Holiday rentals with outdoor seating in Roxbury

This beautiful property has a special place in our hearts. We stayed in the A frame during COVID and we always wanted to come back. This time we stayed in the main house and it was phenomenal. Wish the weather was better for us to use the pool, but next time! It well worth the price. Only an hr from the city and it feels like a full vacation. Wonderful way to lose time time for a few days. We will be back!

We had an amazing time at Marybeth’s suite—it truly felt like a winter wonderland. Our kids had a blast "swimming" in the snow and "rolling" over the gentle hills. Every moment was filled with joy, whether we were relaxing in the sunroom, playing in the snow, or swinging outside. The time spent together as a family, along with our conversations with Marybeth and her family, was truly precious. We can’t wait to return in the summer!

My family and I stayed at this Airbnb during my wedding weekend and it was perfect! The house is beautiful. It had one bedroom and bath downstairs for my grandma to stay in so she didn’t need to go up the stairs. The kitchen is amazing! It was a great distance to the Candlewood Inn where we got married. Jessica was very responsive and always checking in. Would definitely stay here again!

My girlfriends and I had an amazing stay! The house is stunningly gorgeous—even more beautiful than the photos. Every detail was thoughtfully designed, creating the perfect setting for a relaxing and fun getaway. The space was spotless, well-equipped, and incredibly comfortable. We truly had a great time and felt right at home. Highly recommend for anyone looking for a stylish and memorable escape!

My family had a great stay at Amanda's place. It was the perfect vacation spot - we really enjoyed the panorama view! Everything was just as described and we felt right at home.

Wow! This home was such a “wow”—just perfection. The location is spectacular (peaceful and beautiful) and the home was everything you could ask for (a work of art, comfortable, functional, family friendly). We were in town for our son’s graduation from The Woodhall School and Scott’s home was the cherry on top of a perfect weekend. Highly recommend!

Edina and Glen's house was beautiful, spacious, and pristine. It was the perfect setting for a "girls weekend". The grounds were stunning, and made for a great setting. Very close to town, shopping, and wonderful restaurants. We really appreciated that our hosts were very proactive in reaching out and making all instructions clear. They were communicative and flexible. Thank you for having us in your beautiful home! Very memorable weekend.

Check-in was easy. Pretty easy to find with some restaurants close by. It is on a more major road so if you’re sensitive to outside noise this may wake you up. Clean home and hot tub.

Loved this little apartment. It has everything you need and more.

We had a great time at The Ridge House! The property was gorgeous, and the creek is even more stunning in person. The apartment was clean, fresh, and felt very cozy. The kitchen was well stocked to make a meal. Instructions were clear and we had no logistical issues. Thanks for great stay!

this place was amazing. the bed and the pillows were heaven. I enjoyed my stay and would definitely stay here again.

Gracious host, friendly and responded very quickly. The Airbnb itself was pleasant, quite cozy with a pretty backyard/garden area. Would definitely recommend to someone looking to stay in the area

Highly recommend Patrick and Monica’s location. You feel right at home when you walk! The pool and patio views are breathtaking. The beds are very comfortable. Patrick was super responsive to my messages regarding restaurants.

What a beautiful place to stay in the Hudson Valley. The view from the property is just breathtaking. Dan’s place is very clean, open and beautifully furnished. We can’t wait to come back!

Very clean and comfortable! Tatenda is so sweet and responsive. Walkable to Yale and great restaurants, but also includes covered, safe parking in the building. We had fun grilling a dinner by the outdoor pool. Well-equipped workout rooms and the coffeemaker in the lobby was amazing offering a variety of options. We enjoyed everything about this Airbnb and will likely be back! Thank you Tatenda and Hyatus!

The place was beautifully decorated and everything from the plants to the antiques was wonderful to see. This is the perfect place for any stay and they only ask that you respect the possessions. John was very responsive in helping us for a late check in.

Pacers Pasture is on a quiet road giving it a cute country experience in a great small town. The space has an amazing unfenced yard which was great for the dogs. Easy access inside with key entry, and we loved the door entry being toward the back of house for added privacy. The house has very comfortable linens, tons of parking, and the hottest water ever - which was perfect after a cold day adventuring. Aaron provides toiletries, some nice kitchen basics likes spices and teas/coffee, fast wifi-TV streaming, and a cozy space perfect for relaxing. Bonus points for being tastefully decorated and not overly cluttered. Would stay again!

Pete was very great person as a host . She treated us very well and I feel we felt like home great place to stay definitely be back.

Maricela was very responsive and flexible throughout our stay and booking arrangements. Thank you!!

Our stay at Callas loft was amazing! Easy to find and check in. Space was clean and just as pretty as the pictures. Bummed it was rainy when we stayed otherwise we would've spent more time on the deck/patio. If we had forgotten anything (hair ties, shampoo, etc.) we would've been covered! Most of all I really loved the personal touch of the note that greeted us when we arrived of treats for myself and my mom and a toy for our pup that we brought with us. Calla was communicative leading up to our stay and during if we needed anything. I would definitely recommend staying here!

Cristina's home was great for our stay! She was extremely helpful even before we checked in, providing clear instructions on where to park and the location of the entrance. She even left out some toys for our son to play with during our time there. It's small space, but what we needed and exactly as described in the listing. We would absolutely stay here again, when we come back to the area!