Holiday rentals with outdoor seating in Anchorage

Forest Floor Guesthouse

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 paddle boards at Sand Lake.

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.

Cupples Cottage #4: 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.

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.

Modern A-Frame Cabin 1: Hot tub & view!

This newly constructed modern A-Frame offers a unique and luxurious accommodation opportunity. It features a comfortable king bed with crisp linens, keyless entry, washer & dryer, gas fireplace, TV, WiFi, hot tub, and large windows so you can soak up beautiful Alaskan views while surrounded by a tranquil forest. The kitchen and bathroom are stocked with everything you need to feel right at home. Enjoy the cozy and comfortable atmosphere during your private escape.

Overlooking Anchorage!

Come and relax on top of the mountain overlooking Anchorage, Alaska! Walking distance to the Glen Alps Trail Head (Flattop Mountain), but also just a short drive to all the wonderful things to do in and around the Anchorage area, and beyond. ***During snow season, October thru April, you will need all-wheel or 4 wheel drive to access the property. We are also subjected to power outages in our area due to extreme weather conditions***