Photo by Jennifer Brokaw

Holiday Homes in Roxbury

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Featured Holiday Homes in Roxbury

Beautiful Escape! 'Parole LakeHouse' located 90min from NYC & 30min from Beacon
3 bedrooms, iron/ironing board, WiFi, bed sheets
Beautiful Escape! 'Parole LakeHouse' located 90min from NYC & 30min from Beacon
10.0 out of 10, Exceptional, (7)
"Absolutely loved our stay! The house was cozy, comfortable, and well-equipped. The host was responsive and made sure everything was just right. Highly recommend!!"
The price is AU$1,342
includes taxes & fees
30 Sept - 1 Oct
Beautiful Escape! 'Parole LakeHouse' located 90min from NYC & 30min from Beacon
Lakehouse, Private Beach, Kayaks, FirePit, Gym, Movie Room, Pool Table, Air Hock
On the beach, sun-loungers
Lakehouse, Private Beach, Kayaks, FirePit, Gym, Movie Room, Pool Table, Air Hock
9.6 out of 10, Exceptional, (64)
"The good: We had a great time staying here. The first and second floor are beautiful and very well maintained. Both bathrooms and three bedrooms are very clean and have more than enough bath and beach towels. The fire pit and kayaks are also a great touch. The water is just steps away and the view is excellent. Just be sure to bring your own propane and firewood. What could be better? Communication with the host left a lot to be desired. I’m still not sure who runs the property. There are two...
Lakehouse, Private Beach, Kayaks, FirePit, Gym, Movie Room, Pool Table, Air Hock
Lakeside luxury: beautiful, relaxing 4 bedroom home
Property grounds
Lakeside luxury: beautiful, relaxing 4 bedroom home
10.0 out of 10, Exceptional, (13)
"This house was perfect for my group of 6 college friends. We hadn't gotten together in over 10 years and wanted to relax and catch up. The furniture and bedding were extremely comfortable, the kitchen had everything we could possibly need and more! Very spacious home with off-street parking for 6 cars. We loved it here!!! "
Lakeside luxury: beautiful, relaxing 4 bedroom home
Lakeview Estate - Chef's Kitchen - NYC Getaway
Outdoor dining
Lakeview Estate - Chef's Kitchen - NYC Getaway
10.0 out of 10, Exceptional, (21)
"Great stay for 50th birthday "
Lakeview Estate - Chef's Kitchen - NYC Getaway
Candlewood Lakefront 3bd/ 2 bath house w/ 180 degree views!
Outdoor dining
Candlewood Lakefront 3bd/ 2 bath house w/ 180 degree views!
10.0 out of 10, Exceptional, (40)
"We had such a great time! The views are stunning and the house has everything you need to enjoy your stay. The host Kerry was so helpful; we had a small issue with the shower and she had a plumber over within the hour to resolve it. Can’t wait to come back next summer! "
Candlewood Lakefront 3bd/ 2 bath house w/ 180 degree views!
Charming 1870 cape cottage in Litchfield
Outdoor dining
Charming 1870 cape cottage in Litchfield
10.0 out of 10, Exceptional, (32)
"Jeff was so responsive throughout the entire process of getting this VRBO. I was able to get ready for my wedding with our small group and it was such an incredibly beautiful place to do it. The property is gorgeous. The cottage is wonderful, well lit, and charming for sure. We will definitely be returning! "
Charming 1870 cape cottage in Litchfield
Spacious 4-BR house in lake community with beach access and swim-in-place spa.
Fridge, microwave, oven, stovetop
Spacious 4-BR house in lake community with beach access and swim-in-place spa.
2.0 star property
Spacious 4-BR house in lake community with beach access and swim-in-place spa.
Spectacular Short Term Vacation Rental in Kent
Exterior
Spectacular Short Term Vacation Rental in Kent
9.6 out of 10, Exceptional, (76)
"Hosts were great and very responsive and the property was fantastic and really peaceful. Highly recommend staying there!"
Spectacular Short Term Vacation Rental in Kent
Lakefront Home, Close to Mt Southington!
Fridge, microwave, stovetop, dishwasher
Lakefront Home, Close to Mt Southington!
10.0 out of 10, Exceptional, (12)
"Staff very much enjoyed the atmosphere after long days of work. Wonderful Ownership. Thank you so much Susan!"
Lakefront Home, Close to Mt Southington!
The Goshen Glass Chalet
Outdoor dining
The Goshen Glass Chalet
9.4 out of 10, Exceptional, (24)
"Everything was clean, and was a very comfortable home for friends and family."
The Goshen Glass Chalet
Candlewood Lake - Family Getaway with direct lake access. 3775 sqft home.
Property grounds
Candlewood Lake - Family Getaway with direct lake access. 3775 sqft home.
10.0 out of 10, Exceptional, (12)
"The house is huge and is very well equiped. Owners are very responsive to any questions or issues. Wonderful stay for the family."
Candlewood Lake - Family Getaway with direct lake access. 3775 sqft home.
Private Annex/Former Artist Studio
Exterior detail
Private Annex/Former Artist Studio
10.0 out of 10, Exceptional, (42)
"Everything was inviting, lovely, charming."
Private Annex/Former Artist Studio
Traveling Nurse or Business Professional
Exterior
Traveling Nurse or Business Professional
10.0 out of 10, Exceptional, (7)
"The neighborhood was clean, upscale, and beautifully kept. It came with Candlewood Beach access. The second story suite was gorgeous, clean, and well apportioned. The bed was comfortable. The whole house was well maintained and a wonderful,"homey" feel to it. The Hostess was friendly, cheerful, and very accommodating. The house is on the hillside leading to Lake Candlewood. As can be imagined, the views from the windows were outstanding."
Traveling Nurse or Business Professional
Land’s End – Direct Lake Front on Warner Point, Candlewood Lake, CT
Dining
Land’s End – Direct Lake Front on Warner Point, Candlewood Lake, CT
9.8 out of 10, Exceptional, (10)
"Amenities galore in this well equipped beautiful home! Everyone was happily entertained with the many water play options and many indoor games and activities. The dock and lake were frequently used by all as we also rented a pontoon boat. Wonderful location for our large family to spend time together!"
Land’s End – Direct Lake Front on Warner Point, Candlewood Lake, CT
Cozy Lakefront Bungalow w firepit/dock/kayaks
Terrace/patio
Cozy Lakefront Bungalow w firepit/dock/kayaks
10.0 out of 10, Exceptional, (23)
"This is our second time visiting the area and staying at this beautiful home. It's close to many activities for children and adults, easy to access food and services and a beautiful overall area and home. We truly enjoy visiting!"
Cozy Lakefront Bungalow w firepit/dock/kayaks
Peaceful All Season Lake Community Home
Smart TV, fireplace, books
Peaceful All Season Lake Community Home
10.0 out of 10, Exceptional, (7)
"Great location that had everything we needed and was perfect for entertaining friends and family."
Peaceful All Season Lake Community Home
Renovated, one level home in an excellent location
Fridge, microwave, oven, stovetop
Renovated, one level home in an excellent location
10.0 out of 10, Exceptional, (36)
"Perfect for my elderly parents with limited mobility. Close to Marina. Beautiful, quiet neighborhood."
Renovated, one level home in an excellent location
Litchfield County Getaway
Fridge, microwave, stovetop, dishwasher
Litchfield County Getaway
10.0 out of 10, Exceptional, (37)
"We had a wonderful stay at Krystian’s place! The house is wonderful, welcoming and warm. It was very clean, fully equipped, included many special touches and the beds were very comfy. The host was easy to communicate with. We highly recommend this property and appreciate the time we had there. "
Litchfield County Getaway
Gather your family at this country estate
Private kitchen
Gather your family at this country estate
10.0 out of 10, Exceptional, (2)
"once we were able to gain access which took some time, we were pleasantly welcomed and comforted by the charm of this gorgeous farm house. It had everything we needed and more! The beds are extremely comfortable anthehoiiiiisisspspacious yet "
Gather your family at this country estate
Sunrise Bungalow - Lake and Mountains View
Property grounds
Sunrise Bungalow - Lake and Mountains View
10.0 out of 10, Exceptional, (9)
"My husband and I stayed at sunrise bungalow while in the NY/CT area visiting friends and family. The home was immaculate, welcoming and well appointed. Its vibe is where a little euro modern ~ meets the mountains! Morning coffee on the screened in porch, watching the birds at the bird feeder with the lake and mountains in the distance is a great way to begin the day! James responded to all our questions about the homes use, check in and check out policies, so we didn’t have to wonder about...
Sunrise Bungalow - Lake and Mountains View
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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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Other property types in Roxbury

