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Grandmas Cottage on the River and the Rail Trail in Wolfeboro

Cottage near Lake Winnipesaukee in Wolfeboro

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Photo gallery for Grandmas Cottage on the River and the Rail Trail in Wolfeboro

A wooden dock with a hammock and chairs by a lake surrounded by autumn foliage.
A cozy living room with a fireplace, a dining area with a table and chairs, and a kitchen with appliances.
A log cabin with a snow-covered roof, a front porch, and a garage.
A bedroom with a bed, a dresser, a chair, a window, and a lamp.
A kitchen with wooden cabinets, a dining table with chairs, and a refrigerator.

Reviews

10 out of 10
Exceptional

Entire home

2 bedrooms1 bathroomSleeps 6

Popular amenities

  • Kitchen
  • Washer
  • Dryer
  • Pet friendly
  • Free WiFi
  • Air conditioning

Explore the area

View in a map
Wolfeboro, NH
  • Place, Wright Museum
    ‪16 min walk‬
  • Place, Allen Albee Beach
    ‪19 min walk‬
  • Place, Brewster Beach
    ‪3 min drive‬
  • Airport, Sanford, ME (SFM-Sanford Seacoast Regional)
    ‪55 min drive‬

Room options

About the neighborhood

Wolfeboro

On lake.Within 2 miles (3 km) of this Wolfeboro cottage, you'll find Lake Winnipesaukee and Wright Museum. New Hampshire Boat Museum and Allen Albee Beach are also within 2 miles (3 km).
View more Cottages in WolfeboroOpens in a new window

What's nearby

  • Wright Museum - 16 min walk - 0.9 miles
  • Allen Albee Beach - 19 min walk - 1.1 miles
  • New Hampshire Boat Museum - 19 min walk - 1.1 miles
  • Wolfeboro Railroad Depot - 2 min drive - 1.8 miles
  • Brewster Beach - 3 min drive - 1.8 miles

Getting around

  • Laconia, NH (LCI-Laconia Municipal) - 41 min drive

Restaurants

  • ‪Dunkin' - ‬2 min drive
  • ‪Lucas Roasting Company - ‬4 min drive
  • ‪Harvest Market - ‬20 min walk
  • ‪Wolfetrap - ‬5 min drive
  • ‪Bayside Grill and Tavern - ‬4 min drive

About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

Grandmas Cottage on the River and the Rail Trail in Wolfeboro

Just like Grandma’s, with all the comforts of home—full kitchen w/dishwasher, full bath w/washer & dryer, internet & television. 2 separate bedrooms & a common living area w/small outdoor balcony. Located on a small river that connects 2 large lakes. Private dock w/gas grill and outdoor dining table. Kayaks and life vests available. Parking for 2 cars included. Cottage is adjacent to a walking path to downtown Wolfeboro—just over a mile—where there are town docks on Lake Winnipesaukee, lake cruises, shops, restaurants, The Wright WW2 Museum, mini golf, trails for hiking, biking, XC skiing or snowshoeing, ski & bike rentals and more. From the house heading away from downtown, the path leads to a public beach on Lake Wentworth, the NH Boat Museum and single track bike trails. Kingswood Golf Club, Pop Whalen Ice Arena and Abenaki Ski Area are nearby in Wolfeboro.
Wolfeboro is known as “America’s Oldest Summer Resort”!

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The Windrifter Resort
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  • Free WiFi
  • Air conditioning
4.4 out of 5, Excellent, 415 reviews
$115 nightly
The price is $125
Sep 21 - Sep 22
Total with taxes and fees
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Property amenities

Beach

  • Beach towels

Ski

  • Cross-country skiing nearby

Internet

  • Available in the cottage: Free WiFi

Parking and transportation

  • Parking on site

Kitchen

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Electric kettle
  • Microwave
  • Oven
  • Paper towels
  • Refrigerator
  • Stovetop
  • Toaster

Dining

  • Dining table

Bedrooms

  • 2 bedrooms
  • Bedsheets provided

Bathroom

  • 1 bathroom
  • Bathtub or shower
  • Hair dryer
  • Shampoo
  • Soap
  • Toilet paper
  • Towels provided

Living spaces

  • Dining table

Entertainment

  • Books
  • Games
  • Smart TV

Outdoor areas

  • Balcony
  • Firepit
  • Garden
  • Gas grill
  • Outdoor furniture

Laundry

  • Laundry facilities
  • Washing machine

Work spaces

  • Desk

Comfort

  • Air conditioning
  • Heating

Pets

  • Pet friendly
  • Welcoming dogs only
  • 3 pets total

Suitability/Accessibility

  • No elevator
  • Smoking not allowed

Services and conveniences

  • Iron/ironing board

Location highlights

  • Near a health/beauty spa
  • Near a hospital
  • Near the marina
  • On a lake
  • On a river
  • On the waterfront

