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Holiday rentals in Annaka

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Top-rated holiday rentals in Annaka

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Top guest favourite
An outdoor living area features a circular wooden table surrounded by two simple chairs. The space is sheltered by a wooden roof, offering a view of the lush greenery beyond, enhancing the connection with nature.
Home in Hokuto
4.97 out of 5 average rating, 142 reviews

Forests, architecture, and art Yatsugatake Minami Fumoto Blackbird Stopover

Peaceful days with a private forest. Enjoy the sound of birds, the sound of the wind, and the flickering of light in the forest from a comfortable distance. Located at the southern foot of Mt. Yatsugatake at an altitude of 1150 m, it is a place where people who seek the nature and climate of the highlands live, rather than a tourist destination. Spring brings new greenery and buds, cool summers, colorful autumn leaves, and the warmth of a wood stove. There are also plenty of seasonal activities, such as skiing, hiking, river play, hot springs, and Hokuto City, which is surrounded by famous peaks, has many viewpoints where you can enjoy views of Mt. Yatsugatake, the Southern Alps, and Mt. Fuji. There is also an abundance of spring water. Please try to find them. The building was designed and constructed by the Tokei team, and the team operates it as an inn for many people to use. The distinctive architecture is a redesign of an old townhouse using modern construction methods and traditional materials. Inside, you'll find artwork such as murals and stone carvings of black birds, as well as books and photo collections selected by the host, which you can take your time to enjoy during your stay. * The capacity is 4 people, but if it is only adults, the number of people who can stay comfortably is up to 3 people. * The price shown is for up to 2 people, and 10,000 yen will be added to the accommodation fee for each additional person.

Superhost
Cottage in Karuizawa
4.82 out of 5 average rating, 105 reviews

R-villa Karuizawa [Harunire]

* From June 1, 2026, an accommodation tax system will be introduced in Karuizawa Town.Due to this, the accommodation fee has been updated. Located within walking distance (about 900 meters) from Shinano Railway's Naka-Karuizawa Station and about a 15-minute drive from Karuizawa Station, this property is just a one-minute walk from a convenience store (7-Eleven), allowing you to enjoy a carefree stay in Karuizawa! Ideally located for sightseeing and Karuizawa weddings Upon entering the room, you will find a fully renovated, open-concept, and modern living and dining area.Surrounded by the reassuring charm of vintage and carefully crafted interior design, we invite you to spend a relaxing and nostalgic moment in this cozy space. ・Approximately 5–7 minutes on foot to Harunire Terrace and Tombo-no-Yu A spiritually enriching day begins with a morning walk along the Yugawa River, where you can feel its gentle flow and bask in its light. ・Even for long-term stays, the popular local supermarket Tsuruya and other shops are nearby, so you can enjoy a convenient daily life without any inconvenience. There are several different restaurants in the immediate vicinity, so you can enjoy an active stay in Karuizawa 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
An open-concept living space displays natural wood beams and a warm color palette. A dining table is positioned near expansive glass doors, providing views of the garden. A cozy seating area includes a lounge chair and a wood-burning stove, enhancing the inviting ambiance.
Home in Kamikawa
5 out of 5 average rating, 110 reviews

自然素材平家の一棟貸切宿 ドッグラン BBQ 焚き火 温泉 連泊割

It is a spacious, natural material house where you can enjoy the greenery of the garden from any room. You can have barbecues and fires in the garden, and there is a fence so your dog can spend time freely. Also, the garden is lit up at night and beautiful. Enjoy cooking in the spacious kitchen. (Equipped with cooking utensils, condiments, and dishes) An indoor wood stove is also available during the cold season. Experience the comfort of warming up from the inside. Just watching the fire flicker will soothe you. There are also two wonderful hot springs within 10 minutes by car, and the meals at the facility are also popular! (Towels are provided at the inn, please bring toothbrushes) There are many hidden gems, so please feel free to ask ♪ ※ High speed Wi-Fi is available. * We will send a detailed map to those who have booked ▪ ️ Kanto's largest antique market held every Sunday... 3-minute walk ▪ ️ Blueberry picking (June and July) ▪️Tangerine picking (November and December) ▪️ Strawberry picking (January, February, March) ▪ ️ BBQ… Rental 5,000 yen (Grill, mesh, charcoal, igniter, tongs, gloves, paper plates, paper cups, chopsticks included) ▪️Supermarket, butcher shop… 3 minutes by car ▪️Fire pit rental: 4,000 yen (with firewood)