Lakehouse, Private Beach, Kayaks, FirePit, Gym, Movie Room, Pool Table, Air Hock
On the beach, sun-loungers
Lakehouse, Private Beach, Kayaks, FirePit, Gym, Movie Room, Pool Table, Air Hock
9.6 out of 10, Exceptional, (64)
"The good: We had a great time staying here. The first and second floor are beautiful and very well maintained. Both bathrooms and three bedrooms are very clean and have more than enough bath and beach towels. The fire pit and kayaks are also a great touch. The water is just steps away and the view is excellent. Just be sure to bring your own propane and firewood. What could be better? Communication with the host left a lot to be desired. I’m still not sure who runs the property. There are two...
Lakehouse, Private Beach, Kayaks, FirePit, Gym, Movie Room, Pool Table, Air Hock
Spectacular Short Term Vacation Rental in Kent
Exterior
Spectacular Short Term Vacation Rental in Kent
9.6 out of 10, Exceptional, (76)
"Hosts were great and very responsive and the property was fantastic and really peaceful. Highly recommend staying there!"
Spectacular Short Term Vacation Rental in Kent
Lake Cottage, Private Beach, Kayaks, FirePit, Grill, 1 hour & 15 Minutes to NYC!
Beach nearby, beach towels
Lake Cottage, Private Beach, Kayaks, FirePit, Grill, 1 hour & 15 Minutes to NYC!
9.4 out of 10, Exceptional, (82)
"Property was clean, well appointed, wish we could have stayed a bit longer to enjoy more of the lake & fire pit! "
Lake Cottage, Private Beach, Kayaks, FirePit, Grill, 1 hour & 15 Minutes to NYC!
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.