Family-friendly vacation rentals in Boston

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Top-rated family-friendly rentals in Boston

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Top guest favorite
The exterior of a charming brick annex is visible, featuring distinctive arched windows framed by greenery. The facade is adorned with hanging flower baskets, adding a touch of colour. A gravel driveway offers ample parking space, contributing to a welcoming entrance.
Home in Lincolnshire
4.92 out of 5 average rating, 218 reviews

The Annex @ Ormiston House

*AUGUST SPECIAL OFFERS* The Annex@Ormiston offers unique accommodation for up to 4 guests, in a self-contained building adjacent to our family home. It has ample private parking, a secure entrance, a private courtyard and access to a large garden. Downstairs, there's a kingsize bedroom, shower room, lounge and fully equipped kitchen. Upstairs, an additional bedroom contains one or two single beds. The property is a 10 minute walk from the town centre and less than a mile from Pilgrim Hospital.

Guest favorite
The charming cottage exterior features rustic brick walls and a pitched roof, framed by lush green foliage and flower beds. Seating areas with wooden chairs are situated on the lawn, inviting relaxation amidst the serene garden surroundings.
Cottage in Hagworthingham
4.94 out of 5 average rating, 237 reviews

Fairytale Cottage in a Beautiful Garden

Step into this dreamy cottage, secluded within its rambling sunny gardens with ample seating to enjoy the view. Delight and relax in its thoughtfully curated interior. Wake up refreshed within pretty bedrooms tucked into the eaves, and look out over the garden with constant soundtrack of birdsong. Relax by the log burner, or fire up the BBQ after you explore the walks which extends beyond the country lane, even if you only venture as far as the delicious cosy gastro pub, cafes & farm shop nearby

Top guest favorite
The tranquil river reflects the surrounding greenery and the rustic barn structure. A pontoon is visible by the water's edge, alongside outdoor seating that invites relaxation. Trees frame the scene, creating a peaceful atmosphere for enjoying nature.
Barn in Brothertoft
4.98 out of 5 average rating, 207 reviews

The Barn at White House Farm 1800's 3 bed Barn

The Barn is situated in the grounds of White House Farm, on the banks of the River Witham. It's a wonderfully cosy and private barn conversion with a separate private garden which is fully enclosed ideal for Dogs. Self-contained, 2 bedrooms, newly renovated bathroom, kitchen, wood burner and 65” HD TV with Netflix and Free WiFi. Quiet and very peaceful. We also now have a pontoon on The River behind the Barn from which you can launch your paddle boards, canoes or even go wild water swimming!

Top guest favorite
A rural road bordered by neatly trimmed hedges leads to a charming brick cottage, partially shaded by a large birch tree. Surrounding greenery contributes to the tranquil countryside setting, with fields visible in the background under a clear blue sky.
Cottage in Lincolnshire
4.96 out of 5 average rating, 427 reviews

Bresby Cottage, 3 Bedroom Country Cottage

Bresby Cottage is set in a rural farm location surrounded by private secure gardens. The Cottage is fully modernised and is a warm and comfortable. Comprises a cosy living room, fully fitted kitchen, electric oven and hob, fridge freezer, microwave and dishwasher. The washing machine and dryer are situated in the utility. There are two large bedrooms, one twin and a double, a third bedroom is situated off the double and can be utilised as a single bedroom/cot room or simply a dressing room.

Guest favorite
A spacious indoor heated pool area features a serene swimming pool surrounded by artificial grass. Expansive windows allow natural light to flood the room, framing views of the outdoor landscape. Comfortable seating areas are placed nearby, creating a relaxed atmosphere.
Barn in Kirkby on Bain
4.95 out of 5 average rating, 262 reviews

Luxury Annex beside the River Bain Nr Woodhall Spa

A most beautiful luxury annex to the main residence , with an indoor heated luxury swimming pool and 2 person sauna infrared.The property is set on the River Bain ,with open views to the Bain valley. . The pretty village of Kirkby on Bain is just 600 yards away. The Ebbington Arms is a wonderful public house which is well renowned for its excellent food. The Edwardian inland resort of Woodhall Spa is just 4 miles away here you find fantastic restaurants, shops and wonderful walks.

Top guest favorite
The exterior features a rustic brick building with two wooden doors, numbered and flanked by ornamental pots. A hanging planter adds a touch of greenery. Sunlight casts shadows from the structural supports, highlighting the welcoming entrance.
Place to stay in Deeping Saint Nicholas
4.96 out of 5 average rating, 166 reviews

Cosy 1 bedroom space with wetroom and safe parking

Rest and relax in this cosy self-contained room with king sized bed and large wet-room with walk-in shower, surrounded by fields and open spaces, waking up to the peace and tranquility of its semi rural setting. Access to main routes to Stamford, ideal location for visiting events at Burghley House, Rutland Water, Peterborough, Boston and Norfolk. The room is equipped with fridge, microwave, toaster and tea making facilities. Relax just outside your own front door on the terrace.

Top guest favorite
Cottage in Spilsby
4.96 out of 5 average rating, 141 reviews

Retreat to a former Chapel, relax in privacy.