Top guest favourite
Home in Shinano
4.99 out of 5 average rating, 274 reviews

Limited to one group per day, Mökki is a small cottage with a garden by a stream

Mökki means "cottage" in Finnish. Spend your time in a special place surrounded by nature. Guest house Mökki is located in Shinano-cho, a town blessed with forests, lakes and snow in the northern part of Nagano Prefecture, with a wealth of natural areas such as Kurohime Kogen, Lake Nojiri and Togakushi nearby. You can freely use the comfortable building renovated with natural materials such as cedar, cypress, and plaster, the natural garden that creates seasonal scenery, and the forest where the stream flows.In the forest that we have been maintaining, you can see birds, squirrels, and marten, and you can enjoy strolling around looking for wild vegetables and mushrooms, as well as swings and hammocks. We also paid close attention to the interior design and kitchen utensils to make sure you can enjoy "living" in the space. At the gazebo by the stream, you can enjoy BBQ and campfires without worrying about the weather. It is ideal as a base for hiking, fishing, paddle boarding, and golf during the green season, and as a base for winter sports during the snow season. We also offer a celebration cake service for customers celebrating their birthdays or anniversaries.Please check with me in advanced.

Guest favourite
The exterior of a traditional Japanese house is seen at dusk, featuring a sloped roof and wooden elements. Warm lights illuminate the entrance, creating a welcoming atmosphere. Surrounding greenery and a gravel pathway lead into the property, enhancing its rural charm.
Castle in Kumagaya
4.99 out of 5 average rating, 100 reviews

Enjoy a delightful and luxurious stay in a historic mansion | 60 minutes from central Tokyo | Open-air bath | Sauna | BBQ | Karaoke | Private rental

The best time to spend time in a traditional mansion. A time to feel the heart of Japan [Make fun memories / Live Group] It has been renovated into a deluxe room using the original Japanese style in a large 150-year-old mansion.It is a beautiful Japanese beauty, a very calm space, but a fun place to spend, you will have a memorable time. There is a rural landscape around the property, so you can enjoy the countryside, and Kumagaya City is also a place with good access to Saitama's tourist attractions, towns that also pass by the Shinkansen, and sightseeing. BBQ (bring ingredients) In case of rain, you can enjoy under the gate, open-air bath, barrel sauna (equipped with water bath), karaoke, theater room (game corner), listening to music, etc. The open-air bath allows you to bathe while looking out at the garden. (We buy bathing detergent with hot spring ingredients) I want you to feel tired while relaxing and physically relaxing, giving you a healing bath, and having fun with your friends. The sauna is also equipped with a water bath, so you can relax with the open-air bath.

Superhost
Home in Karuizawa
4.92 out of 5 average rating, 109 reviews

Karuiwazawa Oiwake | 1 private villa in the forest | Private garden | 1 bedroom

About a 15-minute drive from Karuizawa Station. A small retreat near the national forest of Karuizawa.Please relax and relax on the spacious terrace overlooking the small birds.Enjoy the quiet villa life while gazing at the stars. ★ The bedroom has 2 double beds (140 cm wide) and 1 single sofa bed.There are usually 2 double beds if you book up to 4 people.If you would like to add a single sofa bed, please contact us by message.(Additional fee: 3,000 yen) It is especially recommended for families. There are quiet villas and houses in the neighborhood of the☆ inn.Please be quiet after 9 pm. Please provide an ID at the time of ★booking or check-in. ☆Early check-in (from 15:00) may be available for an additional fee.Please message me.Depending on the dates, we may decline it. ★ There will be an additional charge for check-in after 9:00 p.m.Please understand. 9:00 PM – 11:00 PM: ¥3,000 There will be an additional charge of 3,000 yen per 2 hours.

