Holiday rentals with outdoor seating in Anchorage

Luxe Mountainside Chalet - The BEST way to live AK

Escape to this secluded 3 BR, 2 BA chalet in the heart of the Chugach Mountains. Endless backcountry hiking, skiing, and sledding starts just outside the door. End the day with a soak in the hot tub under the northern lights set amongst the mountains you just conquered. Looking to relax? Snuggle up to the wood stove or unwind in the 2 person bath tub while still enjoying the breathtaking views from large picture windows. Just 25 min. from Anchorage awaits this private and cozy mountain retreat!

Denali View! Sauna! 1 mile to Glen Alps/Flattop TH

Lone Pine Cottage is nestled against the Chugach State Park. Walk out the front door and explore the meadow of wildflowers below, or the forest next to the cottage which leads directly into the Chugach. The Glen Alps/Flattop Trailhead is 1 mile up the road and provides easy access to amazing hiking, mountain biking, snow shoeing, climbing, and skiing adventures. Enjoy the unobstructed views of Denali/Mt. McKinley, “Sleeping Lady” (Mount Susitna), and the Anchorage skyline from 1600ft elev.

Explore Alaska from Romantic Creekside Chalet

Creekside Chalet is nestled in the forest near Peters Creek in Chugiak, 25 minutes from Anchorage or Wasilla/Palmer. A peaceful & unique retreat just minutes from hiking trails, lakes, winter skiing, & access to Chugach State Park. This property offers wi-fi, large TVs, a full kitchen, open living space, washer/dryer, & private bedroom with blackout curtains. Enjoy a wrap-around deck with outdoor dining & forested pathway to fireplace overlooking the creek. Winter use requires AWD/4WD vehicle.

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.

Cupples Cottage #2: Downtown!

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 3 generations and the property has been reimagined as Cupples Cottages Vacation Rentals, operating since 2017.

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.

Bear Valley Cabin

Fully equipped Guest Cabin near the main home. Sleeps 2. Maximum of 4 (with extra guest fees). * There is 1 Outdoor Security Camera on the garage of the Main Home for safety Treed property, very quiet neighborhood, wildlife: moose, bears, lynx Kitchen, Laundry washer dryer 1 bathroom with shower. 1 Cozy Bedroom with full bed. Futon converts in to full bed. BBQ , patio furniture Great base location for exploring South Central Alaska.

Sleeping Lady Suite

This bright and sunny space is convenientally located for your vacation needs. It is close to the military base, hospitals, and the University of Alaska. The building is also just a quick drive to downtown Anchorage. You will love its rustic charm, quiet neighborhood, privacy, and extra space. Features private patio, fenced yard, washer/dryer. 2 bedroom/1 bathroom. Perfect whether you are enjoying a quick trip, or a long stay.