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Aug 29 - Aug 31
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Oct 17 - Oct 19

Cottages in Middletown

Our top choices for Middletown cottages

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"
$194 nightly
The price is $216
Aug 24 - Aug 25
Total with taxes and fees
Backyard Garden Oasis
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, (60)
"The cottage is a comfortable house. "
Mountain Cottage near Russian River, hiking & downtown, family and pet friendly
Escape to Wine County in your independant Cottage in Downtown Calistoga
Terrace/patio

Escape to Wine County in your independant Cottage in Downtown Calistoga

9.6 out of 10, Exceptional, (22)
"We have stayed many times at the Cottage Grove Inn and it never disappoints. "
$335 nightly
The price is $403
Aug 25 - Aug 26
Total with taxes and fees
Escape to Wine County in your independant Cottage in Downtown Calistoga
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
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, (57)
"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
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
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 "
$199 nightly
The price is $240
Aug 24 - Aug 25
Total with taxes and fees
Comfort and Style in Our Queen Cottage
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
Waterfront Cottage w/ Private Pool & Lake View!
Fridge, microwave, stovetop, dishwasher

Waterfront Cottage w/ Private Pool & Lake View!

9.2 out of 10, Wonderful, (43)
"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!
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."
$340 nightly
The price is $408
Aug 25 - Aug 26
Total with taxes and fees
Escape to wine country in your independent cottage in downtown Calistoga
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!
Windmill Cottage - Peaceful & Quiet on 5 acres
Dining

Windmill Cottage - Peaceful & Quiet on 5 acres

10.0 out of 10, Exceptional, (12)
"Joshua was the best host! "
$470 nightly
The price is $470
Aug 24 - Aug 25
Total with taxes and fees
Windmill Cottage - Peaceful & Quiet on 5 acres
Russian Riverside Cottage in Healdsburg
Fireplace

Russian Riverside Cottage in Healdsburg

8.6 out of 10, Excellent, (9)
"We had a wonderful stay. "
Russian Riverside Cottage in Healdsburg
The Atlas Calistoga - Cottage #2
Iron/ironing board, travel crib, WiFi, bed sheets

The Atlas Calistoga - Cottage #2

10.0 out of 10, Exceptional, (18)
"We recently had a lovely stay. Very conveniently located just a short walk to downtown. Great layout, with a king bed, fireplace, cute small patio with chairs, huge bathroom and a little fridge & coffee station area. The host was super responsive and provided great recommendations for local wine tasting and dinner locations. Lovely small town with cute shops, breakfast & bakery options, wine bars and restaurants. We had a great stay and will definitely be back!"
$439 nightly
The price is $498
Aug 28 - Aug 29
Total with taxes and fees
The Atlas Calistoga - Cottage #2
The Atlas Calistoga - Cottage #3
Exterior detail

The Atlas Calistoga - Cottage #3

10.0 out of 10, Exceptional, (19)
"Great cottage within walking distance to downtown Calistoga."
$505 nightly
The price is $574
Sep 16 - Sep 17
Total with taxes and fees
The Atlas Calistoga - Cottage #3
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!"
$440 nightly
The price is $495
Aug 24 - Aug 25
Total with taxes and fees
True Wine Country Living: 2BR Converted Milkbarn on Family Vineyard
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
Modern Sonoma Stay w/ Spacious Deck, Views & Prime Location Bennett
House (3 Bedrooms) | Interior

Modern Sonoma Stay w/ Spacious Deck, Views & Prime Location Bennett

3.0 star property
Modern Sonoma Stay w/ Spacious Deck, Views & Prime Location Bennett
Private Hot Tub w/ Water Views: Lower Lake Getaway
TV, fireplace

Private Hot Tub w/ Water Views: Lower Lake Getaway

10.0 out of 10, Exceptional, (1)
"Our family of four had a wonderful weekend stay at this well appointed lakeside property."
Private Hot Tub w/ Water Views: Lower Lake Getaway
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!
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
"A very quaint small hotel. Awesome location. "
Karen 3-night trip
Posted 13 hours ago
Hotel E