The Overlook

Check-in is Saturday at 3:00 PM. Check-out is the following Saturday at 10:00 AM. These windows are fixed so our cleaning team can turn the house over between guests.

No, the owner of The Overlook (#539) does not accept pets. Looking for a pet-friendly rental? Filter for "Pet Friendly" on our rentals page.

Submit an inquiry through our website or call Yankee Pedlar at (603) 569-1000. An agent at Yankee Pedlar personally confirms every booking, usually the same day. A deposit of roughly 50% is due at booking and the balance is due 30 days before check-in. We do not accept online payments. Renters mail physical checks (made out to Yankee Pedlar Realtors) to our Wolfeboro office. Leases are signed electronically via DocuSign.

Linens and towels are not provided by the owner at The Overlook (#539), but you can order a full linen package from Yankee Home Services (Winni Linens): sheets, pillowcases, bath and beach towels, kitchen linens, delivered and removed for you. We'll send you an order link after booking.

Yes, The Overlook (#539) is a waterfront rental on Lake Winnipesaukee. The property includes 2 dock slips for your boat. If you don't have a boat, several local marinas rent pontoons, ski boats, and jet skis by the day or week.

Yankee Pedlar Realtors does not permit cancellations. If you find you are not able to come, the tenant is responsible for the entire rental amount no matter when the cancellation occurs. If you confirm in writing, we will attempt to rebook the week(s) on your behalf. If we are able to rebook at full price, the cancellation fee is 20% of the total rent charge plus a $100 administrative fee. If we are not able to rebook the canceled week(s), the tenant remains responsible for the entire rental amount.

The Overlook (#539) is managed directly by Yankee Pedlar Realtors, the oldest agency in Wolfeboro, founded 1940. Booking direct means no OTA service fees (often 15–20%), you speak to a real agent by name when something comes up, and your money goes further for both you and the owner. We've been arranging summers on Lake Winnipesaukee for four generations of guests.