It may be cold in Stowe, Vermont, during the winter, but the cast of Winter House knows how to turn up the heat — and make long-lasting connections.
Season 1 of Winter House, which premiered in October 2021, set the tone for vacation romances. Ciara Miller and Austen Kroll sparked up a relationship as did Andrea Denver and Paige DeSorbo. Fellow Summer House star Lindsay Hubbard also found a hookup buddy in newbie Jason Cameron.
Kyle Cooke and Amanda Batula, for their part, were preparing to get married while filming the show in February 2021. When season 2 began filming in early 2022, things looked very different for the OG stars. Amanda and Kyle were married, having tied the knot in fall 2021, and Craig Conover and Paige had connected outside of the series and begun their own relationship.
When taping season 3 in early 2023, Tom Schwartz’s newly single status made for an even steamier vacation. (He split from wife Katie Maloney in March 2022.)
Amanda Batula
The New Jersey native was invited to film Summer House season 1 after meeting Kyle that year. The twosome became official during the 2017 finale and got engaged one year later. The reality stars’ ups and downs as a couple have been featured heavily on both Summer House and Winter House. Despite a rocky road to the altar, the pair said “I do” in September 2021.
Craig Conover
The Delaware native dated Southern Charm costar Naomie Olindo for three years before splitting in 2017. He moved on with Natalie Hegnauer in early 2020, meeting ahead of the COVID-19 quarantine shutdowns. Craig and Natalie called it quits in 2021.
That same year, Us confirmed that Craig was dating Paige. The twosome’s casual relationship played out on season 6 of Summer House, which filmed in summer 2021. During the season, which aired in early 2022, Craig confessed that he previously hooked up with Kristin Cavallari as rumors surfaced that he and Austen were in a love triangle with the Laguna Beach alum.
During season 8 of Southern Charm, which aired in summer 2022, Craig also revealed that he and ex Naomie hooked up in summer 2021 and that Paige knew all about it. Craig became Instagram official with Paige in winter 2021 — and they were exclusive when they filmed Winter House season 2.
Austen Kroll
Austen briefly dated Southern Charm costar Chelsea Meissner during season 4 of the series in 2017. He moved on with Victoria Bolyard during season 5, which aired in 2018. The beermaker had a fling with Lindsay in 2018, but he didn’t confirm it until four years later.
Madison LeCroy started dating Austen in 2018 as well. The pair dated on and off for two years before Madison exclusively told Us in December 2020 that they were done.
The TV personality was linked to Cavallari in late 2020 and rumored to be in a love triangle with her and Craig. The Hills alum, however, denied the romances in July 2021. Craig, for his part, claimed on Summer House season 6 that he had hooked up with Cavallari and Austen “hates that I was making out [with Kristin].”
While filming season 1 of Winter House in February 2021, Austen sparked a vacation romance with Ciara. When Austen visited the Hamptons that summer he was again flirty with Ciara but also made out with pal Lindsay, causing drama between the ladies. Ciara revealed during the Summer House season 6 reunion that she and Austen hooked up again but were not together.
Austen, meanwhile, was linked to Southern Charm costar Olivia Flowers in late 2021 as they filmed season 8 of the series. He exclusively told Us in May 2022 that he and Olivia were dating. While Olivia told Us in August of that year that they were still seeing each other exclusively, during the season 8 reunion, which filmed in September 2022, she confirmed that they had since broken up.
Kyle Cooke
Kyle proposed to Amanda in 2018 after dating for one year. The twosome’s wedding was postponed amid COVID-19 but they finally tied the knot in September 2021. Their wedding was featured on season 6 of Summer House.
Paige DeSorbo
After joining Summer House during season 3, which filmed in 2018, Paige had a whirlwind romance with Carl. The relationship fizzled out before the end of summer and the New York native moved on with Perry Rahbar. Although Perry briefly appeared on season 4 of the series, the duo called it quits in September 2020.
Us confirmed in October 2021 that Paige and Craig were a couple after they started seeing each other casually earlier that summer.
Luke Gulbranson
The Minnesota native was previously engaged before he struck up romances with a few of his Summer House cast mates. Luke romanced Hannah Berner during season 4 and hooked up with Danielle Olivera in between seasons 4 and 5. When Ciara joined the cast in season 5, she revealed that she had a “history” with Luke.
During season 1 of Winter House, Luke hit on housemate Julia McGuire, but she was in a serious relationship.
Ciara Miller
The nurse had a brief romance with Luke before joining season 5 of Summer House in 2020. During season 1 of Winter House in 2021, she started seeing Austen. The duo’s romance fizzled out due to distance that year. When Austen appeared on season 6 of Summer House in summer 2021, they found themselves in a love triangle with Lindsay as the North Carolina native flirted with both women.
Ciara revealed during the season 6 reunion, which aired in May 2022, that she and Austen had again hooked up. She vowed at the time that it was the last time.
Jason Cameron
Jason had a major crush on season 1 Winter House costar Gabrielle Kniery, but she wasn’t feeling it, so he moved on. The model eventually started spending time with Lindsay in the house and they dated outside the show as well.
Lindsay revealed during season 6 of Summer House, which aired in January 2022, that she suffered a miscarriage during her “last couple of months” dating Jason. It isn’t clear when they broke up, but Lindsay was single while filming the Hamptons series in summer 2021.
