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Holiday houses in Annaka

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Top-rated holiday rentals in Annaka

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Guest favourite
Cottage in Karuizawa
4.82 out of 5 average rating, 133 reviews

Complete renovation of a single-storey old kominka house [Harunire]

* From June 1, 2026, an accommodation tax system will be introduced in Karuizawa Town.Due to this, the accommodation fee has been updated. All the main attractions of Naka-Karuizawa are within walking distance! Within walking distance (about 900 metres) of Shinano Railway's Naka-Karuizawa Station, about 15 minutes by car from Karuizawa Station, and a 1-minute walk to a convenience store You can enjoy a carefree stay in Karuizawa ・A harmonious blend of traditional charm and sophisticated modernity Surrounded by the reassuring charm of vintage and meticulously crafted interiors, enjoy a relaxing and nostalgic moment in this welcoming space. ・Popular Karuizawa tourist spots in the Hoshino area, such as Harunire Terrace and Tonbo-no-Yu, are about 5–7 minutes' walk away. ・Two bedrooms to ensure privacy Main bedroom with a queen-size bed We have provided a Japanese-style room (2 futons) that is like a separate dwelling enveloped in tranquillity. ・A hub supporting a wide range of journeys With the popular local supermarket 'Tsuruya' and other shops nearby, you'll have everything you need for a convenient daily life. There are several different restaurants very close by, so you can enjoy an active Karuizawa experience even if you don't have a car. * Same price for up to 2 people (There will be an additional charge if there are more than 2 people) *There are two parking spaces on the premises

Top Guest favourite
Home in Agatsuma-gun
5.0 out of 5 average rating, 15 reviews

ASAMA HIDEAWAY|Hot spring fed directly from the source|Sauna|BBQ|Entire property rental|About 30 minutes by car from Karuizawa Station

NEW OPENING in July 2026!! ASAMA HIDEAWAY is a luxurious, grown-up hideaway villa nestled at the foot of Mount Asama, designed by architect Keisuke Kajitani. A special location surrounded by a beautiful forest and the babbling of a stream.As you step into the building, which is dominated by a modern, natural black, you are greeted by the overwhelming sense of openness created by the high ceilings and the high-quality interior. The biggest attraction is the completely private spa area located right next to the creek that runs through the property. With a view of dynamic natural rock skin and deep greenery, the "semi open-air bath", and an authentic "sauna and water bath", you can ultimately spend a moment in mind and body. The luxurious outdoor living room is equipped with a BBQ grill and bioethanol fireplace.Enjoy a sophisticated space for adults, where you can enjoy a BBQ amidst the fresh green during the day, and be soothed by the flickering flames and the sound of the stream at night. Kita-Karuizawa is easily accessible from Tokyo, yet it offers the richness of nature brought by Mount Asama and an overwhelming silence that is isolated from the hustle and bustle of the city.Please experience a time that sharpens your five senses, which can only be found here.

Guest favourite
Castle in Nagatoro
4.98 out of 5 average rating, 279 reviews

Large space along the Nagatoro Valley river | Sauna, BBQ, karaoke | Limited to 1 group per day

Live Nagatoro's large resort villa, "Live Nagatoro", with its overwhelming presence and unique atmosphere, provides unforgettable memories for visitors.Luxurious and fun [Make fun memories / Live Group] Spacious and private space to enjoy nature Scenic location downstream of Nagato and Iwamata About 60 minutes from the city center and only 25 minutes by car from Kanetsu Road and Hanazono IC.This property is nestled along the beautiful river of Nagato, where nature remains, while having excellent access. [Charming point] You can play in the river right from the building!1-2min walk from the property to the river.An excitement of adventure through nature's paths. The window overlooks the Arakawa River.In autumn, vibrant autumn leaves spread out, and you can enjoy the scenery of the four seasons. It is equipped with a wood stove and oil stove, so you can rest assured in the winter. You can spend a relaxing time in a completely private space. [There are also plenty of nearby sightseeing spots] Within a 10-minute drive! Nagatoro Iwamata (tourist attraction) · Outdoor experiences such as SAP/Rafting Nagatoro Fishing Center Nagatoro Country Club Get in touch with nature, enjoy the experience, and have a special time that you can only experience here.