Guest favourite
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 Karuizawahigashi
4.98 out of 5 average rating, 204 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 wooden deck features a round hot tub, overlooking a serene lake and surrounding greenery. In the distance, mountains stand against a bright blue sky filled with fluffy clouds, creating a scenic backdrop for relaxation.
Tiny home in Shinano
4.92 out of 5 average rating, 491 reviews

Enjoy the view of Lake Nojiri, with a private sauna, Anoie (あの家)

This house overlooks Lake Nojiri and has a superb view. There are several ski resorts (Myoko, Kurohime, Madarao) about 15-20 minutes away by car, making it a perfect base for winter sports. Enjoy the wood stove sauna and the water bath with a view. There are no private houses around, so you can listen to music and watch movies loudly. Because it is a house located deep in the mountains, we take the best measures, but in the warm season, insects come out. It snows a lot in winter. In autumn, fallen leaves dance. You will also need to adjust the wood stove fire yourself. It's not an easy house to live in, but we promise you a great view and experience. Enjoy cooking with a counter kitchen with a view, condiments and cooking utensils. (There is no equipment for BBQ)

Top 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.
Flat in Isobe
4.91 out of 5 average rating, 355 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

Guest favourite
The log cabin is surrounded by lush greenery, showcasing a wooden deck and balcony with simple railing. Warm light glows from the windows, creating a welcoming ambiance as trees frame the cabin, offering a serene setting in a forested area.
Cabin in Nagano
4.93 out of 5 average rating, 547 reviews

Elegant, Secluded Cabin for Couples & Families

This is a stylish log cabin located in a pristine wooded area at an altitude of 1,300 meters (4,265 feet) in Iizuna, Nagano. The home is the perfect retreat for couples, families or small groups. It features a wood burning stove, large TV, Blu-ray/DVD player, stereo, leather chairs, and full kitchen. Enjoy hiking, skiing, BBQ, golf or hot spring onsen baths in the area. The home is approximately a 20-minute drive from Nagano Station on the JR Hokuriko Shinkansen bullet train and Shinano Railway.

Top guest favourite
A modern kitchen area features wooden cabinetry and a countertop with a sink and stove. A dining table with wooden chairs is seen in the background. Natural light enters through windows, illuminating the open layout that connects to a bright living space.
Place to stay in Karuizawahigashi
4.98 out of 5 average rating, 279 reviews

5 min Walk|Eco-Chic : Nordic Vintage & Always 23°C

Karuizawa Station 5min|Private Nordic Suite Enjoy a unique stay above our 1982-established restaurant. ■ Design & Comfort Produced by haluta, featuring vintage Nordic furniture. High insulation keeps the room at a constant 23°C (73°F) year-round—eco-friendly and cozy in any season. ■ Essentials - Full Kitchen - Washer & Dryer - Free shared workspace next door - Premium Koala Mattresses Savor the aroma of roast chicken from downstairs. Takeout available! 2+ nights min. Request for 1-night.

Top guest favourite
The spacious living area features a comfortable seating arrangement with a large television. Natural light fills the space through wide windows, complemented by warm wood flooring. The connected dining area is visible, showcasing a large table set for meals, alongside the modern kitchen with sleek appliances.
Home in Karuizawa
4.99 out of 5 average rating, 265 reviews

Lampas karuizawa-The best choice for a family trip

"Live like a local in Karuizawa! 🏠" My wife and I welcome you to our lovely home, the perfect retreat for family trips. You will have the entire 1st floor to yourselves. It features 3 bedrooms with 6 beds, a comfortable living room, and a spacious counter kitchen with a large dining table that seats 6. The location is ideal for exploring. Local restaurants, pubs, natural onsen, and the Wild Bird Forest are all just a 10-minute walk or 3-minute drive away. We look forward to hosting you!😀

Popular amenities for Annaka holiday rentals

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  3. Gunma Prefecture
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