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Cupples Cottage #1: Downtown, On-Site Car Rental!

Welcome to the award winning Cupples Cottages! This 600sf flat was recently renovated and is beautifully furnished. When built in 1952 by my late grandfather these units were offered fully furnished providing temporary housing primarily to the construction workers living away from their families working on my grandfather's construction crew. Fast forward over 70 years and 2 generations and the property has been reimagined as Cupples Cottages Vacation & Vehicle Rentals, operating since 2017.

Downtown Portside Hideaway

This newly renovated cottage is in a downtown setting yet out of the bustle of busy city streets. It has a great view of the inlet and port, ands sits above the railyard. The bedroom has a KING size cool foam mattress and full bathroom with shower. On chilly nights enjoy an electric fireplace while cooking in the fully equipped kitchen. The large backyard has a deck with table and chairs, as well as a firepit. There is a desk to work at and high-speed wifi internet, plus a free parking space.

Garden Level Getaway

Experience luxury living in this charming basement apartment with a private walk-out garden entrance. It features a fully equipped kitchenette, dining area, and a cozy seating area with a 55" Samsung Smart TV. A king-size bed awaits in the bedroom. The bathroom features a walk-in shower and radiant in-floor heating. The windows have black-out blinds for a restful night's sleep. Enjoy the convenience of an in-unit washer/dryer and the beauty of your private garden. Rich Fir paneling throughout.

Historic Art Deco Studio

Step into the past without sacrificing modern comfort in this restored 3rd-floor studio, located in the iconic Loussac Building in downtown Anchorage. Just steps from the Anchorage Mushing District, 5th Ave shops, restaurants, and the Coastal Trail, this space offers a rare blend of local history and updated design. Inside, you’ll find an Art Deco-inspired studio with a modern twist: a King bed, Kitchen, full bathroom combo, fast WiFi. Please note: the building does not have an elevator.

New Guest Apartment on the Coastal Trail

Located near the Airport and on the world famous Coastal Trail right on the water of the Cook Inlet, the location boasts a super fast (fastest) internet connection and unlimited downloads for business traveler’s needs. We are in a quiet and safe neighborhood and have free dedicated parking for our guests. Literally 5 minutes to the airport, 5 minutes to downtown and midtown Anchorage by car. We also provide two Bikes and Tennis equipment for your enjoyment during summer months.

Cozy, newly renovated 1-bedroom unit (1)

Enjoy a stylish experience at this centrally-located place. Equipped with amenities and a Roku TV, this renovated apartment has everything you need to make your stay comfortable. This spot is located 9 minutes from the airport, 6 minutes from downtown, and is in walking distance to restaurants and stores. We look forward to hosting you! *Before booking, please read the entire listing description to get an understanding of the pros/cons, sleeping arrangements, house rules, and more.*

Sunny and Warm 1-Bedroom Apartment in Midtown

Cute and remodeled apartment in midtown Anchorage! This apartment has all the necessities to make your time in Anchorage comfortable. Very conveniently located; here you are 5 to 10 minutes from everything in Anchorage. The afternoon and evening sun streams into the apartment, lighting it up. There are black out curtains on all the windows for the summer travelers. Worry not, you can block out the midnight sun if you want!

Chester Creek Getaway Near Downtown w/Washer/Dryer

Welcome to your spacious suite in walking distance from Downtown Anchorage. This two-bedroom space offers a laid-back vibe with modern amenities. The open layout connects the living area to the fully-equipped kitchen. The bedrooms provide a cozy retreat with a queen-sized beds and luggage rack. Conveniently located near dining, shopping, and entertainment options, this spot is perfect for your Anchorage stay.

Downtown Haven - Entire Private Condo

We invite you to stay in our condo located in what we feel is the best part of Downtown Anchorage. (A quick 5min walk to the train depot & only 2 blocks away from where the dowtown Iditarod start is). It's a corner unit on the ground floor of a 1950's residential and business building. Conveniently located near many restaurants, bars & shops all within walking distance of only a block or two.