Family-friendly vacation rentals in Greenwood

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Top-rated family-friendly rentals in Greenwood

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Guest favorite

Cabin in Greenwood

4.92 out of 5 average rating, 140 reviews

Mt Abram ski in & out Sunday River 15 minutes away

This cozy 15 year old log cabin sleeps 6 comfortable and has that log cabin and log furniture feeling and look. Situated on the slopes of Mt Abrams with very easy ski in and out. With a outdoor fireplace on large deck. This is truly your log cabin experience and sking adventure. The cabin has great views of the mountain range for viewing in Fall and Winter. it has 2 King beds, 2 Queen beds, 4 Twin beds, and 1 Full size bunk bed. This log cabin sits half way up Mount Abrams so you ski in and out.

Sep 19 – 26

R6,501 ZAR per night

Guest favorite

Cabin in Greenwood

4.95 out of 5 average rating, 237 reviews

Camp Wigwam on North Pond - Swim,Paddle,Kayak,Fish

Camp Wigwam! Lake cottage on North Pond minutes away from hiking trails, waterfalls, bike trails and more. Stay in comfort with all the amenities. Explore Western Maine or just relax at camp. Watch the nesting pair of bald eagles swoop down to capture fish and hear the loons call. Strong WiFi with Roku streaming. Enjoy any of the 100+ DVDs and the record turntable. Near Bethel with lovely restaurants, bars and other venues. Great for kids, couples and families. Easy to get to all year round.

Sep 22 – 29

R4,366 ZAR per night

Superhost

Apartment in Norway

4.84 out of 5 average rating, 393 reviews

Remodeled Downtown Norway 1.5 Bedroom, 1 Bath Apt

Newly renovated and remodeled 1.5 Bedroom (both Queen Beds), and 1 full Bathroom on the 1st floor of a 2 floor Townhouse. In Downtown Norway Maine, 3 doors down from the local coffee shop (Cafe Nomad), and steps from downtown shops and the farmers market. Less than a 5min drive from Lake Pennesseewassee and great restaurants like 76 Pleasant. 10 minute drive from Norway Country Club, 20min from the Oxford Casino, and 40minutes from Bethel. Bright, airy, modern relaxed feel to the apartment.

Jan 16 – 23

R2,762 ZAR per night

Guest favorite

Cabin in Weld

4.97 out of 5 average rating, 156 reviews

Colby's Cabin

Beautiful, off-the-grid, rustic log cabin on 10 acres one mile up a 4-wheel drive trail. Located in a wilderness region minutes to Webb Lake, Tumbledown Mountain & Mt. Blue State Park. Trails of all kinds right out the front door. In the middle of Maine’s finest hiking, hunting, fishing, and boating. A perfect place for adventure, romance, celebration or serenity. An escape from the electronic world, the cabin has solar and battery lights but no power generator. (See Winter Conditions below)

Jan 5 – 12

R1,643 ZAR per night

Guest favorite

Home in Bridgton

4.91 out of 5 average rating, 273 reviews

Lake Region Comfort, Close to Everything!

Come enjoy the Highland Lake area known for its clear water, boating and fishing! Just a few miles away from Shawnee Peak which offers both day/night skiing. Also a few miles away is downtown Bridgton where there is the Magic Lantern movie theater and the drive-in theatre. Downtown also offers shopping and many options for superb dining. This single-family residence will provide you with 2 bedrooms, a newly renovated kitchen, sliders to deck, bathroom, living room with large panel tv and WiFi.

Sep 13 – 20

R2,882 ZAR 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.

Apr 3 – 10

R2,294 ZAR per night

Superhost

Cabin in Waterford

4.89 out of 5 average rating, 125 reviews

Jewett Pond Retreat

Relax in the Western Maine Foothills at our cabin on Jewett Pond. The main cabin has 672 sq ft of finished living space with bedroom (queen bed), bathroom, basic kitchen, great room (queen sleeper sofa), and screened porch. There is an additional rustic bunkhouse with two twin beds. This space is ideal for a couple or adventurous family who enjoys swimming, canoeing, hiking, fishing, or sitting on the screened porch with a good book and pine forest backdrop. Canoe included with booking.

Aug 31 – Sep 7

R3,669 ZAR per night

Guest favorite

Apartment in Jackson

4.97 out of 5 average rating, 504 reviews

Studio, pet friendly, river views, Jackson NH

Sunny studio with king bed, private entrance, garage parking. Small but complete kitchen (under counter refrigerator). Great views of the Wildcat river. WiFi, cable. 1 mile to Jackson cross country trails and close to the village of Jackson. Non smoking. The space is 500 square feet. There is a two night minimum stay. Pet friendly. Starting in 2025, we will allow 1 dog without charge. You will be charged $40/stay for a second dog. Please supply information on breed and size.

Nov 18 – 25

R2,377 ZAR per night

Guest favorite

Home in Andover

4.97 out of 5 average rating, 107 reviews

Cozy comfortable mobile home on private farm.

My place is close to the great outdoors! Hiking, biking, horseback riding, swimming and all water sports. We are an easy drive to three wonderful ski areas.. You’ll love my place because of the coziness, the location, the views and all the outdoor activities in the western mountains of Maine.. My place is good for couples, solo adventurers, business travelers, families (with kids), and furry friends (pets). In season you can enjoy fresh vegetables from our gardens.

Nov 17 – 24

R2,042 ZAR per night

Guest favorite

Home in Bethel

4.95 out of 5 average rating, 109 reviews

Sunday River Bethel Village ! Walk to Restaurants

2 Bdrm, 1 Bth, Cozy Rental located in Bethel Village. 400 yds from The Bethel Inn. Walk to Bethel Village Restaurants & Shops. Home is in residential area with plowed sidewalks and well lit street. Ideal for a mature quiet couple or similar who are into skiing / enjoying the Bethel area and respectful of the property and neighbors. small dog ok, no cats.

Jul 5 – 12

R3,425 ZAR per night

Guest favorite

Home in Paris

4.94 out of 5 average rating, 129 reviews

Just a get away!!

My place is close to great views - for fall time - half hour to ski area's -oxford casino 7 miles away - hour drive to Mt Washington or Portland - Plenty of hiking area's- Oxford plains speed way 3 miles - , restaurants and dining . Read all { House Rules } it's under things to know, on the bottom left, before making reservation - Thank You

May 5 – 12

R2,006 ZAR per night

Guest favorite

Condo in Newry

4.88 out of 5 average rating, 234 reviews

Sunday River Locke Mountain Ski In/ Ski Out Pool

Hard to find, ski in/ski out 1 BR unit in prestigious Locke Mtn Townhomes. Apartment is located on the Tempest ski run (White Cap chair) in the lower level of our own townhouse. Ski right to your front door, then relax in the beautiful outdoor pool/jacuzzi. Nightly price covers 2 people. Extra guests are an extra $25 per person, per night.

Jun 16 – 23

R2,525 ZAR per night