Vacation rentals in Middletown, CT

65 available vacation rental offers

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Best Vacation rentals and Airbnb offers in Middletown, CT

Newly Remodeled 1-BR Close to Everything yet Very Private - Middletown, CT

Newly Remodeled 1-BR Close to Everything yet Very Private

Holiday Home, Middletown

Newly Remodeled 1-BR Close to Everything yet Very Private is a holiday home in Middletown, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base…

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About Newly Remodeled 1-BR Close to Everything yet Very Private

Newly Remodeled 1-BR Close to Everything yet Very Private is a holiday home in Middletown, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,166.

From$118/night
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Chic Suite with Recliner - Webster Hill Suite 1W - Middletown, CT

Chic Suite with Recliner - Webster Hill Suite 1W

Apartment, Middletown

Chic Suite with Recliner - Webster Hill Suite 1W is a apartment in Middletown, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Chic Suite with Recliner - Webster Hill Suite 1W

Chic Suite with Recliner - Webster Hill Suite 1W is a apartment in Middletown, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: kitchen, with kitchen, parking, free parking, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,262.

From$127/night
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Stylish and cozy home away from home. Located in Central meriden - Middletown, CT

Stylish and cozy home away from home. Located in Central meriden

Apartment, Middletown

Stylish and cozy home away from home. Located in Central meriden is a apartment in Middletown, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable…

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About Stylish and cozy home away from home. Located in Central meriden

Stylish and cozy home away from home. Located in Central meriden is a apartment in Middletown, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,387.

From$135/night
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Peaceful lake cottage #2 - Middletown, CT

Peaceful lake cottage #2

Cottage, Middletown

Peaceful lake cottage #2 is a cottage in Middletown, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About Peaceful lake cottage #2

Peaceful lake cottage #2 is a cottage in Middletown, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,486.

From$144/night
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Browse Vacation Rentals with a Pool in Middletown, CT

Add a pool to the search when you want an easy place to cool off between outings.

The Bevin House B&B - Middletown, CT

The Bevin House B&B

B & B, Middletown

The Bevin House B&B is a b & b in Middletown, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family…

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About The Bevin House B&B

The Bevin House B&B is a b & b in Middletown, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free breakfast, pool, free wifi, and for couples.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,064.

From$266/night
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The Bevin House Bed & Breakfast - Middletown, CT

The Bevin House Bed & Breakfast

B & B, Middletown

The Bevin House Bed & Breakfast is a b & b in Middletown, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time…

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About The Bevin House Bed & Breakfast

The Bevin House Bed & Breakfast is a b & b in Middletown, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free breakfast, pool, free wifi, and gym.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,098.

From$270/night
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Home away from home Hot Tub and Pool in Middletown home of Wesleyan university - Middletown, CT

Home away from home Hot Tub and Pool in Middletown home of Wesleyan university

Holiday Home, Middletown

Home away from home Hot Tub and Pool in Middletown home of Wesleyan university is a holiday home in Middletown, with pool access and kitchen access. This stay gives travelers a comfortable…

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About Home away from home Hot Tub and Pool in Middletown home of Wesleyan university

Home away from home Hot Tub and Pool in Middletown home of Wesleyan university is a holiday home in Middletown, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, hot tub, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $4,706.

From$495/night
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Country retreat with pool, brook and waterfall, 2 hours from NYC and Boston - Middletown, CT

Country retreat with pool, brook and waterfall, 2 hours from NYC and Boston

Holiday Home, Middletown

Country retreat with pool, brook and waterfall, 2 hours from NYC and Boston is a holiday home in Middletown, with pool access, kitchen access, and a quieter setting. This stay gives…

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About Country retreat with pool, brook and waterfall, 2 hours from NYC and Boston

Country retreat with pool, brook and waterfall, 2 hours from NYC and Boston is a holiday home in Middletown, with pool access, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, hot tub, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $6,164.

