Vacation rentals in Oakham

4.99 out of 5 average rating, 143 reviews

A secure garden area features a circular glass table surrounded by four wooden chairs. Two reclining lounge chairs are placed in a grassy space. The garden is bordered by wooden fencing and dense greenery, with blooming flowers adding a touch of color.

Townhouse in Manton

Entire House - Osprey Cottage, Manton in Rutland.

Osprey Cottage in Manton is a beautifully presented end terrace property which sleeps 4 guests. One bedroom with a king size bed, a second bedroom that can be configured either as single beds (2’6” wide) or a king, and a stylish bathroom. Finished in a contemporary style with modern facilities including Wi-Fi(74mb), TV, a well-equipped kitchen with dishwasher and washing machine. There is a garden with a shed and we welcome well-behaved dogs(£20 charge applies). Bedding and towels are included.

Chalet in Breedon on the Hill

A warm interior is highlighted by wood-paneled walls and large windows offering views of the surrounding fields. A modern television is mounted above a sleek fireplace. The area includes a cozy sofa and a wooden coffee table, complemented by a decorative rug.

4.92 out of 5 average rating, 102 reviews

The Barley Country Lodge with hot tub

Superbly equipped luxury lodge nestled in private grounds at Breedon on the Hill. Enjoy spacious warmth for year round breaks or extended stays. Explore great walks, cycling or riding and visit many local attractions. A lovely place to relax in comfort with 300 + 5 star reviews for our properties. There are two pubs in the village an easy walk away. There are two bedrooms, a fully equipped kitchen for dining and a spacious main room cosy sofas and soft lighting. perfect for evening relaxation.

A peaceful scene depicts the still water reflecting the nearby stone buildings and lush greenery. Tall grasses line the banks, enhancing the natural tranquility of the environment. The stone pathway is visible, leading toward a residential area in the background.

4.94 out of 5 average rating, 366 reviews

Millstream Cottage

A Charming Grade 2 listed stone built terraced cottage with an allocated parking space outside the property, conveniently located in the picturesque market town of Bakewell. Very quiet but ideally positioned to explore the beautiful Peak District. There is a bus stop nearby where you can access transport to Manchester and Sheffield. Ideal for families or couples. Highchair and travel cot available on request. A welcome pack will be provided on your arrival to get your stay of to a great start.

An aerial view showcases the charming stone cottage surrounded by landscaped gardens and mature trees. A gravel driveway leads to a patio area furnished with a dining set, while the expansive lawn invites relaxation. The scenic countryside is visible in the background.

5 out of 5 average rating, 211 reviews

Luxury 2 Bedroom Cottage (Sleeps 4) Stunning Views

*AirBnB Best New Host Finalist 2022* A stunning 2 bedroom (Sleeps 4) luxury cottage, nestled in the Peak District countryside, with superb views over Chatsworth House. Outdoor dining, farm animals, private parking (with electric charging) & tranquil walks - all within a short drive of Bakewell, Matlock & the beautiful Derbyshire Dale villages. Fully equipped with everything you will need for your stay, including: Netflix, Amazon Prime & Disney+ BBQ for outdoor dining. Family & Dog Friendly

4.89 out of 5 average rating, 122 reviews

A scenic landscape features rolling hills adorned with vibrant purple heather under a colorful sky at sunset. The backdrop showcases distant valleys, while large boulders in the foreground highlight the natural beauty of the area.

Townhouse in Derbyshire

Period town house, right in the Heart Of Bakewell

Fabulous loft style living right in the heart of beautiful Bakewell Shops, pubs, restaurants, River and amazing walks on your doorstep. Ideal to explore the stunning dales. Parking permit supplied for 1 vehicle. Sleeps 8 guests in 2 bedrooms & can sleep up to 12 with the use of sofa beds in the lounge area (£25 pppn on request) All in a modern and bright setting. Fully fitted and well equipped kitchen. Fast wi-fi Adaptable sleeping arrangements, to accommodate larger groups and families.

4.93 out of 5 average rating, 283 reviews

A private decked balcony offers a seamless connection to nature, surrounded by lush greenery. The entrance to the loft is visible, featuring large double doors that invite natural light into the interior space, showcasing the blend of outdoor and indoor living.

Apartment in Bedford

51 ½ - Self Contained Loft Space - Sleeps 2

A fully refurbished self contained loft apartment We can offer either super king or twin beds dependant upon your requirements (Please confirm upon booking) Private staircase, decked balcony, open plan living, aircon/heating, TV, armchairs & breakfast bar/table. Kitchen includes combi oven, ceramic hob and fridge . Bedroom offers aircon/heating, TV and double glazed window looking onto open views. Modern en suite bathroom includes a spacious walk in shower fresh towels & basic toiletries.

4.94 out of 5 average rating, 123 reviews

Cabin in Willington

🥇Holiday Lettings Beech Lodge > Luxury 🏆 Cabin > King Beds > Marina Location > 🐕✅

Rob invites you to stay at Beech Lodge. Located on the original, established side of the Marina within the gated community. Looking for the best price, try Searching ‘Book Holiday Lettings Beech Lodge’ In Your Browser now. Set in a quiet and attractively maintained landscaped area and a short walk away from the bustling centre and all the amenities that the Marina has to offer. It’s the original show home for the lodge development it is attractively fitted out to a high standard.

4.94 out of 5 average rating, 145 reviews

A charming entryway is framed by lush greenery and vibrant flowers, leading to a well-lit cottage. Soft lights illuminate the path which is lined with gravel, creating a welcoming atmosphere. The cottage features a combination of wood and white exterior, enhancing its rustic appeal.