When Jason returned to Vermont for season 2 of Winter House, which filmed in early 2022, it appeared that he had his sights set on newbie Rachel Clark, not Lindsay, who had moved on with Carl. Jason and Rachel’s vacation romance, however, didn’t last. The florist confirmed in November 2022 that she was dating someone new.
Lindsay Hubbard
When fans met Lindsay on season 1 of Summer House she was dating Everett Weston. The duo split after one year and their breakup was revealed on season 2 of the series in 2018. Lindsay hooked up with Austen in 2018 but kept it quiet for years.
The publicist was briefly linked to costar Carl during the summer of 2019 but settled down Stephen Traversie that same year. Us confirmed in January 2021 that Lindsay and Stephen called it quits in fall 2020.
She moved on with Jason, whom she met filming Winter House in February 2021. The pair’s romance ended in summer 2021 after she suffered a miscarriage.
Lindsay sparked romance speculation with Carl again in September 2021 when they were spotted getting cozy at Amanda and Kyle’s wedding. Carl exclusively confirmed to Us in January 2022 that he and Lindsay were a couple. He proposed in August 2022 but they ended their engagement one year later.
Andrea Denver
During season 1 of Winter House, Andrea was flirty with all the ladies, but he and Paige quickly became an item. The pair continued to casually date outside of the show — including sharing romantic moments on season 6 of Summer House, which filmed that summer. While Paige became getting more serious with Craig, Andrea realized he still had feelings for a former flame, whom he was seeing before heading to the Hamptons.
In February 2022, Andrea announced that he would not return to Winter House. Instead, he was going to focus on his relationship with model Lexi Sundin. “I didn’t feel like it was the right time for me [to leave to film the show],” he exclusively told Us in March 2022. “I reconnected with a person that really matters to me and she was my priority. I feel like it was too soon to go on vacation with my friends.”
Rachel Clark
Rachel joined the cast of Winter House for season 2 after saving the day at Amanda and Kyle’s wedding as their last-minute florist. The New York resident quickly adapted to life on camera and sparked a romance with costar Jason while in Vermont. Despite their steamy connection, Rachel revealed in November 2022 that she was “in love” and “very happy” — with someone other than the model.
“I wasn’t looking for someone ‘better’ than Jason, because Jason is wonderful,” she told Entertainment Tonight after going public with her boyfriend, Thomas Altamirano, earlier that month. “In the end, I was just looking for something different, and I don’t think there’s anything wrong with that. I found my person, and I hope so much so that Jason finds his person.”
Kory Keefer
The Winter House season 2 newbie was single heading into filming in early 2022. During the show, he had a vacation romance with housemate Jess Stocker. After making his Bravo debut, Keefer started dating Summer House newcomer Sam Feher, which fans saw play out on season 7 of Summer House. The twosome confirmed their relationship in April 2023. By December of that year, Feher had called things off after he was flirty with other girls, including Malia White and Jordan Emanuel on season 3 of Winter House.
“I had said [‘I love you’] to him and he never said it to me,” Feher revealed during a January 2024 interview on the “Not Skinny But Not Fat” podcast. “I didn’t break up with him because I don’t love him, I broke up with him because he doesn’t love me.”
Danielle Olivera
Danielle dated Summer House costar Carl Radke before she joined the Bravo series on season 2. It was later revealed that Danielle hooked up with costar Luke between season 4 and 5. She introduced fans to boyfriend Robert Sieber during season 5 but confirmed in February 2023 that they had split. Danielle, who joined Winter House for season 3, appeared to have a vacation fling with newbie Alex Propson, according to the trailer.
Tom Schwartz
The Vanderpump Rules star, who made a cameo on season 2 of Winter House before becoming a full-time cast member on season 3, announced in March 2022 that he and Katie Maloney had split. The pair were together more than 10 years. Tom made headlines in summer 2022 for kissing Pump Rules costar Raquel Leviss before news broke that she had an affair with Tom Sandoval. Schwartz kisses Below Deck’s Katie Flood in the season 3 Winter House trailer.
Malia White
The Below Deck Mediterranean star briefly dated Wes Walton during season 2 of the series. Malia moved on with fellow yachtie Tom Checketts in 2019 but the pair split in fall 2020. Malia later dated another Below Deck star in chef Jake Baker. The twosome went public in summer 2021 and Malia confirmed in February 2023 that they were done. Malia joined the Winter House cast for season 3 and according to the September 2023 trailer she is interested in Kory.
Brian Benni
The Family Karma star announced his split from Monica Shah in 2021. He appeared to be single when he joined season 3 of Winter House in 2023.
Katie Flood
The Below Deck Mediterranean personality dated deckhand Jack Stirrup before she appeared on season 6 of the Bravo show. According to the Winter House season 3 trailer, Katie gets cozy with Schwartz.
Jordan Emanuel
Fans first met Jordan on season 1 of Summer House: Martha’s Vineyard. After joining the cast for season 3 of Winter House, she finds herself in a love triangle with Danielle and Alex.
Alex Propson
During season 4 of Below Deck Sailing Yacht, which aired in summer 2023, Alex had a flirtation with shipmate Mads Herrera. The pair hinted at an off-camera romance after the season but Mads revealed during the reunion that Alex had an on-off girlfriend. Coming into Winter House season 3, Alex appeared to have his sight set on both Danielle and Jordan.
Casey Craig
Casey is new to the Bravo family, joining the group for season 3 of Winter House. Casey appears to be single.