From$645/night
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Best Middletown, CT vacation rentals with parking

Find vacation rentals that make arriving by car easier.

All New Studio apartment in center of town - Middletown, CT

All New Studio apartment in center of town

Apartment, Middletown

All New Studio apartment in center of town is a apartment in Middletown, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About All New Studio apartment in center of town

All New Studio apartment in center of town is a apartment in Middletown, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,166.

From$118/night
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Once the old Schools house now a newly furnished Apartment - Middletown, CT

Once the old Schools house now a newly furnished Apartment

Holiday Home, Middletown

Once the old Schools house now a newly furnished Apartment is a holiday home in Middletown, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Once the old Schools house now a newly furnished Apartment

Once the old Schools house now a newly furnished Apartment is a holiday home in Middletown, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,166.

From$118/night
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Seasons Hospitality offers all new 1Br with tons of charm - Middletown, CT

Seasons Hospitality offers all new 1Br with tons of charm

Apartment, Middletown

Seasons Hospitality offers all new 1Br with tons of charm is a apartment in Middletown, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for…

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About Seasons Hospitality offers all new 1Br with tons of charm

Seasons Hospitality offers all new 1Br with tons of charm is a apartment in Middletown, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,166.

From$118/night
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Historic Mansion 1841 - The listed price is per Bedroom, Private Entrance - Middletown, CT

Historic Mansion 1841 - The listed price is per Bedroom, Private Entrance

B & B, Middletown

Historic Mansion 1841 - The listed price is per Bedroom, Private Entrance is a b & b in Middletown, with parking and room for a group. This stay gives travelers a comfortable base for…

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About Historic Mansion 1841 - The listed price is per Bedroom, Private Entrance

Historic Mansion 1841 - The listed price is per Bedroom, Private Entrance is a b & b in Middletown, with parking and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: parking, free parking, ac, air conditioning, and tv.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,827.

From$201/night
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Best Pet-Friendly Vacation Rentals in Middletown, CT

Bring your pet along with stays that welcome four-legged travelers.

Tiny, Budget Friendly 1 Bedroom Central CT - Middletown, CT

Tiny, Budget Friendly 1 Bedroom Central CT

Apartment, Middletown

Tiny, Budget Friendly 1 Bedroom Central CT is a apartment in Middletown, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Tiny, Budget Friendly 1 Bedroom Central CT

Tiny, Budget Friendly 1 Bedroom Central CT is a apartment in Middletown, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pet friendly, pets friendly, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $965.

From$100/night
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East Haddam CT Country Loft - Middletown, CT

East Haddam CT Country Loft

Holiday Home, Middletown

East Haddam CT Country Loft is a holiday home in Middletown, with pet-friendly space and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About East Haddam CT Country Loft

East Haddam CT Country Loft is a holiday home in Middletown, with pet-friendly space and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, pet friendly, pets friendly, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,457.

From$162/night
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SPACIOUS AND QUIET - Middletown, CT

SPACIOUS AND QUIET

Apartment, Middletown

SPACIOUS AND QUIET is a apartment in Middletown, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

Read more

About SPACIOUS AND QUIET

SPACIOUS AND QUIET is a apartment in Middletown, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,571.

From$162/night
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fashionably cozy place - Middletown, CT

fashionably cozy place

Apartment, Middletown

fashionably cozy place is a apartment in Middletown, with pet-friendly space and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About fashionably cozy place

fashionably cozy place is a apartment in Middletown, with pet-friendly space and parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, pet friendly, pets friendly, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,640.

From$183/night
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Best Middletown, CT vacation rentals with a kitchen

Compare stays with kitchen access for longer trips and easier meals.

