Search Ossipee Cottage Rentals from CA $159

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
Aug 29 - Aug 31
In two weeks
Sep 5 - Sep 7
In one month
Sep 19 - Sep 21
In two months
Oct 17 - Oct 19

Browse Select Ossipee Cottages

Our top choices for Ossipee cottages

Lakefront home with private beach, access to dock/fishing/kayaks/boat slip
Property grounds

Lakefront home with private beach, access to dock/fishing/kayaks/boat slip

8.4 out of 10, Very good, (11)
"Very peaceful this time of the year. Weather was great for late September. Have rented several places in the area and can say this was one of if not the best "
Lakefront home with private beach, access to dock/fishing/kayaks/boat slip
Chalet-style lakefront home with private dock, beach, kayak, canoe & epic view
Exterior

Chalet-style lakefront home with private dock, beach, kayak, canoe & epic view

9.4 out of 10, Exceptional, (11)
"Very clean comfortable house"
Chalet-style lakefront home with private dock, beach, kayak, canoe & epic view
Tranquil lakefront cottage with private beach, boat slip & fishing kayak access
Terrace/patio

Tranquil lakefront cottage with private beach, boat slip & fishing kayak access

9.2 out of 10, Wonderful, (29)
"The location is superb and the home is clean and the check in was easy. The home is not large but feels larger with the outdoor space very relaxing. Would rent again for sure."
Tranquil lakefront cottage with private beach, boat slip & fishing kayak access
Kayaks, kids secret room, fishing, fire pit, ev charger.
Smart TV, DVD player, books

Kayaks, kids secret room, fishing, fire pit, ev charger.

10.0 out of 10, Exceptional, (16)
"Renting with these guys you instantly feel welcomed and loved. Ive been in hospitality all my love and can 100% guarantee you will want to return! The location is amazing-private-beautiful- the house is walking into a dream- caters to families, makes vacationingneasy!!! Youll regret not booking with ghem!"
Kayaks, kids secret room, fishing, fire pit, ev charger.
Picturesque studio in bay-front locale just steps to water w/WiFi & kitchenette
Outdoor dining

Picturesque studio in bay-front locale just steps to water w/WiFi & kitchenette

8.8 out of 10, Excellent, (16)
"Nice location on the lake."
The price is CA $207
CA $431 total
includes taxes & fees
Aug 25 - Aug 26
Picturesque studio in bay-front locale just steps to water w/WiFi & kitchenette
Cozy Cottage 2 Bedroom With Amazing View <br>
Interior

Cozy Cottage 2 Bedroom With Amazing View <br>

10.0 out of 10, Exceptional, (26)
"This place was just as described and just what our little group was looking for. It was clean and convenient to all the main attractions of Lake Winnepesaki. "
Cozy Cottage 2 Bedroom With Amazing View <br>
Maine Lakehouse near N. Conway Beach Access/Pool table/Screened Porch/gas grill
Fridge, microwave, oven, stovetop

Maine Lakehouse near N. Conway Beach Access/Pool table/Screened Porch/gas grill

10.0 out of 10, Exceptional, (1)
"Great location with easy access to the lake. Community had kayaks, sandy beach and shaded picnic area. The house had a lot of space and included games to entertain the kids. "
Maine Lakehouse near N. Conway Beach Access/Pool table/Screened Porch/gas grill
Cozy, Pet-Friendly Escape Near Lake & Mountains
Outdoor dining

Cozy, Pet-Friendly Escape Near Lake & Mountains

10.0 out of 10, Exceptional, (38)
"The property was very nice and clean. We enjoyed our stay very much!"
Cozy, Pet-Friendly Escape Near Lake & Mountains
Maine Fall Foliage: Lakefront Home in Limerick!
TV, table tennis

Maine Fall Foliage: Lakefront Home in Limerick!

