Holiday rentals in Middleton

4.98 out of 5 average rating, 172 reviews

Guest suite in Lebanon

Rustic Rose Cottage of Historic West Lebanon

Rustic guest suite on serene four acres. Abutting colonial cape style house and West Lebanon Historic District date back to early 18th Century. Private parking & entrance, queen memory foam mattress, steam sauna, kitchen and laundry supplies, and desk and high speed wifi for telework. Minutes from Skydive New England, Prospect Hill Winery or McDougal Orchard. 30min to Portsmouth NH, Maine beaches, and Lake Winnipesaukee. Just over an hour to the White Mountains, Portland ME or the Boston area.

4.97 out of 5 average rating, 239 reviews

Farm stay in Alton

Mountain View - Modern & Beautiful

Kick back and relax in this stylish apartment space, with its own entrance around the back of the home! Modern construction w/ a king bed, large outdoor patio space w/ mountain views. A well-equipped kitchen/dining/living room combination that is great for short term or long term stays. Although there are other guest on the property you will have a private space to call your own and enjoy. Only 5 min from Lake Winnipesukee, 20 min to Wolfeboro, 25 min to Gunstock and 25 min to Bank of Pavilion

Place to stay in Moultonborough

4.96 out of 5 average rating, 108 reviews

Secluded cabin with off grid capabilities

If your looking for a place to get away from it all and just relax this is the place for you! Located in the Northern Lakes Region on a major wildlife corridor this rustic hunting cabin has off the grid accessories including battery powered lights, outside cold shower with an outside sink and a outhouse. There are walking trails and abundant wildlife from deer, bear, moose and coyotes all of which you may encounter. The peepers will lull you to sleep at night. Pristine beach and hiking close by.

4.9 out of 5 average rating, 520 reviews

Treehouse in Sanford

Luxury Year-round Treehouse with private hot tub

The Canopy is one of 5 luxurious tiny homes that make up Littlefield Retreat, a tranquil woodland village of 3 treehouses and 2 hobbit houses – each with its own private hot tub and dock. To see all five dwellings, click on the photo to the left of “Hosted by Bryce”, then click “Show more…”. This 15-acre forest retreat on Littlefield Pond offers our guests an experience that feels like a trip up to the woods of northern Maine, but is closer to home and to all the attractions of southern Maine.

4.94 out of 5 average rating, 171 reviews

Home in Middleton

Blue Breeze - Private lakefront w/ Hot Tub

This huge lakeside house is a great experience for all of your friends and family to enjoy all the New Hampshire lakes region has to offer. There is incredible nature all around! Some of our favorites nearby: 11min to a nearby brewery 12min to a great breakfast spot 14min to a farm stand and pick-your-own produce 17min to a nearby winery 21min to Hannafords grocery store 22min to Alton Bay 25min to Wolfeboro 29min to Mt. Major with views of Winnipesaukee 38min to Gunstock mountain for skiing

4.98 out of 5 average rating, 153 reviews

Flat in Alton

Pretty & Peaceful….close to Lake Winni!

Welcome to your Alton Bay retreat! Come relax & make lasting memories. Very clean, well stocked full kitchen & bath. Across the street is 200 acres of picturesque hiking trails & fishing. Turn left at the end of driveway and enjoy a scenic walk along Winni. Quiet location but close enough to Lake Winnipesaukee, Mt Major, Wolfeboro, Bank of Pavillion, boat launches, & docks, beaches, restaurants, shopping, sking, snowmobiling, boat rides, scuba diving, biking, kayaking, leaf peeping!

4.96 out of 5 average rating, 303 reviews

Guest house in Acton

The LOTUS welcomes you, stay a while

The Lotus is your zen home away from home. Enjoy peace and tranquility on your private back deck, the amazing salt water hot tub (exclusively use) new sauna (extra $88 per day) heated outdoor shower, deep bathtub (showering is tricky for people taller then 5'5)with bluetooth speaker.Comfortable king size bed with European bedding will let you get some much needed rest. Enjoy walks on our 12 ac property or any of the lakes near by for any kind of year round outdoor experience. Welcome :)

4.97 out of 5 average rating, 152 reviews

Cottage in Middleton

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.

