Kid-friendly vacation rentals in Ashland

Find and book unique kid-friendly rentals on Airbnb

Top-rated kid-friendly rentals in Ashland

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

Guest favorite
Guesthouse in Ashland
Charming cottage, walk to town.
Our guests at The Ashland Cottage are always thrilled upon arrival, "It's gorgeous!" The cottage offers exactly what Ashland visitors are seeking: Comfort and charm, ample amenities and a walkable location. The cottage is newly constructed yet designed with the same Craftsman appeal as our 1920s residence. As a separate house with a private entrance, the cottage offers spacious living with high ceilings, natural light and inspiring views.. all within a 10 minute walk to theaters and downtown
Nov 20 – 27
$148 per night
4.97 out of 5 average rating, 422 reviews
Guest favorite
Guesthouse in Ashland
Charming Guest House - One block from Downtown!
This private, comfortable, two story guest house is located one block from Downtown! With stylish furniture, a large furnished private deck, and a space that can comfortably sleep 4, it's sure to give you a great visit. Enjoy a short walk to Shakespeare (6-8 mins per iPhone map), great coffee shops, Lithia Park, amazing restaurants, or stay in and enjoy the view off the private second story deck. We feel fortunate to offer such a lovely space in such a great location. PA number on file.
May 27 – Jun 3
$120 per night
4.98 out of 5 average rating, 502 reviews
Guest favorite
Guesthouse in Ashland
Historic Cottage close to plaza
Whimsical, cozy cottage located off quiet alley behind our main residence. Low-key, friendly neighborhood in the Skidmore Historic District. Front porch and back patio. Park your car and never get back in until it's time to leave. Street parking with a walk of about 200 yards to the cottage. Just 4 blocks from downtown. Full kitchen & laundry. A light-filled groovy hideaway. (Our wifi is good, but if you are doing zoom meetings, don't expect perfection.)
Nov 24 – Dec 1
$146 per night
4.96 out of 5 average rating, 169 reviews

Popular amenities for Ashland kid-friendly rentals

Kid-friendly house rentals

Guest favorite
Home in Ashland
Coyote Moon
Jan 16 – 23
$200 per night
4.95 out of 5 average rating, 173 reviews
Guest favorite
Home in Ashland
Ashland Haus Retreat - 1 block from downtown!
Feb 16 – 23
$181 per night
4.91 out of 5 average rating, 190 reviews
Guest favorite
Home in Ashland
Secluded Forest Log House 15 minutes to Ashland
Aug 5 – 12
$191 per night
4.98 out of 5 average rating, 236 reviews
Guest favorite
Home in Ashland
ABBOTT'S COTTAGES - Avocet
Mar 12 – 19
$159 per night
4.87 out of 5 average rating, 113 reviews
Guest favorite
Home in Ashland
Casa Bella
Oct 29 – Nov 5
$315 per night
4.95 out of 5 average rating, 101 reviews
Guest favorite
Home in Ashland
High Street Cottage, Artist's Garden Cottage
Dec 31 – Jan 7
$166 per night
4.96 out of 5 average rating, 129 reviews
Guest favorite
Home in Phoenix
The Country Oasis- Where City and Country Meet.
Apr 29 – May 6
$186 per night
4.96 out of 5 average rating, 208 reviews
Guest favorite
Home in Ashland
The Madrone House, mountain views.
Mar 17 – 24
$270 per night
4.91 out of 5 average rating, 118 reviews
Guest favorite
Home in Trail
Log Cabin w/Treehouse & Zip Line on Rogue River
Sep 10 – 17
$407 per night
4.95 out of 5 average rating, 210 reviews
Guest favorite
Home in Grants Pass
Gateway to Cathedral hills
Oct 21 – 28
$134 per night
4.97 out of 5 average rating, 281 reviews
Guest favorite
Home in Trail
Quiet Riverfront Cottage | 40 mins to Crater Lake
Dec 9 – 16
$148 per night
4.94 out of 5 average rating, 151 reviews
Superhost
Home in Grants Pass
Modern House in town with Hot Tub and fenced yard.
Aug 22 – 29
$84 per night
4.8 out of 5 average rating, 236 reviews

