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.

SaltWater Cottage

This one BR newly renovated cottage is in downtown, yet peaceful and private. Very well appointed, It overlooks the port, rail yard, and Cook Inlet. Steps away from bikes trails and within blocks of restaurants and city life, most downtown attractions are within walking distance. It is a few minutes walk to museums, convention centers, and the rail depot. Equipped with a king sized, cool memory foam mattress in the bedroom and fully equipped kitchen, this vintage cottage is like brand new!

Views Alaskan Prospect Heights Guesthouse

Settle down in a light filled, private, comfy guesthouse w/great views safe & secure privacy on wooded upper hillside w/parks/hiking, skiing, wildlife. Easy drive to airport/downtown. Ideal for business/leisure visitors. 5G WIFI. Mild temps & snow make Anchorage a winter playground. Sunsets & views from a private deck/Family friendly with plenty of room to roam. Make wonderful memories. Open dates Feb 22-26, March 29-April 17, Sept 7-18, Sept 23-Oct 31 & select open dates in Nov/Dec

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.

The Downtown Anchorage Grand Four Bedroom

Come stay in this unique, and exquisite home located in the cozy downtown neighborhood. Massive outdoor deck, soaring ceilings through the home , and a loft net with a rock climbing wall that kids and adults enjoy! We have a large chef kitchen with all the amenities, modern bathrooms, Master bathroom with a tub and an above skylight, and a designated working desk. All the bedrooms are equipped with the most comfortable beddings, extra linens and towels, essentials and so much more.

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.

Peaceful Suite - South Anchorage: The Cozy Bear

Welcome to the Cozy Bear in Anchorage! We welcome you to our peaceful, residential Lower Hillside neighborhood on a quiet cul-de-sac in Southeast Anchorage near Abbott Community Park & Far North Bicentennial Park. The Cozy Bear is centrally located 15 minutes from the airport with easy highway access for epic adventures and sightseeing! We are a husband-and-wife team living the dream in Alaska! We’re on hand to support our guests as little or as much as they wish.

The White House Anchorage - 1 BR

Location! Location! The White House Anchorage is located in the heart of the city. » About 10-15 minutes from the airport » Walking distance to everything downtown Anchorage has to offer » Go for a walk/run or a bike ride on the acclaimed Tony Knowles Coastal Trail » Walk to Westchester Lagoon Parking is available on property in addition to free on-street parking along the front of the house. High speed wifi is available on all corners of the property.

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.

Hillside Haven - Cozy & Bright!

Convenient, calm and spacious 1 bedroom, 1 bathroom apartment on the Anchorage hillside. Just a few minutes from all of the conveniences of the city, but tucked away in a quiet neighborhood close to trails, parks, Hilltop Ski Area, the Alaska Zoo, and lots of other fun adventures! Features include fully equipped laundry room and kitchen, Smart TV, and super fast WiFi. Settle in and enjoy a quiet, cozy, hillside retreat.