Three Windham hotels are urging the town Planning Board to reject Windham Mountain Club’s proposal for a 26-room luxury hotel, citing low occupancy rates at existing hotels and arguing the town doesn’t need more lodging.
The owners of Wylder, Christman’s Windham House, and Albergo Allegria submitted letters to the Planning Board after the club introduced the proposal at a June 18 meeting. They said the club’s hotel proposal would compete directly with their businesses and questioned whether the town could support additional rooms.
All three described low or declining occupancy at their hotels. Wylder averaged 32% occupancy during the past 12 months, according to internal figures cited by its chief executive officer, John Flannigan. Kate Christman, the owner of Christman’s Windham House, said its occupancy was consistently below 30% and that it was fully booked for just one weekend last year. The owners of Albergo Allegria Hotel said their winter occupancy was 40% lower than before Windham Mountain’s 2023 rebranding.
Windham Mountain Club President Kristen Leach has said the planned hotel, with rooms expected to cost $1,000 to $1,200 a night, would appeal to potential club members and occupy a higher price tier than Windham’s existing hotels.
The hotel would replace eight townhouses approved in April as part of the club’s redevelopment plan. It would also change the approved use of the Resort Drive site from residential to commercial, requiring a new review under the State Environmental Quality Review Act.
Leach said the idea for the hotel grew out of what the club sees as a need for five-star accommodations in Windham. The hotel would offer valet parking and be open to both the public and club members. A small cafe and bar would be reserved for hotel guests.
Some existing hotel owners see the market differently. The Planning Board heard from Wylder at its July 16 meeting but couldn’t act on the proposal because it lacked a quorum.
Planning Board members Claudia Lane, Ray Curtis, and Michael Troccoli didn’t participate because of ties to the club. Planning Board Chair Lisa Jaeger later said one is a ski instructor, another works part time for the club, and the third is a club member. She declined to say which description applied to each person, calling that information “irrelevant.”
The board needs three eligible members for a quorum, leaving Jaeger, Nate Holdridge, and alternate John O’Neill as the only members eligible to vote. Holdridge was absent.
Jaeger invited Flannigan to read his letter.
“I’m going to allow that as privilege of the floor, just because there’s not much we can do tonight anyway,” Jaeger said. “But the board is concerned, and we do want to make sure our community feels heard.”
Flannigan said Wylder’s occupancy figures contradicted Leach’s assertion at the June meeting that Windham lacked bed space.
“There’s a lot of rooms in Windham,” he said. “There’s not enough visitors.”
Flannigan said Wylder’s prices placed it in the same luxury market the club intends to enter, putting the hotels in direct competition.
Wylder is a 111-room boutique hotel at the site of the historic Thompson House resort on state Route 296 in Windham. The Thompson House, established in 1880, was family-owned and operated for over 140 years until Flannigan took over the property in 2021. It reopened as Wylder in 2022. Wylder also operates a hotel on Tilghman Island in southeastern Maryland.

Rates listed on Wylder’s website for stays later this month started at just over $200 per night for two people in a standard room, and exceeded $500 for larger suites. Some weekend rates started above $550. The hotel’s four-bedroom Farmhouse was listed at $2,000 a night.
“Guests seeking upscale accommodations will inevitably compare these properties, and the mountain’s hotel will compete directly with existing local businesses for the same customer base,” he said. “We’re selling rooms for $400, $600, $1,200, $1,800 a night. We’re a luxury hotel.”
Windham has at least 10 hotels, along with numerous short-term rentals. Other hotel operators in Windham didn’t respond to multiple requests for comment. A search for “Windham” on Airbnb returned more than 1,000 listings across the mountaintop region, and roughly 240 in Windham.
A spokesperson for Airbnb didn’t return a request for comprehensive data on short-term rental listings in the town.
Christman said in her letter to the board that she was “concerned that the additional hotel in Windham is redundant given the abundance of lodging options in town.”
“Windham boasts a full range of accommodations from basic camping all the way to luxury accommodations with everything in between,” Christman said. “This new lodging option will take further business away from existing hotels, as Airbnbs have done.”
Christman’s Windham House, established in 1805, describes itself as “the oldest continuously operating inn in the Great Northern Catskills.” Its summer room rates are about $200 a night. The inn, on state Route 23, also has a restaurant and 27 holes of golf across two courses.
Leach said the club didn’t expect its hotel to compete directly with existing properties. She said Windham lacked the type of accommodation the club plans to offer.
“For a five-star, luxury room, there is not that on the mountaintop,” she said.
Windham Mountain Club also owns The Outpost, a hotel on state Route 23, as well as the Mountainside and Winwood condominium developments. It developed more than 50 townhouses that are owned by individual buyers. Townhouse buyers receive access to the club’s standard membership plan.
Leach said that occupancy at The Outpost was also low but declined to provide a rate, saying only that it was similar to the figures cited by Wylder and Christman’s. She said the proposed hotel could attract potential club members who now choose condominiums or short-term rentals instead of The Outpost, even after its lobby and rooms were renovated over the winter.
“We’ve done renovations on it,” she said. “We’ve upgraded it. However, we find that most people of the caliber of club level, membership-wise, that might be coming to Windham to check it out, really want to stay in Whisper Creek, or they’ll go the Airbnb route versus a hotel.”
Whisper Creek is a condominium complex on Resort Drive. Its units are individually owned, and Brainard Ridge Realty handles sales and rentals there.
Leach said Wylder and Eastwind, a boutique hotel on state Route 23 that opened in 2018, offered luxury experiences but that the club intended to enter a higher-priced tier.
Eastwind’s listed nightly rates ranged from just over $250 for its least expensive accommodations to more than $500 for larger rooms. It also operates hotels in Oliverea, a hamlet of Shandaken, and in Lake Placid.

