A new opportunity for your large family or reunions to stay in “The Oldest Summer Resort in America” in a historic colonial home located a few minutes from downtown. This 1870’s home was turned into “The Oaks” in the early 1900’s as an Inn for visitors over a hundred years ago to take in the Crescent Lake view. Your gathering will enjoy the beautiful character of the old Inn while utilizing modern amenities.
5 Bedrooms, 3 bathrooms will beautifully accommodate your group of 10 with 3 queen beds, 1 king and 2 twins. The home is well equipped for your family to cook together, watch movies from a big screen, make memories from the game collection, take advantage of toys, puzzles and dress ups for kids, 2 player arcade, foosball, piano, outdoor games, and firepit. With a convenient location near the Cotton Valley Rail Trail which is a 15 mile trail that leads you to Wolfeboro, three different lakes, one beach, dirt biking trails and many resting benches. It will only take a 5–10 minute walk to arrive at Mast Landing docks, a bakery and a World War 2 Museum. A lovely 15-minute walk to great pizza, grocery store, mini-golf, Dunkins, pickleball, tennis, basketball and playground. A short five-minute walk past those amenities is the timeless marina town of Wolfeboro with a variety of shops including great coffee, restaurants and of course ice cream! During your stay we can provide you with passes to the three town beaches within a 5-10 minute drive. For those who need to get some work done there is a bedroom with a desk, in addition the house has an office, exercise equipment and a hallway desk for extra study space.
The downstairs of the home is the location of the • large well stocked kitchen • living room • game spaces • dining (that can accommodate 15+ people) • a fireside room (perfect for a card game or quieter conversation), • a beautiful guest room with many touches of the historic nature of the home including antique crown molding along the cathedral ceilings graced with a beautiful chandelier • bedroom with two twin beds • adorable laundry room if needed • bathroom with shower
The Upstairs has • the dedicated office with exercise equipment • an additional desk in the hallway • two queen bedrooms • bathroom with tub • Master bedroom with King posterbed and private bathroom with walk in shower
The Outdoor spaces include • gas grill • seating area • firepit • grass area • lawn games • parking for 4-5 cars (if more is needed just let us know and we should be able to accommodate)
Guest access You’ll receive a key code a week before your arrival and more details about the home.
Other things to note Many years ago the old barn from the original Oaks Inn was torn down and made into a separate living space where the owners currently reside (shared wall). We are happy to help in anyway you need during your stay but also know that the entrances and parking areas are separate to allow for your privacy. We are just excited that this home may one day welcome visitors to Wolfeboro and encourage your larger family gatherings or reunions to have a space to get together and enjoy one another in this beautiful location.
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Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
About the area
Wolfeboro
Wolfeboro is home to this holiday home. Clark House Museum and Castle in the Clouds are local landmarks, and the area's natural beauty can be seen at Lake Winnipesaukee and Wentworth State Park. New Hampshire Boat Museum and Hampshire Pewter Co. are also worth visiting.
Laconia, NH (LCI-Laconia Municipal) - 37 min drive
Restaurants
Wolfetrap Grill And Rawbar - 3 min drive
Dunkin' - 15 min walk
Lucas Roasting Company - 3 min drive
Burnt Timber Tavern - 16 min walk
Back Bay Boathouse - 3 min drive
Frequently asked questions
Is Family Retreat in Wolfeboro: 5BR/3BA, Lake Views pet-friendly?
Yes, this property allows dogs (limit 1 total).
How much does it cost to stay at Family Retreat in Wolfeboro: 5BR/3BA, Lake Views?
As of 5 May, 2026, prices found for a 1-night stay for 2 adults at Family Retreat in Wolfeboro: 5BR/3BA, Lake Views on 12 May, 2026 start from S$859, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.
How much is parking at Family Retreat in Wolfeboro: 5BR/3BA, Lake Views?
On-site parking is available at the property.
What time is check-in at Family Retreat in Wolfeboro: 5BR/3BA, Lake Views?
Check-in begins at 3:00 PM.
What time is check-out at Family Retreat in Wolfeboro: 5BR/3BA, Lake Views?
Checkout is at 11:00 AM.
Where is Family Retreat in Wolfeboro: 5BR/3BA, Lake Views located?
Situated in Wolfeboro, this holiday home is 0.6 mi (0.9 km) from Wright Museum and 2.5 mi (4.1 km) from Lake Winnipesaukee. Wolfeboro Railroad Depot and Cate Park are also within 1 mile (2 km).
About the host
Hosted by Andrew and Julie Brenner
Premier Host
They consistently provide great experiences for their guests