Title: Book the Best ADVENTURE Hotels in Wineglass in 2025 | Expedia.ca [Vacation Rentals in Livingston](https://expedia.ca/Livingston-Vacation-Rentals.d8604.Travel-Guide-VacationRentals)[Flights to Livingston](https://expedia.ca/Cheap-Flights-To-Livingston.d8604.Travel-Guide-Flights)[Things to do in Livingston](https://expedia.ca/Things-To-Do-In-Livingston.d8604.Travel-Guide-Activities)[Wineglass Car Rentals](https://expedia.ca/Car-Rentals-In-Wineglass.d553248635976480080.Car-Rental-Guide)[Wineglass Vacations](https://expedia.ca/Wineglass.d553248635976480080.Destination-Travel-Guides) ![Default HTG hotel image](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_lodging_v2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Hotels & Resorts for Couples in Wineglass, MT from CA $242 ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) ![bed illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check availability on Wineglass Hotels & Resorts for Couples Tonight [Oct 8 - Oct 9](https://www.expedia.ca/Hotel-Search?regionId=553248635976480080&startDate=2025-10-08&endDate=2025-10-09&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 9 - Oct 10](https://www.expedia.ca/Hotel-Search?regionId=553248635976480080&startDate=2025-10-09&endDate=2025-10-10&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=553248635976480080&startDate=2025-10-10&endDate=2025-10-12&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=553248635976480080&startDate=2025-10-17&endDate=2025-10-19&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Wineglass Hotels & Resorts for Couples ![Terrace/patio](https://images.trvl-media.com/lodging/114000000/113400000/113396700/113396648/577c24ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/114000000/113400000/113396700/113396648/e6e660e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Single Room](https://images.trvl-media.com/lodging/114000000/113400000/113396700/113396648/76f06daf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/114000000/113400000/113396700/113396648/efb1dd73.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wandering Buffalo Bozeman 9.4/10 Exceptional (33) "Great staff, beautiful property, great area," CA $222 CA $242 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Bozeman-Hotels-Wandering-Buffalo.h113396648.Hotel-Information) ![Restaurant](https://images.trvl-media.com/lodging/68000000/67550000/67546700/67546615/8498a844.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/68000000/67550000/67546700/67546615/d7864503.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/68000000/67550000/67546700/67546615/a7fc2251.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, premium bedding, desk, laptop workspace](https://images.trvl-media.com/lodging/68000000/67550000/67546700/67546615/fc5dcf8f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Residence Inn by Marriott Bozeman Downtown Bozeman 9.2/10 Wonderful (386) "Had a great stay." CA $250 CA $272 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Bozeman-Hotels-Residence-Inn-By-Marriott-Bozeman-Downtown.h67546615.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/90000000/89990000/89989600/89989582/56f36a09.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/90000000/89990000/89989600/89989582/345674d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV](https://images.trvl-media.com/lodging/90000000/89990000/89989600/89989582/dfaa3a55.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/90000000/89990000/89989600/89989582/fcd6a6ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Historical Charm with Modern Comforts Livingston 9.8/10 Exceptional (12) "Probably the best VRBO we’ve stayed in. So charming, so clean and the perfect location for a long weekend in Livingston. " CA $383 CA $1,088 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Livingston-Hotels-Sweetwater-Guest-House.h89989582.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/111000000/110660000/110652500/110652458/d7857973.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/111000000/110660000/110652500/110652458/d3276a4e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, travel crib, WiFi](https://images.trvl-media.com/lodging/111000000/110660000/110652500/110652458/dc8d9174.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/111000000/110660000/110652500/110652458/b2dc5f58.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Trout House- An Authentic Montana Cabin, Perfect for Yellowstone Adventures! Livingston 9.8/10 Exceptional (19) "The property was absolutely amazing and the house was fully furnished and well equipped. Our host Jennifer was awesome and we will be back. Could not be happier with our experience at this property." CA $180 CA $395 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Livingston-Hotels-Montana-Getaway-Near-Yellowstone.h110652458.