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Middletown Holiday Rentals

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Middletown holiday rentals

A covered porch with two grey upholstered chairs and a small table, wooden railings, and a window with a curtain.

1. Tangerine Cottage spacious home

Tangerine Cottage spacious home
Middletown
The price is HK$1,216
HK$2,236 total
includes taxes & fees
12 Oct - 13 Oct
Tangerine Cottage spacious home
A fenced outdoor area with a red umbrella, a white building, and a natural landscape in the background.

2. 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 HK$769
HK$1,553 total
includes taxes & fees
1 Oct - 2 Oct
Garden house with gas fireplace
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, (377 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 HK$1,122
HK$1,252 total
includes taxes & fees
28 Sept - 29 Sept
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 HK$1,264
HK$1,409 total
includes taxes & fees
28 Sept - 29 Sept
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, (133 reviews)
"Nice place to be in with your dog, very good for comfortable stay"
United States
NEERJA
The price is HK$830
HK$946 total
includes taxes & fees
28 Sept - 29 Sept
Wildhaven Sonoma Glamping
A small, single-story house with a front porch, a chimney, and a door with a window above it.

6. 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 HK$2,424
HK$3,149 total
includes taxes & fees
5 Oct - 6 Oct
Private Napa Valley Cottage, Peaceful, Walkable & Thoughtfully Designed
A small, single-story house with a front porch, a chimney, and a door with a window above it.

7. 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 HK$2,659
HK$3,485 total
includes taxes & fees
29 Sept - 30 Sept
Private Napa Valley Cottage, Peaceful, Pet Friendly, and Walkable to Downtown
A kitchen with a stainless steel faucet, a microwave, and an oven.

8. 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 HK$1,530
HK$2,255 total
includes taxes & fees
28 Sept - 29 Sept
Suites On Main
A house with a porch, a wooden door, and two rocking chairs. There are two suitcases and a table with bottles on the porch.

9. 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 HK$2,424
HK$3,164 total
includes taxes & fees
5 Oct - 6 Oct
Escape to wine country in your independent cottage in downtown Calistoga
A hallway with wooden walls and a blue door, leading to a room with a bed and a table.

10. 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 HK$699
HK$1,680 total
includes taxes & fees
28 Sept - 29 Sept
Cobb Mountain Chalet Main Floor
An outdoor seating area with a table, candles, and a potted plant.

11. 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 HK$1,718
HK$2,132 total
includes taxes & fees
28 Sept - 29 Sept
Comfort and Style in Our Queen Cottage
A wooden pier extending over calm water with mountains in the background.

12. 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 HK$459
HK$962 total
includes taxes & fees
3 Oct - 4 Oct
Lake front unit #6 right by the water
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 HK$1,045
HK$1,547 total
includes taxes & fees
28 Sept - 29 Sept
Bungalow on the lake
A single-story cabin with a small porch, situated on a hillside overlooking a body of water and mountains.

14. 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 HK$621
HK$708 total
includes taxes & fees
28 Sept - 29 Sept
The Ranch at Lake Sonoma
A wooden pathway leading to a house with a view of a lake and mountains.

15. 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 HK$1,020
HK$2,090 total
includes taxes & fees
28 Sept - 29 Sept
Watefront Getaway w/ Mtn Views & Dock in Clearlake
A view from a room with a large sliding glass door to a deck overlooking a lake.

16. 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 HK$572
HK$1,189 total
includes taxes & fees
5 Oct - 6 Oct
Overlooking Clearlake From The Living Room
A spacious lobby with a large sofa, a coffee table, and a leather armchair. A fireplace is visible in the background, and there is a staircase leading to an upper level.

17. Sonoma Stonehouse, Wine Country Vibes

Sonoma Stonehouse, Wine Country Vibes
2.0 star property
Santa Rosa
8.0 out of 10, Very good, (1 review)
"Muy bonito diseño interior en ambos la recepción y el cuarto."
Mexico
Tara
Sonoma Stonehouse, Wine Country Vibes
A modern kitchen with stainless steel appliances, grey cabinets, and a marble backsplash.

18. The Parlour House at the Fainting Couch

The Parlour House at the Fainting Couch
Cobb
The price is HK$4,709
HK$5,548 total
includes taxes & fees
28 Sept - 29 Sept
The Parlour House at the Fainting Couch
A covered outdoor deck with a table and chairs, a grill, and a bottle of wine.

19. 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 HK$628
HK$1,470 total
includes taxes & fees
28 Sept - 29 Sept
Cobb Mountain Chalet King Size Suite
A modern living room with a built-in bench, a wooden coffee table, and a dining area with chairs.

20. 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, (11 reviews)
"Enjoyed our stay and everything was as described. Very friendly staff. "
United States
Mete Y.
The price is HK$2,424
HK$3,623 total
includes taxes & fees
28 Sept - 29 Sept
Fully furnished apartment tucked away on-site at UpValley Inn & Hot Springs
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

Hotel E

Hotel E

10/10 Excellent
"Great spot on the town square. Cute. Clean. Loves it"
Rhiannon 2-night trip
Posted 3 hours ago
Hotel E

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 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 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 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.