Kid-friendly apartment rentals

Guest favorite
Apartment in Ashland
Modern Crash Pad | Pet Friendly | West Wing
Jun 6 – 13
$131 per night
4.95 out of 5 average rating, 632 reviews
Guest favorite
Apartment in Ashland
Winner 2023 Best of Ashland! Our Carriage House
Oct 25 – Nov 1
$168 per night
4.86 out of 5 average rating, 236 reviews
Guest favorite
Apartment in Grants Pass
Peace on the Rogue river Studio
Apr 12 – 19
$94 per night
4.94 out of 5 average rating, 757 reviews
Guest favorite
Apartment in Medford
Suite Comice (Sanitized daily)
Apr 7 – 14
$61 per night
4.95 out of 5 average rating, 345 reviews
Guest favorite
Apartment in Grants Pass
Light and Bright! Entire 2 Bedroom Apt!
Sep 30 – Oct 7
$65 per night
5.0 out of 5 average rating, 148 reviews
Guest favorite
Apartment in Grants Pass
West Park Unit B
Oct 22 – 29
$72 per night
4.96 out of 5 average rating, 422 reviews
Superhost
Apartment in Medford
Broken Chair Ranch
Apr 14 – 21
$131 per night
4.91 out of 5 average rating, 159 reviews
Guest favorite
Apartment in Medford
Suite Madrona
Oct 21 – 28
$82 per night
4.99 out of 5 average rating, 233 reviews
Superhost
Apartment in Medford
Designer 1 BD Apt | W/ W&D | Near I-5 & DT
Dec 12 – 19
$102 per night
4.85 out of 5 average rating, 433 reviews
Guest favorite
Apartment in Grants Pass
Great location to I-5 and city! King bed!
Jul 14 – 21
$72 per night
4.82 out of 5 average rating, 199 reviews
Guest favorite
Apartment in Grants Pass
Peaceful Secluded Getaway in the forest
Apr 23 – 30
$57 per night
4.94 out of 5 average rating, 160 reviews
Guest favorite
Apartment in Grants Pass
1940s Vintage apartment steps from the Rogue River
Jun 14 – 21
$175 per night
4.97 out of 5 average rating, 202 reviews

Kid-friendly condo rentals

Guest favorite
Condo in Medford
Peaceful, quiet, pet-friendly home with a king bed
Feb 23 – Mar 2
$105 per night
4.85 out of 5 average rating, 115 reviews
Guest favorite
Condo in Rogue River
The Executive Suite
Feb 10 – 17
$130 per night
4.89 out of 5 average rating, 102 reviews
Superhost
Condo in Ashland
Spacious Modern Condo Walk To Downtown & OSF
Dec 17 – 24
$138 per night
4.88 out of 5 average rating, 26 reviews
Superhost
Condo in Ashland
Mahar Homes - Plaza North 201 Suite Alexander
Sep 17 – 24
$358 per night
5.0 out of 5 average rating, 3 reviews
Guest favorite
Condo in Phoenix
Phoenix OR Duplex-Full House Rental (1,100 Sq Ft)
Aug 22 – 29
$109 per night
4.99 out of 5 average rating, 69 reviews
Guest favorite
Condo in Jacksonville
Selah House!
Jun 20 – 27
$242 per night
4.91 out of 5 average rating, 11 reviews
Guest favorite
Condo in Medford
Bella Vista
Aug 1 – 8
$150 per night
5.0 out of 5 average rating, 61 reviews
Condo in Grants Pass
Modern, retro updated bungalow
Jul 4 – 11
$70 per night
4.17 out of 5 average rating, 6 reviews
Superhost
Condo in Ashland
Mahar Homes - Plaza North 203 Windsor Suite
Dec 31 – Jan 7
$299 per night
5.0 out of 5 average rating, 3 reviews
Superhost
Condo in Ashland
Mahar Homes - Plaza North 202 Suite Sonoma
Mar 24 – 31
$274 per night
5.0 out of 5 average rating, 4 reviews
Superhost
Condo in Medford
Cozy Historic Carnegie Suite Downtown Medford 1bd
Dec 16 – 23
$101 per night
4.73 out of 5 average rating, 11 reviews
Guest favorite
Condo in Rogue River
Black Pearl
Sep 25 – Oct 2
$124 per night
4.92 out of 5 average rating, 60 reviews

Quick stats about vacation rentals that are kid-friendly in Ashland

Total rentals

30 properties

Rentals with dedicated workspaces

10 properties have a dedicated workspace

Pet-friendly rentals

20 properties allow pets

Family-friendly rentals

10 properties are a good fit for families

Total number of reviews

1.5K reviews

Nightly prices starting at

$50 before taxes and fees

Destinations to explore

  1. Airbnb
  2. United States
  3. Oregon
  4. Jackson County
  5. Ashland
  6. Kid-friendly rentals