Luxury STR- Family Retreat in NH

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Luxury STR- Family Retreat in NH

Tony EisenhauerPro Member
Rental Property Investor · Oxford Massachusetts · Member since 2021 · 5 posts · 3 votes

Investment Info:

Single-family residence buy & hold investment in Mount Hamilton.

Purchase price: $600,000
Cash invested: $250,000

Peak & Pine Retreat is a spacious, family-friendly mountain getaway in Bartlett, NH, in the heart of the White Mountains. This charming post-and-beam home blends rustic character with modern comforts and plenty of room for groups to relax. Just minutes from Attitash, Story Land, and North Conway, it offers the perfect mix of adventure and peaceful wooded surroundings—making it an ideal basecamp for year-round mountain vacations. 🏔️🌲

What made you interested in investing in this type of deal?

This was our first luxury STR, we were focused on high design, high amenity and high cash flow here.

How did you find this deal and how did you negotiate it?

This house was on market but needed a full renovation and design.

How did you finance this deal?

DSCR 75% LTV loan

How did you add value to the deal?

We fully renovated this house and lot, completely transforming it into what it is now.

What was the outcome?

We are the top 5% in our market and projected to hit or exceed our income goals for the year

Lessons learned? Challenges?

Alot of lessons learned here, contractors in markets you haven't done renovations before can become a problem. Also, timelines and Reno budgets sometimes get pushed and extended.

Did you work with any real estate professionals (agents, lenders, etc.) that you'd recommend to others?

No

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  • Michael Eskenasy
    Investor · Pacific Northwest · Member since 2026 · 538 posts · 309 votes
    7mo
    First off, I think you’re already doing something right if you’re consistently filling the winter months with medium-term stays. That’s actually a pretty solid baseline for an STR in a seasonal market. New Hampshire STR markets tend to be very season-driven, especially around ski areas and lakes. In many places the average occupancy is only around the mid-50% range annually, which means a lot of properties naturally have slower periods outside peak travel seasons.  A couple things I’d think about with a property like yours: 1. Seasonal positioning Winter demand is obvious (ski trips), but the guest profile outside winter is different. In NH those tend to be lake visitors, hiking groups, fall foliage travelers, or weekend family retreats. Sometimes it helps if the listing title and first few photos highlight those experiences instead of just the house itself. 2. The first few photos Airbnb search is basically a click-through game. If the first images are mostly interior shots, you might test leading with the view, outdoor space, fire pit, lake access, or nearby activities—whatever makes someone imagine the trip. 3. Minimum stay / pricing strategy A lot of shoulder-season travel is short weekend trips, not week-long vacations. If minimum nights or pricing are set assuming peak season demand, you may be filtering out those bookings. 4. Guest segments outside ski season You mentioned medium-term winter renters. Outside peak months you might attract remote workers, traveling professionals, or long-weekend family trips if the listing highlights things like workspace, fast Wi-Fi, etc. Overall, I wouldn’t necessarily assume something is “wrong” with the listing. In many seasonal markets the reality is that demand just changes dramatically throughout the year, and the listings that perform best tend to adjust their positioning depending on the season. Curious if you’ve looked at the summer occupancy for comparable listings nearby—that’s usually the easiest way to see whether it’s a listing issue or just how the local market behaves.
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    • Patrick McCannPro Member
      Realtor · NH · Member since 2022 · 113 posts · 59 votes
      6mo
      Quote from @Michael Eskenasy:
      First off, I think you’re already doing something right if you’re consistently filling the winter months with medium-term stays. That’s actually a pretty solid baseline for an STR in a seasonal market. New Hampshire STR markets tend to be very season-driven, especially around ski areas and lakes. In many places the average occupancy is only around the mid-50% range annually, which means a lot of properties naturally have slower periods outside peak travel seasons.  A couple things I’d think about with a property like yours: 1. Seasonal positioning Winter demand is obvious (ski trips), but the guest profile outside winter is different. In NH those tend to be lake visitors, hiking groups, fall foliage travelers, or weekend family retreats. Sometimes it helps if the listing title and first few photos highlight those experiences instead of just the house itself. 2. The first few photos Airbnb search is basically a click-through game. If the first images are mostly interior shots, you might test leading with the view, outdoor space, fire pit, lake access, or nearby activities—whatever makes someone imagine the trip. 3. Minimum stay / pricing strategy A lot of shoulder-season travel is short weekend trips, not week-long vacations. If minimum nights or pricing are set assuming peak season demand, you may be filtering out those bookings. 4. Guest segments outside ski season You mentioned medium-term winter renters. Outside peak months you might attract remote workers, traveling professionals, or long-weekend family trips if the listing highlights things like workspace, fast Wi-Fi, etc. Overall, I wouldn’t necessarily assume something is “wrong” with the listing. In many seasonal markets the reality is that demand just changes dramatically throughout the year, and the listings that perform best tend to adjust their positioning depending on the season. Curious if you’ve looked at the summer occupancy for comparable listings nearby—that’s usually the easiest way to see whether it’s a listing issue or just how the local market behaves.

       Mountain bike travel is really starting to take off in NH as well.

      [email protected]603-818-9095
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