Middletown Vacation Rentals

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Check prices for these dates

In two weeks
Apr 3 - Apr 5
In two months
May 15 - May 17
In three months
Jun 12 - Jun 14
In four months
Jul 10 - Jul 12

Our top choices for Middletown vacation rentals

Porch

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
The price is ￥32,989
￥36,783 total
includes taxes & fees
Mar 21 - Mar 22
Backyard Garden Oasis
Property grounds

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.
The price is ￥16,415
￥36,012 total
includes taxes & fees
Mar 22 - Mar 23
Garden house with gas fireplace
Front of property

The Ranch at Lake Sonoma

The Ranch at Lake Sonoma
1.0 star property
Geyserville
9.4 out of 10, Exceptional, (3 reviews)
"Nice camping spot "
United States
Evelyn
The price is ￥12,501
￥14,251 total
includes taxes & fees
Mar 21 - Mar 22
The Ranch at Lake Sonoma
Apartment, 1 Bedroom (Sonoma Stonehouse in Boutique Hotel) | Iron/ironing board, free WiFi

Sonoma Stonehouse, Wine Country Vibes

Sonoma Stonehouse, Wine Country Vibes
2.0 star property
Santa Rosa
The price is ￥13,628
￥41,146 total
includes taxes & fees
Mar 22 - Mar 23
Sonoma Stonehouse, Wine Country Vibes
Lake

Clear Lake Cottages & Marina

Clear Lake Cottages & Marina
2.5 star property
Clearlake
9.0 out of 10, Wonderful, (331 reviews)
"The property was beautiful, stayed a night in cottage - 24, it has 2 queen beds a comfortable couch and sitting chair , coffee table and 4 chair and table dinette. The cottage has plenty of room, 2 flat screen tvs, heater and air worked great! Nice grounds to walk around and friendly staff. Close to town for restaurants. Excellent choice for a stay in Clearlake !"
United States
Rob
The price is ￥22,506
￥25,094 total
includes taxes & fees
Mar 22 - Mar 23
Clear Lake Cottages & Marina
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
The price is ￥22,729
￥42,604 total
includes taxes & fees
Mar 22 - Mar 23
Watefront Getaway w/ Mtn Views & Dock in Clearlake
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
The price is ￥44,037
￥57,703 total
includes taxes & fees
Mar 22 - Mar 23
Escape to wine country in your independent cottage in downtown Calistoga
Terrace/patio

Lakefront Family Getaway | Dock, Hot Tub, Kings

Lakefront Family Getaway | Dock, Hot Tub, Kings
Lakeport
10.0 out of 10, Exceptional, (24 reviews)
"Very Nice House"
United States
Chandy O.
The price is ￥38,631
￥122,450 total
includes taxes & fees
Mar 24 - Mar 25
Lakefront Family Getaway | Dock, Hot Tub, Kings
Living area

Mandala Springs Wellness Retreat Center

Mandala Springs Wellness Retreat Center
3.5 star property
Cobb
8.8 out of 10, Excellent, (30 reviews)
"Very clean room, friendly staff, great to walk around "
United States
Victoria
The price is ￥25,428
￥28,352 total
includes taxes & fees
Apr 1 - Apr 2
Mandala Springs Wellness Retreat Center
Interior

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.
The price is ￥78,762
￥98,631 total
includes taxes & fees
Mar 22 - Mar 23
The Carriage House Sonoma • Hot Tub • Vineyard Views • Complimentary Bottle
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
The price is ￥44,037
￥57,229 total
includes taxes & fees
Mar 22 - Mar 23
Escape to Wine Country in your independant Cottage in Downtown Calistoga
Room, 1 Bedroom | Outdoor dining

Rouge Cobb Mountain Hotel - Cabin 2

Rouge Cobb Mountain Hotel - Cabin 2
2.0 star property
Cobb
The price is ￥16,806
￥36,493 total
includes taxes & fees
Mar 23 - Mar 24
Rouge Cobb Mountain Hotel - Cabin 2
Exterior

Rainbow Lodge

Rainbow Lodge
2.0 star property
Lakeport
4.4 out of 10, (17 reviews)
"Friendly manager at check in, quiet location, conveniently located. Room was adequately "
United States
Daniel
The price is ￥11,532
￥15,226 total
includes taxes & fees
Mar 22 - Mar 23
Rainbow Lodge
Property grounds

Bungalow on the lake

Bungalow on the lake
Clearlake
7.8 out of 10, Good, (8 reviews)
"Great little cottage for a good price. "
United States
Danielle C.
The price is ￥23,360
￥33,863 total
includes taxes & fees
Apr 1 - Apr 2
Bungalow on the lake
Property grounds

