Holiday rentals with a fireplace in Anchorage

Apartment in Anchorage

Cupples Cottage #3: 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.

7–14 Feb

Condo in Girdwood

Spacious Mountainside Studio

Located on the 3rd floor (walk up) in the Timberline Building, condo is very spacious and in walking distance to the Alyeska resort and several great restaurants and shops. Hiking, biking, or skiing are right outside the front door! The building is typically very quiet, making it great for families or travelers seeking a peaceful reprieve in the great little town of Girdwood. The space is ideal for 1-3 people but can accommodate 4. We hope you enjoy your Girdwood adventure as much as we do!

15–22 Oct

Apartment in Anchorage

Studio in Girdwood at base of Alyeska

Studio condo at the base of Alyeska. Wake up and walk downstairs to enjoy a delicious Bake Shop breakfast. Spend an adventurous day on the mountain or take a relaxing stroll through the small town of Girdwood. End the day with a drink and appetizer at the Sitzmark while listening to fun, local music. The murphy bed sleeps two adults. The hideaway bed in the couch can be used if need be, but please confirm with us beforehand. We cherish time at our special condo and hope you love it as well!

5–12 Sep

Guest suite in Anchorage

Modern colorful "sweet"

Your private “sweet" is through our home's shared (street-level) entry. We are 5.1 miles from ANC airport (13 min by car or approx $20-$22 Uber/Lyft/taxi). Fred Meyer grocery is .7 mile away (15 min walk); Costco is 1.7 miles. Behind your interior “front door” is your Queen bed; TV room; kitchenette; and bathroom with tiled walk-in shower and the best backside feature ever: heated bidet toilet. We live and work upstairs. There's plenty of space for all. We can host only humans age 13+.

Guesthouse in Anchorage

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 temperatures & snow make Anchorage a great winter playground. Sunsets & views from a private deck/Family friendly with plenty of room to roam. Make wonderful memories of Alaska. Available in 2024 include April 1-4, Sept 20-30 & more dates in fall.

1–8 Mar

Condo in Anchorage

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.

8–15 Jan

Condo in Anchorage

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.

22–29 Jan

Guest suite in Anchorage

Hillside Holiday Base Camp

Welcome to your home away from home in Anchorage, Alaska! The house is in a quiet neighborhood on the base of the Chugach Mountains. This private location is nicely wooded, features mountain views, and is conveniently located adjacent to Anchorage's world class hiking, biking, and skiing trails. The Alaska Zoo and Anchorage Golf Course are also very close. Grocery stores and excellent restaurants are just a few minutes away.

8–15 Apr

Apartment in Anchorage

Deb's Place

Walk to downtown, the famous Coastal Trail, quaint eateries, elegant restaurants, fabulous bakeries, local brew pubs, and more! This unit is a walkers delight. Enjoy easy access to downtown and our famous Coastal Trail (great for birding, running, biking) without needing a car! Owners are very knowledgeable about local restaurants as well as hiking, biking, and other activities. We are happy to share what we know!

2–9 Jun