Things to do

  • Kayak
  • Optional golf privileges
  • Water sports equipment
  • Basketball nearby
  • Birdwatching nearby
  • Fishing nearby
  • Golfing nearby
  • Hiking/biking trails nearby
  • Horseback riding nearby
  • Hunting nearby
  • Ice skating nearby
  • Jet skiing nearby
  • Kayaking nearby
  • Motor boating nearby
  • Mountain biking nearby
  • Mountain climbing nearby
  • Sailing nearby
  • Snowmobiling nearby
  • Swimming nearby
  • Water skiing nearby
  • Water tubing nearby
  • Wildlife walks nearby

Safety features

  • Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
  • Smoke detector (host has indicated there is a smoke detector on the property)
  • Fire extinguisher
  • Deadbolt lock

General

  • Garden

Policies

Check-in

Check-in time starts at 4:00 PM
Contactless check-in available

Check-out

Check-out before 11:00 AM
Contactless check-out available

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools

Rules

Wolfeboro has a sound ordinance from 11pm to 7am. Do not leave food or trash outside as it attracts wildlife, including bears and coyotes.
You are responsible for any damage to the property caused by your dog(s). Please remove pet waste from the property (secure waste bags in trash is ok)
By NH law, all under 18 must wear a life vest when on a boat or kayak, etc. One life vest for each person onboard must also be stowed onboard.

Pets

  • Pets are welcome
  • Only dogs are allowed
  • Maximum 3 pets
  • Service animals are exempt from fees
  • Note from host: Pet fee is $150 per stay

Children and extra beds

  • Children are welcome.

Events

No events allowed

Smoking

Smoking is not permitted

Important information

You need to know

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
Onsite parties or group events are strictly prohibited
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a deadbolt lock
This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card, or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
    This property is managed by a private host, not a professional engaged in trade or business. This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children. If you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room. Onsite parties or group events are strictly prohibited. For guests' safety, the property includes a carbon monoxide detector, a fire extinguisher, a smoke detector, and a deadbolt lock in each accommodation.

Frequently asked questions

How close is Grandmas Cottage on the River and the Rail Trail in Wolfeboro to the airport?

This cottage is 26.8 mi (41-min drive) away from the Laconia, NH (LCI-Laconia Municipal) airport, the closest popular airport to the property.

How much does it cost to stay at Grandmas Cottage on the River and the Rail Trail in Wolfeboro?

As of Sep 1, 2026, prices found for a 1-night stay for 2 adults at Grandmas Cottage on the River and the Rail Trail in Wolfeboro on Sep 2, 2026 start from $606, 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.

Does Grandmas Cottage on the River and the Rail Trail in Wolfeboro have an airport shuttle?

Airport shuttle services are not available at this cottage.

How close is Grandmas Cottage on the River and the Rail Trail in Wolfeboro to the beach?

This cottage is 1.3 mi (3-min drive) from Allen Albee Beach and 1.6 mi (3-min drive) from Brewster Beach. Don't forget your sunscreen!

Does Grandmas Cottage on the River and the Rail Trail in Wolfeboro offer free breakfast?

This cottage does not offer free breakfast.

Is there a casino at Grandmas Cottage on the River and the Rail Trail in Wolfeboro?

No, there is no casino at this cottage.

What time is check-in at Grandmas Cottage on the River and the Rail Trail in Wolfeboro?

Check-in begins at 4:00 PM.

Is there free parking at Grandmas Cottage on the River and the Rail Trail in Wolfeboro?

Free parking is not available at this cottage.

Does Grandmas Cottage on the River and the Rail Trail in Wolfeboro have a pool?

This cottage does not have a pool.

Does Grandmas Cottage on the River and the Rail Trail in Wolfeboro have a spa?

There are no spa services available at this cottage.

How close is Grandmas Cottage on the River and the Rail Trail in Wolfeboro to downtown Wolfeboro?

This cottage is 1.1 mi away from Wolfeboro.

Grandmas Cottage on the River and the Rail Trail in Wolfeboro Reviews

Reviews

10

Exceptional

Rating 10 - Excellent. 20 out of 20 reviews
Rating 8 - Good. 0 out of 20 reviews
Rating 6 - Okay. 0 out of 20 reviews
Rating 4 - Poor. 0 out of 20 reviews
Rating 2 - Terrible. 0 out of 20 reviews

10/10

Cleanliness

Reviews

Verified review

10/10 Excellent

The F.

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had the best time here, would 100% go back. Very quiet and relaxing and the hosts were great.
Stayed 8 nights in Sep 2025
Verified review

10/10 Excellent

Nicole C.