Superhost
Home in Ikahomachi Ikaho
5.0 out of 5 average rating, 3 reviews

5 Ikogabo Onsen, 3 minutes by car from Ishidangai, 2 bedrooms, 3 DB / Ikogabo Festival from 18 to 20 September / 70 minutes by car to Kusatsu Onsen

Ikaho Shuku BASE】 3 minutes by car from Ikaho Ishidan! A private rental accommodation that is ideal as a base for sightseeing in Kusatsu and Karuizawa Welcome to "Ikaho Shuku BASE", located in the Ikaho area, where the rich nature and hot spring atmosphere remain! It is in a prime location just 3 minutes by car from the popular "Ikaho Ishidan Street", and is a very convenient location as a base for sightseeing drives to the Kusatsu and Karuizawa areas. There are two bedrooms in the spacious building, and it can comfortably accommodate up to eight people. There is free parking for 3 cars on the premises, so you can feel at ease even on a group trip with multiple cars. The building is equipped with Wi-Fi, and there is also a fully equipped kitchen where you can enjoy cooking. It's perfect for creating memories on a family trip or in a group of friends. Please enjoy a relaxing time with your loved ones in a calm, private space. 20 minutes by car or 40 minutes by bus from JR Shibukawa Station. A single-storey house (50 m²) in a quiet residential area in Ikabo-cho, Shibukawa City. (50 m²). The Ikaho bus stop is far away, so a car is we recommend using a car. <Note> Cameras are installed outside only. Please refrain from booking for one person.

Superhost
A spacious sunlit dining area features a wooden table surrounded by chairs, offering views of the lush garden outside. Large glass doors open to a wooden deck, enhancing the connection to nature. A soft light filters through a translucent ceiling.
Home in Kamikawa
4.97 out of 5 average rating, 140 reviews

Hirake, made from natural materials. Dog run, BBQ, campfire, playing in the river, hot spring, discount for consecutive stays.

It is an open natural material Heike house where you can enjoy the greenery of the garden from every room. In the garden, there are barbecues, fires, and fences, so your dog can stay freely. Also, the garden is lit up at night and is beautiful. Enjoy cooking in the spacious kitchen.(Fully equipped with cooking utensils, condiments, plates) There are also two great hot springs that can be reached in 10 minutes by car, and the meals in the facility are also popular! (Please bring towels and tooth brushes with you) Access to Nagatoro, Chichibu, and Ikaho Onsen is also good🚗 I recommend playing in the beautiful nearby river in the summer! There are many recommendations for hidden gems, so please do not hesitate to contact us♪ * There is high-speed Wi-Fi. * We will send a detailed map to the person who made the reservation Kanto's largest antique market is held ▪️every Sunday... 3-minute walk ▪️Blueberry Picking (July) ▪️Orange Hunting (Nov.12) ▪️BBQ... rental 5,000 yen (Grill, net, charcoal, lighter, chakkaman, gloves, paper plates, paper cups, chopsticks) ▪️Supermarkets, butchers... 3 minutes by car ▪️Fire pit rental... 4,000 yen (with firewood) * There is a security camera at the entrance.

Top Guest favourite
A well-maintained garden path leads to a traditional two-story house framed by lush greenery. Sunlight filters through the leaves, illuminating various shrubs and trees surrounding the home. The clear blue sky above creates a serene outdoor environment.
Home in Chichibu
4.96 out of 5 average rating, 281 reviews

Minsu Aoyama is an entire Japanese-style house.

[Floor plan and facilities] [Ground floor] ◾️ Tea room (8 tatami mats) ◾️ Floor space (8 tatami mats, can be used as a bedroom) ◾️ Dining kitchen (gas stove,  Oven range, rice cooker, refrigerator,  Each has tableware and air conditioning) ◾️ Western music (analogue records, CD listening/   Air conditioning available) ◾️ Toilet ◾️ Bathroom [2nd floor] ◾️ Bedrooms (8 tatami mats, 7 tatami mats, 5 tatami mats,  Shared air conditioning in both rooms) ◾️ Toilet ◾️ Courtyard (BBQ barbecue grill,  Table rental available)  ⭐️Advance booking required  ⭐️Period (April to November) [Nearby] (about 10 minutes by car) ○ Hot spring facilities ○ Winery ○ Whiskey brewery ○ Golf course ○ Sujin Shrine (Ryusei Festival) ○ Fruit road (strawberry, grape, blueberry) ○ Convenience store ○Supermarket ○ Ryusei Kaikan Roadside Station/Agricultural Products Direct Sales Office (a few minutes on foot)

