 3
Charming King Cottage
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

Calistoga Inn Restaurant and Brewery

Calistoga Inn Restaurant and Brewery

10/10 Excellent
"Had a great time. Bathrooms were clean and always available. Room was clean, simple, had A/C."
Christina 2-night trip
Posted 9 hours ago
Calistoga Inn Restaurant and Brewery

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 vacation rentals in Middletown?

Yes, we offer vacation rentals close to top attractions in Middletown, or you can go with a secluded option if you'd like a relaxing place to 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 vacation rentals that Middletown has to offer?

Beautiful Wine Country Vacation Home - St. Helena Short Term Permit PL-24-021: This vacation home rental near Middletown is located in the city center and has a fireplace, a patio, and a barbecue grill 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 you can cook with friends or family. Make the most of the selection of games in this rental home to help you unwind.

How many vacation rentals are there in Middletown?

Expedia has 10 vacation 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 vacation rentals like in Middletown?

Vacation rentals are private properties you can stay in for several days or longer in Middletown. Vacation rentals offer extras like WiFi and washers and dryers so you'll have a home away from home. If you're concerned about cleanliness, a vacation rental can provide a sense of safety away from shared hotel elevators and busy lobbies while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a standard hotel, which makes a vacation rental a great choice for a family trip or a small group gathering.