Holiday houses in Annan

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Top-rated holiday rentals in Annan

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Guest favourite
Cottage in Powfoot
4.91 out of 5 average rating, 108 reviews

Beach, Period 3 Bed Cottage with Great Kitchen

Ideal for the family or trips with friends, our period cottage is beautifully situated directly overlooking an Arts and Crafts style Bowling Pavilion and the large beach immediately beyond. The house sleeps 6 in 3 bedrooms, has a big well-equipped kitchen, wi-fi and a comfy lounge with a wood and coal burning fire. Relax or find an adventure. Powfoot is peaceful with a bar and restaurant. There's free putting at the door, golf, lots of nature, nearby outlet shopping, the Solway coast and more!

Guest favourite
Cabin in Dumfries and Galloway
4.94 out of 5 average rating, 127 reviews

Studio Lodge Dumfries Cosy With Stunning Views

Studio Lodge is a charming stylish lodge nestled amid beautiful countryside, perfect for a romantic retreat or a family holiday. Close to Dumfries, 7 Stanes, Solway Firth and an array of castles, museums, pubs and eateries. Located in a lovely rural position on the edge of a small family run lodge park. Step inside this charming detached single storey lodge from the fully enclosed decking overlooking beautiful fields and country side to find a well equipped bright and comfortable home from home.

Top Guest favourite
The exterior of a uniquely shaped cabin is presented, featuring a wooden facade and large glass doors. An outdoor seating area is seen under a covered porch, adorned with string lights. A fire pit is positioned for warmth, with trees in the background.
Cabin in Dumfries and Galloway
4.92 out of 5 average rating, 345 reviews

Luxury Rural Cabin with Wood Fired Hot Tub

Glencartholm Farm by Wigwam Holidays is part of the UK's No1 glamping brand that has been providing guests with 'great holidays in the great outdoors' for over 20 years! Situated in a beautiful rural location in Dumfries and Galloway, we also run an Alpaca Farm. Beautiful views and quiet surroundings are what will greet you whilst you relax in the private hot tub. We have 4 luxury ensuite cabins with wood fired hot tubs and the capacity to accomodate for couples, families and group bookings.

Top Guest favourite
The bungalow is set within a spacious garden, illuminated softly by outdoor lighting. A pathway leading to the entrance is lined with decorative trees. The scene is framed by a twilight sky, enhancing the natural surroundings.
Home in Gretna
4.97 out of 5 average rating, 150 reviews

Orchard Cottage @ Gretna

The cottage sleeps 6 with a wood fired hot tub Just off the M6/M74 2 bed cottage set in a large private garden with ample parking Ideally located Gretna Green Weddings Designer Outlet Hidden River/ Annan Distillery Hetland Hall weddings Hadrian's Wall The Lake District Coastal Path National Cycle Route 7 South West Scotland Coast Wood fired Hot Tub is available at £50 per night - payable on arrival to allow flexibility, this can take 2/3 hours to heat up depending on the time of year

Top Guest favourite
A wooden cabin is showcased with an arched roof and large glass double doors. Two chairs are positioned on a covered porch, overlooking a well-maintained grassy area enclosed by wooden fencing. Trees and open fields are visible in the background.
Guesthouse in Dumfries and Galloway
4.98 out of 5 average rating, 451 reviews

Sea Views-Scotland-Cluaran Cabins-Solway Breeze

With views over looking the solway shore onto the beautiful mountains in Lake District, we offer this self catering cabin, with your own private and secure garden for any four legged friends you may wish to bring with you. Situated in a rural location with amazing walks on your doorstep. Our local town amenities are within a 2mile walk or 5minute drive. There are many tourist attractions near by that can either be reached by car, bus or train. This accommodation offers something for everybody.

Top Guest favourite
The entrance features a bright yellow door framed by two decorative topiary plants in square pots. Flanking the door are two windows with white frames, allowing natural light to enhance the warm tones of the stone exterior.
Cottage in Halleaths
5 out of 5 average rating, 255 reviews

Converted Stables - Scenic 'Courtyard Cottage'

'Courtyard Cottage' is situated in a courtyard - previously stables and tastefully converted to a high standard. Easy driving distance of the A74(M), with good rail & bus links. The cottage provides the ideal base to enjoy the many cultural and outdoor activities available in the area. Plenty of lovely walks, sailing, fishing, wild life and great night skies. Perfect to kick back and relax after a day of exploring the many attractions and scenery. parking is available.

Top Guest favourite
An open living space features a yellow sofa and various seating options surrounding a round dining table. A staircase with black railings leads to an upper level, while a large screen television is mounted on the wall. Natural light filters through the windows, highlighting the modern décor.
Barn in Annan
5 out of 5 average rating, 243 reviews

Annan, Dumfries & Galloway, Scotland Barn - 2 Bed

Watchhall Annexe is a recently converted barn, situated on the edge of the Royal Burgh Town of Annan. Attached to Watchhall House, it overlooks the Solway Firth and has views of the Lake District hills. It is within a 10-minute drive of the M6/M74 corridor on the Scottish-England border at Gretna. The area boasts lots of lovely places to eat and relax. Ideal for walking and cycling. Gretna Gateway Outlet Village and famous wedding venue is just a 10-minute drive away.

