Vacation rentals in Ossipee

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Top-rated vacation rentals in Ossipee

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Guest favorite

Farm stay in Alton

4.97 out of 5 average rating, 165 reviews

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

Apr 8 – 15

G$22,382 GYD per night

Guest favorite

Guest suite in Conway

4.99 out of 5 average rating, 422 reviews

Mountain View Studio

This over-garage studio has a private entrance, a queen-sized bed, a futon, gas fireplace, kitchenette & bathroom. There is a refrigerator/freezer, microwave, coffeemaker & toaster but no oven/stovetop. There is a small gas grill available May-Oct. We have beautiful mountain views & are located 10 minutes from downtown. NOTE: Our driveway is long and steep. 4WD/AWD vehicles are often needed to safely get up our driveway in the winter. Also, you will hear the garage door when it opens & closes.

May 19 – 24

G$24,817 GYD per night

Guest favorite

Cabin in Conway

4.95 out of 5 average rating, 294 reviews

N. Conway…Cozy Cabin, Centrally Located

Our newly renovated cabin is family friendly (childproofed), stylish, and cozy with lovely wooden accents throughout! It is newly furnished and has brand new mattresses! This cabin is wonderfully located just off of Westside Rd. a mere skip away from Echo Lake, Cathedral Ledge, Diana's Baths etc...It is a 5 - 8 minute drive to North Conway Village and Cranmore Ski Resort; and a 5 - 8 minute drive from Settler's Green Outlets, grocery stores etc...with numerous other popular destinations nearby.

Apr 14 – 21

G$23,176 GYD per night

Guest favorite

Apartment in Tuftonboro

4.97 out of 5 average rating, 267 reviews

Apartment CenterTuftonboro minutes from Wolfeboro

This is a spacious lower- level apartment 1000 sq ft in our home . Our guests will have complete privacy with convenience parking . It features a large master bedroom and cozy second bed room. You have a large private kitchen , living room , a bathroom and laundry room . Our area offers many activities as well as shopping in historic down town Wolfeboro. A very short drive to all the best things that Lake Winnipesaukee offers. Please read all our description before booking . Thanks so much

Jun 13 – 20

G$31,816 GYD per night

Guest favorite

Guesthouse in Conway

4.97 out of 5 average rating, 123 reviews

Private, quiet contemporary studio apartment.

Experience the glory of the seasons from our newly remodeled studio apartment nestled in the woods of New Hampshire’s White Mountains. The apartment has its own private entrance, clean, modern furnishings with a soft contemporary color scheme. We live at the end of a 2.8 mile state designated scenic dirt/gravel road, on 50 acres with a beaver pond, relaxing spaces and colorful gardens. All of this is within 20 minutes of North Conway's shopping and its' majestic mountains, lakes and rivers.

Jan 22 – 29

G$25,502 GYD per night

Guest favorite

Guest suite in Albany

4.89 out of 5 average rating, 361 reviews

Mountain Hideaway

Two private rooms with full bath in private home. Includes separate entrance sharing only a mud room. Downstairs room has a refrigerator, microwave, and toaster oven, coffee and tea provided. Located in a beautiful rural setting with mountain views adjacent to the National Forest and Tin mt conservation center. Only 1 mile from the Kancamangus Highway, route 16 and Conway. Minutes from outdoor activities: skiing, biking hiking, paddling and snowshoeing. Many restaurants and shops nearby.

Jan 25 – Feb 1

G$21,726 GYD per night

Superhost

Cottage in Freedom

4.78 out of 5 average rating, 441 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.

Dec 11 – 18

G$30,550 GYD per night

Superhost

Apartment in Porter

4.86 out of 5 average rating, 319 reviews

The Carriage House Apartment

A unique and inviting second floor apartment. Located in what was originally a carriage repair shop. Renovated into living space, the apartment offers a comfortable living room with high ceilings and exposed beams. A well equipped kitchen area, bedroom with two double beds and full bathroom. Our beautiful area offers a variety of activities including a scenic town beach a short walk down the road, hiking trails for all level, antique shops, great restaurants, seasonal fairs, and orchards.

Mar 11 – 18

G$23,361 GYD per night

Guest favorite

Chalet in Freedom

4.93 out of 5 average rating, 181 reviews

Cute cottage with lake access at beach club.

My entire house just waiting to be enjoyed! A great get away for relaxing. King Pine ski hill is close by for winter fun. Summertime, I am a member of the Lake Ossipee Village Beach Club on Broad Bay, the most sandy beach with facilities. Enjoy the beach! Nearby, Freedom Town Forest trails await hiking/biking or Goodhue Boat Co. has boat rentals. If shopping is a must, Conway is 20 minutes north as are other ski hills. Antique/resale shops are nearby. Guests love the updated décor.

Oct 19 – 26

G$41,185 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.

May 7 – 14

G$24,803 GYD per night

Guest favorite

Guesthouse in Brownfield

4.88 out of 5 average rating, 379 reviews

Mountain Treehouse Guesthouse

Spacious post and beam room adorned with king bed, full kitchen, bath, living area, and laundry. The guest house is located on 40 acres of wilderness with mountain views, and walking trails on the property. Just two miles from Stone Mountain Arts Center, 15 minutes from Fryeburg village, and only 25 minutes to neighboring North Conway, NH. A great retreat for all seasons. TV, High-Speed Internet, AC, Heat, Ceiling Fans, New Construction.

