Holiday rentals with outdoor seating in Anchorage

Cupples Cottage #4: 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.

Alpenglow Loft ~ 1Br/Ba W&D Radiant Charmer

Unique modern loft 1 bedroom/1 bathroom apartment. Cool A/C in bedroom, spiral staircase, sunny floor-to-ceiling windows and live plants. Comfortably furnished, conveniently located between Midtown and Downtown Anchorage. This charming home base is perfect for embarking on your Alaskan getaway. The unit is equipped with a full-size washer/dryer, 43” Smart TV, stocked kitchen, and fast Wi-Fi for your convenience. However, due to the spiral staircase, we do not recommend this unit for children.

Forest Floor Apartment

The lower level of our Jewel Lake Home with a separate entry, and fun backyard. This is a recent remodel; an eclectic space with vintage wood ceilings and a blend of industrial+ modern detailing. We are 5 minute drive from the airport, and guests can enjoy Alaskan wilderness right from this space. A forested trail system lies right behind our house for walking and biking. Guests may collect eggs from our chickens, use our forest-side hot tub, stoke the firepit, or use the canoe at Sand Lake.

Charming 1 Bedroom Duplex Apartment

Our duplex is conveniently located in a highly desirable neighborhood nestled between Turnagain and Spenard. This daylight-basement unit has a living room, kitchen, separate bedroom, bathroom, and laundry facilities. It is super comfortable for 2 people, and cozy for 4 with a pull-out sofa bed. This home is 3.5 miles from the airport and is centrally located for any adventures you may have planned. The Coastal trail, grocery store, and several dining options are within walking distance.

Private backyard, firepit, mtn views, full kitchen

Quiet guest suite of a family home outside the city with private backyard: •Full kitchen and private entrance •Fire pit and gas grill •On-site laundry (shared) •20 minutes to the airport/5-15 minutes to the best hiking trails •Mountain views and sounds of Rabbit creek from the valley below One review: "...amazing find in Anchorage...extremely clean, convenient and in a beautiful location. Hosts were well organized...Impressed with the professionalism exhibited by these property owners."

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.

5 min walk to Flattop Trailhead! Aurora! Sauna!

Nestled in a forest of Mountain Hemlocks hundreds of years old, the home is located in a quiet neighborhood only a 5-6 minute walk from the Glen Alps/Flattop Trailhead providing the most direct and easy access to Chugach State Park. There are endless possibilities for hiking, climbing, and skiing from the house. Or, if you prefer to sit and relax and read a book, the view from the deck or living room couch of the Anchorage skyline and Denali/Mt. McKinley is spectacular.

Waterfront View of Denali, Alaska Range and Ocean.

Nestled within a private corner of Bootleggers Villa is a Brand New Private Suite with a personal entrance and private patio. Located near downtown offices, and suffused with the feeling of privacy and security. Our location is a short stroll to downtown Anchorage, and an easy drive to adventurous Alaska. Outdoor comfort with sunset-facing private patio. Enjoy, barbecues and relax with a view of Cook Inlet, the Alaska Range all from charming Bootlegger’s Cove.