#2 *Beautiful 1 BR Apartment - Central CT* - Middletown, CT

#2 *Beautiful 1 BR Apartment - Central CT*

Apartment, Middletown

#2 *Beautiful 1 BR Apartment - Central CT* is a apartment in Middletown, with pet-friendly space, kitchen access, and room for a group. This stay gives travelers a comfortable base for…

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About #2 *Beautiful 1 BR Apartment - Central CT*

#2 *Beautiful 1 BR Apartment - Central CT* is a apartment in Middletown, with pet-friendly space, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: hot tub, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,291.

From$141/night
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Luxury Loft (perfect for business or pleasure) - Middletown, CT

Luxury Loft (perfect for business or pleasure)

Apartment, Middletown

Luxury Loft (perfect for business or pleasure) is a apartment in Middletown, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Luxury Loft (perfect for business or pleasure)

Luxury Loft (perfect for business or pleasure) is a apartment in Middletown, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, washer, and dryer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,535.

From$159/night
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Beautifully Lit Spacious 3-Bedroom House!! - Middletown, CT

Beautifully Lit Spacious 3-Bedroom House!!

Holiday Home, Middletown

Beautifully Lit Spacious 3-Bedroom House!! is a holiday home in Middletown, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring…

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About Beautifully Lit Spacious 3-Bedroom House!!

Beautifully Lit Spacious 3-Bedroom House!! is a holiday home in Middletown, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,569.

From$167/night
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Lovely Family sized 3 bedroom Colonial home, close to restaurant. - Middletown, CT

Lovely Family sized 3 bedroom Colonial home, close to restaurant.

Holiday Home, Middletown

Lovely Family sized 3 bedroom Colonial home, close to restaurant. is a holiday home in Middletown, with parking, kitchen access, and room for a group. This stay gives travelers a…

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About Lovely Family sized 3 bedroom Colonial home, close to restaurant.

Lovely Family sized 3 bedroom Colonial home, close to restaurant. is a holiday home in Middletown, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,243.

From$234/night
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Our Favorite Family-Friendly Vacation Rentals in Middletown, CT

Plan a trip with stays that give families more room to spread out.

Life on the Farm - Middletown, CT

Life on the Farm

Apartment, Middletown

Life on the Farm is a apartment in Middletown, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About Life on the Farm

Life on the Farm is a apartment in Middletown, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,352.

From$147/night
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Comfy and Equipped for a Small Family - Webster Hill Suite1E - Middletown, CT

Comfy and Equipped for a Small Family - Webster Hill Suite1E

Apartment, Middletown

Comfy and Equipped for a Small Family - Webster Hill Suite1E is a apartment in Middletown, with kitchen access and room for a group. This stay gives travelers a comfortable base for…

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About Comfy and Equipped for a Small Family - Webster Hill Suite1E

Comfy and Equipped for a Small Family - Webster Hill Suite1E is a apartment in Middletown, with kitchen access and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free wifi, kitchen, with kitchen, kids friendly, and kids friendly videos or books.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,548.

From$157/night
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Family-Friendly Lakeside Cottage with Spectacular Sunset Views Pet-Friendly! - Middletown, CT

Family-Friendly Lakeside Cottage with Spectacular Sunset Views Pet-Friendly!

Cottage, Middletown

Family-Friendly Lakeside Cottage with Spectacular Sunset Views Pet-Friendly! is a cottage in Middletown, with pet-friendly space, kitchen access, and room for a group. This stay gives…

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About Family-Friendly Lakeside Cottage with Spectacular Sunset Views Pet-Friendly!

Family-Friendly Lakeside Cottage with Spectacular Sunset Views Pet-Friendly! is a cottage in Middletown, with pet-friendly space, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,683.

From$175/night
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Cozy Lakefront Cottage #6 - Middletown, CT

Cozy Lakefront Cottage #6

Cottage, Middletown

Cozy Lakefront Cottage #6 is a cottage in Middletown. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

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About Cozy Lakefront Cottage #6

Cozy Lakefront Cottage #6 is a cottage in Middletown. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, dryer, ac, air conditioning, and internet.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,066.

From$208/night
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