Lake front unit #6 right by the water

Lake front unit #6 right by the water
Clearlake
8.4 out of 10, Very Good, (23 reviews)
"Maureen was very accommodating "
United States
JOSH
The price is ￥9,234
￥19,358 total
includes taxes & fees
Mar 22 - Mar 23
Lake front unit #6 right by the water
Interior

Beautiful Wine Country Vacation Home - St. Helena Short Term Permit PL-24-021

Beautiful Wine Country Vacation Home - St. Helena Short Term Permit PL-24-021
St Helena
10.0 out of 10, Exceptional, (255 reviews)
"Enjoyed it so much that I’m coming back in two weeks! "
United States
Thomas H.
The price is ￥260,436
￥333,911 total
includes taxes & fees
Mar 22 - Mar 23
Beautiful Wine Country Vacation Home - St. Helena Short Term Permit PL-24-021
Outdoor pool

Wine Country Villa, Brush Creek, Heated Pool & Hot Tub

Wine Country Villa, Brush Creek, Heated Pool & Hot Tub
Santa Rosa
10.0 out of 10, Exceptional, (20 reviews)
"Wonderful hosts, wonderful experience "
United States
Edward G.
The price is ￥134,077
￥265,547 total
includes taxes & fees
Apr 1 - Apr 2
Wine Country Villa, Brush Creek, Heated Pool & Hot Tub
Smart TV, fireplace, DVD player, books

Wine Country Retreat w/ Pool, Hot Tub, Backyard & Game Nights Near Wineries

Wine Country Retreat w/ Pool, Hot Tub, Backyard & Game Nights Near Wineries
Santa Rosa
10.0 out of 10, Exceptional, (14 reviews)
"Great property and owner really cared about our stay being great."
United States
Todd J.
Wine Country Retreat w/ Pool, Hot Tub, Backyard & Game Nights Near Wineries
Exterior

Guinda's Finest Nature Get-Away!

Guinda's Finest Nature Get-Away!
Guinda
9.8 out of 10, Exceptional, (8 reviews)
"Wonderful location, beautiful view."
United States
George M K.
The price is ￥42,617
￥66,135 total
includes taxes & fees
Mar 24 - Mar 25
Guinda's Finest Nature Get-Away!
Interior

The Estate at Sycamore- Sonoma Wine County Retreat

The Estate at Sycamore- Sonoma Wine County Retreat
Santa Rosa
9.4 out of 10, Exceptional, (35 reviews)
"Beautiful house in a quiet neighborhood. Very spacious bedrooms, very nice bathrooms. Communication was excellent. Will definitely be staying again. "
United States
Rodney S.
The price is ￥95,840
￥176,001 total
includes taxes & fees
Mar 26 - Mar 27
The Estate at Sycamore- Sonoma Wine County Retreat
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

Mount View Hotel & Spa

Mount View Hotel & Spa

10/10 Excellent
"Very much enjoyed my stay. The staff was very friendly and helpful. The spa services were the best! A big thank you to Stacy and Kelsee for their excellent spa service, ahhhhh so nice! The hotel is walking distance to so many shops and the town is very quaint. I will definitely go back again. "
Lisa 4-night trip
Posted 14 hours ago
Mount View Hotel & Spa

Find out more about Middletown

Search for holiday rentals in Middletown on Expedia! You can easily find your home rentals, villas, holiday apartments in Middletown using one of the methods below:

  • View our selection of featured holiday rentals in Middletown
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Look no further and take a look at our great range of rental properties in Middletown!

Frequently asked questions

Can I find vacation rentals in Middletown?

Yes, we offer vacation rentals close to top attractions in Middletown, or you can go with a secluded option if you'd like a relaxing place to stay. Middletown is known for its hot springs and wineries. Make sure you have time to check out the spas and casinos during your trip.

What are some of the best vacation rentals that Middletown has to offer?

Luxury Vineyard Guest House with Amazing Views, Pool, Pickle Ball & Tennis!: This vacation home rental near Middletown is located in the city center and has an outdoor pool, a fireplace, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. It offers a balcony, a garden, and a selection of games so you can immerse yourself in your vacation.

How many vacation rentals are there in Middletown?

Expedia has 11 vacation rentals for your stay in Middletown.

What can I see and do in Middletown?

Explore the area and family-friendly sights such as SingleThread Farm at Dry Creek, or get out into nature at a spot like Boggs Mountain Demonstration State Forest. Other places in town to visit include Twin Pine Casino and Robert Louis Stevenson State Park.

What are vacation rentals like in Middletown?

Vacation rentals are private properties you can stay in for several days or longer in Middletown. Vacation rentals offer extras like WiFi and washers and dryers so you'll have a home away from home. If you're concerned about cleanliness, a vacation rental can provide a sense of safety away from shared hotel elevators and busy lobbies while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a standard hotel, which makes a vacation rental a great choice for a family trip or a small group gathering.