Superhost
A spacious living area features a comfortable sofa and colorful chairs around a dining table. Natural light filters in through sheer curtains covering a window. A small coffee table is placed on a textured rug, complementing the warm wooden flooring.
Home in Karuizawa
4.96 out of 5 average rating, 222 reviews

Izumiya house1, a good location for sightseeing access near Izumiya station

IZUMIYA is a newly built, single-family home located about a 7-minute walk from the north exit of Karuizawa Station. The house has 2 units and rents 2 buildings. It is in a good location within walking distance of the popular outlet mall, Kyukaruizawa Ginza, and Unba Pond, and you can also enjoy the beautiful nature unique to Karuizawa. It is very convenient, with a convenience store, supermarket, and delicious restaurants nearby. You can spend a spacious time renting one building, and it is equipped with a kitchen, furniture, and appliances necessary for daily life, so you can stay with your family and friends as if you were living in Karuizawa. Small children are also welcome. We keep the rooms clean and use a professional cleaning service for the towels and linens so that guests can feel at ease. Please let us know if you'd like to be flexible with check-in times, etc.

Superhost
A vibrant display of blooming flowers features clusters of purple and pink petunias, interspersed with green foliage. The lush garden bed is bordered by dark stones, providing a natural contrast to the bright colors of the blossoms.
Home in 高崎市
4.87 out of 5 average rating, 219 reviews

Please have a relaxing time on the sunny veranda side of the two rooms that are pure Japanese-style.

It is a pure Japanese-style bungalow single unit constructed 30 years ago. Feel free to use the pans, microwave, oven, and utensils in the spacious private kitchen, enjoy your meals and unwind. Rest peacefully in the tatami mat room on Japanese futons lined with pillows. Parking is also available for up to 2 station wagon sized vehicles. In addition, due to the enforcement of the new Private Lodging Law (Residential Accommodation Business Law) on June 15, 2018, government agencies are required to fill in the list of guests, and foreigners who do not have an address in Japan are required to present their passports.Therefore, we ask for permission to fill in the guest list and present your passport and copy at the time of staying.We appreciate your understanding.

Guest favourite
A wooden deck extends from the house, furnished with a dining table and chairs. Lush greenery frames the view, with trees and a body of water visible in the background under a clear blue sky.
Home in Karuizawa
4.95 out of 5 average rating, 113 reviews

[Riverside House] A riverside villa in Karuizawa with a sauna and fireplace

We have renovated a villa along the river in the forest of Karuizawa. Great location is about 2,500 ㎡! Feel the extraordinary feeling of the garden and outdoor dining where you can run around, the living room has a large sofa and fireplace. The bathroom can also be enjoyed in the JAXSON jetted tub, a large sauna for 4 people in the metos, and a rain shower in the water bath. This renovated old villa is set in a nature-rich environment.Please be aware in advance that insects may appear in your room during your stay when making your booking.If you have excessive allergies to insects, etc., please avoid booking.

Guest favourite
The room features a low table surrounded by tatami mats, providing a comfortable and traditional setting. Bright yellow curtains frame the windows, allowing natural light to fill the space. A television set is positioned nearby, creating a cozy atmosphere for relaxation.
Apartment in Annaka
4.9 out of 5 average rating, 365 reviews

40 minutes to Karuizawa, next to a hot♨ spring, with a golf course and ski resort close by, 2DK room

◆ Overview 3-minute walk from the nearest station 2DK room with tatami mats and kotatsu for relaxing There is a day-use hot spring with good water quality next door♨ ・ It is a quiet and calm environment with lots of nature Bicycles We have one available, so please feel free to use it☀ However, you are responsible for any accidents, etc. (no insurance) ◆ Neighborhood information ・ Karuizawa: About 40 minutes by car ・ Ikaho Onsen: About 60 minutes by car ・ Kusatsu Onsen: About 90 minutes by car ・ Tomioka Silk Mill: About 20 minutes by car

