Photo by Matthew Walls

Search Middletown Cottages

Start date: Check-in selected.
To Date
End date: Check-out

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Jan 9 - Jan 11
In two months
Feb 20 - Feb 22
In three months
Mar 20 - Mar 22
In four months
Apr 17 - Apr 19

Our top choices for Middletown cottages

Exterior
Backyard Garden Oasis

Cottage in Middletown

Backyard Garden Oasis
3.0 star property
9.6 out of 10, Exceptional, (51)
"Cute garden area, quiet, nice all inclusive spot"
United States
Jodi
$178 nightly
The price is $198
Dec 26 - Dec 27
Total with taxes and fees
Backyard Garden Oasis
House (2 Bedrooms) | Interior
Watefront Getaway w/ Mtn Views & Dock in Clearlake

Cottage in Clearlake

Watefront Getaway w/ Mtn Views & Dock in Clearlake
3.0 star property
$209 nightly
The price is $230
Jan 1 - Jan 2, 2026
Total with taxes and fees
Watefront Getaway w/ Mtn Views & Dock in Clearlake
Property grounds
True Wine Country Living: 2BR Converted Milkbarn on Family Vineyard

Cottage in Forestville

True Wine Country Living: 2BR Converted Milkbarn on Family Vineyard
10.0 out of 10, Exceptional, (11)
"Ideal for a relaxing time in wine country! The winery on property is fantastic and highly recommend it!"
United States
Paul H.
$440 nightly
The price is $495
Jan 15 - Jan 16, 2026
Total with taxes and fees
True Wine Country Living: 2BR Converted Milkbarn on Family Vineyard
Property grounds
Comfort and Style in Our Queen Cottage

Cottage in Calistoga

Comfort and Style in Our Queen Cottage
9.8 out of 10, Exceptional, (49)
"The cottage was very well appointed, very clean and comfortable. we really enjoyed our 2 night stay!Communication, check in and out were a breeze!Thank you!!"
United States
Kevin T.
$359 nightly
The price is $430
Jan 11 - Jan 12, 2026
Total with taxes and fees
Comfort and Style in Our Queen Cottage
Exterior
Wine Country Cottage in downtown Santa Rosa, CA

Cottage in Santa Rosa

Wine Country Cottage in downtown Santa Rosa, CA
9.8 out of 10, Exceptional, (62)
"Tim and Caroline’s cottage was perfect for our two night stay. We loved how close it was to the shops and restaurants in downtown Santa Rosa. Definitely recommend."
United States
Adam R.
$362 nightly
The price is $383
Jan 4 - Jan 5, 2026
Total with taxes and fees
Wine Country Cottage in downtown Santa Rosa, CA
Exterior
Escape to Wine County in your independant Cottage in Downtown Calistoga

Cottage in Calistoga

Escape to Wine County in your independant Cottage in Downtown Calistoga
9.6 out of 10, Exceptional, (30)
"Great place! Clean, and very close to everything!"
United States
Levi J.
$305 nightly
The price is $368
Jan 4 - Jan 5, 2026
Total with taxes and fees
Escape to Wine County in your independant Cottage in Downtown Calistoga
Exterior
Charming King Cottage

Cottage in Calistoga

Charming King Cottage
9.8 out of 10, Exceptional, (11)
"This property was amazing!! Very clean, comfortable and exactly as described in the listing. Our host reached out personally to make sure we had the check in instructions. When we come back to Calistoga we will stay here again!!"
United States
Rich S.
$382 nightly
The price is $458
Jan 11 - Jan 12, 2026
Total with taxes and fees
Charming King Cottage
Terrace/patio
Escape to wine country in your independent cottage in downtown Calistoga

Cottage in Calistoga

Escape to wine country in your independent cottage in downtown Calistoga
10.0 out of 10, Exceptional, (3)
"We made the Calistoga CA area our base for our recent trip and the Cottage Grove Inn served as a great place to stay."
United States
Anonymous traveler
$305 nightly
The price is $368
Jan 4 - Jan 5, 2026
Total with taxes and fees
Escape to wine country in your independent cottage in downtown Calistoga
Exterior
Escape to Wine Country in your independant Cottage in Downtown Calistoga

Cottage in Calistoga

Escape to Wine Country in your independant Cottage in Downtown Calistoga
10.0 out of 10, Exceptional, (2)
"Loved everything Ellen was very accommodating ,pleasant and polite As well as professional The furnishings were very up scale and same style as my home One suggestion The tv should be more accessible so it does not block AC when pulled out from the wall I’m not being critical because I love this place. I will stay there every time I would ever be close to Calistoga. AND I adore Ellen personally and professionally!!👍❤️"
United States
Ronny
$301 nightly
The price is $364
Jan 4 - Jan 5, 2026
Total with taxes and fees
Escape to Wine Country in your independant Cottage in Downtown Calistoga
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
"We had a wonderful, relaxed time at Golden Haven."
Susanne 3-night trip
Posted 3 days ago
Golden Haven Hot Springs

Find out more about Middletown

Middletown Cottages information

Number of reviews
208
Accommodation
112 Cottages
Lowest Price
$198
Highest Price
$495

Frequently asked questions

How much do cottages in Middletown cost?
Prepare to pay between $198 and $495 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.

Explore a world of travel with Expedia