Cottage vacation rentals in Wolfeboro

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Top-rated cottage rentals in Wolfeboro

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Guest favorite

Cottage in Northwood

4.91 out of 5 average rating, 216 reviews

Cottage near lake! Includes canoe! Dog friendly!

Come relax, sit by the fire pit, walk the dirt roads & trials! Walk 2 min. to the boat launch/swim area & enjoy the canoe. WIFI. 500 mbps. Yard: grill out, make s'mores by the fire pit, play horse shoes. Inside: play games, complete puzzles, cuddle up and watch movies. Outings: Antique Alley, Chucksters, Stonehouse Pond, Meadows State Park, Portsmouth,Concord. *Sleeps 4. *PET FEE $25 per dog/ night. 1-2 behaved dogs. Dogs only due to health concern for cleaner. *Wear life jackets provided.

Feb 24 – Mar 3

G$33,384 GYD per night

Guest favorite

Cottage in Alton

4.87 out of 5 average rating, 159 reviews

1B Cottage w/kayaks-Lake Winnipesaukee View/Access

Quaint 1 bedroom cottage w/views of Lake Winnipesaukee available year-round. Our deck is literally on Lake Winnipesaukee and a 3 minute walk from the cottage. Here you will be able to enjoy gorgeous views, participate in lake activities such as swimming off our dock, using our kayaks, diving board, etc. The public beach is steps away, along with restaurants, ice cream, water sport rentals, mini-golf & entertainment. Perfect for couples or small family & is pet friendly. Cottage has heat & AC.

Nov 24 – Dec 1

G$38,640 GYD per night

Guest favorite

Cottage in Plymouth

4.91 out of 5 average rating, 394 reviews

Plymouth's Historic Doll House; A tiny house

The Doll House has everything you’ll need at under 700 square feet. This fully-outfitted, historic, full-house rental has a complete kitchen, living room, two-bedrooms, bath, back sitting room, front farmer's porch and beautiful gardens and sitting areas. The Doll House is within easy walking distance to the Town Common, great restaurants and shopping, the Flying Monkey, and PSU. We are just a few minutes' drive to the Barn on the Pemi and Holderness School. NH Rooms Tax; License #059528.

Feb 18 – 25

G$34,258 GYD per night

Superhost

Cottage in Freedom

4.79 out of 5 average rating, 442 reviews

Lakefront, Beach Private, Amazing Views, & pets!

Lakefront House, contemporary, amazing views, large deck, private lake beach & dock, steps from house (swimming). Very fast internet, multiple users. Private free parking. Fully equipped kitchen, AC, Smart TV & Modern shower room. Laundry Equipment, all Linen supplied. Sun trap West Facing Deck with loungers for relaxation. Canoe, life preservers & paddles included. 2 Fire pits & Grill. Boat put-in locally. Following cleaning codes: Airbnb & other authorities. Please ask any questions.

Mar 19 – 26

G$31,342 GYD per night

Guest favorite

Cottage in Gilford

4.88 out of 5 average rating, 192 reviews

Ski Gunstock, Concerts, Lake Hiking

One dog friendly, with host permission, contact host before booking My place is close to, restaurants, movies, concerts , the lake, and family-friendly activities. You’ll love my place Close to Lake Winnipesaukee, walk to Bank Of NH Pavillion Gunstock, Weirs Beach and Mt. Major. Is good for couples, solo adventurers, business travelers, and 1 dog friendly (with permission ). Just updated. There's a grill, picnic table, fire pit :) Quiet location Gunstock and, winter sports, zip line!

Feb 19 – 26

G$36,643 GYD per night

Guest favorite

Cottage in Gilmanton

4.97 out of 5 average rating, 203 reviews

Cozy Cottage Near Crystal Lake

Cozy guest cottage tucked away in the quiet town of Gilmanton. On a small hill with just a short walk down to Crystal Lake to launch your kayak or take a dip. This adorable year round camp has many necessities and is the perfect place to unwind. Less than a mile to the local beach and boat launch. Only 15 minutes to Alton Bay & Lake Winnipesaukee, and close to Gunstock Mt., Tilton shopping & restaurants and the Weirs. Come enjoy the mountains and lakes in the beautiful Lakes Region!

