Search Middletown Cottages

  • 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
Apr 17 - Apr 19
In two months
May 29 - May 31
In three months
Jun 26 - Jun 28
In four months
Jul 24 - Jul 26

Our top choices for Middletown cottages

Exterior

Backyard Garden Oasis

Backyard Garden Oasis
3.0 star property
Middletown
9.6 out of 10, Exceptional, (51 reviews)
"Cute garden area, quiet, nice all inclusive spot"
United States
Jodi
$209 nightly
The price is $233
Apr 10 - Apr 11
Total with taxes and fees
Backyard Garden Oasis
Outdoor dining

Garden house with gas fireplace

Garden house with gas fireplace
Middletown
10.0 out of 10, Exceptional, (1 review)
"We were not originally planning on staying in Middletown but were pleasantly surprised on arrival. The Garden House is very comfortable and convenient to many things in town. Linda, our host had special little touches that made the stay relaxing. Number one the shower is amazing! I looked forward to it every evening the pressure and hot water is perfect and the quality shampoos and soaps provides smelled wonderful! The kitchen is well stocked if you are cooking during your stay. And there is...
United States
kelsie i.
$202 nightly
The price is $223
Apr 6 - Apr 7
Total with taxes and fees
Garden house with gas fireplace
House (2 Bedrooms) | Interior

Clear Lake Living! Pet-friendly Gem w/ Fenced Yard

Clear Lake Living! Pet-friendly Gem w/ Fenced Yard
3.0 star property
Lakeport
$376 nightly
The price is $420
Apr 7 - Apr 8
Total with taxes and fees
Clear Lake Living! Pet-friendly Gem w/ Fenced Yard
Exterior

Escape to Wine County in your independant Cottage in Downtown Calistoga

Escape to Wine County in your independant Cottage in Downtown Calistoga
Calistoga
9.6 out of 10, Exceptional, (35 reviews)
"Perfect little cottage within walking distance to everything in downtown Calistoga! Bed was so comfy and the fireplace made it feel extra cozy. We definitely want to stay here again!"
United States
Cameron D.
$319 nightly
The price is $383
Apr 6 - Apr 7
Total with taxes and fees
Escape to Wine County in your independant Cottage in Downtown Calistoga
Exterior

Escape to Wine Country in your independant Cottage in Downtown Calistoga

Escape to Wine Country in your independant Cottage in Downtown Calistoga
Calistoga
10.0 out of 10, Exceptional, (2 reviews)
"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
$317 nightly
The price is $381
Apr 6 - Apr 7
Total with taxes and fees
Escape to Wine Country in your independant Cottage in Downtown Calistoga
Exterior

Charming King Cottage

Charming King Cottage
Calistoga
9.8 out of 10, Exceptional, (11 reviews)
"Nice comfortable cottage."
United States
Michael E. S.
$220 nightly
The price is $250
Apr 6 - Apr 7
Total with taxes and fees
Charming King Cottage
Terrace/patio

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, (3 reviews)
"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
$319 nightly
The price is $383
Apr 6 - Apr 7
Total with taxes and fees
Escape to wine country in your independent cottage in downtown Calistoga
Exterior

Wine Country Cottage in downtown Santa Rosa, CA

Wine Country Cottage in downtown Santa Rosa, CA
Santa Rosa
9.6 out of 10, Exceptional, (72 reviews)
"Good location for coffee and restaurant. Nice backyard "
United States
vicki a.
$395 nightly
The price is $419
Apr 22 - Apr 23
Total with taxes and fees
Wine Country Cottage in downtown Santa Rosa, CA
Outdoor spa tub

The Carriage House Sonoma • Hot Tub • Vineyard Views • Complimentary Bottle

The Carriage House Sonoma • Hot Tub • Vineyard Views • Complimentary Bottle
Kenwood
9.0 out of 10, Wonderful, (2 reviews)
"Such a cute place! The turn into the property is a bit hidden right before the bridge but once you find it the house is so secluded with plenty of space. The kitchen was fully stocked and had everything you could think of. Did a wine tasting with their tasting room and everyone was so welcoming and sweet. Thank you! "
United States
Sara W.
$570 nightly
The price is $630
Apr 14 - Apr 15
Total with taxes and fees
The Carriage House Sonoma • Hot Tub • Vineyard Views • Complimentary Bottle
Outdoor dining

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.
$470 nightly
The price is $531
Apr 6 - Apr 7
Total with taxes and fees
RustRidge Bed and Breakfast - Rustridge Cottage
Property grounds

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
$199 nightly
The price is $226
Apr 6 - Apr 7
Total with taxes and fees
Comfort and Style in Our Queen Cottage
Exterior detail

Farm Country Cottage in Downtown Geyserville, Vineyard Views + UNTI Wine

Farm Country Cottage in Downtown Geyserville, Vineyard Views + UNTI Wine
Geyserville
10.0 out of 10, Exceptional, (1 review)
"WELL......if I wasn't so ecstatic to share my joy, I would be selfish and not want anyone else to discover this gem...This place is THE DREAM. It's giving all the vibes: Gorgeous wine country, iconic farm meets industrial design AND adorable goats, mustangs and a cutey cow? I mean come on! Coffee and wine stocked....walk anywhere in town...Space is private and peaceful and Danae was such a gracious host when I had any questions...I wished I could have stayed a week. I'll be back for sure, and...
United States
Lauren K.
$327 nightly
The price is $362
Apr 13 - Apr 14
Total with taxes and fees
Farm Country Cottage in Downtown Geyserville, Vineyard Views + UNTI Wine
House (2 Bedrooms) | Interior

Watefront Getaway w/ Mtn Views & Dock in Clearlake

Watefront Getaway w/ Mtn Views & Dock in Clearlake
3.0 star property
Clearlake
$245 nightly
The price is $270
Apr 6 - Apr 7
Total with taxes and fees
Watefront Getaway w/ Mtn Views & Dock in Clearlake
Microwave, oven, stovetop, dishwasher

Enchanting Vineyard cottage nestled in the wine country!

Enchanting Vineyard cottage nestled in the wine country!
Santa Rosa
$630 nightly
The price is $696
Apr 8 - Apr 9
Total with taxes and fees
Enchanting Vineyard cottage nestled in the wine country!
Exterior

The Atlas Calistoga - Cottage #1

The Atlas Calistoga - Cottage #1
Calistoga
10.0 out of 10, Exceptional, (17 reviews)
"Great space, impeccably appointed, amazing location. Would stay again. "
United States
Kris R.
$770 nightly
The price is $871
Apr 26 - Apr 27
Total with taxes and fees
The Atlas Calistoga - Cottage #1
House (3 Bedrooms) | Interior

Dock, Slip & Launch: Waterfront Home on Clear Lake

Dock, Slip & Launch: Waterfront Home on Clear Lake
3.0 star property
Kelseyville
$633 nightly
The price is $702
Apr 13 - Apr 14
Total with taxes and fees
Dock, Slip & Launch: Waterfront Home on Clear Lake
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

The Sandman Santa Rosa Sonoma, an Ascend Collection Hotel

The Sandman Santa Rosa Sonoma, an Ascend Collection Hotel

8/10 Good
"nice breakfast, great pool, unfriendly bar keeper. Overall a great place"
Troy 1-night trip
Posted 1 hour ago
The Sandman Santa Rosa Sonoma, an Ascend Collection Hotel

Find out more about Middletown

Middletown Cottages information

Number of reviews
194
Accommodation
112 Cottages
Lowest Price
$223
Highest Price
$871

Frequently asked questions

How much do cottages in Middletown cost?
Prepare to pay between $223 and $871 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