Top Guest favourite
The Capsule House is nestled among autumn foliage, with vibrant orange and yellow leaves surrounding the unique architectural structure. The building features distinct circular windows and a wooden facade, offering a harmonious blend with the natural landscape.
Holiday home in Miyota
5.0 out of 5 average rating, 25 reviews

Capsule House-K, a monumental capsule house in nature designed by Kisho Kurokawa

CAPUSULE HOUSE-K is a private house designed by Kisho Kurokawa. It was created based on the concepts of Metabolism and Homo Mobius. This building is composed of the same capsules as the Chugin Capsule Tower Building, which is also a metabolism building, and was completed in 1973, the year after the building was completed. Until now, it has been open only to a few people and was a little-known building, but in 2019, the restoration was started by Kisho Kurokawa's son, and now it is open to the public with the interior of that time.

Guest favourite
A modern A-frame living area showcases large glass doors that connect the indoor space with a wooden deck. Natural wood walls and flooring create a warm environment. A cozy sitting area includes a three-seater sofa and a coffee table, complemented by a pellet stove.
Home in Shimonita
4.96 out of 5 average rating, 54 reviews

NEW! A-Frame House in Minami Karuizawa

“A-FRAME HOUSE” is a newly built & highly unique triangle shaped house located in beautiful Minami Karuizawa. Gaze for hours at the surrounding trees and mountains through the eight meter tall South facing triangular window. Step outside onto the 20 square meter wood deck and fully immerse yourself in nature. The modern Western style interior will make you feel like you’re in Europe or North America. Come and unwind in a one-of-a-kind home and enjoy the tranquil beauty of Minami Karuizawa.

Popular amenities for Annaka holiday rentals

Other great holiday rentals in Annaka

Guest favourite
A spacious living area is depicted, featuring large windows that invite natural light and offer views of the surrounding greenery. A modern sectional sofa and a circular coffee table are located on light hardwood flooring. The room's open design enhances the sense of openness.
Home in Karuizawa
4.98 out of 5 average rating, 84 reviews

[Big call for applications for October, the best season for autumn leaves!] View of Mt. Asama! Enjoy the birdsong, tranquillity, convenience and stunning views!

Superhost
Cabin in Oazakitakaruizawa
5.0 out of 5 average rating, 3 reviews

【Noël Kitakaruizawa Notch】Pets, Sauna & Jacuzzi

Guest favourite
A traditional-style room features natural wood accents and a low wooden table surrounded by cushions. A television is mounted on the wall, and a dining area is visible in the background. Light is gently diffused through the window, illuminating the space.
Home in Annaka
4.96 out of 5 average rating, 25 reviews

[Kanauya] Kyu-Usui Pass Promenade, Tetsudo Bunka Mura 3 minutes by car, Karuizawa 25 minutes, whole house rental, 2 nights or more

Guest favourite
A spacious living area features a large, dark-colored sofa and a dining table for gatherings. Light enters through multiple windows with shoji screens, illuminating the harmonious blend of traditional design and modern comfort.
Home in Tomioka
5.0 out of 5 average rating, 77 reviews

Jugoya Villa: A soothing house that blends tradition and modernity. Maximum 13 guests. Roofed BBQ. Families welcome

Guest favourite
A spacious onsen bathing area is surrounded by wooden walls and large windows, allowing natural light to illuminate the space. Stone flooring complements the wooden features, while two benches and two wash stations with mirrors are positioned near the edges. A deep, stone-lined onsen bath is centrally located.
Villa in Tsumagoi
5.0 out of 5 average rating, 57 reviews

AsamaMori : a private onsen villa in Kitakaruizawa

Superhost
Home in Karuizawa
5.0 out of 5 average rating, 3 reviews

NEW OPEN | Forest Riverside Villa | Dog Run &Sauna

Guest favourite
Home in Oazakitakaruizawa
5.0 out of 5 average rating, 9 reviews

The Cabin by Deep Gorge|焚き火と陶器を楽しむ森の一棟貸し

Superhost
Home in Takasaki
4.81 out of 5 average rating, 31 reviews

6 minutes by car from Takasaki Station | P3 parking spaces, 4 bedrooms | A house in a retro-modern building | A hot spring leisure trip to Ikaho, Minakami and Kusatsu