Jul 19 – 26

G$28,629 GYD per night

Guest favorite

Guest suite in Meredith

4.9 out of 5 average rating, 234 reviews

Downtown! Studio w 3/4 Bathroom. Private Entrance!

This is one room with a queen bed and a 3/4 bathroom. Breakfast nook, mini-fridge, microwave, coffee maker. This room comes with it's own seperate entrance, private bathroom, and private patio (Patio is not open in the winter). Also we have off street parking for one or two cars. I am new to hosting, so for now please a two person max. Walking distance to downtown. Less than 100 yards and you are in the middle of downtown Meredith.

Aug 28 – Sep 4

G$18,677 GYD per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Ossipee vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Ossipee's top sights

Yankee Smokehouse26 locals recommend

McDonald's7 locals recommend

Pizza Barn20 locals recommend

Harley Jacks Burgers and Brews12 locals recommend

Dunkin'16 locals recommend

Jake's Seafood and Grill18 locals recommend

Other great vacation rentals in Ossipee

Guest favorite

Home in Albany

4.81 out of 5 average rating, 371 reviews

Cozy Guest Suite in White Mountain National Forest

Aug 29 – Sep 5

G$15,679 GYD per night

Guest favorite

Apartment in Tamworth

4.89 out of 5 average rating, 143 reviews

The Village House

Mar 17 – 24

G$25,470 GYD per night

Guest favorite

Guesthouse in Loudon

4.97 out of 5 average rating, 238 reviews

Pastoral Farm in NH

Sep 21 – 28

G$24,161 GYD per night

Guest favorite

Guest suite in Conway

5.0 out of 5 average rating, 257 reviews

CloverCroft - "Far from the madding crowd."

Jul 18 – 25

G$28,526 GYD per night

Guest favorite

Apartment in Campton

4.92 out of 5 average rating, 167 reviews

White Mountain is a Special Place

Oct 15 – 22

G$19,540 GYD per night

Guest favorite

Home in Center Harbor

4.98 out of 5 average rating, 235 reviews

Guest House in the Woods

Dec 14 – 21

G$34,134 GYD per night

Guest favorite

Cabin in Tamworth

4.99 out of 5 average rating, 104 reviews

Mountainside Retreat! Great Views! Cosy & Private!

Jul 18 – 25

G$36,999 GYD per night

Guest favorite

Cottage in Conway

4.95 out of 5 average rating, 281 reviews

20ft from the Water with Mountain View!

Dec 12 – 19

G$39,669 GYD per night

Show all

Quick stats about vacation rentals in Ossipee

Total rentals
140 properties
Rentals with dedicated workspaces
60 properties have a dedicated workspace
Pet-friendly rentals
50 properties allow pets
Family-friendly rentals
120 properties are a good fit for families
Total number of reviews
4.8K reviews
Nightly prices starting at
G$8,364 GYD before taxes and fees

Frequently Asked Questions

How much does it cost to stay in house rentals in Ossipee?
Experience the best of Ossipee with our house rentals, starting at about $40 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there vacation rentals with a dedicated workspace in Ossipee?
Yes! Work meets play with ease at over 60 vacation rentals in Ossipee featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there family-friendly vacation rentals in Ossipee?
Ossipee has more than 120 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
Do chalet rentals in Ossipee have wifi?
Absolutely! We offer over 10 chalet rentals with wifi in Ossipee. Enjoy a tailored experience with all the comforts you desire.
Where should I stay in Ossipee?
Make yourself at home in Ossipee by choosing from our most frequently booked neighborhoods. We have over 60 vacation rentals in Effingham Falls, and over 60 vacation rentals in West Ossipee.
Do cottage rentals in Ossipee have air conditioning?
Absolutely! We offer over 10 cottage rentals with air conditioning in Ossipee. Enjoy a tailored experience with all the comforts you desire.
Are there pet-friendly vacation rentals in Ossipee?
Four-legged friends are welcome in Ossipee. Choose from more than 50 vacation rentals for guests traveling with pets.
What are the most popular amenities for Cottage Rentals in Ossipee?
Enhance your stay in our Cottage Rentals with the most popular amenities: over 20 homes with wifi, over 10 homes with air conditioning, over 10 homes with a bbq area, and more. Indulge in the ultimate retreat, tailored to your preferences.

Vacation rentals in Ossipee

Top-rated vacation rentals in Ossipee

Vacation rentals for every style

Cottages

Houses

Hotels

Popular amenities for Ossipee vacation rentals

Stay near Ossipee's top sights

Other great vacation rentals in Ossipee

Home in Albany

Apartment in Tamworth

Guesthouse in Loudon

Guest suite in Conway

Apartment in Campton

Home in Center Harbor

Cabin in Tamworth

Cottage in Conway

Quick stats about vacation rentals in Ossipee

Total rentals

Rentals with dedicated workspaces

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Frequently Asked Questions

How much does it cost to stay in house rentals in Ossipee?

Are there vacation rentals with a dedicated workspace in Ossipee?

Are there family-friendly vacation rentals in Ossipee?

Do chalet rentals in Ossipee have wifi?

Where should I stay in Ossipee?

Do cottage rentals in Ossipee have air conditioning?

Are there pet-friendly vacation rentals in Ossipee?

What are the most popular amenities for Cottage Rentals in Ossipee?

Destinations to explore