Vacation rentals in Greenwood

4.91 out of 5 average rating, 85 reviews

Cottage in Windham

Tranquil waterfront cottage

Jo-AnnRating, 5 stars7 months ago

This Lakeside Retreat was a perfect weekend escape for two couples. In late September, we seemed to have the pond to ourselves and enjoyed sharing time around the firepit overlooking the lake. The Bathroom was spacious and one level up from the bedrooms downstairs. The kitchen had everything needed to prepare an excellent meal. I would highly recommend this cabin to a a small group of friends or family looking for a great location near Portland and Lake area attractions.Our host Bobbi was very responsive.

4.94 out of 5 average rating, 169 reviews

Condo in Intervale

Upscale retreat w/ panoramic White Mountain views

ChrisRating, 5 stars6 months ago

We really enjoyed our stay at Lisa’s house in our white mountains foliage trip. Very quiet and stunning views of the mountains in color right in the living room. Secluded location but very short drive to Jackson and Conway. We would be happy to return again. Highly recommended!

4.83 out of 5 average rating, 114 reviews

Home in Conway

A Large Vacation Home with hot tub, game room +

DeirdreRating, 5 stars2 months ago

Beautiful spacious home for a large group. Beds were very comfortable and we all had a great time in the game room and hot tub. Very convenient location. Note: there are very few kitchen basics- remember to pack trash bags, cleaning products, paper towels, plastic wrap, cooking oil, etc

4.94 out of 5 average rating, 127 reviews

Home in Windham

Waterfront Gem walkable to Restaurants!

RachaelRating, 5 starstoday

Beautiful house on the pond! Perfect for our family of 4. It was comfortable and relaxing. Amy is a wonderful host! She checked in and made sure we had everything we needed. We really enjoyed our stay! Hoping to stay again sometime.

4.99 out of 5 average rating, 175 reviews

Cabin in Bartlett

Cozy White Mountain Chalet - Minutes to Everything

ArianeRating, 5 stars1 month ago

Stayed through the weekend for a quick ski trip and Kris’s was the perfect spot! Beds were super comfortable, and since we all were coming straight from work, checking in/ out was super easy! Thank you and we hope to be back soon!

4.98 out of 5 average rating, 54 reviews

Home in Jackson

The Sommet-Magical Views- Main house+Guest cottage

ChrisRating, 5 stars2 months ago

We loved the views at the Sommet. The house was spacious enough for all 6 of us without even spending much time in the guest house. We found the beds comfortable and the 3 bathrooms were helpful. The kitchen was pretty well stocked and we ended up eating in 5 out of 7 nights. The Uno, Jenga and Clue were big hits with the whole family. Thanks!

4.84 out of 5 average rating, 351 reviews

Home in Conway

Private In Village, HotTub, 1 bedroom, Fire Place

IsaacRating, 5 stars2 weeks ago

Perfect place for a weekend getaway for my wife and I. The house is comfortable and cozy to hang out at, we loved the fireplace in the living room and of course the hot tub! Quiet and secluded property while still only a 5-10 min walk to a ton of great shops/restaurants. We loved it!

5 out of 5 average rating, 6 reviews

Home in Harrison

2BR Lake House on Private Beach w/hot tub & sauna

JasonRating, 5 stars6 months ago

This is place is a gem. The lake is beautiful and the beach is very private. The house has a nice layout and is both spacious and cozy. This was our second year staying here and we plan to come back again! Dina is very responsive and great to work with.

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What guests are saying

Dream Vacation Home - Full Amenities & Hot Tub

5 out of 5 average rating, 62 reviews1 month ago

Group of mid 30 something’s stayed here for a long ski weekend! Plenty of space for us to spread out! Did a lot more hanging around the house than initially planned thanks to uncooperative weather, but there was plenty of games/puzzles in the house for us to use!

Home in Bethel

What guests are saying

All seasons Lake House next to ski areas

4.92 out of 5 average rating, 13 reviews6 months ago

Had a great stay at the cabin. The lake and surrounding mountains are beautiful. Lake was fun to fish off dock and using canoe. Nearby town Bethel has a few nice restaurants and there are a number of easily accessible day hiking spots nearby. The beds are super comfortable as well. Overall a great stay!

Cabin in Greenwood

What guests are saying

Charming mountain retreat with endless views

4.97 out of 5 average rating, 33 reviews6 months ago

Scott's place had a beautiful view of the Fall foliage, mountains, and Sebago Lake in the distance. the property was peaceful and a true escape from city life. The place has a definite country feel. Scott and Kath were very responsive to all of our questions and requests. Plenty of space for our party of 3. Would stay there again.

Vacation home in Cornish

What guests are saying

Relaxing Mountaintop Escape | Incredible Views!

4.91 out of 5 average rating, 22 reviews6 months ago

Thank you Jeremiah and Lisseth, we had a great stay! Everything was clean, organized, and had everything we needed for a wonderful time. Main st's of NH Conway were 15-20minutes away, dunkins 15minutes, mostly everything was close enough. The view from the balcony and bedroom were amazing. I will be staying here again for sure. Thank you!

Home in Bartlett

What guests are saying

The Bellemark | Lakefront Cabin + Amazing Views!