“Wylder, Eastwind, they do a wonderful job and there is a clientele for that,” Leach said. “We felt that this hotel doesn’t encroach on their business at all because it’s a step above that. It’s not at all trying to dilute what they do. It’s a phenomenal luxury experience that they offer. We’re just trying to go to the next level above that.”
Leslie and Marianna Leman, owners of Albergo Allegria Hotel on state Route 296, cited the 40% decline in their hotel’s winter occupancy in arguing that the proposed hotel would compete with existing businesses.
“If Windham Mountain Club’s primary season does not call for additional hotel rooms to ‘address a shortage of lodging in Windham,’ why would its secondary season require more rooms?” they wrote.
Albergo Allegria Hotel opened in 1982. According to the hotel’s website, rooms currently range from $139 to $189 per night.

Leach said July 22 that while she didn’t know exactly why Albergo Allegria’s occupancy rates had decreased, it shouldn’t solely be attributed to the rebranding of the Windham Mountain Club.
“Since we became the club, they also faced having their neighbors, Wylder, in business,” Leach said. “They’re right next door to them.”
Windham Mountain rebranded as Windham Mountain Club in 2023 and shifted toward a member-focused model, while the ski area remained open to the public. Standard year-round membership costs $250,000, plus annual dues.
The club is also introducing a $150,000 seasonal membership covering April through November. It is nonrefundable and nontransferable and carries full annual dues. Potential members must be referred by current members or reviewed by a club committee and invited to apply.
The club reserves a limited number of winter tickets for local residents and hotelgoers and offers free passes to Windham-Ashland-Jewett students.
Leach said the hotel owners’ comments had prompted her to consider how the club could communicate more regularly with other businesses.
“I left that meeting, no matter how shocked I was, how disappointed I was in the Planning Board’s approach, going back to my table, saying, ‘What can I do to bridge that gap that they clearly feel?’” she said. “Maybe we need to get out there more often and find out what’s going on in their world or how we can help.”
The objections would not cause the club to abandon the proposal, she said.
“But we’re not going to stop,” Leach said. “We really want this hotel.”
Leach also said she was disappointed that the Planning Board had not told her in advance that Flannigan would speak at the July 16 meeting. She called for the appointment of additional alternates to prevent delays when members must recuse themselves.
“They need to look for more stand-ins that can step up,” she said. “You run into that situation, then it just delays and delays.”
Planning Board attorney Allyson Phillips said the board’s previous approval of the club’s master plan didn’t cover the hotel amendment, which would require its own review under the State Environmental Quality Review Act, referred to as SEQR.
Phillips said under a SEQR review, the board isn’t able to directly take into account potential economic impacts like business competition. However, those effects can be considered under certain zones of interest.
“We aren’t concerned with business competition as part of SEQR, but we have to and are required to look at the secondary impacts that a use and any business competition that it creates, whatever that economic impact is, the effect that can have on an interest that is protected within the zone of interest under SEQR, such as our community character,” she said.
The Planning Board is scheduled to resume its review at its Aug. 6 meeting. If it again lacks a quorum, consideration could be delayed until September because O’Neill, one of only three members eligible to vote, plans to be away later in August.
Connor Greco is a staff reporter for The Overlook covering Windham, Hunter, and surrounding Greene County communities. Send correspondence to connor@theoverlooknews.com.