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had a wonderful stay at Grandma’s with our two little boys and dog. It was clean, cozy and a perfect location for our weekend ice fishing trip! We enjoyed walking the rail trail, watching ducks by the dock, passing snowmobiles, and playing puzzles/games. Highly recommend for a family getaway. We would definitely stay again.
Stayed 3 nights in Feb 2026
Verified review

10/10 Excellent

Laura B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Booked a summer getaway for my husband, my dog, and me. We had a great time - the house was comfortable and clean, and the location was excellent!
Stayed 4 nights in Jul 2025
Verified review

10/10 Excellent

Marc

All excellent
Stayed 4 nights in Nov 2025
Verified review

10/10 Excellent

Claudia M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Awesome location right on the water and the rail trail yet close to town; we enjoyed the use of the kayaks, and our child loved fishing right off the dock. House was clean and had everything we needed. Owner was very responsive to questions. Easy check-in and check-out. Definitely a place to come back to!
Stayed 3 nights in Aug 2025
Verified review

10/10 Excellent

Elizabeth F.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Family trip

Great for a quick trip with young swimmers! The dock was a great depth for jumping off over and over :-)
Stayed 5 nights in Aug 2024
Verified review

10/10 Excellent

Shawn S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great Spot

Stayed for new years eve and was perfect for the fam. Kids explored outside in the morning and fed the ducks on the river.
Stayed 1 night in Dec 2023
Verified review

10/10 Excellent

Chris C.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Peaceful

Great time with the family.
Stayed 2 nights in Jul 2023
Verified review

10/10 Excellent

Samantha T.

Liked: Cleanliness, check-in, communication, location, listing accuracy

july 4th trip

great property accommodations for the whole family, walk out to the water right from the backyard with convenient grill and outdoor dining set up, kayaks and paddle boards definitely got some miles put on them, excellent stay and very responsive host
Stayed 3 nights in Jul 2024
Verified review

10/10 Excellent

Rob and Julie S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Terrific location

This was just what we needed! Cute cottage in a perfect location. Nice dock. Easy paddle access to both Wentworth and Crescent lakes, and walking to town on the rail trail.
Stayed 3 nights in Aug 2024
Verified review

10/10 Excellent

Christine P.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wonderful!

Everything was just the way it’s described. Great location. Clean and good communication with owner. Thank you so much for a lovely stay in a beautiful location.
Stayed 2 nights in Jul 2024
Verified review

10/10 Excellent

Jorge

Liked: Cleanliness, check-in, communication, location, listing accuracy

February Winter Escape

Grandmas cottage was just as described and really felt like visiting with grandma. The location was superb with an easy access to the trail into town. The views of the water from the porch were astounding. Overall a great stay and will definitely try to be back during the warmer months.
Stayed 3 nights in Feb 2024
Verified review

10/10 Excellent

Laura B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Michigander

Great location! Perfect for water-sports and proximity to town. Had just about everything we needed. Cottage could use a drainboard and sharper knives and a few more cooking utensils. Otherwise, it was as advertised.
Stayed 3 nights in Sep 2023
Verified review

10/10 Excellent

Erin M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wonderful

Perfect! My daughter and I fished, swam, used the kayaks, walked into town and binged on our favorite new netflix series. Check in and out was easy. We will be back. Thank you so much!
Stayed 2 nights in Jun 2023
Verified review

10/10 Excellent

Donna G.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great time on Smith River

We really loved our time at Grandma's Cottage. Everything was just as advertised and Wendy Rae responded promptly to any questions we had. The location on the Smith River was perfect for exploring both Crescent Lake and Lake Wentworth in our small powerboat which we were able to tie up at the property's dock. It was also fun to just sit on the nice wide dock and watch whatever happened to float by...kayakers, paddleboarders, slow-moving motor boats, etc. Lake Wentworth is big and beautiful! If the weather hadn't cooperated there were plenty of games and puzzles to keep us entertained. We would definitely stay here again.
Stayed 3 nights in Aug 2023
Verified review

10/10 Excellent

Noly R.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wonderful. Exactly as advertised.

It was the husband, myself, four kids and our dog. Everyone had a wonderful time. The cabin is exactly as described “grandma’s cabin” But everything is neat and quaint but up to date. Some of the regular stuff I bring as usual was not even needed. The area is quite and although a traffic area for some boats going to the larger lake. Everyone is friendly and respectful of the limits and other people enjoying the lake. The kids really enjoyed paddle boarding and the kayaks. We will definitely planning a return trip. 🙂
Stayed 4 nights in Jun 2023
Verified review

10/10 Excellent

Meg O.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Quick Getaway

Last minute trip to a new area for us and found Grandma's cabin on VRBO and so glad we did. The place was on the river between two lakes and had all the comforts of home. The cabin is small but immaculate and really all we needed for a friends getaway. We came with our clothes and pretty much everything else was provided. The front stairs and dock are fairly new and so sturdy. The back deck was perfect for morning coffee looking over the river but was a bit shaky so hopefully that's the next project. The hill to go down to the dock was fairly steep and since I have a bad knee just used the front stairs to go to the dock so it wasn't an issue. We didn't get to use the provided kayak or paddleboard since it was such a short trip and poured one of the days but would definitely come back. The proximity to the rail trail was awesome and we enjoyed walking around downtown Wolfeboro and visiting the local restaurants and coffee locations. I have stayed in many VRBO locations and have to say how clean this cabin was. For a place that accepts dogs, you would never know it. Hopefully next time we can bring our dog and she too can enjoy this home away from home!
Stayed 3 nights in Aug 2023
Verified review

10/10 Excellent

Ashley C.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 4 nights in May 2025

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