5 out of 5 average rating, 18 reviews7 months ago

This was a beautiful spot. We loved the little table in the living room, which was filled with games and infant toys. There were outlet covers and reasonably kid proofed so we could let our baby crawl around. The view was beautiful, rooms were clean, and the space was nicely decorated. There were kayaks, fire wood, a wood burning fire place, and fire pit outside. We didn’t have much time, but if we’d spent a few days here, it would have been neat to take advantage. The view is definitely the selling point. Mountains surrounding a lake, boats every so often, miss coming up from the water. It was just a very nice little slice of mountainous Maine.

Cabin in Fryeburg

What guests are saying

#1 View in Maine, Theater, HTub, Xbox, Golf, Lake

5 out of 5 average rating, 87 reviews1 week ago

A true gem! Its impossible not to be impressed by the mountain views that this place offers, for me it's one of a kind! You can see they care a lot about the house, the movie theater is a lot of fun and adds a lot to the house, the rooms are spacious and comfortable, the arcade and the hot tub are the cherry on top. The host was nice and responsive the whole trip! I would love to come back and spend more time in this amazing home! Don't think twice, just book it

Home in Woodstock

What guests are saying

Contemporary family/Dog friendly home Silverlake

4.96 out of 5 average rating, 27 reviews9 months ago

From the very beginning Tamara was a responsive host and provided clear instructions and lots of recommendations for things to do in the area. The house was as described and we loved staying here. The house was clean and spacious and perfect as a home base for our outings and to relax with our family. We had movie and game nights, made s’mores using the fire pit, and our two dogs enjoyed the fenced backyard. Highly recommend staying here and Tamara as a host.

Home in Silverlake

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Stay near Greenwood's top sights

Mt Abram Family Resort75 locals recommend

The Local Hub51 locals recommend

Maggie's Nature Park21 locals recommend

Bucks and Lapham Ledges Hiking Trail10 locals recommend

True North Adventureware9 locals recommend

Deepwood Farm9 locals recommend

Other great vacation rentals in Greenwood

5 out of 5 average rating, 15 reviews

Home in Greenwood

Cozy Greenwood Condo!

AnnieRating, 5 stars1 month ago

This condo, conveniently on the ground floor, and was clean and inviting. The wood stove provided warmth and ambiance. The furnishings included a modern well appointed coffee bar, ski themed decorations and two comfortable couches to gather around the wood stove after a day outside of adventuring. There was a mud room for outdoor clothing and boots and the bed was comfortable. The artwork in the bedroom is a fun ski-themed print. A lovely ski weekend.

4.82 out of 5 average rating, 96 reviews

Home in Tamworth

Lakefront HotTub, Fireplace, Shop, Ski, Hike, Swim

ShaunaRating, 5 stars2 months ago

The place is clearly well taken care of with attention to detail. This would be a great place any time of year. Miriam and the home were very accommodating. I would return to this location with great peace of mind.

5 out of 5 average rating, 6 reviews

Home in Harpswell

The Hideaway, In Harpswell Maine

NikkiRating, 5 stars6 months ago

We had a great long weekend at The Hideaway! The house was clean and very comfortable for 5 adults. There is a fire pit in the backyard, but plan ahead for firewood as the closest market does not sell it (we found some at Zach's Country Store in Brunswick). It's a great location with beautiful views and great restaurants nearby. We would definitely stay here again!

5 out of 5 average rating, 22 reviews

Apartment in Bartlett

Large Family Apartment

KarenRating, 5 stars1 month ago

Kevin's place was great! Very clean, comfortable and in good area as we stayed for a week of skiing. Easy to get to Attitash ski resort and quick drive to Wildcat Mountain. Kevin was easy to communicate with and would return again next year for sure!

4.97 out of 5 average rating, 63 reviews

Home in Gray

cozy 3 bedroom ranch with deck and screen porch

MichaelRating, 5 stars3 months ago

The house is lovely and, if it’s not new, it sure feels that way. In a very quiet area with tons of outdoor space yet just a mile or two from more main roads. Had a lovely white Christmas/Hanukkah with fresh snow on the 24th. Diana was a great host, always answering questions promptly and rolling with some last minute travel issues. Would love to stay here in warmer months to take advantage of the outdoors and the lovely sun porch.

4.92 out of 5 average rating, 179 reviews

Cabin in Bartlett

Mountain View Retreat, Near skiing, shopping

JaimeRating, 5 stars3 months ago

We absolutely loved our stay! Plenty of room for 8 guests (and more!!) in a beautiful setting. There was many helpful amenities, like kitchen items, and plenty of towels. The location is perfectly centered to many popular things to do. James was always very responsive to questions left clear instructions. We highly recommend staying here and hope to do so again in the future.

4.75 out of 5 average rating, 20 reviews

Home in Otisfield

Log Cabin *15 acres*hunting* snowmobile*skiing

NinaRating, 5 stars3 months ago

great place for a group of friends to get away from the city ! hot tub was spacious, pool table was a great addition to the house, and the large property was awesome for exploring the woods. overall, 10/10 would definitely come back !! only downside, there were only 11 forks for 12 guests !