Family-friendly vacation rentals in Oakham

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Top-rated family-friendly rentals in Oakham

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Guest favorite

Cottage in Cottesmore

4.98 out of 5 average rating, 122 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. The cottage comfortably accommodates up to 5 people, offering surprisingly spacious living. Enjoy free Netflix and WiFi.

Guest favorite

Condo in Tilton on the Hill

4.9 out of 5 average rating, 126 reviews

The Hayloft: Popular Hideaway - Sleeps 3.

After our storming success for 6 years with our cosy Hayloft Apartment, we have totally refitted the bathroom, installed a brand new kitchen and added a single bedroom / study. Fresh paint, blinds and carpets throughout! Guests have dedicated parking [Now with EV Charging] a private patio for sunny breakfasts, lunches or sundowners. Home-cooked ready meals are available in the fridge or freezer when you arrive. Message when you book and we can supply details. The Welcome pack's a big hit.

Guest favorite

Place to stay in Stonton Wyville

4.98 out of 5 average rating, 247 reviews

'Posie' at West View Farm Lodges

Your Lodge is close to Foxton Locks, Market Harborough, Rutland Water, Melton Mowbray, Uppingham, International Space Centre. You’ll love my place because of the views, the location, the people, the ambiance, and the outdoors space. My place is good for couples, solo adventurers, business travelers, families (with kids), and furry friends (pets). Private hot tub! Please note that there is an additional charge of £20 per pet per stay. Note: min 3 night stay. dogs must not scare sheep or horses.

Guest favorite

Loft in Stainby

4.93 out of 5 average rating, 166 reviews

Studio in quiet countryside setting

This self contained, open plan studio sleeps 2 in either 2 single or 1 kingsize bed(s). As a matter of course, the bed is always made up as super king size, so if you would prefer singles please request at time of booking. There is a separate shower room and small kitchen area with small fridge, mini oven and hob. The Studio has an A shape ceiling so please make yourself aware of this and avoid banging your head. Situated in a delightful countryside setting between Stamford and Grantham.

Guest favorite

Farm stay in Rutland

4.92 out of 5 average rating, 137 reviews

The Old Stables Retreat, Northfield Farm

Quiet, romantic retreat on small family-run working farm w. rare & native breed cattle & sheep. Fascinating place to learn about food & the countryside. Great place to stay & explore one of England's most lovely countryside areas. Farm shop, open for 20 + yrs, sells a wide range of home grown & home butchered meats & local flour, beers, ready meals & pies. Nr. Rutland Water, & Melton Mowbray, of pie fame, Stamford & Leicester. Great pubs abound, as do walks & entertainment of every kind.

Guest favorite

Home in Greetham

4.87 out of 5 average rating, 108 reviews

Puddleduck Cottage

Thismodernised property in Greetham village, Rutland consists of 2 bedrooms (one double and one twin), living room, garden room, kitchen and shower room (downstairs) with brand new shower unit . The cottage has gas central heating and a wood burner. Excellent location for the British Bird Fair, Burghley House as well as sports and leisure activities around Rutland water. Amenities in the village: community shop/post office. 2 pubs:The Wheatsheaf and The Plough.

Guest favorite

Cottage in Rutland

4.94 out of 5 average rating, 145 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.

Guest favorite

Home in Stamford

4.96 out of 5 average rating, 252 reviews

Detached Victorian Cottage, Stamford

The cottage is located on a private lane with free parking. Stamford's stunning historic architecture, quaint independent shops and fabulous pubs are moments from the door. Short walk from the railway station. The cottage is ideal for a couple or group of 3. Being in town, there are daytime background noises of a a nearby laundry and occasional workman in the area but people don't generally find these a problem.

Guest favorite

Cabin in Harby

4.97 out of 5 average rating, 282 reviews

Self contained Oak Framed Studio in Village garden

Situated in the Vale of Belvoir, this self-contained, open plan studio sleeps two people comfortably and includes a fully equipped kitchen, shower room, high speed Wifi and Smart TV. Surrounded by countryside, Harby is ideal for walking, cycling and being in the great outdoors. There are an abundance of public footpaths in the Vale and we can provide plenty of inspiration and maps!

Guest favorite

Cottage in Burley

4.98 out of 5 average rating, 396 reviews

Cosy Country Cottage near Rutland Water

Gamekeeper Lodge is a characterful, modern and luxurious self catering cottage; and forms a totally private annexe to our Grade 2 listed thatched cottage in the heart of Rutland. The property was designed in 1795 by John Nash, who also designed Buckingham Palace and overlooks the original thatched game larder. Situated only 2 miles from Rutland Water.

Guest favorite

Cottage in Leicestershire

4.94 out of 5 average rating, 301 reviews

Self contained rural cottage.

Self contained rural accommodation with private entrance. Sitting room with log fire and kitchen with oven, fridge, microwave and Nespresso machine. Double bed with own bath / shower room. The second bedroom (also with a double bed) will only be let with the first as one booking as they share the bathroom.

Guest favorite

Cottage in Gumley

4.97 out of 5 average rating, 180 reviews

Self-contained coach house in peaceful location

Self contained coach house adjoining our family home half a mile from Gumley village. Beautiful secluded location with far reaching views over open countryside. The perfect base for exploring the local area. Foxton locks are about a mile away, and the historic town of Market Harborough a 10 minute drive.