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/97000000/96140000/96138600/96138522/4d63954c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/97000000/96140000/96138600/96138522/84af4ad3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/97000000/96140000/96138600/96138522/72591220.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/97000000/96140000/96138600/96138522/6c290039.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Glamping under the Montana stars #2 Livingston 9.2/10 Wonderful (31) "Unforgettable stay, so peaceful and just breathtaking!" CA $251 CA $492 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Livingston-Hotels-Glamping-Under-The-Montana-Stars-2.h96138522.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/106000000/105230000/105224600/105224535/ad913122.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/106000000/105230000/105224600/105224535/6caee45e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/106000000/105230000/105224600/105224535/7f348ee5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/106000000/105230000/105224600/105224535/9e5163b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### NEW Farm Stay Cabin close to Livingston, Yellowstone, Bozeman, fishing, hiking Livingston 9.8/10 Exceptional (10) "Great location and the kids loved being on the farm! Owners and neighbors were wonderful." CA $244 CA $301 total includes taxes & fees Nov 6 - Nov 7 [](https://www.expedia.ca/Livingston-Hotels-NEW-Modern-Cabin-On-A-Farm-With-A-View.h105224535.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/28000000/27500000/27494200/27494137/baa22621.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/28000000/27500000/27494200/27494137/5754bf8c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/28000000/27500000/27494200/27494137/8c77a6c4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/28000000/27500000/27494200/27494137/b4f3a55c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bridger Creek Luxury near Bozeman & Bridger Bowl Skiing - Legends Chalet Bozeman 9.4/10 Exceptional (40) "Had a great spring break skiing at Bridger — amazing location from the house! We love Bozeman and are so happy to have stayed in a comfortable and clean place. Thank you!" CA $279 CA $949 total includes taxes & fees Oct 13 - Oct 14 [](https://www.expedia.ca/Bozeman-Hotels-Bridger-Creek-Luxury-Near-Bozeman-Bridger-Bowl-Skiing-Legends-Chalet.h27494137.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/113000000/112670000/112668500/112668492/5c003073.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/113000000/112670000/112668500/112668492/ef1cde8f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, offices](https://images.trvl-media.com/lodging/113000000/112670000/112668500/112668492/c07e33a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/113000000/112670000/112668500/112668492/b51d4afc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Ultra charming historic home just a few blocks from Downtown Livingston, MT Livingston 10/10 Exceptional (3) "Great place in a great location with easy walk to restaurants in town. Place is very clean and well stocked. Veronica is a great host and super responsive. Would highly recommend." CA $418 CA $774 total includes taxes & fees Oct 9 - Oct 10 [](https://www.expedia.ca/Livingston-Hotels-Ultra-Charming-Historic-Home-Just-A-Few-Blocks-From-Downtown-Livingston.h112668492.Hotel-Information) ![Smart TV, books](https://images.trvl-media.com/lodging/69000000/68150000/68147600/68147518/ff6ddb56.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/69000000/68150000/68147600/68147518/e4486d99.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/69000000/68150000/68147600/68147518/2060e07b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/69000000/68150000/68147600/68147518/f0797aba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Downtown Lovely - Historic yet modern space downtown Livingston 9.4/10 Exceptional (46) "Beautiful building with lots of history, very nice place to be!" CA $121 CA $417 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Bozeman-Hotels-Fresh-And-Cozy-Apartment-In-Historical-Downtown-Livingston-Sleeps-2-4.h68147518.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/73000000/72550000/72542400/72542390/863c4ae5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/73000000/72550000/72542400/72542390/5aff2b36.