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Check prices for these dates

Next weekend
22 Aug - 24 Aug
In two weeks
29 Aug - 31 Aug
In one month
12 Sept - 14 Sept
In two months
10 Oct - 12 Oct

Featured Cottages in Middletown and around

Mountain Cottage near Russian River, hiking & downtown, family and pet friendly
Terrace/patio

Mountain Cottage near Russian River, hiking & downtown, family and pet friendly

9.2 out of 10, Wonderful, (58)
"The cottage is a comfortable house. "
Mountain Cottage near Russian River, hiking & downtown, family and pet friendly
Backyard Garden Oasis
Property grounds

Backyard Garden Oasis

3.0 star property
9.6 out of 10, Exceptional, (49)
"Cute garden area, quiet, nice all inclusive spot"
The price is €185
includes taxes & fees
16 Aug - 17 Aug
Backyard Garden Oasis
Escape to Wine County in your independant Cottage in Downtown Calistoga
Terrace/patio

Escape to Wine County in your independant Cottage in Downtown Calistoga

10.0 out of 10, Exceptional, (21)
"We have stayed many times at the Cottage Grove Inn and it never disappoints. "
The price is €353
includes taxes & fees
18 Aug - 19 Aug
Escape to Wine County in your independant Cottage in Downtown Calistoga
Comfort and Style in Our Queen Cottage
Dining

Comfort and Style in Our Queen Cottage

9.8 out of 10, Exceptional, (48)
"Great place to stay. Clean and well appointed and in a great location for access to sites, vineyards, and restaurants "
The price is €210
includes taxes & fees
17 Aug - 18 Aug
Comfort and Style in Our Queen Cottage
ALL INCLUSIVE AMENITIES:Kayak,SUP,Pedal Boat,PingPong,Pickleball,Movie Nt &MORE!
Terrace/patio

ALL INCLUSIVE AMENITIES:Kayak,SUP,Pedal Boat,PingPong,Pickleball,Movie Nt &MORE!

9.2 out of 10, Wonderful, (11)
"Cottage appeared newly remodeled and had everything we needed. Great access to the lake and private dock."
ALL INCLUSIVE AMENITIES:Kayak,SUP,Pedal Boat,PingPong,Pickleball,Movie Nt &MORE!
Sunny View Cottage in the Beautiful Wine Country
Fridge, microwave, oven, stovetop

Sunny View Cottage in the Beautiful Wine Country

10.0 out of 10, Exceptional, (273)
"Quiet setting great location!!"
Sunny View Cottage in the Beautiful Wine Country
TREE HOUSE, WITH INDOOR/OUTDOOR SHOWER, PRIVATE DECK, POOL & INFIINITY HOT TUB
Exterior

TREE HOUSE, WITH INDOOR/OUTDOOR SHOWER, PRIVATE DECK, POOL & INFIINITY HOT TUB

TREE HOUSE, WITH INDOOR/OUTDOOR SHOWER, PRIVATE DECK, POOL & INFIINITY HOT TUB
Waterfront Cottage w/ Private Pool & Lake View!
Fridge, microwave, stovetop, dishwasher

Waterfront Cottage w/ Private Pool & Lake View!

9.2 out of 10, Wonderful, (40)
"Nice little house, good for a couple or small family. Great view of the lake in the back yard."
Waterfront Cottage w/ Private Pool & Lake View!
Santini Farmhouse | Complimentary tasting at Croix Winery included!
Exterior

Santini Farmhouse | Complimentary tasting at Croix Winery included!

10.0 out of 10, Exceptional, (48)
"Everything was perfect"
Santini Farmhouse | Complimentary tasting at Croix Winery included!
Healdsburg Plaza Gem--Complimentary wine tasting at Croix included!
Property grounds

Healdsburg Plaza Gem--Complimentary wine tasting at Croix included!