May 27 – Jun 3

G$33,824 GYD per night

Guest favorite

Cottage in Middleton

4.96 out of 5 average rating, 136 reviews

Beautiful Lakeside Cottage

Beautiful, quiet and secluded lakeside cottage. Enjoy amazing sunsets on our pristine lake. Swim, kayak, fish or just relax and take in the natural beauty. COVID UPDATE: We know everyone has different levels of concern regarding the virus. Please know that while we feel our sanitation and cleanliness of the Cottage is exceptional, we have doubled our efforts providing multiple cleanings between guests. This is a NON-SMOKING property. We are sorry, but we cannot accommodate pets.

Sep 27 – Oct 4

G$35,386 GYD per night

Superhost

Cottage in Parsonsfield

4.9 out of 5 average rating, 120 reviews

Riverpine Retreat - clean&bright waterfront home

Tucked away in a small town, minutes away from the New Hampshire border, located 2 minutes off of rt. 25 (direct route from Portland ME to NH) The ultimate family or couples getaway. Plenty of room in the back yard for any and all yard games, while also enjoying the firepit, "game shed" and 75ft of water frontage where you can swim, fish, or launch your kayaks from the dock into the Ossipee River. Wireless internet is available and reaches the back yard. The 'cabin' has 2 bedrooms.

Jun 8 – 15

G$27,435 GYD per night

Guest favorite

Cottage in Brownfield

5.0 out of 5 average rating, 210 reviews

Taproot Cottage at Stone Mountain

Taproot Cottage is cozy, quiet, comfortable and nestled in the beautiful White Mountain foothills of Brownfield, ME. Just one mile from the Stone Mountain Arts Center, 30 minutes to North Conway, NH, and easy access to hiking trails, mountain vistas, and the Lakes Region of western Maine. It offers a well-equipped kitchen/dining/ living room combination, full bath, a relaxing sunroom with full-sized futon for additional sleeping, and a loft bedroom with a queen bed.

Jul 30 – Aug 6

G$24,728 GYD per night

Guest favorite

Cottage in Middleton

4.96 out of 5 average rating, 141 reviews

☀ Fox & Loon lake house: hot tub/pedal boat/kayaks

Escape to a peaceful, lakeside retreat with a secluded sun-lit deck and private dock with incredible views of Sunrise Lake, plus a 4-person hot tub, and seasonal amenities like a pedal boat, two kayaks, a SUP board, gas fire table, central A/C, a pellet stove, and snowshoes. Enjoy nearby activities like hiking, leaf peeping, skiing, and visiting scenic towns, local vineyards and breweries — or simply relaxing in a beautiful lakefront setting!

Oct 29 – Nov 5

G$73,235 GYD per night

Guest favorite

Cottage in Conway

4.95 out of 5 average rating, 282 reviews

20ft from the Water with Mountain View!

This cozy cottage sits 20 ft from Pequawket Pond. We are the only cottage in this association that has 2 floors and directly on the pond. It has a spiral staircase that leads downstairs to the bedroom downstairs with walk out access. We are located within minutes to the Mount Washington Valley and all the amenities the valley has to offer. Ski resorts galore! We also have a kayak and 2 paddle boards available for our guests to use!

Nov 3 – 10

G$39,548 GYD per night

Guest favorite

Cottage in Sugar Hill

4.99 out of 5 average rating, 169 reviews

Tasseltop Cottage in Sugar Hill

Our guest house, affectionately known as the “shanty” is in a very private setting on our property in Sugar Hill. We are located about 25 minutes from the Brenton Woods Ski area and also Loon Mountain ski area. Cannon Mountain is about a 15 minute drive. Our property abuts the Toad Hill Farm wedding venue and is a 5 minute drive from the cottage. The Bishop Farm wedding venue is a 12 minute drive from the cottage.

Nov 18 – 25

G$25,096 GYD per night