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/73000000/72550000/72542400/72542390/17af24c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/73000000/72550000/72542400/72542390/6202cecc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Kelly Canyon Retreat: 17 Acres of Privacy & Paradise in Bozeman Bozeman 9.4/10 Exceptional (10) "This was a very clean, updated cabin with many amenities. We thoroughly enjoyed our stay and would book again for sure! " CA $445 CA $1,156 total includes taxes & fees Nov 1 - Nov 2 [](https://www.expedia.ca/Bozeman-Hotels-Bozeman-Retreat-17-Acres-Of-Privacy-Paradise.h72542390.Hotel-Information) Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply. [View all properties](https://expedia.ca/Hotel-Search?startDate=2025-10-22&endDate=2025-10-23®ionId=553248635976480080&adults=2&nearby_group=recreation&sort=RECOMMENDED&openPlayBack=true) ## Top Wineglass Hotel Reviews ![Country Motor Inn](//images.trvl-media.com/lodging/5000000/4930000/4928400/4928334/314881f0_y.jpg) ### Country Motor Inn 10/10 Excellent "Gave high ratings because it far surpassed our expectations based on the photos on the booking site we used. Our room had clearly been updated since those photos. Very comfortable bed, friendly staff, new air conditioner, and next to a charming downtown area." [](https://expedia.ca/Bozeman-Hotels-Country-Motor-Inn.h4928334.Hotel-Information) ![Murray Hotel](//images.trvl-media.com/lodging/9000000/8120000/8116500/8116451/1383f0db_y.jpg) ### Murray Hotel 10/10 Excellent "Such a cool spot in a great little town. We loved staying at the historic Murray." [](https://expedia.ca/Bozeman-Hotels-Murray-Hotel.h8116451.Hotel-Information) ![Super 8 by Wyndham Livingston Yellowstone](//images.trvl-media.com/lodging/1000000/460000/459900/459869/ab42d40c_y.jpg) ### Super 8 by Wyndham Livingston Yellowstone 10/10 Excellent "It was a convenient location and met our expectations. Beds were comfortable and the room was larger than expected. We would stay again in the future." [](https://expedia.ca/Bozeman-Hotels-Super-8-By-Wyndham-Livingston.h459869.Hotel-Information) ![Yellowstone Valley Lodge, an Ascend Collection Hotel](//images.trvl-media.com/lodging/5000000/4510000/4501700/4501686/6e412f2a_y.jpg) ### Yellowstone Valley Lodge, an Ascend Collection Hotel 10/10 Excellent "This was an amazing experience. On the banks of the Yellowstone River, we enjoyed a breathtaking view every morning, whether sunny or overcast. The breakfast, provided by Chef Lisa, was the perfect variety and blend of sweet treats and healthy options. We had an amazing dinner at the Yellowstone Grill that would rival any of the top restaurants in Montana. They were very pet friendly and their half mile walking path by the river allowed our Kirby the opportunity to stretch his legs after a long day riding in the truck around the park. Getting up early to enjoy the wonder of the night sky is something that will stay with me for the rest of my life. All in all, I cannot think of a better place for someone who wants to be close to Yellowstone Park, yet far enough to enjoy the peace and quiet of Montana." [](https://expedia.ca/Bozeman-Hotels-Yellowstone-Valley-Lodge.h4501686.Hotel-Information) ![Top Rated Charming MT Cabin w Hot Tub, 10min Dwtn, MSU, 1hr Big Sky/Yellowstone](//images.trvl-media.com/lodging/20000000/19440000/19438100/19438076/394397da_y.jpg) ### Top Rated Charming MT Cabin w Hot Tub, 10min Dwtn, MSU, 1hr Big Sky/Yellowstone 10/10 Excellent "This was by far the best cabin we’ve ever stayed in! It was equipped with everything we needed to feel at home, and was super convenient to town and beautiful hiking locations! This trip was incredible for my family and especially in part to the lovely cabin. The creek was so peaceful and the hot tub was clean and beautiful. Thank you so very much for sharing this little slice of heaven with us. We definitely hope to be back!" [](https://expedia.ca/Bozeman-Hotels-Top-Rated-Charming-MT-Cabin-W-Hot-Tub.h19438076.Hotel-Information) ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - Other - More ways to book - [4 Star Hotels in Livingston](https://www.expedia.ca/4Star-Livingston-Hotels.s40-0-d8604.Travel-Guide-Filter-Hotels) - [Business Hotels in Bozeman](https://www.expedia.ca/Bozeman-Hotels-Business-Hotel.0-0-d757-tBusinessHotel.Travel-Guide-Filter-Hotels) - [Adults Only Resorts & in Montana](https://www.expedia.ca/Destinations-In-Montana-Adults-Only-Resorts.0-0-d228-tAdultsOnlyResorts.Hotel-Filter-Destinations) - [Business Hotels in Montana](https://www.expedia.ca/Destinations-In-Montana-Business-Hotel.0-0-d228-tBusinessHotel.Hotel-Filter-Destinations) - [Green Hotels in Montana](https://www.expedia.ca/Destinations-In-Montana-Green-Sustainable.0-0-d228-tGreenSustainable.Hotel-Filter-Destinations) - [Hotels with Bar in Montana](https://www.expedia.ca/Destinations-In-Montana-Hotels-With-Bar.0-0-d228-tHotelswithBar.Hotel-Filter-Destinations) - 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