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Holiday Homes in Madison

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Featured Holiday Homes in Madison

Mountainside Villas at Massanutten by Tripforth

3.5 star property
9.0 out of 10, Wonderful, (321)
"Town home was beautiful! We will def.stay again. "
Mountainside Villas at Massanutten by Tripforth

Mountainside Villas 2 Bedroom

9.8 out of 10, Exceptional, (11)
"Very closed to ski area. House is very spacious and clean."
Mountainside Villas 2 Bedroom

Charming 1800s Farmhouse on 47 Acres — Riverfront w/Views, Hot Tub, Pet-Friendly

9.6 out of 10, Exceptional, (188)
"We had a great time sitting on the porch relaxing. "
Charming 1800s Farmhouse on 47 Acres — Riverfront w/Views, Hot Tub, Pet-Friendly

Pet friendly! Free Rec passes w/ Mass Resort!

9.0 out of 10, Wonderful, (21)
"great location and amenities"
Pet friendly! Free Rec passes w/ Mass Resort!

Resort Amenities, Mountain Views, Sauna!

2.0 star property
9.4 out of 10, Exceptional, (13)
"Perfect location to anything you want to do on the resort. Would definitely stay again."
Resort Amenities, Mountain Views, Sauna!

Massanutten's Woodstone Meadows by Tripforth

4.0 star property
9.0 out of 10, Wonderful, (217)
"Nice and quiet place to stay over the weekend and food was great "
Massanutten's Woodstone Meadows by Tripforth

Massanutten Resort by Tripforth

3.0 star property
7.8 out of 10, Good, (152)
"The rooms are fully equipped "
Massanutten Resort by Tripforth

The Summit at Massanutten Resort by Tripforth

3.5 star property
9.2 out of 10, Wonderful, (63)
"Beautiful resort, clean & spacious condo. Lots of activities for the family to enjoy. I recommend staying away from the timeshare presentation they offer guest. "
The Summit at Massanutten Resort by Tripforth

Great Five-Bedroom Massanutten Lodge for You to Relax -Military Discounts Avail

8.0 out of 10, Very good, (109)
"Perfect house for three family groups. 5 bedrooms & lots of space. We cooked all meals at home over our 3 night stay. The adults & kids enjoyed the pool at fitness center , and mini golf.kids enjoyed"
Great Five-Bedroom Massanutten Lodge for You to Relax -Military Discounts Avail

Hot Tub*Resort Rec Included*Pets*Games

9.4 out of 10, Exceptional, (28)
"Loved this place! It was perfect for our family. I’m glad the spiral staircase had a secure gate for the safety of our toddlers."
Hot Tub*Resort Rec Included*Pets*Games

Be Our Guest at Massanutten Resort

9.8 out of 10, Exceptional, (149)
"This was a lovely well equipped rental in a lovely setting.. "
Be Our Guest at Massanutten Resort

Maple Highlands: Under 1 Mile to Lift! Mountaintop Estate with 2 Scenic Decks

9.2 out of 10, Wonderful, (82)
"We enjoyed our stay in this house. It was a great time with family & friends."
Maple Highlands: Under 1 Mile to Lift! Mountaintop Estate with 2 Scenic Decks

5 BDRM Dog Friendly, Lake Access Getaway w/Playground, Fire Pit & more

10.0 out of 10, Exceptional, (12)
"Perfect home for our yearly Christmas gathering. Would definitely book again and highly recommend this property. "
The price is NZ$961
includes taxes & fees
18 Aug - 19 Aug
5 BDRM Dog Friendly, Lake Access Getaway w/Playground, Fire Pit & more

Newly renovated entire guest suite in Orange County.

10.0 out of 10, Exceptional, (43)
"Myla was such a wonderful hostess. She shared cucumbers from her garden with us. This place was like a home away from home. Cozy and had everything you need. We stayed here 5 nights. My dog loved trying to hunt the squirrels. And the flowers smelled amazing when you stepped outside every morning. I highly recommend staying here. "
The price is NZ$219
includes taxes & fees
11 Aug - 12 Aug
Newly renovated entire guest suite in Orange County.

New 6 bedroom Massanutten home with 3 king beds steps from all the attractions

10.0 out of 10, Exceptional, (52)
"Perfect home for a family gathering with 15 people. Family/dining room made for an ideal gathering area where everyone could catch-up and hang out. Bottom level with a pool table was another good place to hang out. Outdoor decks were also ideal places to relax. Numerous bedrooms and large beds were great for adults. Steep driveway but we were able to park 4 cars by the house and another 2 by the road (park on the same side as the house). Would definitely stay here again!"
New 6 bedroom Massanutten home with 3 king beds steps from all the attractions

Peaceful mountain farmhouse, close to Shenandoah NP, wineries and more

10.0 out of 10, Exceptional, (37)
"Our family of 4 stayed at the house. Everything was as described, and we appreciated the owners' attention to detail. We enjoyed being in the woods and would stay again!"
Peaceful mountain farmhouse, close to Shenandoah NP, wineries and more

The Play House by Zen Living

10.0 out of 10, Exceptional, (7)
"Nice and Spacious no one was on top of one another we really enjoyed our stay."
The Play House by Zen Living

Huge Mod Farmhouse Pets Hot Tub Firepit | 11 Min to ShenNatl or Massanutten Park

10.0 out of 10, Exceptional, (3)
"We truly enjoyed our stay at this vacation home. It was incredibly comfortable, with plenty of space for everyone. The two kitchens were a great bonus, the hot tub was perfect for relaxing, and there was ample parking for all our vehicles. Highly recommend!"
The price is NZ$918
includes taxes & fees
17 Aug - 18 Aug
Huge Mod Farmhouse Pets Hot Tub Firepit | 11 Min to ShenNatl or Massanutten Park

5BR Movie Theater, Hot Tub, Bowling, Fire Pit!

The price is NZ$1,531
includes taxes & fees
31 Aug - 1 Sept
5BR Movie Theater, Hot Tub, Bowling, Fire Pit!

🏔Mountain retreat⛷ 400Mbps | Hot Tub | BBQ | Pets | Deck | 3300ft2 | King Bed

10.0 out of 10, Exceptional, (62)
"Enjoyed our stay at this lovely getaway - clean, pleasant and roomy home. "
The price is NZ$695
includes taxes & fees
17 Aug - 18 Aug
🏔Mountain retreat⛷ 400Mbps | Hot Tub | BBQ | Pets | Deck | 3300ft2 | King Bed
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Madison Hotel Reviews