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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Middletown cottages

A wooden deck with wicker furniture and a metal table, overlooking a vineyard and hills.

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 €184
includes taxes & fees
1 Oct - 2 Oct
Garden house with gas fireplace
A wooden pathway leading to a house with a view of a lake and mountains.

2. 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 €241
includes taxes & fees
4 Oct - 5 Oct
Watefront Getaway w/ Mtn Views & Dock in Clearlake
A wooden deck with a round table and two chairs, surrounded by a white railing.

3. 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 €232
includes taxes & fees
1 Oct - 2 Oct
Comfort and Style in Our Queen Cottage
A hot tub with a blue light, surrounded by a wooden fence and string lights.

4. 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 €204
includes taxes & fees
5 Oct - 6 Oct
Hot tub lake wine Cottage State Park 4 mins away
A small, single-story house with a front porch, a chimney, and a door with a window above it.

5. 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 €414
includes taxes & fees
13 Oct - 14 Oct
Private Napa Valley Cottage, Peaceful, Pet Friendly, and Walkable to Downtown
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 €381
includes taxes & fees
5 Oct - 6 Oct
Private Napa Valley Cottage, Peaceful, Walkable & Thoughtfully Designed
A house with a porch, a wooden door, and two rocking chairs. There are two suitcases and a table with bottles on the porch.

7. 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 €381
includes taxes & fees
5 Oct - 6 Oct
Escape to wine country in your independent cottage in downtown Calistoga
A small, single-story house with a porch, a red door, and two bicycles parked outside.

8. 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 €291
includes taxes & fees
12 Oct - 13 Oct
Charming King Cottage
A modern building with a metal exterior, a wooden door, and a small window on the side.

9. 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 €353
includes taxes & fees
22 Oct - 23 Oct
Country Carriage House in Downtown Geyserville, Vineyard Views
A two-story house with a covered porch, a stone pathway, and a well-maintained garden with various shrubs and trees.

10. The Atlas Calistoga - Cottage #1

The Atlas Calistoga - Cottage #1
Calistoga
10.0 out of 10, Exceptional, (19 reviews)
"Great space, impeccably appointed, amazing location. Would stay again. "
United States
Kris R.
The Atlas Calistoga - Cottage #1
A building with a sign that reads "Russian River Brewing Company."

11. Wine Country Cottage in downtown Santa Rosa, CA

Wine Country Cottage in downtown Santa Rosa, CA
Santa Rosa
9.8 out of 10, Exceptional, (80 reviews)
"Lovely vacation rental"
United States
suzanne g.
The price is €368
includes taxes & fees
7 Oct - 8 Oct
Wine Country Cottage in downtown Santa Rosa, CA
A wooden deck with a round table and two chairs, surrounded by a metal railing, overlooking a forested area.

12. RustRidge Bed and Breakfast - Rustridge Cottage

RustRidge Bed and Breakfast - Rustridge Cottage
St Helena
8.0 out of 10, Very good, (3 reviews)
"We had a magical time. The horses, pool, Vinyard and hospitality was wonderful. What a special ranch. Oh and the breakfast! Delicious!!"
United States
ila m.
The price is €466
includes taxes & fees
11 Oct - 12 Oct
RustRidge Bed and Breakfast - Rustridge 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

Flamingo Resort & Spa Santa Rosa Sonoma, Tapestry by Hilton

Flamingo Resort & Spa Santa Rosa Sonoma, Tapestry by Hilton

8/10 Good
"Great place for a staycation! Close to many restaurants, shops, and easy access to nearby towns for different activities. Staff were always friendly and helpful. We got lucky and the resort was not too busy so there was plenty of spaces for the pool, no wait at the restaurant, etc. also if you are an early morning person their cafe opens at 6:30 am which was great! There are also plenty of cafes nearby that open early. The not so great: if you are a light sleeper or bothered by noise overall beware it can get noisy. We stayed from Thursday to the weekend and we could hear everything happening at the pool, music from the venue, and other guests in the hallways being a bit loud at night but we didn’t mind as much since it was not all night. We traveled with our toddler and she had a great time and her sleep was not disrupted."
Alexander 2-night trip
Posted 3 hours ago
Flamingo Resort & Spa Santa Rosa Sonoma, Tapestry by Hilton

Find out more about Middletown

Middletown Cottages information

Number of reviews
215
Accommodation
124 Cottages
Lowest Price
€184
Highest Price
€466

Frequently asked questions

How much do cottages in Middletown cost?
Prepare to pay between €184 and €466 per night for cottages in Middletown. No matter your budget, a wonderful stay is just a click or two away on Expedia. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
Are there any family-friendly cottages in Middletown?
If you're looking to get back to nature in Middletown, we recommend Backyard Garden Oasis. With a 3-star rating and amenities like pillow top mattresses and a barbecue grill, you'll find it easy to settle in at this family-friendly cottage. Check in to your hotel and then make your way to some attractions that will keep everyone entertained in Middletown. Cobb Mountain should be at the top of your list.
Why book your cottage in Middletown with Expedia?
We think a getaway should be a walk in the park, so if you're looking for cottages in Middletown at an affordable rate, Expedia has your back. Save those pennies and choose an economical option far from the hustle and bustle, or splurge on a 5-star cottage to treat your loved ones.
How can I find cheap cottages in Middletown?
With Expedia's user-friendly filter tool, sourcing cheap cottages in Middletown is a breeze. To discover properties that are friendly on the wallet, narrow your search results by amenities, star rating and budget.
What is there to do in Middletown near my cottage?
Once you've checked in to your hotel, set out and discover the awesome things Middletown has on offer. Beaver Creek Vineyards is a top attraction to add to your must-see list.