9.8 out of 10, Exceptional, (43)
"Great location. Clean.. Great communication with property manager. The problem is that the second bedroom is really the attic, and even with window AC was 10 degrees hotter than first floor. Also colder at n ight so in warmer months this could potentially be a problem."
Healdsburg Plaza Gem--Complimentary wine tasting at Croix included!
1 Bedroom Cottage Walking Distance to Down Town
Fridge, microwave, oven, stovetop

1 Bedroom Cottage Walking Distance to Down Town

10.0 out of 10, Exceptional, (56)
"Walking distance to many good coffee shops, bakeries, restaurants and shops while being in a very quiet area for a good nights sleep!"
1 Bedroom Cottage Walking Distance to Down Town
Great Price! Sunset Beach Cottage with Lovely garden, beach, and boat dock!
Outdoor dining

Great Price! Sunset Beach Cottage with Lovely garden, beach, and boat dock!

9.8 out of 10, Exceptional, (29)
"Beautiful property in a beautiful location. "
Great Price! Sunset Beach Cottage with Lovely garden, beach, and boat dock!
True Wine Country Living: 2BR Converted Milkbarn on Family Vineyard
Outdoor dining

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!"
The price is €432
includes taxes & fees
17 Aug - 18 Aug
True Wine Country Living: 2BR Converted Milkbarn on Family Vineyard
Chalk Hill Cottage Close to Wineries
Exterior

Chalk Hill Cottage Close to Wineries

9.8 out of 10, Exceptional, (40)
"The Chalk Hill cottage was the perfect getaway for Sonoma wine lovers. Located in Alexander Valley and close to great wineries."
Chalk Hill Cottage Close to Wineries
Warm And Cozy Mountain And Lake View Haven 2 Bedroom Cottage by RedAwning
Cottage, 2 Bedrooms | Private kitchen

Warm And Cozy Mountain And Lake View Haven 2 Bedroom Cottage by RedAwning

3.0 star property
Warm And Cozy Mountain And Lake View Haven 2 Bedroom Cottage by RedAwning
Escape to wine country in your independent cottage in downtown Calistoga
Terrace/patio

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."
The price is €358
includes taxes & fees
18 Aug - 19 Aug
Escape to wine country in your independent cottage in downtown Calistoga
Heron House--Complimentary wine tasting at Croix included!
Outdoor spa tub

Heron House--Complimentary wine tasting at Croix included!

10.0 out of 10, Exceptional, (23)
"We had a fabulous stay. Great house with a great location. It was lovely waking up and going outside to enjoy the river and woods around us. 5 min drive from Healdsburg main streets with great stores and restaurants. Enjoyed our drive to the coast, redwoods, and vineyards! Would stay again!"
Heron House--Complimentary wine tasting at Croix included!
Spacious Kelseyville Home w/ Large Lakefront Deck!
Outdoor dining

Spacious Kelseyville Home w/ Large Lakefront Deck!

3.0 star property
10.0 out of 10, Exceptional, (1)
"I wish the grill had worked, but I love it."
Spacious Kelseyville Home w/ Large Lakefront Deck!
Enjoy a Slice Of Country--Two miles to Downtown Healdsburg
Terrace/patio

Enjoy a Slice Of Country--Two miles to Downtown Healdsburg

10.0 out of 10, Exceptional, (62)
"Very clean, very beautiful, very quiet! A perfect place to stay while visiting Healdsburg."
Enjoy a Slice Of Country--Two miles to Downtown Healdsburg
ALL INCLUSIVE AMENITIES:Kayak,SUP,Pedal Boat,PingPong,Pickleball,Movie Nt &MORE!
Terrace/patio

ALL INCLUSIVE AMENITIES:Kayak,SUP,Pedal Boat,PingPong,Pickleball,Movie Nt &MORE!

9.4 out of 10, Exceptional, (15)
"We had such a good time. The lake was close by so we got to enjoy all our toys. Angelique was super nice very relaxed environment. Pet friendly and our dogs had a great time."
ALL INCLUSIVE AMENITIES:Kayak,SUP,Pedal Boat,PingPong,Pickleball,Movie Nt &MORE!
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 hotel in the downtown Santa Rosa area. Great location for restaurants and walking around so many options to choose from."
Edwin 1-night trip
Posted 13 hours ago
Hotel E

Frequently asked questions

How much do cottages in Middletown cost?
Prepare to pay between €185 and €432 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.