Vacation rentals in Middletown

Lorraine's Loft

- Escape to Lorraine’s Loft - a modern studio with stunning countryside views. - Add our Birthday, Anniversary or Romance package for a special touch! Available on request. - Slip into cosy robes & unwind with unlimited use of our large, premium hot tub. - Private entrance, large covered deck, balcony. - Close to Cookstown’s shops & restaurants yet peaceful & relaxing. -Full kitchen for home-cooked meals or order take away from a local fave. - 55" TV with Netflix, Disney + & Prime Video.

Lemnagore Lodge

Cosy self-catering apartment located between 2 beautiful estates. The house is surrounded by green and lush farmland and an old railway line. We are only 12 minutes away from beautiful Armagh. It is a good shopping town with plenty of restaurants, cafes, leisure centre, museums and planetarium. There are ple of parks and forests nearby, for that peaceful walk. Our place is ideal for families, couples, and the lone traveller alike. Welcome basket on arrival with tea, coffee, milk, and water.

Tullydowey Gate Lodge

Situated beside the village of Blackwatertown on the border between counties Tyrone and Armagh. Tullydowey Gate Lodge is a Grade B1 listed property built in 1793. Restoration of the gate lodge was completed in 2019 and undertaken with the utmost regard for the history of the building with many of the existing 18th century features sympathetically maintained whilst providing the comforts of 21st century living in a traditional country cottage style turning it once again into a real eye catcher.

Killeavy Cottage

Enjoy the lovely setting of this romantic spot in nature. Killeavy Cottage is the perfect antidote to the modern fast paced world. Killeavy Cottage is nestled between the magnificent Slieve Gullion mountain and the calm, tranquil waters off Camlough Lake in a picturesque rural setting close to the bustling shopping city of Newry, and not for from the lively town of Dundalk. A unique location with breath-taking scenery with access to bike trails and Hill walking at Slieve Gullion Forest Park.

Homely Village House

This quaint, fully equipped self catering cottage, is situated in the heart of Glaslough village, just a 5 minute walk to the castle estate entrance. It is ideally located beside the village shop, Olde Bar and children's playground (Tennis/Basketball courts). Garden and BBQ area are available for guests to use. We also offer bespoke soul soothing activities including equine therapy, lakeside meditation, creative writing, breathwork, yoga, electric bike tour of the village and so much more.

Diamond View Apartment

A modern, newly furnished apartment located in center of diamond in Monaghan Town. This space is perfect for groups or families. Within 1 minute walking distance of all the bars and restaurants, shopping boutiques. The Westenra Arms hotel is just across the street while both the Hillgrove Hotel and Four Seasons Hotel is both less than 2km a 4 minute drive. Perfect location for wedding guests, Music Festival visitors or families visiting the area. The Castle Leslie Estate is a 13 minute drive.

Lower Lough Lodge with Hottub & Bbq

Kick back and relax in this calm, stylish space.lough lodge is situated at the foothills of the Cooley mountains on the north side of the picturesque Carlingford lough and mourne mountains 5 minute walk up to reach the Tain trial and 5 minute walk down to reach the omeath/carlingford greenway its a 1 bedroom sleeps up to 4 people with a sofa bed in living room ,bedroom living room/dining area outside balcony to enjoy a relaxing stay with hot tub and bbq stunning views in a peaceful setting

Balance Treehouse - Luxury high in the tree tops

High in the tree tops as you look out over the craggy Heather covered hills, stone ditched fields and winding narrow roads. Take a deep breath, relax and reconnect with nature. A unique hand crafted resort, boasting a natural rustic look with full modern connectivity. Accessed via a private rope bridge, a hot tub, outdoor net/hammock, outdoor shower built for two and super king bed complete with glass roof for star gazing. All fully controlled by voice commands.

Ireland’s #1 River Retreat Hot Tub~Sauna~Plunge

One of Ireland's most popular & unique Airbnb escapes for couples. Just 1 hour north of Dublin & 1 hour south of Belfast, our little well-being sanctuary awaits The amenities of this space have been specially designed for you to let go and disconnect from the stresses of life There is no better place to emerge into the depths of nature and discover the great benefits of natural hot and cold therapy in Ireland We invite you to: Rest | Relax | Recharge

5 bed Cottage Sleeps up to 10 in Glaslough Village

Spacious, self catering end terrace 5 bedroom house located in the heart of Glaslough Village. Boasting the title of the country's Tidiest Village, Glaslough is an historic, picturesque village with a playground, Tennis court, local shop, pubs and restaurants in close proximity. The Hunting lodge, Equestrian centre and hotel is a short 5 minute walk. Up to ten guests can comfortably stay in our spacious, cosy house. Private parking for up to 4 cars.

Hilltop Hideaway | Private escape + HotTub & Views

Perched on a mountaintop with breathtaking panoramic views, this one-of-a-kind dome-shaped Glamping Pod is your private sanctuary — there’s only one pod on the entire site, so you’ll have the whole space to yourself. This secluded retreat offers 360 uninterrupted views. Ideal for a digital detox, this is the perfect off-grid escape to disconnect from everyday stresses and reconnect with nature under the stars.

Keepers House, Castle Leslie Estate

A cut stone period two bed house, recently renovated and formerly the game keepers house, located in the heart of the Castle Leslie Estate. The house sits at the top of a small hill, with views of a lake through the trees that surround the house. Perfect for quiet get aways with friends or the family as well as those visiting for weddings and events at Castle Leslie.