Villa in Wicken

The Koya

Beautiful garden cottage set in large garden but self contained and fully equipped, with underfloor heating and private patio. Open plan with airy and bright double height main living space and bedroom mezzanine, stunning bathroom. Ideal for a couple or family with young children. Easy to reach both Cambridge and Newmarket as well as Ely which is 15 minutes drive away. Very close to Wicken Fen so great for walkers and nature lovers. Host is flexible with check-in and check-out times.

A small terrace area features a gravel surface surrounded by greenery. Two metal chairs and a round table are set against the backdrop of the cottage and rolling hills, providing a serene space for outdoor relaxation.

4.97 out of 5 average rating, 160 reviews

Swiss Cottage, a heritage cottage, stunning views

Overlooking the beautiful tree-lined Derwent valley, the South facing Swiss Cottage is uniquely situated to offer panoramic views of the entire gorge and the picture perfect village of Matlock Bath, complete with an array of pretty lights, below. It provides the seclusion of a mountain retreat and access to all the village has to offer by way of a range of eateries from vegan to seafood, excellent pubs and entertainment for children from the Heights of Abraham to rowing on the river.

A cozy living area is highlighted by a log burner set within a rustic stone fireplace. A soft armchair and a television are positioned near shelves containing books, creating a warm space for relaxation.

4.92 out of 5 average rating, 107 reviews

Stylish cottage inc. breakfast, sleeps 4

FREE Breakfast at the Old Original Bakewell pudding shop Welcome basket on arrival - Loaf of Bakewell Bakery bread, Pint of milk, bottle of Wine, bottle of local beer and the Old Original Bakewell Pudding Within a minuet’s walk of the shops, restaurants, pubs, cafes and the river Wye and large car parks *Walking, climbing and cycling on your door step *Outdoor area for al fresco dining *Cosy log burner in the living area *One parking space included *free WI-FI *Small dogs allowed

4.8 out of 5 average rating, 218 reviews

Cottage in Carsington

Luxury SC Cottage Lake views 6-8 Guests

FULLY REFURBISHED -Fabulous Lakeside cottage with unrivalled views over Carsington Water. The property is South facing, set in over an acre of garden. Beautiful walks, cycling, water & outdoor activities on your doorstep. Fantastic village gastro pub - The Miners Arms (2 min walk) central to over 100 attractions. A Hot tub can be hired in ready for use on arrival (extra charge) Please ask for details. Weekend breaks (Friday-Monday) or Midweek breaks (Monday - Friday)

4.97 out of 5 average rating, 288 reviews

An outdoor patio area is featured, with a comfortable seating arrangement and a fire pit on a gravel surface. Lush green grass extends to the horizon, framed by scenic countryside views beneath a partly cloudy sky.

Hut in Derbyshire

Hillside Hut - with hot tub & private garden

Hillside Hut is our charming, newly developed, hut located in a secluded position on our smallholding in rural Derbyshire. With its own driveway and dedicated parking, it is situated in a very private spot enjoying stunning countryside views. Enjoy the most magnificent sunsets as you kick back and relax in this calm, stylish space. Bring your wellies! There are many countryside walks from the front door and fantastic dog-friendly village pubs within walking distance.

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Popular amenities for Oakham vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Oakham's top sights

The Lord Nelson17 locals recommend

The Admiral Hornblower16 locals recommend

The Grainstore Brewery & Tap12 locals recommend

Gates Garden Centre12 locals recommend

Hitchen's Barn11 locals recommend

Fika8 locals recommend

Other great vacation rentals in Oakham

4.93 out of 5 average rating, 29 reviews

Home in Loughborough

Luxurious five bedroom barn-style retreat.

4.88 out of 5 average rating, 8 reviews

A sleek fireplace is framed by a gold-tone border, featuring dark stones arranged inside. Nearby, a clear glass vase holds fresh tulips, adding a touch of color to the elegant black backdrop.

Home in Peterborough

6bed Perfect stay! Contractors welcome!

4.96 out of 5 average rating, 169 reviews

Farm stay in Derbyshire

Luxury newly converted oak cottage

Cabin in Sutton Bonington

A wooden hot tub is positioned against a dark wall, featuring a smooth, rounded edge. A uniquely designed, carved wooden wall piece adds texture. Pendant lighting casts a warm glow, illuminating the space, while a vintage sink is mounted on the wall, completing the rustic atmosphere.

4.83 out of 5 average rating, 6 reviews

Countryside Stay | Sleeps 4 | Hot Tub | BBQ

Camper/RV in Lincolnshire

A spacious deck is visible, featuring a round table and four woven chairs, arranged for outdoor seating. Surrounding railings provide safety, while an area for drying laundry is seen in the distance. Soft grass lines the perimeter, contributing to a relaxed outdoor setting.

4.89 out of 5 average rating, 9 reviews

P nf caravan holidays

4.72 out of 5 average rating, 29 reviews

Home in Beeston

Spacious 4BDR home, off-Street parking sleeps 7

5 out of 5 average rating, 4 reviews

A modern bathroom features a freestanding bath positioned under a skylight, allowing natural light to fill the space. A floating vanity with a round mirror is installed beside the bath, complemented by neat stacks of white towels. Stylish wooden accents enhance the contemporary design.

Barn in Derbyshire

Springwood Barn No1 Forest Exclusive County Escape