Top Guest favourite
A spacious lounge area features two leather sofas, accent pillows, and a wooden coffee table on a light rug. Exposed wooden beams create an open atmosphere, while warm lighting fixtures enhance the bright space, which connects to the dining area in the background.
Cottage in Dumfries and Galloway
5 out of 5 average rating, 122 reviews

DISTILLERY(The Stables) with private HOT TUB

*SPECIAL OFFER* 2 NIGHT WEEKEND BREAKS BETWEEN FRI. 21st NOV. 2025 - MON. 30th MARCH 2026. Get in touch for details. Distillery Luxury Holiday Cottages are situated in a unique position nestled between our own Distillery Stud and the Annandale Distillery(the First or Last in Scotland)Spacious sandstone stable conversions completed to v high standard in October 15.

Top Guest favourite
The exterior of the wooden pod is shown, featuring a curved roof and double glazed French doors. A picnic table is positioned on a gravel area nearby, surrounded by blooming plants and foliage. Sunlight highlights the natural beauty of the outdoor space.
Hut in Cumbria
4.92 out of 5 average rating, 653 reviews

The Eden Hideaway - Luxury Pod

Stunning views and walks, looking straight over the River Eden onto the Lake District fells. Situated in an Area of Outstanding Natural Beauty, this newly built wooden pod provides a comfortable, warm and cosy stay for people looking for a countryside retreat to relax and unwind in. Situated on Castletown Estate you can walk out of the garden gate and straight onto the river side with access to walks not publicly available.

Guest favourite
A cozy window seat is adorned with a plush cushion and a soft throw, inviting relaxation. Natural light filters through the large window, framing a scenic view of rolling hills and a blue sky with scattered clouds.
Cottage in Eastriggs
4.93 out of 5 average rating, 387 reviews

Rural 2 bed cottage, wood-fired hot tub & food

Moorside Cottage is a stylishly renovated holiday cottage annexed to, but separate from, family-run farm, Moorside Farm. Set in the beautiful Scottish countryside it offers a real taste of country living and the good life: comfy-chic rooms, modern, open-plan kitchen, home-grown food and homemade meals, fantastic views and plenty of fresh air. This peaceful, family-friendly place is perfect for a short or long-term getaway.

Guest favourite
A kitchen corner features a vintage-style fireplace with dark blue detailing. Green floral wallpaper adorns the walls, while decorative plates and potted plants add touches of color. Open shelving displays neatly arranged white dinnerware above a wooden countertop with metal cookware beneath.
Home in Dumfries and Galloway
4.9 out of 5 average rating, 204 reviews

The Old Schoolhouse

A Victorian Schoolhouse, now a cozy and stylish home. The Old Schoolhouse has 3 bedrooms, shower room & en suite bathroom. Wood stove in the lounge, open fire in the kitchen, and central heating. Light, bright, with a large garden looking onto the fields beyond- snowdrops in the spring, cherries in summer, and apples in autumn. The occasional escapee hen wandering about. The perfect place for a proper holiday.

Top Guest favourite
A stone retreat is set against a backdrop of rolling hills, illuminated by soft evening light. The exterior showcases natural stone walls and multiple rooflines, with a wooden entrance visible. Surrounding grass and a few shrubs frame the entrance, providing a tranquil atmosphere.
Barn in Askham
4.99 out of 5 average rating, 108 reviews

Wild boar barn

Wild Boar offers nothing short of spectacular views across the Lake District National Park. This retreat is perfect for couples looking to explore of the grid and away from hustle and bustle of everyday life. We have lots of walking routes right out of your front door onto the fellside, we are actually on the hillside of a wainwright Loadpot. 1 master bedroom, beautiful master bathroom and downstairs w/c

Popular amenities for Annan holiday rentals

When is the best time to visit Annan?

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Avg. price$180 NZD$197 NZD$187 NZD$182 NZD$199 NZD$204 NZD$219 NZD$213 NZD$195 NZD$192 NZD$189 NZD$182 NZD
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Frequently Asked Questions

  • Are there family-friendly vacation rentals in Annan?

    Annan has more than 10 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Are there pet-friendly vacation rentals in Annan?

    Four-legged friends are welcome in Annan. Choose from more than 10 vacation rentals for guests traveling with pets.

  • Are there vacation rentals with a dedicated workspace in Annan?

    Yes! Work meets play with ease at over 10 vacation rentals in Annan featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Where should I stay in Annan?

    Make yourself at home in Annan by choosing from our most frequently booked neighborhoods. We have over 90 vacation rentals in Annan, and over 90 vacation rentals in Howes.

Quick stats about holiday rentals in Annan

  • Total holiday rentals

    Explore 20 holiday rentals in Annan

  • Nightly prices starting at

    Annan holiday rentals start at $69 NZD per night before taxes and fees

  • Verified guest reviews

    Over 2,090 verified reviews to help you choose

  • Family-friendly holiday rentals

    10 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    20 of Annan holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Annan rentals

  • 4.7 Average rating

    Annan stays receive an average rating of 4.7 out of 5 from guests

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