4.96 out of 5 average rating, 534 reviews

Loft in Barrington

Sunny, secluded studio loft apartment

Fully furnished studio apartment above home owners' garage with private entrance. Secluded 5.5 acre lot of land surrounded by beautiful woods. Vaulted ceilings with ladder to loft with queen bed. Big, sunny south-facing windows overlooking back yard and gardens. Homeowners are a laid-back, married gay couple, living in the main house with their 5 year old daughter. LGBTQ friendly home that welcomes kind guests of any race, religion, gender, and orientation. A minute from Route 125.

4.99 out of 5 average rating, 104 reviews

Cottage in Alton

Lake view cottage #2 in Alton Bay on Winnipesaukee

Cottage #174 is one of our 3 cottages. This cozy STUDIO cottage (225 SF ) has a queen size bed/den area , fully equipped kitchen and Full Bath. AC, Wi-Fi , TV with ROKU included. Cottage has its own outside space overlooking the lake with table and chairs making it the perfect setting to relax and enjoy the beautiful lake views. The entire area is fenced in. See other listings Lake view cottage #1 &3 in Alton Bay on Winnipesaukee SEE INFO BELOW ABOUT EXTRA BOAT SLIP

5 out of 5 average rating, 204 reviews

Cabin in South Berwick

Romantic A-Frame cabin in the woods

Modern cabin tucked privately in the forest. Loaded with modern amenities make it perfect for a romantic getaway. Unwind in the hot tub looking up at the sky full of stars. Take a Sauna while being surrounded by nature all around. Relax by the fire pit. Located in the majestic forest of mount agamenticus, the extensive trail system is off our road. Short drive to the Ogunquit/ york beaches, outlets at Kittery and near Portsmouth, Dover and Portland restaurant scenes.

4.96 out of 5 average rating, 187 reviews

Cottage in Middleton

☀ 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!

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Other great holiday rentals in Middleton

4.89 out of 5 average rating, 37 reviews

Cottage in Middleton

Chase Cottage on Sunrise Lake – Lakefront

LisaRating, 5 stars9 months ago

We loved our extended weekend at Gerda’s lakefront property. It was clean, easy check-in, everything we could have needed was there, and the set up was awesome!! We enjoyed swimming, floating, and beautiful campfires. Gerda was very responsive and kind. It was the perfect birthday getaway. Thanks Gerda!!

4.91 out of 5 average rating, 80 reviews

Flat in Alton

Downtown, Super Private & Cozy Loft Style Apt.

KlaudiaRating, 5 stars4 months ago

We spent almost a month in this place and felt at home the entire time. The place was very well equipped and we lacked nothing. It was clean and the hosts even took care of snacks and bath products. Contact with Parvaneh was easy and we always got a quick response. We would definitely come back to this place.

4.94 out of 5 average rating, 34 reviews

Cottage in New Durham

Waterfront Rustic Cabin

Cathie And ChrisRating, 5 stars10 months ago

This was our 2nd stay at the Red Cabin. We and our dog enjoyed our stay and love the peace, quiet, sunsets, and loons of Chalk Pond and the Selt trails nearby. We tried some new restaurants and recommend Ellacoya and The Breeze for dinner and Ames Farm Inn for breakfast. We highly recommend staying here. Both hosts are great!

4.87 out of 5 average rating, 31 reviews

Apartment in Lebanon

Quiet place on Milton 3 Ponds water front

JohnRating, 5 stars1 day ago

An absolute beautiful home…. We loved it so much we extended our stay!

5 out of 5 average rating, 33 reviews

Home in Shapleigh

Luxury Lakefront Paradise w/ Private Beach

LeslieRating, 5 stars4 days ago

My family and I had a serene experience staying here. Although the weather was mostly rainy or cloudy, we loved the lake location and maximized the indoor, outdoor, and nearby activity options. The hosts were so responsive, regardless of the question, and made this a truly delightful visit. This was my parents’ first Airbnb experience and it set the bar higher than I could have imagined! My family and I are already talking about coming back!!

4.95 out of 5 average rating, 22 reviews

Home in Milton

The Ranch at the Ponderosa

MatthewRating, 5 stars8 months ago

This place is amazing! Very private and secluded. Perfect for a family get together. The house was spotless and well appointed. Claudine was very responsive to any questions. Would definitely stay here again!