With unspoilt views over countryside, our former Chapel on the Lincolnshire Wolds doorstep offers the perfect place to enjoy a memorable relaxing stay. Visit all that this County has to offer, including miles of lovely beaches, followed by snug winter evenings in front of a Log Burner, or warm summer evenings relaxing on the Patio, perhaps observing the wildlife. There is a myriad of tracks and paths around for walkers and cyclists alike. We offer comfort with a homely feel.

Top guest favorite
A quaint dining area is visible, featuring a small table set with tableware. A large window allows natural light to illuminate the space, showcasing greenery outside. A stable door is open, providing additional access to the outside garden.
Cottage in Lincolnshire
4.98 out of 5 average rating, 149 reviews

School Cottage - Cosy 1 bedroom Country Cottage

A cosy mid terraced 1 bedroomed cottage in the small village of Ewerby, near Sleaford. Ideally situated for weddings, sight seeing, or a romantic break in the country. The cottage features an open plan lounge & kitchen with log burner, smart TV, cooker, fridge/freezer & microwave. Winding stairs lead up to the luxurious & cosy bedroom with a standard double bed & en-suite shower room. This is a non smoking cottage & parking is on the street in this safe & peaceful village.

Guest favorite
A scenic outdoor area is highlighted with a picnic table and a firepit, overlooking the tranquil lake. Nearby, a black storage unit is present, and several cabins are visible in the background against a clear blue sky.
Cabin in Boston Lincolnshire
4.9 out of 5 average rating, 1,106 reviews

Adults Only Cabin With Log Burning Hot Tub

In the middle of nowhere but only 8 miles from Boston town, 12 miles from Skegness Beach and 3 miles from the sea/coast boasting award winning RSPB nature reserves and marshes. 28 cabins on a 3 acre lake. Pet and children are more than welcome.We have an orchard for you to walk around and even a dog agility area (Bookable). Double cabins with Finnish hot tubs (Adults only, charges apply for wood/firelighters). Twin cabins pet/child friendly. Double cabins pet/child friendly.

Top guest favorite
The exterior of a semi-detached cottage displays a whitewashed facade and a traditional green front door. Two brick chimneys rise from a sloped roof, while windows with white frames provide symmetry across the front. A sign above the doorway details the establishment's historical significance.
Home in Stickney
4.87 out of 5 average rating, 521 reviews

Honeysuckle Cottage, 2 bedroom cottage

A historically significant building,Honeysuckle Cottage has been beautifully restored. The front has been kept with the original front door but actually it is semi detached. It has exposed ceiling beams and natural wood furniture. The vintage decor adds to the homely feel of this two-bed cottage, perfectly equipped for a couple or small family to stay. Easy to access by car or bus, this cottage provides the escape of the countryside with the convenience of a large village.

Top guest favorite
The caravan is set on a grassy area, featuring a spacious deck. Surrounding trees provide a natural backdrop, while a gravel pathway leads to the entrance. The exterior is light-colored, with multiple windows allowing ample natural light.
Camper/RV in Stickford
4.95 out of 5 average rating, 528 reviews

Static Caravan on private garden

Situated in Stickford at the base of the Lincolnshire Wolds this is a great place to explore Lincolnshire. Wonderful dog friendly beaches 25 minutes away with plenty of walking and fishing locally. The historic city of Lincoln is 45 minutes, and the seaside town of Skegness is 15 miles away. The caravan is situated in our garden which has a large pond so children must be supervised at all times. We have 3 dogs, and free ranging chickens so visiting dogs must be on leads.

Guest favorite
A spacious bedroom features a wooden bed frame with a light-colored mattress. The room showcases exposed wooden beams and warm wooden flooring. Flanking the bed are bedside tables with lamps, and a wooden chair is positioned nearby. A large window allows natural light to fill the space.
Guesthouse in Martin Dales
4.92 out of 5 average rating, 218 reviews

Self contained rustic charm in Woodhall Spa

We want to share with you a piece of Lincolnshires best kept secret. With it’s stunning skies, beautiful riverside walks, and the charming village of Woodhall Spa a 5 minute drive away, our barn offers you a peaceful haven away from the stresses of everyday life. The barn has a large bedroom with king size bed, a sitting room with a double sofa bed and TV, kitchenette, shower room and small mezzanine with table and chairs. There is space to park on the shared drive.

Popular amenities for Boston family-friendly rentals

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MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$31,129 GYDG$33,845 GYDG$34,890 GYDG$32,800 GYDG$33,427 GYDG$33,636 GYDG$36,352 GYDG$34,890 GYDG$35,099 GYDG$28,622 GYDG$30,502 GYDG$27,369 GYD
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Quick stats about vacation rentals that are family-friendly in Boston

  • Total vacation rentals

    Explore 40 vacation rentals in Boston

  • Nightly prices starting at

    Boston vacation rentals start at G$14,624 GYD per night before taxes and fees

  • Verified guest reviews

    Over 1,120 verified reviews to help you choose

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wi-Fi availability

    40 of Boston vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Boston rentals

  • 4.7 Average rating

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