9.4 out of 10, Exceptional, (24)
"We had a great stay at this beautiful lake house ! You couldn’t ask for a more relaxing vacation directly on the water . We enjoyed kayaking , fishing , swimming, paddle boarding and having fires at night . The hosts are wonderful and supply pretty much everything you would need ! We almost brought our big lobster steamer pot but we didnt have room for it but thankfully they had one in the shed and we had lobsters and steamers by the lake ! The house is well equipped, clean and lots of beds ....
Maine Fall Foliage: Lakefront Home in Limerick!
Stunning lakefront gem with full water view, beach access & dock
TV

Stunning lakefront gem with full water view, beach access & dock

10.0 out of 10, Exceptional, (11)
"A perfect little cottage for a getaway for two, to the lake. Great experience and would happily return someday."
Stunning lakefront gem with full water view, beach access & dock
Cozy Cottage on Lake Winni
Dining

Cozy Cottage on Lake Winni

9.2 out of 10, Wonderful, (38)
"This cabin was close to most attractions in the area. The cabin was clean and was perfect for our stay!"
Cozy Cottage on Lake Winni
Newly Renovated Cottage 4 in Alton Bay, NH
Private kitchen

Newly Renovated Cottage 4 in Alton Bay, NH

8.8 out of 10, Excellent, (3)
"Communication was amazing, check in was a delightful, the house itself was perfect "
The price is CA $159
CA $363 total
includes taxes & fees
Sep 16 - Sep 17
Newly Renovated Cottage 4 in Alton Bay, NH
Steps to Saco River: Outdoor Rec Hub in White Mtns
House (2 Bedrooms) | Interior

Steps to Saco River: Outdoor Rec Hub in White Mtns

3.0 star property
Steps to Saco River: Outdoor Rec Hub in White Mtns
Maine Lakefront Cottage Rental with Sandy Beach
Dining

Maine Lakefront Cottage Rental with Sandy Beach

9.2 out of 10, Wonderful, (43)
"Loved the lake and location. Planning on stay again."
Maine Lakefront Cottage Rental with Sandy Beach
Cozy cottage near Lake Kanasatka with kayaks , dog-friendly
Fridge, microwave, oven, stovetop

Cozy cottage near Lake Kanasatka with kayaks , dog-friendly

6.8 out of 10, (5)
"Good"
Cozy cottage near Lake Kanasatka with kayaks , dog-friendly
Winnipesaukee house w/ dock included.
Exterior

Winnipesaukee house w/ dock included.

9.4 out of 10, Exceptional, (6)
"Property was beautifully decorated and brand new. The views of the lake were incredible."
Winnipesaukee house w/ dock included.
Charming 3-bedroom cottage on Halfmoon Lake in Alton with Dock, Beach, WiFi, AC
Property grounds

Charming 3-bedroom cottage on Halfmoon Lake in Alton with Dock, Beach, WiFi, AC

10.0 out of 10, Exceptional, (3)
"We had an incredible stay at The Loon’s Nest! Everything was great from the moment we arrived: check-in was a breeze and we enjoyed a complimentary welcome bottle of wine on the back deck overlooking the gorgeous lake! We had everything we needed for our stay and the entire cottage was very clean and had all new appliances. We definitely took advantage of being right on the water, using the kayaks provided and taking in the amazing views! I would recommend Loon’s Nest to anyone looking for a...
Charming 3-bedroom cottage on Halfmoon Lake in Alton with Dock, Beach, WiFi, AC
Dog-friendly lakefront cottage with private dock, air hockey, water access, W/D
Property grounds

Dog-friendly lakefront cottage with private dock, air hockey, water access, W/D

9.2 out of 10, Wonderful, (10)
"Clean, comfortable, equipped, and the location is fantastic!"
Dog-friendly lakefront cottage with private dock, air hockey, water access, W/D
Cottage with great beach.
Property grounds

Cottage with great beach.

2.0 star property
10.0 out of 10, Exceptional, (6)
"We loved our stay at this cute, quaint cottage. The location was perfect just steps from Crescent lake and an easy kayak ride to Lake Wentwprth. Janis was very welcoming and the property was nice and clean. Will stay again! "
Cottage with great beach.
Harold's Camp: The cutest waterfront right on Lake Winnipesaukee ⚓️
Property grounds

Harold's Camp: The cutest waterfront right on Lake Winnipesaukee ⚓️

10.0 out of 10, Exceptional, (15)
"Great experience!"
Harold's Camp: The cutest waterfront right on Lake Winnipesaukee ⚓️
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Ossipee Hotel Reviews

The Wolfeboro Inn

The Wolfeboro Inn

10/10 Excellent
"Classic NewEngland charm"
anthony 2-night trip
Posted 14 hours ago
The Wolfeboro Inn