Lodging Image

Middletown Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

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 vacation rentals

Terrace/patio

1. Tangerine Cottage spacious home

Tangerine Cottage spacious home
Middletown
The price is AED 635
AED 1,113 total
includes taxes & fees
4 Oct - 5 Oct
Tangerine Cottage spacious home
Property grounds

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 AED 360
AED 727 total
includes taxes & fees
1 Oct - 2 Oct
Garden house with gas fireplace
Lake

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 AED 526
AED 586 total
includes taxes & fees
27 Sep - 28 Sep
Clear Lake Cottages & Marina
Meeting facility

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 AED 497
AED 554 total
includes taxes & fees
27 Sep - 28 Sep
Mandala Springs Wellness Retreat Center
Deluxe Cabin, 1 Queen Bed, Patio, Garden View | Laptop workspace, WiFi (free), bed sheets

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 AED 346
AED 394 total
includes taxes & fees
26 Oct - 27 Oct
Wildhaven Sonoma Glamping
Exterior

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 AED 1,135
AED 1,474 total
includes taxes & fees
5 Oct - 6 Oct
Private Napa Valley Cottage, Peaceful, Walkable & Thoughtfully Designed
Exterior

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 AED 1,245
AED 1,632 total
includes taxes & fees
29 Sep - 30 Sep
Private Napa Valley Cottage, Peaceful, Pet Friendly, and Walkable to Downtown
Superior Suite, Ensuite, Garden View (Couryard Suite #1) | Private kitchen

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 AED 716
AED 1,056 total
includes taxes & fees
27 Sep - 28 Sep
Suites On Main
Terrace/patio

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 AED 1,135
AED 1,482 total
includes taxes & fees
5 Oct - 6 Oct
Escape to wine country in your independent cottage in downtown Calistoga
Interior

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 AED 327
AED 786 total
includes taxes & fees
28 Sep - 29 Sep
Cobb Mountain Chalet Main Floor
Dining

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 AED 804
AED 999 total
includes taxes & fees
27 Sep - 28 Sep
Comfort and Style in Our Queen Cottage
Property grounds

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 AED 215
AED 450 total
includes taxes & fees
27 Sep - 28 Sep
Lake front unit #6 right by the water
Property grounds

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 AED 544
AED 784 total
includes taxes & fees
9 Oct - 10 Oct
Bungalow on the lake
Exterior

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 AED 291
AED 332 total
includes taxes & fees
27 Sep - 28 Sep
The Ranch at Lake Sonoma
Property grounds

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 AED 507
AED 1,011 total
includes taxes & fees
26 Oct - 27 Oct
Watefront Getaway w/ Mtn Views & Dock in Clearlake
Lobby sitting area

16. 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
The price is AED 1,396
AED 2,152 total
includes taxes & fees
23 Oct - 24 Oct
Sonoma Stonehouse, Wine Country Vibes
Coffee/tea maker, fridge, oven, dishwasher

17. The Parlour House at the Fainting Couch

The Parlour House at the Fainting Couch
Cobb
The price is AED 2,205
AED 2,602 total
includes taxes & fees
27 Oct - 28 Oct
The Parlour House at the Fainting Couch
Outdoor dining

18. 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 AED 294
AED 688 total
includes taxes & fees
28 Sep - 29 Sep
Cobb Mountain Chalet King Size Suite
Interior

19. 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 AED 1,135
AED 1,693 total
includes taxes & fees
27 Sep - 28 Sep
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Middletown Hotel Reviews

Golden Haven Hot Springs

Golden Haven Hot Springs

10/10 Excellent
"The hot spring pools are so nice and relaxing!"
Arturo 2-night trip
Posted 2 hours ago
Golden Haven Hot Springs

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 12 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.