Cottage vacation rentals in Oakham

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Top-rated cottage rentals in Oakham

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Guest favorite

Cottage in Wing

4.88 out of 5 average rating, 223 reviews

Quiet Rural Chapel Conversion (Architectural Gem)

Stylish & unique, self- contained historic Chapel conversion overlooking stunning scenery, (Chater Valley) tucked away at the edge of Conservation Village, 5 min drive from R.Water. Private. Sleeps 4 1 king-size & 1 small DBL Kids 8+ welcome Park free outside 2 min walk from King's Arms, Award winning Pub. Quiet & very rural. Grade ii Listed. Modern interior feat. in "Living Etc" & won a local design award Helpful owners next door Completely OPEN PLAN INTERNAL WALLS ONLY AROUND BATHROOM

Apr 9 – 16

G$27,928 GYD per night

Guest favorite

Cottage in Cottesmore

4.98 out of 5 average rating, 109 reviews

Quiet Lane Retreat: The Bee Cottage Rutland

Welcome to our charming cottage located on a tranquil lane in Rutland. Just a quick 5-min drive from Rutland Water, this 17th-century cottage is a picture-perfect gem that has undergone a refurbishment. The thatched roof adds to its undeniable charm. Step inside and be greeted by original features like low ceilings, doorways and exposed beams, creating an authentic atmosphere.T he cottage comfortably accommodates up to 5 people, offering surprisingly spacious living. Enjoy free Netflix and WiFi.

Dec 27 – Jan 3

G$59,838 GYD per night

Guest favorite

Cottage in Stoke Albany

5.0 out of 5 average rating, 167 reviews

Converted Barn overlooking fields.

Built in 1634, the Barn is on the edge of a village 5m from Market Harborough in Leicestershire. We converted it in 2017, and it's on our property, but separate from it. Light and airy, it's open plan downstairs, with areas for cooking, dining and relaxing. French doors lead out onto a pretty courtyard garden, with stone steps up to a raised area, where you can watch the sunset over the fields. Upstairs there's a well-equipped bedroom and bathroom with far reaching views over the countryside.

May 13 – 20

G$21,273 GYD per night

Guest favorite

Cottage in Stamford

4.97 out of 5 average rating, 252 reviews

Pea Cottage - A beautiful countryside retreat

Pea Cottage is a secretive, luxury cottage full of surprises. You're getting more than just a gorgeous place to hang out; the host has lined up a thoughtful selection of extras to make the most of your romantic break. These include a Prosecco Treasure Hunt, use of a tandem, an old fashioned record player, homemade "Scrum-Pea Cider", a choice of two walks and three hand-picked pubs to enjoy a memorable meal. Pea Cottage is 5 miles from Stamford, one of the prettiest market towns in the country.

Mar 26 – Apr 2

G$47,799 GYD per night

Guest favorite

Cottage in Rutland

4.96 out of 5 average rating, 118 reviews

Beautiful Georgian cottage within a walled garden

This unique family-friendly Georgian cottage, is located in the very heart of Oakham. Quiet location, set within a secluded red brick walled garden next to Oakham Castle, and All Saints Church. You will have full use of the property and private garden with summer house, outside seating and dining areas. Facilities include king and double beds, plus a double sofa bed in a second sitting room leading off the main bedroom. Bathroom with shower, kitchen, lounge, dining room & toilet/utility.

Aug 27 – Sep 3

G$51,452 GYD per night

Guest favorite

Cottage in Empingham

5.0 out of 5 average rating, 116 reviews

Primrose Hall Holiday Cottage Rutland

Primrose Hall is a beautifully renovated, Grade 2 listed stone barn conversion. It is ideally situated in the Rutland village of Empingham, within walking distance of Rutland Water’s North Shore. Empingham nestles in the Gwash Valley, equidistant from the charming Georgian town of Stamford, and Rutland’s county town, Oakham. The village has a shop, medical centre, hairdressing salon and pub just 250m away. The local area also benefits from many other very good pubs, restaurants and cafes.

Feb 27 – Mar 6

G$35,677 GYD per night

Guest favorite

Cottage in Kibworth Harcourt

4.94 out of 5 average rating, 158 reviews

Willow Cottage

The accommodation was once a barn dating back to 1900. It is a contemporary conversion within the rear garden of the main house. The property incorporates everything needed for a great stay. It is completely private and self-contained. The ground floor consists of an open plan living room/kitchen and is accessed by two large patio doors. A staircase leads to a light and airy bedroom with a king size bed, drawers and a wardrobe. There is an en-suite bathroom with walk-in shower.

Aug 4 – 11

G$18,775 GYD per night

Guest favorite

Cottage in Tugby

4.96 out of 5 average rating, 109 reviews

Attractive Cottage for relaxing country stay

This light and airy cottage situated in the heart of the village accommodates 8 guests in 4 spacious bedrooms, 1 en-suite, family bathroom and downstairs WC. Living area is stylish open plan, with 2 seating areas and dining area leading out onto patio and cottage garden overlooking the church and opposite the village school. A short walk to Fox & Hounds pub, and ideally placed for cycling and walking, with easy access to Market towns of Uppingham, Oakham and Stamford.

Jan 2 – 9

G$41,080 GYD per night

Guest favorite

Cottage in Wing

4.84 out of 5 average rating, 225 reviews

Idyllic Thatched Country Cottage - a hidden gem!

Situated in the picturesque village of Wing, this adorable thatched cottage is nestled in the grounds of beautiful Cedar House. The property was fully renovated in March 2021 and is the ideal getaway location to explore everything that stunning Rutland has to offer. The cottage is only 5 minute drive to Rutland Water, Uppingham and Oakham, so you have everything you wish to experience during your stay on your doorstep. Historic Stamford is also only 20 mins away.

Sep 26 – Oct 3

G$26,592 GYD per night

Guest favorite

Cottage in Rutland

4.93 out of 5 average rating, 116 reviews

Daphne's cottage

Our comfortable stone built self-contained cottage, situated 1/2 mile from the A1 in a rural village called Stretton. The cottage contains .. 2,Bedrooms .. room 1 with a double bed and room 2, with 2 single beds (which are "Zip and link beds") by request can be turned in to a King size bed. shower room .. with a large comfortable shower cubicle (unfortunately no bath) a front room and fully equipped kitchen. You also have your own private Patio area.

Mar 21 – 28

G$29,972 GYD per night

Guest favorite

Cottage in Market Harborough

4.93 out of 5 average rating, 121 reviews

Cobblers Cottage, Market Harborough

Hidden away in the heart of the town, this quirky home makes the ideal stopover for couples or singles. The dedicated workspace and super-fast WiFi makes it ideal for business travellers. Built in 1904 as a church hall, it later became a cobbler's workshop before under-going a conversion into a fabulous open-plan, one-bedroomed, detached home, set in it's own wrap-around, private courtyard garden.

Feb 21 – 28

G$21,431 GYD per night

Guest favorite

Cottage in Haselbech

4.9 out of 5 average rating, 281 reviews

Our Cosy Cottage of Hearts ♥️

Our Cosy Cottage of Hearts! If you need a place to come and totally chill out then this is the place, Haselbech is a peaceful village where you can walk, cycle and explore all day long! OR snuggle up and do nothing but read a good book, cook nice food and relax. We live only 10 minutes away and will help with anything we can! Good pubs are not far away and there is so much to do in the area.

Nov 16 – 23

G$24,357 GYD per night